Caribbean Family Villas

Caribbean Family Villas

The Caribbean is a great destination choice for families or multiple families traveling together. With a private kitchen and enough space for everyone, a Caribbean villa rental can be the most economical accommodation choice. Whether you are seeking a beachfront villa, a private island or a hillside villa with an amazing view, our favorite family villas section provides some of the best villas in the Caribbean for your family vacation.

There's really no island quite like Calivigny. This gem was purchased in 2000 by a couple who wanted to create a ... 20 BR rate available. Calivigny Island is located just south of Woburn Bay, Grenada

Grenada

Beachfront | Pool | AC

from $132000/Nt
25 25
Details
The Pearls of Long Bay are the gems of Providenciales. Each home has a theater-style media room, two pools, tons ... Has specials. The Pearls of Long Bay Estate consist of Pearl East, Pearls West and Lidia House

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $22500/Nt
23 23
Details
Necker Island is the place to go if you want the ultimate privacy, luxury, and pampering. You can rent out ... Has specials. The Beach pool at Necker Island

Necker Island, BVI, British Virgin Islands

Beachfront | Pool | AC

from $87500/Nt
17 11
Details
This private island resort is perfect for a casual, relaxing vacation for any group of travelers. Every activity you can ... Thatch Caye photo

Belize

Near Beach

from $9100/Nt
15 15
Details
Over Yonder Cay is the pinnacle of luxury. It's a private island in the Bahamas with a full staff of ... 6 BR rate available. Over Yonder Cay is a spectacular exclusive private island south of Nassau in the Bahamas

Exuma and Cays, Bahamas

Beachfront | Pool | AC

from Call for rates
15 12
Details
Ani Villa Estate - Dominican Republic is a property that doesn't skimp on luxury. There's pools with massive water slides, ... 10 BR rate available. Ani Villa Estate in The Dominican Republic has an amazing infinity edge pool with Caribbean views

Cabrera, Dominican Republic

Pool

from $10500/Nt
14 14
Details
Seaclusion Estate combines two gorgeous properties into one luxurious villa rental. The villas sit on the world’s most beloved ... Has specials. Seaclusion Villa and Seascape Villa combined comprise the Seaclusion Estate in Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $13800/Nt
14 14+
Details
This estate can easily accommodate large groups thanks to fourteen large bedrooms, indoor and outdoor dining areas, and sprawling patios. ... 4, 5, 6, 7, 8, 9, 10, 11, 12 & 13 BR rates available.
Has specials. The stunning infinity pool at Mes Amis Villa overlooks the beauty of Baie Rouge

Terres Basses (French side), St. Martin

Pool

from $1357/Nt
14 14+
Details
Combining the words, "Luxurious" and "All-Inclusive" can almost sound paradoxical. But at Three Bees at Harbour Island, Bahamas these two ... 8 BR rate available. Three Bees is located on Harbour Island Bahamas

Harbour Island, Bahamas

Beachfront | Pool | AC

from Call for rates
13 13
Details
Arrecife 23/24/25 make up a luxurious estate with resort amenities like a full staff, beautiful landscaping, pristine pools, and glamorous design. ... Arrecife 23/24/25 Estate at Punta Cana Resort photo

Punta Cana, Dominican Republic

Pool

from $4390/Nt
13 13+
Details
Although Bella Casa is super spacious, it manages to create an intimate atmosphere. You can easily relax with your family ... 4, 5, 6, 7, 8, 9, 10 & 11 BR rates available.
Has specials. La Bella Casa is located in Terres Basses overlooking the La Samanna Hotel and Baie Longue Beach

Terres Basses (French side), St. Martin

Pool

from $1071/Nt
12 12
Details
Golden Clouds is one to remember because it has meditation gardens that wind throughout the property, and several spots dedicated ... 7, 8, 9, 10 & 11 BR rates available.
Has specials. Golden Clouds Villa is located on Jamaica's north coast in the village of Oracabessa

Ocho Rios, Jamaica

Pool

from $1571/Nt
12 12
Details
2, 3, 4, 5, 6, 7 & 8 BR rates available. Enjoy relaxing by the pool and spectacular views of the Sir Francis Drake Channel beyond

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from $5000/Nt
10 9
Details
The Beach House is the biggest and most impressive accommodation on the island. If you want to vacation in style, ... The Beach House at Calivigny Island

Grenada

Beachfront | Pool | AC

from $57000/Nt
10 10
Details
This beachfront estate combines two villas into one luxurious rental. The St. James Estate enjoys an oceanfront location on Paynes ... The St. James Estate is located on Paynes Bay Beach and is comprised of The One and The Villa

Barbados

Beachfront | Pool | AC

from $3000/Nt
10 10+
Details
This beachfront vacation rental is a tranquil, luxurious place to take your family, friends, or wedding party. With ten bedrooms, ... Aerial views of the Samsara property and surrounding area

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $6050/Nt
10 7+
Details
Surrounded on three sides by green, tropical foliage, Le Chateau des Palmiers is ideal for any luxury vacation. The villa ... 6 BR rate available.
Has specials. Le Chateau des Palmiers is located directly on Plum Bay Beach

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $5000/Nt
10 10+
Details
Imagine having a bonfire on the beach after a long day of fun swimming, playing in the sand, tennis and ... Has specials. The luxurious resort like pool is just steps away from the ocean at Flor de Cabrera

Cabrera, Dominican Republic

Beachfront | Pool | AC

from $2900/Nt
10 9+
Details
If you do things with an all or nothing attitude, you'll flip over Le Bleu Villa. It's hard to think ... 5, 7 & 9 BR rates available.
Has specials. Le Bleu Villa its on 2.5 acres of beachfront in Little Harbor

Anguilla

Beachfront | Pool | AC

from $6750/Nt
10 10
Details
Silent Waters Villa is a sprawling villa just outside of Montego Bay that offers everything you could possibly need for ... 5, 6 & 9 BR rates available. Aerial View of Silent Waters

Montego Bay, Jamaica

Pool

from $2482/Nt
10 6
Details
The cove on which Crystal Springs Villa rests is like a clip out of a castaway movie. It is private ... 7 & 8 BR rates available.
Has specials. Crystal Springs is a beautiful Estate located right on the beach

Barbados

Beachfront | Pool | AC

from $8150/Nt
10 11
Details
For large groups wanting extreme luxury, the oceanfront Ani Villa Estate is a perfect choice. There are two separate villas, ... 8 BR rate available. Ani Estate Anguilla - North and South

Anguilla

Pool

from $8425/Nt
10 10
Details
I recommend Casa Sunshine for family vacations or big celebrations with friends. With 10 bedrooms and three levels of air-conditioned interiors, ... 4, 5, 6, 7, 8 & 9 BR rates available.
Has specials. Casa Sunshine photo

Guana Bay (Dutch Side), St. Martin

Beachfront | Pool | AC

from $1143/Nt
10 10
Details
This estate is perfect for family reunions or staff retreats. The sheer size of it all makes you feel like ... 5, 6 & 8 BR rates available. The Hawksbill Villa Estate

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $7500/Nt
10 10
Details
Pool area for Arrecife Villas

Punta Cana, Dominican Republic

Pool

from $2790/Nt
9 9
Details
Yarari Royale is one of a kind when it comes to luxury. You'll be spoiled by daily housekeeping, full butler ... 5, 6, 7 & 8 BR rates available. Yarari Royale is a beautiful home located in Cap Cana

Cap Cana, Dominican Republic

Pool

from $2430/Nt
9 9+
Details
La Dolce Vita is super luxurious and spacious. There's seven different lounges inside the villa and tons around the property's ... Has specials. La Dolce Vita sits beachfront on a beautiful stretch of Long Bay Beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $17000/Nt
9 9
Details
One Perfect Day is a well-equipped, charming villa. It has a five-star kitchen with tons of appliances, massive outdoor space, ... One Perfect Day Villa is located on the Peterborg Peninsula overlooking Magens Bay

St. Thomas, USVI

Near Beach | Pool

from $5500/Nt
9 9+
Details
Bella Vita has a gorgeous location right on Babalua Beach. Hang around the beach with the villa’s stand up ... Has specials. Bella Vita is a contemporary villa located near Babalua Beach

Providenciales, Turks and Caicos

Beachfront | Pool | AC

from $5950/Nt
9 7+
Details
This villa may be painted pink, but it has all the luxury and amenities you'd expect in a five-star Caribbean ... La Palmeraie is located on Harbour Island in the Bahamas

Harbour Island, Bahamas

Beachfront | Pool | AC

from Call for rates
9 8
Details
Nirvana and Mirador are lovely on their own, but even better together. Both properties are ideal for couples getaways or ... Has specials. Nirvana and Mirador ar the located in Fitts Village on and amazing stretch of sandy beach

Barbados

Beachfront | Pool | AC

from $3375/Nt
9 9+
Details
This ultra-modern villa is a great choice for any multi-generational family vacation. It's golf course location keeps kids a few ... 5, 6, 7 & 8 BR rates available. Arrecife Royale is located in the renowned Punta Cana Resort on the golf course

Punta Cana, Dominican Republic

Pool

from $2430/Nt
9 9+
Details
If you’re looking for luxury, Nevaeh has it in abundance. Not only does it sit on a gorgeous, private ... 5, 6, 7 & 8 BR rates available. Nevaeh is located on a beautiful stretch of Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $6800/Nt
9 8+
Details
Located on picture-perfect Grace Bay Beach, Seaclusion epitomizes luxury island lifestyle. The design is ultra-modern, with sleek finishes, cutting-edge technology, ... Has specials. Seaclusion photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $9600/Nt
9 9+
Details
Kiko has a great location that truly can't be beat. It's in Paynes Bay on Barbados's Platinum Coast, which is ... 6 & 8 BR rates available. Villa Kiko is located on Payne's Bay

Barbados

Beachfront | Pool | AC

from $7500/Nt
9 9+
Details
Capri Villa is the perfect venue for your next birthday, anniversary, wedding, or retreat. The villa is in Cap Estate, ... 5, 6, 7 & 8 BR rates available. Capri Villa photo

Cap Estate, St. Lucia

Near Beach | Pool

from $850/Nt
9 9+
Details
"Cerulean" means "heaven," and this private resort attends to all the details of your stay to create your personal heaven. ... Has specials. The beautiful Cerulean Villa on Barnes Bay in Anguilla

Anguilla

Beachfront | Pool | AC

from $14286/Nt
9 9+
Details
Sitting directly on Long Bay Beach, Casa Varnishkes is an opulent, gated estate perfect for families or larger group gatherings. ... 6 BR rate available.
Has specials. Luxurious private swimming pool at Casa Varnishkes

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1970/Nt
9 9+
Details
A La Mer Villa is one of the most spacious, well-designed villas on St. John. Its exterior has so many ... 8 BR rate available. A La Mer sits on St. John's coastline near Grat Cruz Bay

Great Cruz Bay, St. John

Near Beach | Pool

from $5280/Nt
9 9+
Details
Santosha sits right on Long Bay Beach and is perfect for beach weddings, anniversaries, and any special event. You can't ... 5, 6, 7 & 8 BR rates available.
Has specials. Santosha is located along a beautiful stretch of Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $5000/Nt
9 9
Details
“Nevaeh” is “heaven” backwards, and the villa's golf simulator, movie theater, media room, and gym are just a few of ... 5, 6, 7 & 8 BR rates available. Nevaeh is located on a beautiful stretch of Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $5000/Nt
9 8+
Details
Coconut Walk was designed to maximize views and luxury. You can see the ocean from almost everywhere in the house, ... Coconut Walk Villa at twilight

Grand Cayman, Cayman

Beachfront | Pool | AC

from $4450/Nt
8 6+
Details
This two-story home is ideal for families to share or for a few couples. The bedrooms are spread out over ... La Serena Villa features a private dock that brings you to a beautiful private sandy beach

Punta Cana, Dominican Republic

Beachfront | Pool | AC

from $3950/Nt
8 6+
Details
Ani Villas - Larimar is ideal for any group of travelers who wants the full luxury experience. There’s a ... 4, 5 & 6 BR rates available. The swimming pool at the Larimar Villa overlooks the Caribbean

Cabrera, Dominican Republic

Pool

from $4925/Nt
8 8
Details
Villa Del Mare is the ideal oceanfront villa. It's near Rum Point, which is one of Grand Cayman's most elegant ... Villa Del Mare is in an ideal oceanfront location near Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $3750/Nt
8 8
Details
English Harbour #048 is a hidden gem. With eight bedrooms, three pavilions and an extensive exterior, the villa is large enough ... 5 BR rate available. English Harbour #048 is located on Windward Bay

English Harbour, Antigua

Near Beach | Pool

from $2714/Nt
8 7
Details
Silver Sands is modern, luxurious, fully staffed, and beachfront. The villa has its own stainless steel pool, and Thompson Cove ... 6 BR rate available. Silver Sands Villa is located along Thompson's Cove on the world famous Grace Bay

Providenciales, Turks and Caicos

Beachfront | Pool | AC

from $4200/Nt
8 7+
Details
Footprints Estate is the place to be for your next group getaway. With two villas and eight bedrooms total, there’... Has specials. Footprints Estate is located on Alleynes Bay Beach

Barbados

Beachfront | Pool | AC

from $3500/Nt
8 7+
Details
Coconut Walk is a gorgeous choice for a group vacation. The villa is modern, elegant, and well-designed for large parties. ... Coconut Walk is an oceanfront estate on Seven Mile Beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $4450/Nt
8 7+
Details
Villa Del Mare has plenty of space for your next large group vacation. Whether you’re bringing your family, friends, ... Villa Del Mare is located on Rum Point Drive and has a great beach area

Grand Cayman, Cayman

Beachfront | Pool | AC

from $3750/Nt
8 8
Details
Fischer’s Reef is a great beachfront villa for large groups. There are four king suites, three queen suites, and ... Fischer's Reef Villa is located in Rum Point right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2950/Nt
8 8+
Details
Kaiku is a fun choice for your next luxury beachfront vacation. The house sits right on the beach and has ... 7 BR rate available. Kaiku is located on the Rum Point end of the island directly on Bio-luminescent Bay

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1850/Nt
8 6+
Details
If you want to breathe in the ocean air and relax, Arrecife 17 is an excellent choice for your next vacation. ... Arrecife 17 is located in Punta Cana with beautiful Caribbean views

Punta Cana, Dominican Republic

Pool

from $3750/Nt
8 8+
Details
Emerald Cay combines natural beauty with state-of-the-art technology for the ideal modern getaway. The master suite is a great example ... Aerial views of Emerald Cay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $30000/Nt
8 8+
Details
If you’re traveling with a large group and want plenty of space to spread out and relax, English Harbour #46 ... 7 BR rate available. English Harbour #46 is located on a hillside above Windward Bay and English Harbour

English Harbour, Antigua

Pool

from $5700/Nt
8 8+
Details
Just two minutes from the beach, Bluff House and Cottage is great for families and friends traveling together. The main ... 6 BR rate available.
Has specials. Bluff House and Cottage are located very near by Sandy Lane Bay

Barbados

Near Beach | Pool

from $2300/Nt
8 8
Details
Mango Bay is a large estate featuring seven bedrooms, a full on-site staff, and easy access to some of Barbados ... 6 & 7 BR rates available.
Has specials. Mango Bay's patio sits right on the beach

Barbados

Beachfront | Pool | AC

from $5200/Nt
8 7+
Details
If you want to not only see the water from your villa but be able to step right into it, ... 2, 4, 6 & 7 BR rates available. Beach Court Villa is settled at the western end of Shoal Bay Beach

Anguilla

Beachfront | Pool | AC

from $1100/Nt
8 8
Details
Fabrizia Villa is a great property for groups or a family with older children. This vacation rental has 8 bedrooms, several ... 3, 4, 5, 6 & 7 BR rates available. Fabrizia Villa offers a great pool nestled on the hillside over Gustavia Harbor

Gustavia, St. Barts

Near Beach | Pool

from $2571/Nt
8 9
Details
From the inviting front exterior to the contemporary furnishings, from the large pool to the quiet beach, Kaiku Villa is ... 7 BR rate available.
Has specials. Kaiku is located on the Rum Point end of the island directly on Bio-luminescent Bay

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1850/Nt
8 6+
Details
Your trip to the Dominican Republic should be nothing short of quiet and relaxing, and Casa Kimball will help redefine ... Casa Kimball is located on the north coast of the island of the Dominican Republic

Cabrera, Dominican Republic

Near Beach | Pool

from $3250/Nt
8 8
Details
Mullins Mill is truly where the living is easy. With a full staff to anticipate your every desire, you'll have ... 4 & 6 BR rates available.
Has specials. There is a beautiful ridge side pool at Mullins Mill

Barbados

Pool

from $1960/Nt
8 8
Details
If you want to hear the ocean from every room, then Sunrise Villa is the perfect setting for your next ... Sunrise Villa photo

Cabrera, Dominican Republic

Beachfront | Pool | AC

from $1500/Nt
8 8
Details
Plantation House is a huge luxury villa in Royal Westmoreland near Barbados's West Coast. It's eight bedrooms and three-story design ... 5 & 6 BR rates available.
Has specials. Grand views of the pool and the ocean beyond from the balcony at Plantation House

Barbados

Pool

from $1515/Nt
8 8
Details
Located on a hillside in St. John, Eco Serendib is a spacious 8-suite villa that serves as an ideal setting ... 1 & 5 BR rates available.
Has specials. The pool and ocean views from Eco Serendib

Rendezvous Bay, St. John

Pool

from $2850/Nt
8 8+
Details
The Beach House's high-class architecture and contemporary style is enough to make you want to stay forever, but that's not ... 3 & 5 BR rates available.
Has specials. The Beach House features an amazing pool and outdoor area

Anguilla

Beachfront | Pool | AC

from $8900/Nt
8 9+
Details
Sentosa Villa is the perfect vacation rental if you want a luxurious getaway on Grace Bay Beach with resort amenities. ... Sentosa is located along a beautiful stretch of Grace Bay Beach

Providenciales, Turks and Caicos

Beachfront | Pool | AC

from $15000/Nt
8 8
Details
I would strongly recommend this villa for a vacation with extended family. There's a guest cottage that's great for a ... 5, 6 & 7 BR rates available.
Has specials. Prudence is located in Old Queen's Fort, St James' on the West Coast

Barbados

Near Beach | Pool

from $1435/Nt
8 6
Details
You'll never lack entertainment here at Fischer's Reef. Have a cornhole tournament by the pool, read in the gazebo, or ... Fischer's Reef Villa is located right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2950/Nt
8 8+
Details
Darsena 20 is the perfect large group villa. Not only is it a resort villa in a gated community, it's also ... Darsena 20 Villa photo

Casa de Campo, Dominican Republic

Pool

from $2540/Nt
8 10
Details
Pearl East will make you feel like royalty. I love this villa for large family reunions and get-togethers with all ... 5, 6 & 7 BR rates available.
Has specials. Aerial view of Pearl East

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $5500/Nt
8 8+
Details
Pearl West is incredible. This villa is right on Long Bay, which is one of the most private beaches on ... 5, 6 & 7 BR rates available.
Has specials. Exterior Pearl West

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $5500/Nt
8 8+
Details
Martello House is pretty spectacular. It has two pools, a game room, and a media room to entertain your guests, ... 6 BR rate available.
Has specials. Stunning views from the infinity edged swimming pool

Barbados

Pool

from $1880/Nt
8 8+
Details
Our Cayman Cottage is pretty impressive. This villa was made for family reunions, with ample space for kids and adults ... Has specials. Our Cayman Cottage sits along a beautiful stretch of beach on the north side of Grand Cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1195/Nt
7 6+
Details
Impulse is honestly one of a kind. There's sculptures and statues throughout the space, waves of colored lights in the ... 6 BR rate available. Expansive living area has endless views of the ocean

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $3571/Nt
7 7
Details
Evolution is going to revolutionize your next family vacation. Not only is there a specific children's bedroom, but there's also ... Evolution Vill offers it all - right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2139/Nt
7 7+
Details
Tatenda is a great family villa because its far enough from cruise traffic and tourist spots to actually relax, but ... Tatenda Villa is a beautiful beach front home just along South Sound

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2139/Nt
7 7
Details
This luxury villa is absolutely beautiful and has plenty of room for any group. The outdoor space is amazing, with ... The pool and beautiful beach at Kaia Kamina

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2859/Nt
7 7+
Details
Middle Cay is the perfect-sized, perfectly stocked private island for two families to share for a tropical getaway. The location ... Middle Cay photo

Harbour Island, Bahamas

Pool

from $7000/Nt
7 6+
Details
Beach Enclave is unique not only because it sits on Long Bay, but also because it has a resort feel ... 6 BR rate available.
Has specials. A boardwalk to the beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $6180/Nt
7 6+
Details
Villa Londali is a great family villa, thanks to its location, bedrooms, and amenities. It's in Punta Cana Resort, which ... Villa Londali is located in the Punta Cana Resort and has amazing lake and golf course views

Punta Cana, Dominican Republic

Pool

from $2290/Nt
7 7
Details
This wedding-friendly villa is within walking distance to amazing resort amenities, restaurants, and an 18-hole golf course in a gated ... Has specials. Casa de Suenos is located within the gated Los Suenos Resort community

Costa Rica

Pool

from $1250/Nt
7 7
Details
If you've been dreaming of a five-star luxury vacation, Royal Island is hard to beat. This private island retreat has ... Royal Island is located four miles from North Eleuthera, and 40 miles northeast of Nassau

Eleuthera Island, Bahamas

Beachfront | Pool | AC

from $17400/Nt
7 6+
Details
If you love the sea, Cayman Castle and Guesthouse is the place to be. This expansive villa enjoys an oceanfront ... Cayman Castle and Guesthouse are located on Gun Bay in Grand Cayman

Grand Cayman, Cayman

Near Beach | Pool

from $1295/Nt
7 7+
Details
Twin Palms really stands out, and not just for its unique ocean view. The beach is silky soft, has great ... Twin Palms is located near Rum Point on a beautiful stretch of ocean

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1250/Nt
7 5
Details
If you want a beachfront villa with private bedrooms, a generous lap pool, and amazing snorkeling, Mora is a great ... Villa Mora is located on a beautiful beachfront in South Sound

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1650/Nt
7 7
Details
Our Cayman Cottage is a massive, oceanfront escape perfect for your next Grand Cayman vacation. It’s secluded on the ... Our Cayman cottage is located on the island's East End

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1195/Nt
7 6+
Details
Zenaida offers a great experience at an exceptional value. The beach is down a short, private path, and the villa ... 3, 4, 5 & 6 BR rates available. Zenaida Beach & Tennis Estate is located just above Sandy Hill Beach

Anguilla

Beachfront | Pool | AC

from $950/Nt
7 7
Details
This seaside villa is 7,000 square feet and is on 3.5 acres of land with gorgeous panoramic views. Between the pool, hot ... 3, 4 & 5 BR rates available. Paradise Villa is located near Blowing Point

Anguilla

Pool

from $1200/Nt
7 5+
Details
Private, secluded, and peaceful, La Koubba Villa will give you a lifetime of vacation memories. This 8000 sq.ft. fully air-conditioned ... 6 BR rate available. La Koubba Villa sits on the white sands of Sapodilla Bay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1786/Nt
7 7+
Details
If you are looking for a waterfront villa with the ultimate location, Vieux Caribe is the perfect choice. This island ... 5 BR rate available. Private pool deck at Vieux Caribe Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1225/Nt
7 7+
Details
It is probably the short walk to Guana Bay Beach that will please you the most when you stay at ... 3, 4, 5 & 6 BR rates available.
Has specials. Alizee Villa sits on a hillside above Guan Bay

Guana Bay (Dutch Side), St. Martin

Near Beach | Pool

from $930/Nt
7 7
Details
Tamarind Villa is an ideal choice for a family with young children. It has 7 bedrooms, with two cribs and one ... 3 & 4 BR rates available. Tamarind Villa photo

Cap Estate, St. Lucia

Pool

from $575/Nt
7 7
Details
Offering king-size beds and an en-suite bathroom for each of the five bedrooms, La Plage is a villa conveniently located ... 5 BR rate available. Luxurious Lorient Bay beachside pool deck at La Plage

Lorient, St. Barts

Beachfront | Pool | AC

from $5714/Nt
7 7
Details
Fustic House is a legendary vacation destination. The villa was built in the 18th century, but it’s been extremely ... Has specials. Amazing private swimming pool at Fustic House

Barbados

Near Beach | Pool

from $4030/Nt
7 7
Details
La Belle Creole is a great choice for a family vacation. There are seven bedrooms total, and six of them ... 3, 4, 5 & 6 BR rates available. La Belle Creole photo

Saint Jean, St. Barts

Pool

from $1571/Nt
7 6
Details
If you are looking for a completely stunning location for your family getaway, Coral House might just be it. With ... 5 BR rate available. Coral House sits on a beautiful stretch of the world famous Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $5500/Nt
7 7+
Details
This is a fantastic property for large families or groups that are working within a budget. There is plenty of ... Has specials. Twin Palms Villa - the namesake beautiful palm trees

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1250/Nt
7 4
Details
Villa Mora balances luxury, access, and spaciousness. With 8,000 square feet and beachfront access, everyone in your party will have plenty ... Has specials. Villa Mora is located beachfront in South Sound

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1650/Nt
7 7+
Details
Cayman Castle has plenty of opportunity for fun! It has access to a beach, tons of room outside to take ... Spectacular views, infinity edge pool and oceanfront lounging await at Cayman Castle

Grand Cayman, Cayman

Near Beach | Pool

from $1295/Nt
7 7+
Details
Wake up to the soothing sounds of the ocean and fall asleep to the cooling trade winds. Huge arcs throughout ... The entertainment patio and pool area at Conched Out Villa

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1557/Nt
7 7
Details
If you want your own private beachfront home with plenty of room for all 17 of your guests, Seascape is for ... Seascape Villa

Grand Cayman, Cayman

Beachfront | AC

from $3000/Nt
7 5
Details
Jamoon is the place to be for family reunions, couples getaways, and girls trips. Kids and adults alike love the ... 3, 4, 5 & 6 BR rates available.
Has specials. Private resort style pool and outdoor entertainment area at Jamoon

Barbados

Pool

from $1290/Nt
7 6+
Details
Jolly Harbour's Palm Point Villa is THE retreat for wedding parties, family reunions, or any group of 16 who are ready ... 1, 2, 3, 4, 5 & 6 BR rates available. Palm Point Villa is located right on Jolly Harbour

Jolly Harbour, Antigua

Beachfront | Pool | AC

from $1800/Nt
7 7+
Details
If you want a private, oceanfront villa with a secluded beach, On The Rocks is a great choice. This villa ... Has specials. On the Rocks Villa is located in the Beach Bay community

Grand Cayman, Cayman

Near Beach | Pool

from $950/Nt
7 4
Details
Villa Corales 28 is a beautiful oceanfront villa in Punta Cana

Punta Cana, Dominican Republic

Near Beach | Pool

from $5250/Nt
7 7+
Details
Cosmos is perfect if you love being outside and want to be one with nature. You could rent The Lodge ... 4, 5 & 6 BR rates available. Cosmos photo

Soufriere, St. Lucia

Pool

from $950/Nt
7 7
Details
Grace Too is the ideal beachfront escape. With wraparound porches and room for 16, it was made for big families and ... Has specials. The beachside pool at Grace Too - main beach house

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2864/Nt
6 5+
Details
Wake Up is super modern, well-equipped, and gorgeously designed. There's tons of space to relax outside by the pool or ... Wake Up Villa is located on the beautiful Flamands Beach

Flamands, St. Barts

Beachfront | Pool | AC

from $12143/Nt
6 6
Details
Yellow Bear Villa is great for your family's next vacation! Parents, have a babysitter watch the kids while you go ... Yellow Bear Villa - Very large pool and outdoor areas

Punta Cana, Dominican Republic

Pool

from $1750/Nt
6 6+
Details
This villa is totally serene. There's more than enough activities - pool and beach toys, kayaks, snorkeling, and a huge ... Casa Barana is located on Thompson Cove and has amazing ocean views

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $1550/Nt
6 5+
Details
Villa Acajou is a lovely getaway for the guest who wants to be on the water all day, every day. ... 4 BR rate available. Acajou Villa has a magical backyard

Leeward, Turks and Caicos

Near Beach | Pool

from $990/Nt
6 5+
Details
If you want a fully-staffed villa that has activities for everyone, then Villa Corales 114 is perfect for you. There's a 72 ... Villa Corales 114 has a decadent lawn and pool area

Punta Cana, Dominican Republic

Near Beach | Pool

from $2211/Nt
6 6+
Details
This family-friendly villa has a private pool, gorgeous hillside views, and is in the prime location for Antigua's sailing events. ... 5 BR rate available. Al fresco dining for eight

English Harbour, Antigua

Pool

from $850/Nt
6 6
Details
I love this villa because it's secluded, designed with tons of windows, and has private beach access. Willoughby Bay is ... 3, 4 & 5 BR rates available. Villa Liene at Daniel Bay is situated in Willoughby Bay

English Harbour, Antigua

Beachfront | Pool | AC

from $1161/Nt
6 6
Details
Ani Villas - Amber is a beachfront resort property that doesn't skimp on luxury. There’s not one, but two ... 4 & 5 BR rates available. Enjoy amazing sunsets from the beach at the Amber Villa

Cabrera, Dominican Republic

Pool

from $4925/Nt
6 6
Details
I love Villa Blackstone for family vacations. There's two bedrooms that are connected, a super safe pool terrace with crystal ... 2 & 4 BR rates available. Villa Blackstone is nestled in the hillside above Marigot Bay

Marigot, St. Barts

Pool

from $2857/Nt
6 6
Details
Big Chill is perfect for big families who want to chill in paradise! Its location on the Leeward Canal is ... Has specials. Big Chill Villa has a canal front pool with great areas to relax and entertain

Leeward, Turks and Caicos

Pool

from $2000/Nt
6 6+
Details
Kandara is great if you're looking for space and privacy. The villa has 8,000 square feet of space, an acre of ... Kandara Villa is located on Anguilla's West End

Anguilla

Near Beach | Pool

from $2330/Nt
6 6+
Details
Seaclusion will make you feel like royalty. There's more chandeliers and ocean views that I can count, and the exterior ... 4 & 5 BR rates available.
Has specials. Seaclusion is located just steps away from an amazing white sand beach

Barbados

Beachfront | Pool | AC

from $3750/Nt
6 5
Details
Salacia is a gorgeous, family-friendly choice for a luxurious vacation on Grace Bay Beach. It sits on 1.5 acres with over 200 ... Salacia Villa in Grace Bay offers amazing amenities

Grace Bay, Turks and Caicos

Near Beach | Pool

from $6900/Nt
6 6
Details
Casa de Campo is amazing for family vacations because there's something for everyone. It has tennis courts, a country club, ... Las Colinas 17 is located directly on the golf course in Casa de Campo

Casa de Campo, Dominican Republic

Pool

from $1430/Nt
6 6+
Details
Mandala is a perfect Punta Cana family villa, with all the bedrooms upstairs or in the guest house and the ... Mandala Villa is located right on the La Cana Golf Course

Punta Cana, Dominican Republic

Pool

from $1750/Nt
6 6+
Details
These resort villas are perfect for any group that wants to vacation in style. The villas range from three to ... 5 BR rate available.
Has specials. The elegant Shore Club Villas feature private swimming pools

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $6000/Nt
6 8
Details
Les Lataniers has a uniquely Caribbean charm, and I love how the owners have combined antique decor with modern amenities. ... 4 & 5 BR rates available. Villa Les Lataniers sits at the very end of Anse des Cayes

Anse des Cayes, St. Barts

Pool

from $2857/Nt
6 6
Details
This beachfront villa is a great choice if you want to take your family to Turks and Caicos, and you ... Has specials. Beach Enclave Beach Front Villa Plus 1 Bedroom Cottage at Long Bay photo

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $6080/Nt
6 6+
Details
Kempa Kai is luxurious, gorgeous, and unforgettable. Its modern design is both beautiful and practical, while the exterior is packed ... Kempa Kai villa is located on a nature preserve near Rum Point

Grand Cayman, Cayman

Beachfront | AC

from $3950/Nt
6 7
Details
Casa Patron is a great villa if you and your guests want plenty of space in a gated community. The ... Has specials. Casa Patron Villa is located just above Colina

Costa Rica

Pool

from $850/Nt
6 5+
Details
If you and your friends want to take a family vacation, Harmon Estate is perfect. Thanks to the main house ... Has specials. The Harmon Estate Villa is located in the Eco Golf Community

Costa Rica

Pool

from $1000/Nt
6 6
Details
Amalia is a gorgeous villa for a luxurious St. Martin vacation. I love how its architecture frames the views and ... 5 BR rate available.
Has specials. Amalia Villa is located on a hillside overlooking Guana Bay

Guana Bay (Dutch Side), St. Martin

Pool

from $1857/Nt
6 7
Details
White Coral is a bright, modern villa right on the Leeward Canal. The six bedrooms are great for a family ... White Coral Villa is located right on the Leeward Canal

Leeward, Turks and Caicos

Pool

from $1700/Nt
6 6
Details
Dei Sogni is an totally gorgeous, luxurious choice for your next family vacation. The entire villa opens to the outdoors, ... Dei Sogni is located right on a very desirable stretch of Lorient Beach

Lorient, St. Barts

Beachfront | Pool | AC

from $8571/Nt
6 6
Details
Sea Rocks is an easy choice for a family getaway or couples' vacation. The lap pool is great for morning ... 3 & 5 BR rates available. Sea Rocks is on the northern coast near Shoal Bay Village

Anguilla

Pool

from $750/Nt
6 6
Details
Corales 50 is ideal for a family or couples who want a resort experience without sacrificing privacy. It's near the beach, ... Corales 50 is situated in Punta Cana on the golf course only several hundred yards from the ocean

Punta Cana, Dominican Republic

Pool

from $1800/Nt
6 6+
Details
Tree House is an incredible family vacation rental within minutes of the sea, marina, dining, and activities. It feels tranquil ... Has specials. Tree House Villa is located on Grace Bay

Providenciales, Turks and Caicos

Near Beach | Pool

from $3500/Nt
6 5+
Details
Blue Dragon is dramatic, luxurious, and spacious. It's minutes from Gouverneur's shops and activities, and a short hike from the ... Blue Dragon sits on the hillside above Gouverneur

Gouverneur, St. Barts

Pool

from $10000/Nt
6 6
Details
CieloMar is one of the most stunning villas in the Caribbean. It has everything you could want in a vacation ... CieloMar is perched on the hillside above Peninsula Papagayo in a gated community

Costa Rica

Pool

from $7143/Nt
6 7+
Details
This gorgeous family-friendly villa is perfect if you have older children. Each of the bedrooms has exterior access, and there's ... 4 & 5 BR rates available.
Has specials. Mapai is located in Terrasse de Cul de Sac and looks out to Pinel Island

Cul de Sac (French Side), St. Martin

Pool

from $957/Nt
6 6+
Details
Footprints villa offers an amazing location on the most envied coast on Turks & Caicos: Grace Bay. Its modern technology, air-conditioning, ... Footprints villa is located on a beautiful stretch of Grace Bay Beach

Grace Bay, Turks and Caicos

Pool

from $3500/Nt
6 6
Details
Corales 60 is the place to be for an elegant, tranquil vacation. This luxury villa would be perfect for couples and ... Corales 60 Villa is located on the Golf Course in the Punta Cana Resort & Club

Punta Cana, Dominican Republic

Pool

from $2211/Nt
6 6+
Details
Ammonite is an amazing villa for your next vacation with family or friends. Not only does it have a full ... Ammonite Villa is located in Punta Cana on the golf course just a short distance away from the ocean

Punta Cana, Dominican Republic

Pool

from $6000/Nt
6 6+
Details
If you’re looking for all the comforts of home with a gorgeous tropical setting, Amarone is the place to ... Amarone Villa is located on South Sound Road with a beautiful stretch of white sand beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1300/Nt
6 6+
Details
Moon Kai is a great family vacation villa on a barefoot beach in Cayman Kai. The villa is designed for ... Moon Kai is located right on a white sandy beach with in walking distance to Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1950/Nt
6 6
Details
Alta Gracia pulls out all the stops. This villa is part of Punta Cana Resort, but it feels like a ... Alta Gracia Villa is located in Punta Cana near a beautiful golf course

Punta Cana, Dominican Republic

Pool

from $2300/Nt
6 6
Details
Villa de Agua has all the amenities of a classic Caribbean rental, and the design is magazine-worthy. If you love ... Villa de Agua is located in Punta Cana on the ocean ans just moments from Corales Beach

Punta Cana, Dominican Republic

Pool

from $4500/Nt
6 6+
Details
Cabuya is one of the most gorgeous villas on Providenciales's eastern coast. This villa has it all: a beachfront location, ... 5 BR rate available. Cabuya Villa is located in Leeward on a beautiful stretch of white sand beach

Leeward, Turks and Caicos

Beachfront | Pool | AC

from $4300/Nt
6 6+
Details
Z'Abricot is a great option for your next family vacation. All of the bedrooms are interior access only, there's a ... 4 & 5 BR rates available.
Has specials. Villa Z'Abricot is located near Orient Bay

Orient Bay (French side), St. Martin

Pool

from $686/Nt
6 4
Details
Escape to pure luxury on this huge 4.5-acre estate that is just minutes from beaches, restaurants, and shops! Chateau Margot ... 3, 4 & 5 BR rates available. Chateau Margot Villa photo

Bordeaux, St. John

Pool

from $857/Nt
6 5+
Details
Azzurra Castle is just the place for families or four couples to vacation together. There are six air-conditioned bedrooms, including ... 4 BR rate available. Azzurra Castle sits on the southwest shore of Greneda's L'Anse aux Epines

Grenada

Pool

from $2200/Nt
6 6+
Details
At Summer Heights, you can jumpstart your day with coffee in bed while you watch the sailboats and yachts head ... Summer Heights is located on a hillside above Nanny Cay

Tortola, BVI, British Virgin Islands

Pool

from $895/Nt
6 5+
Details
This villa is easily large enough for five couples traveling together or a family vacation. There's tons of space, and ... 2, 3 & 4 BR rates available. Loblolly Villa photo

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

from $486/Nt
6 6
Details
This beachfront property is made for relaxation. The patio area around the pool is surrounded by cushioned loungers, so you ... 2, 4 & 5 BR rates available. Caribbean Wind Villa is located on the beach at Mahoe Bay

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

from $929/Nt
6 6
Details
This is a great place to combine work and play. There's every amenity you could want, from a fully equipped ... Luxurious resort style pool in a lush tropical setting at Sol y Sombra

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from $2075/Nt
6 6+
Details
Baraka Point has a ton of privacy and great beach access. You can snorkel around the reef right outside the ... 3 BR rate available. Baraka Point is an amazing Villa Estate on the western Coast of Virgin Gorda

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from $3786/Nt
6 6+
Details
Two beaches to choose from, a large private pool, gated entrance, and views of the Caribbean waters are among the ... 4 & 5 BR rates available.
Has specials. La Salamandre is located in Terres Basses with views of Simpson Bay

Terres Basses (French side), St. Martin

Near Beach | Pool

from $1414/Nt
6 6
Details
Due to its architectural significance, Estate Belvedere has a very naturalistic flare, and is well-suited for up to five couples ... 3, 4 & 5 BR rates available. Enjoy relaxing poolside at Estate Belvedere

St. Croix, USVI

Pool

from $860/Nt
6 6+
Details
Only minutes from the beach, tennis, and shopping, Encore has spacious living areas both inside and out. The gazebo and ... 4 & 5 BR rates available.
Has specials. Encore Villa is located in Terres Basses and is nestled amongst beautiful tropical foliage

Terres Basses (French side), St. Martin

Pool

from $979/Nt
6 6
Details
Bajacu Villa has a totally unique design that gives you the best of both worlds: hilltop views and easy ocean ... Bajacu is located on a private hilltop in Turtle Cove

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $7000/Nt
6 7+
Details
Location, location, location! Petite Plage 5 is a sprawling beachfront property sleeping up to 12 guests offering privacy, one of the largest ... Has specials. A resort like pool and amazing ocean views

Grand Case (French side), St. Martin

Beachfront | Pool | AC

from $2829/Nt
6 6+
Details
Valentina has everything you could want for a quiet, relaxing vacation. There's fitness equipment and a lap pool so you ... 3 & 4 BR rates available. Valentina Villa is located at the eastern end of Pointe Milou

Pointe Milou, St. Barts

Pool

from $3143/Nt
6 6
Details
Inside and out, Pelican Vista offers the best of Providenciales. You can enjoy the view inside, or find a spot ... 4 & 5 BR rates available.
Has specials. The pool and palapa at Pelican Vista Villa

Grace Bay, Turks and Caicos

Near Beach | Pool

from $1570/Nt
6 5
Details
Colibri Cottage is ideal for a nature-centric getaway in St. Lucia. The villa has gorgeous views of Petit Piton and ... 2 & 4 BR rates available. Colibri Cottage sits on a hill above Soufriere Bay

Soufriere, St. Lucia

Near Beach | Pool

from $415/Nt
6 6
Details
Le Reve will have you hooked from the first glance. Palm trees, sandy beaches, and gorgeous ocean views fill the ... Le Reve Villa is located on a private stretch of beach in Baie Rouge

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $6429/Nt
6 7+
Details
Located within the gated community of Sandy Lane Estate, Moon Dance Villa is ideal for couples who want a tropical ... 4 BR rate available.
Has specials. Luxurious pool and backyard at Moon Dance Villa

Barbados

Pool

from $1300/Nt
6 6+
Details
Always Villa, recently entirely renovated, is decorated in appealing white to showcase its clean lines, as well as gleaming polished ... 4 & 5 BR rates available.
Has specials. Always Villa is located in Terres Basses

Terres Basses (French side), St. Martin

Pool

from $1357/Nt
6 6
Details
Views of tropical greenery, Caribbean waters, and the hills beyond can be enjoyed firsthand at Maison de Reve Villa. Six ... 4 & 5 BR rates available.
Has specials. Maison de Reve is located on a hillside in the Terres Basses area

Terres Basses (French side), St. Martin

Near Beach | Pool

from $857/Nt
6 6+
Details
Triton Villa is nestled into its own hillside enclave above Lockrum Bay and Little Harbour. This villa shares a secluded ... 4 & 5 BR rates available. Triton Villa is located on LockRum Bay

Anguilla

Near Beach | Pool

from $2200/Nt
6 6+
Details
Spacious and colorful, Mare Blu Villa overlooking Rendezvous Bay is the ideal getaway for your St. John vacation. Up to 12 ... 3, 4 & 5 BR rates available. Mare Blu Villa photo

Rendezvous Bay, St. John

Pool

from $1571/Nt
6 8
Details
This Happy Bay hideaway has plenty of space for everybody to relax - especially several couples traveling together. Ocean 5 is ... 4 & 5 BR rates available. Ocean 5 Villa sits on a Hillside in Mt. Choisy

Happy Bay (French Side), St. Martin

Near Beach | Pool

from $829/Nt
6 6+
Details
Located in Saline, Dunes Villa is an ideal selection for families with young children or four couples. With 6 bedrooms (2 king ... Amazing pool at Dunes Villa

Saline, St. Barts

Near Beach | Pool

from $8571/Nt
6 6
Details
With three secluded villas offering accommodations for up to 12, an on-site chef, and a chapel, Little Whale Cay is a ... 3 BR rate available. Little Whale Cay private island retreat in the Berry Islands

Berry Islands, Bahamas

Pool

from $16250/Nt
6 6
Details
Vintage charm and private cabins make Nelson Gay House an ideal spot for a wedding or family reunion. The size ... 4 & 5 BR rates available.
Has specials. Nelson Gay House is located on Godings Beach and has beautiful gardens

Barbados

Beachfront | Pool | AC

from $2200/Nt
6 6+
Details
Cumulus Villa is just a short walk from Lorient Beach, and was built with all the latest amenities in mind. ... 3 & 4 BR rates available. Cumulus Villa photo

Lorient, St. Barts

Near Beach | Pool

from $1707/Nt
6 6
Details
Antilles Pearl is a super luxurious, fully staffed, beachfront villa in one of the best spots on Anguilla. There's a 50... 5 BR rate available.
Has specials. Antilles Pearl is located on Shoal Bay Beach

Anguilla

Beachfront | Pool | AC

from $3200/Nt
6 6
Details
Sandyline Villa is one of the most luxurious estates on St. Martin. The exterior amenities are endless, and the villa’... 5 BR rate available.
Has specials. Plenty of loungers surround the swimming pool

Terres Basses (French side), St. Martin

Near Beach | Pool

from $4429/Nt
6 7
Details
The name says it all at Go Easy Villa. This villa enjoys water and island views, a gourmet kitchen, numerous ... 4 BR rate available.
Has specials. Go Easy Vill at Sugar hills offers a beautiful pool area

Barbados

Pool

from $1695/Nt
6 6+
Details
Book Ani Villa South if you need a family friendly, wheelchair accessible vacation rental. This 6-bedroom villa is ultra modern ... Ani Villa South in Anguilla is an excellent destination in the Caribbean

Anguilla

Pool

from $6775/Nt
6 6
Details
Vistamar Villa has plenty of room for any family vacation or special event. With six bedrooms and lots of living ... Has specials. Vistamar features a poolside gazebo and an ample sundeck

Barbados

Pool

from $1800/Nt
6 5
Details
Jable has gorgeous views, gorgeous design, and gorgeous amenities. Every spot in the villa is outfitted for luxury and comfort, ... 3, 4 & 5 BR rates available. Tucked away on a hillside Jable Villa has a private pool that provides some amazing views

Petite Saline, St. Barts

Pool

from $2571/Nt
6 6+
Details
As one of the few six-bedroom villas on the island, Panache Villa delights with magnificent views and unforgettable sunrises and ... 3 & 5 BR rates available. Panache Villa has amazing views over Rendezvous Bay

Rendezvous Bay, St. John

Pool

from $857/Nt
6 7
Details
The impression one gets when walking into this villa, is simply elegant Caribbean. It features a clean white interior with ... 3, 4 & 5 BR rates available.
Has specials. Amazing views of the harbor from Paradiso Villa

Oyster Pond (Dutch side), St. Martin

Pool

from $929/Nt
6 6+
Details
Le Caprice is designed for days of sunbathing and unwinding. The large pool is surrounded by a sprawling sundeck, and ... 4 & 5 BR rates available. Le Caprice Villa is located on a hilltop above Baie Rouge in Terres Basses

Terres Basses (French side), St. Martin

Near Beach | Pool

from $1142/Nt
6 6
Details
There’s something for everyone at Sandalwood House. You can enjoy a round of golf and a romantic dinner for ... 3 & 4 BR rates available.
Has specials. Twilight on the patio at Sandalwood Cottage

Barbados

Near Beach | Pool

from $975/Nt
6 7
Details
Children are welcome at Silver Rainbow Villa, which offers 5 bedrooms, 5 en-suite baths, 1 full bath, and outdoor showers. It has private ... 3 BR rate available. Silver Rainbow Villa looks out into Petit Cul De Sac

Petit Cul de Sac, St. Barts

Near Beach | Pool

from $7143/Nt
6 6
Details
Tamarind Villa is located in Providencials' best neighborhood, right on Grace Bay Beach. The views from both inside and outside ... Tamarind Villa is located on the shores of Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1934/Nt
6 6+
Details
With lots of space indoors and out, a great beachfront location, and easy access to water sports and entertainment, Serenity ... Serenity House Villa is located directly on Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1307/Nt
6 6+
Details
With the ability to accommodate up to 12 guests, Eclipse Villa in Vitet is perfect for large families or couples traveling ... 3, 4 & 5 BR rates available. Eclipse Villa is located on the hillside in Vitet a few minutes away from Lorient Beach

Camaruche, St. Barts

Pool

from $1857/Nt
6 6
Details
Monkey's Run Villa is a spacious home with the finest of everything. Five comfortable bedrooms with en suite baths, a ... 5 BR rate available.
Has specials. Monkey's Run has a great pool and outdoor space

Barbados

Pool

from $1800/Nt
6 5+
Details
Royal Belize is an exclusive private island rental with seclusion, luxury, and full service. There are three villas and a ... 3 & 5 BR rates available. Royal Belize Private Island

Belize

Beachfront | AC

from $6500/Nt
6 6+
Details
Casa Grande is totally relaxing. Its super open, has great views, and is steps from a private part of Grace ... 5 BR rate available. Casa Grande is located directly on Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2557/Nt
6 5+
Details
When you arrive at Bon Temps Villa, the first thing to do is stake out your chaise lounge. While everyone ... 4 & 5 BR rates available. Bon Temps is located on the west side of Pointe Milou looking out into the Caribbean

Pointe Milou, St. Barts

Pool

from $3143/Nt
6 6
Details
Le Manoir de Lurin Villa is not your typical rental. Of course, it is larger than most with its 6 bedrooms ... 1, 2, 3 & 5 BR rates available. Le Manoir de Lurin Villa photo

Lurin, St. Barts

Pool

from $2143/Nt
6 7
Details
Mani Villa has everything you need for a luxury vacation, with a three-level infinity pool, a gourmet chef, and a ... 5 BR rate available. Mani Villa is located in the Turtle Tail area on Providenciales

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $1350/Nt
6 5+
Details
Get a gorgeous view of Dawn Beach and great access to Phillipsburg in one package at Dawn Beach Villa. Just ... 2, 3, 4 & 5 BR rates available.
Has specials. Beautiful views of the Caribbean form the pool at Dawn Beach Villa

Dawn Beach (Dutch side), St. Martin

Near Beach

from $372/Nt
6 6
Details
Whether you are vacationing with others or having a quiet family trip, Amberley House is ready to meet your needs. ... 4 BR rate available.
Has specials. Poolside view of Amberley House

Barbados

Near Beach | Pool

from $1750/Nt
6 5
Details
Perched on the coast, Sun Salutations Villa has spacious, modern interiors and stunning views that make it an ideal spot ... The perfect image for Sun Salutations Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2499/Nt
6 5+
Details
Finding the perfect mix of oceanfront and privacy for a larger family can be difficult at times, but Coconut Villa ... Has specials. Coconut Beach villa is right on the Beach near Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $745/Nt
6 4
Details
Facing the impressive coast of the Caribbean Sea in Rum Point, Moon Kai Villa has six bedrooms that provide you ... Has specials. Moon Kai has a beachfront pool where you can lounge in the Caribbean sun

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1950/Nt
6 6
Details
Villa Susanna is a tropical paradise secluded above Marigot Bay. It's wooden exterior and lush gardens contrasts beautifully with the ... 2, 3 & 4 BR rates available. Aerial view of Villa Susanna

Marigot Bay, St. Lucia

Near Beach | Pool

from $1700/Nt
6 7
Details
Villa Colibri has a sleek and modern design that belongs on a magazine cover. There's a swimming pool with different ... 2, 3, 4 & 5 BR rates available.
Has specials. You'll find contemporary class at Colibri Villa.

Anguilla

Pool

from $945/Nt
6 6
Details
This villa offers guests luxury, starting with its view of the 13th hole of the Royal Westmoreland Resort's golf course. ... 4 & 5 BR rates available.
Has specials. Beautiful pool and outdoor area at Westerings

Barbados

Pool

from $1800/Nt
6 6
Details
This six-bedroom Clairmont Overlook Villa is absolutely perfect for large family getaways, employee retreats, or for a group of friends ... 1, 2, 3, 4 & 5 BR rates available. Clairmont Overlook photo

St. Croix, USVI

Pool

from $629/Nt
6 6+
Details
I love this villa's clean lines and all-white interior, and how quiet and private it is. Not only is C'est ... Has specials. C'est La Vie Villa is located on Plum Bay Beach

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $4714/Nt
6 6
Details
Mandalay Villa’s design, features, and amenities will make you feel like royalty the instant you arrive. This 5-bedroom beach ... The palatial pool area

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $10000/Nt
6 7+
Details
Tranquility Cove lives up to its name. This beachfront villa sits mere feet from the South Sound, with plenty of ... Tranquility Cove Villa has a luxurious infinity edge pool

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2139/Nt
6 6+
Details
If you want a modern villa that will leave you and your friends speechless, book Cascade. The pools here come ... 4 BR rate available. Cascade Villa is located right on Babalua Beach

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $1857/Nt
6 6+
Details
This villa is unique because of the four-level design. The bedrooms are really spread out, so guests have privacy that ... 3, 4 & 5 BR rates available. Villa Coco Rock is located on a secluded Petit Cul de Sac hillside

Petit Cul de Sac, St. Barts

Pool

from $1321/Nt
6 6
Details
Hidden Cove is perfect if you love being on the water and want a bit of privacy. It's near great ... Has specials. An aerial view of Hidden Cove Villa - it is located just adjacent to the Bio-luminescent Bay

Grand Cayman, Cayman

Near Beach | Pool

from $600/Nt
6 5
Details
Villa Oceania has a beautiful pool and shaded back patio

Cap Cana, Dominican Republic

Pool

from $4070/Nt
6 6+
Details
Sirena is a great choice for families who want to soak up the island. Punta Cana is a resort community ... Villa Sirena is located in Punta Cana on the La Cana golf course

Punta Cana, Dominican Republic

Near Beach | Pool

from $2670/Nt
6 6
Details
The best thing about this villa is easily the location. It's right on South Sound Beach, which is calm and ... Amarone Villa is a luxurious home on the South Coast

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1300/Nt
6 7
Details
Point of View is a great villa rental for large groups of travelers who want to be near the beach ... Point of View Villa is located on a picturesque Caribbean beachfront

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2859/Nt
6 6+
Details
Maison Blanc Bleu is breathtaking. The pool is huge, and the deck leaves plenty of room if you use the ... 4 & 5 BR rates available. Maison Blanc Bleu Villa photo

Lurin, St. Barts

Pool

from $5000/Nt
6 6
Details
I love Alta Bella because it's so peaceful. It's perfect for kids and family gatherings at a really great value. ... Alta Bella Villa sits on a inlet just on chalk Sound

Chalk Sound, Turks and Caicos

Near Beach | Pool

from $1351/Nt
6 6
Details
If you want a luxurious resort experience with zen-inducing Balinese design and nonstop ocean views, then you'll fall in love ... 3 BR rate available. A private cabana sits beachfront at Love Pumpkin

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $12225/Nt
5 5
Details
Tip of the Tail is so private, you'll feel like you have the island all to yourself. It has an ... Tip of the Tail Villa sits on the peninsula for which it is named

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $4800/Nt
5 6
Details
Beach Enclave Ocean View Villas are stunning beachfront villas perfect for travelers who appreciate elegant design and want to spend ... 3 & 4 BR rates available.
Has specials. The pool and view of the ocean from Beach Enclave Ocean View Villas

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $2950/Nt
5 5
Details
Crystal Waters, formerly known as Mudslide, is the perfect villa for your next family vacation. Every room is oversized, and ... Crystal Waters Villa sits beach front near the popular Water Cay and Kaibo Yacht Club

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1000/Nt
5 4
Details
This spacious, historic estate is ideal for family reunions. The large patio area and infinity pool are great for holiday ... Langarra Estate photo

St. Thomas, USVI

Pool

from $1081/Nt
5 5+
Details
Magens Hideaway photo

St. Thomas, USVI

Pool

from $1265/Nt
5 4+
Details
Hesperides is one of a kind. The location couldn't be better either, because it's close to Sapodilla Bay and Las ... Hesperides House has amazing uninterrupted ocean views

Taylor Bay/Sapodilla Bay, Turks and Caicos

Pool

from $1629/Nt
5 5
Details
The Beach House is right on the beach and has its own dock, so if you love the sea its ... The Beach House photo

St. Thomas, USVI

Beachfront | AC

from $1300/Nt
5 4+
Details
Coral Pavilion is chic and elegant, the perfect vacation rental if you want to feel like royalty. You’ll love ... The luxury pool at Coral Pavilion Villa sits just a few yard from the beautiful Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4950/Nt
5 5
Details
Hilltime is perfect for any family or couples who want to relax by the sea with minimal fuss. This villa ... Hilltime Villa is located on the north coast of Cayman in Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $695/Nt
5 4
Details
White Cottage is a great vacation rental for anyone who loves the ocean and privacy. It's in a quiet region ... White Cottage is a great beachfront villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1139/Nt
5 3
Details
Great Bluff Estate is perfect for groups who want privacy and space. It's fully gated, and sits on the quiet, ... Has specials. Great Bluff Estates sits along the beautiful northern coast of Grand cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $995/Nt
5 7
Details
Nirvana's bohemian design adds a homey touch to the five star amenities, and having your own private beach is the ... Nirvana photo

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1469/Nt
5 4
Details
Alinna is a gorgeous one-level villa with views of Chalk Sound. I love it for family vacations or couples' getaways, ... Alinna sits just along Chalk Sound with beautiful water views

Chalk Sound, Turks and Caicos

Pool

from $1700/Nt
5 6+
Details
Second Chances is a great choice for a relaxed getaway. It's 200 meters from Grace Bay, so you can go to ... Second Chances Villa has plenty of outdoor space for relaxing and entertaining

Leeward, Turks and Caicos

Near Beach | Pool

from $1950/Nt
5 6
Details
Dragonkey is a great villa for families who want to stay in a modern, chic villa that has top-notch technology. ... 2, 3 & 4 BR rates available. Dragonkey Villa is located in Mahogany Run overlooking the Caribbean

St. Thomas, USVI

Pool

from $568/Nt
5 3+
Details
The Five Bedroom Beach Level residences are perfect for families or four couples to share. They're right on Grace Bay ... Has specials. The Grace Bay Club Estate

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4320/Nt
5 4+
Details
Casa de la Playa is perfect for two families who want to vacation on St. Martin's glamorous west coast. It ... Has specials. Casa de la Playa Villa is located on Baie Longue in Terres Basses

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $3614/Nt
5 5
Details
This five-bedroom beachfront resort villa is absolutely gorgeous. It's on Long Bay, which is the quieter, windier sister to Grace ... Has specials. Beach Enclave Beach Front Villas on Long Bay

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $5700/Nt
5 5
Details
Nirvana is ideal for couples who want to vacation on the beach in style. The pool isn't massive, but who ... 4 BR rate available.
Has specials. Nirvana's pool deck and lounges

Barbados

Beachfront | Pool | AC

from $1500/Nt
5 5
Details
Lime Tree is a cool villa to stay in because it combines Mediterranean architecture with cushy amenities. The master bedroom ... Lime Tree Villa sits on a tropical hillside in the Peter Bay area

Peter Bay, St. John

Pool

from $1786/Nt
5 4+
Details
La Case Créole is a great family vacation villa. It has six bedrooms spread across two levels, and every ... 3 & 4 BR rates available. La Case Créole is located on a hilltop above St. Jean Bay

Saint Jean, St. Barts

Pool

from $1929/Nt
5 5
Details
Mirabelle is ideal if you want the beauty of Turks and Caicos without the crowds of Grace Bay. Sapodilla Bay ... Mirabelle sits on a beautiful stretch of Sapodilla Bay Beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1429/Nt
5 5+
Details
This luxury rental sits right on Paynes Bay and is the only unit in the complex to have a private ... 3 & 4 BR rates available.
Has specials. The Villa at the St. James is located beachfront on Paynes Bay Beach

Barbados

Beachfront | Pool | AC

from $1300/Nt
5 5
Details
Three Dolphins isn't only gorgeous inside, it also has amazing sea views with St. Martin in the distance. The villa ... Three Dolphins sits in a beautiful location with great ocean views

Anguilla

Near Beach | Pool

from $1850/Nt
5 4+
Details
This waterfront villa would be great for a few couples or a large family. There's two queen suites upstairs and ... 2 & 4 BR rates available. Water's Edge Villa is located on Blowing Point

Anguilla

Near Beach | Pool

from $600/Nt
5 5
Details
Windfall is an amazing family vacation destination for any age group. It has three king suites, one queen, and two ... Has specials. Windfall Villa's open-air pool with retractable canopy

Barbados

Pool

from $1750/Nt
5 6
Details
Casa Oasis is the place to go for a family vacation in Costa Rica. The two double suites, ping pong, ... Has specials. Casa Oasis Villa is located above Los Sueños popular Eco Golf Course

Costa Rica

Pool

from $1500/Nt
5 5
Details
Casa Puesta del Sol manages to be extremely chic and elegant without feeling stuffy or uncomfortable. It has high ceilings, ... Has specials. Casa Puestra del Sol Villa is located the neighborhood of Vista Tres Bahias in Los Suenos

Costa Rica

Pool

from $1000/Nt
5 5
Details
Casa Pacifica is ideal for four couples or adult families. Four of the five bedrooms have king beds, and the ... Has specials. Casa Pacifica is located in the hills of the Los Suenos Resort

Costa Rica

Pool

from $1000/Nt
5 5
Details
Seagrace is a bright, modern villa right on the water. It has gorgeous views, tons of natural light, and a ... Seagrace Villa is located on the Ailla Canal in the gated community of Leeward

Leeward, Turks and Caicos

Pool

from $1100/Nt
5 4
Details
Emerald Pavilion is the place to stay for a luxurious, beachfront vacation. This villa was designed by Paul Duesing Partners ... Has specials. Emerald Pavilion Villa is located on Emerald Point beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $6000/Nt
5 5
Details
Abita Kai is a great choice for a multi-generational family vacation. With three bedrooms spread across two levels of the ... Has specials. Abita Kai is located on a beautiful stretch of white sand beach in Cayman Kai

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1000/Nt
5 5
Details
Westland Heights 9 is a chic choice for your next Barbados vacation. It's on the west coast, which is one of ... Westland Heights 9 is located in a community on the west coast

Barbados

Pool

from $1500/Nt
5 5
Details
Vision Beach is a gorgeous, luxurious villa on Turks and Caicos’s most envied location: Grace Bay Beach. Not only ... Hot tub with-in the pool

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $6500/Nt
5 5+
Details
Seascape is the perfect place for five couples to experience the best part of Turks and Caicos. This chic five-bedroom ... Has specials. Seascape Villa is located on a beautiful stretch of Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4200/Nt
5 5+
Details
Residence 3 enjoys luxurious design inside and out, from the open exterior to the elegant living area. The kitchen is well-designed ... Has specials. The Residences are located directly on Grace Bay Beachfront and each have private infinity pools

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4800/Nt
5 5+
Details
The Residences at Seafire 5 Bedroom is a beachfront resort villa with luxurious amenities, an ideal location, and modern interiors. Guests ... The Residences at Seafire are located directly on Seven Mile Beach

Grand Cayman, Cayman

Beachfront | AC

from $2500/Nt
5 4
Details
Bajan Heights is a luxurious villa with five-star amenities, daily housekeeping, and a private chef. The villa is in a ... Bajan Heights is located in Royal Westmoreland

Barbados

Pool

from $1500/Nt
5 5
Details
Looking for luxury? Crystal Waters has it in spades. This beachfront villa has an ideal location within walking distance of ... Crystal Waters Villa is located just across the street from the Kaibo Yacht Club

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1000/Nt
5 4
Details
If you’re traveling with a large group, Ocean Kai is a great villa! It’s spacious, the bedrooms are ... Ocean Kai Villa is located in Cayman Kai near Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $925/Nt
5 5+
Details
Blue Water is the place to be for large groups. There are five bedrooms that can all accommodate couples, although ... Blue Water Villa is located on Rum Point Drive on a beautiful stretch of white sand beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $900/Nt
5 4+
Details
Great Bluff Estates is a fun, gorgeous place to be on Grand Cayman’s beachfront. There are several levels to ... Great Bluff Estates sits along the beautiful northern coast of Grand cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $995/Nt
5 7
Details
Pease Bay House is a luxurious, gorgeous villa that’s totally equipped for your next beachfront vacation. A large part ... Pease Bay House sits along a secluded sandy beach in Bodden Town

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1495/Nt
5 5+
Details
Two Rainbows is a fantastic choice for your next family vacation if you want total relaxation. This villa is on ... Two Rainbows is located within walking distance to the Rum Point Club

Grand Cayman, Cayman

Beachfront | Pool | AC

from $900/Nt
5 4+
Details
Tolumnia is a beautiful, spacious villa for group vacations. There’s tons of lounging space outside around the pool and ... 2, 3 & 4 BR rates available. Tolumnia is located on an acre of national park overlooking the bay of Willoughby

English Harbour, Antigua

Pool

from $627/Nt
5 4+
Details
Rotunda is a great, family-friendly villa rental with gorgeous views and privacy. It’s elevated above Peter and Trunk Bay, ... Has specials. Rotunda Villa is located above Peter Bay and Trunk Bay

Bordeaux, St. John

Pool

from $1700/Nt
5 5+
Details
If you want the resort experience without the crowds, Beach Enclave at Grace Bay is for you. Each villa enjoys ... Beach Enclave at Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $7600/Nt
5 4+
Details
Vacationing will be as much fun for your kids as it is for you at Sand Castle Villa. It has ... 3 BR rate available.
Has specials. Pool with view of ocean

Anguilla

Beachfront | Pool | AC

from $2000/Nt
5 5+
Details
Casa Bougainvillea is the ideal spot for guests who love water sports and beach combing. Situated right on the water's ... Casa Bougainvillea Villa has a beautiful private pool

St. Thomas, USVI

Beachfront | Pool | AC

from $800/Nt
5 4
Details
The open floor plan and high vaulted ceilings throughout this villa, coupled with the stone and tile work, keep the ... 2, 3 & 4 BR rates available. Silk Cotton Villa photo

St. Thomas, USVI

Pool

from $624/Nt
5 5
Details
Whether you're here to work or to play, you'll find something for everyone in your party at Sea Star. Kick ... Sea Star Villa is located on Cabrita Point

St. Thomas, USVI

Beachfront | Pool | AC

from $1399/Nt
5 5+
Details
The Carib House is located on the south coast of Antigua, and is perfect for your next getaway, honeymoon or ... 2, 3 & 4 BR rates available. The Carib House photo

Antigua

Near Beach | Pool

from $600/Nt
5 4
Details
Crystal Sea View Villa is spacious, well-equipped, and conveniently located. There’s plenty of space for everyone to relax, with ... 1, 2, 3 & 4 BR rates available. Crystal Seaview Villa is located on a hillside in the Cruz Bay area overlooking Chocolate Hole

Chocolate Hole, St. John

Pool

from $571/Nt
5 4+
Details
Casa Cervo is just steps away from the white sands of Baie Rouge with its secluded beaches, blue skies, and ... 3 & 4 BR rates available.
Has specials. Casa Cervo is an idyllic beach front villa - located directly on Baie Rouge

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $1281/Nt
5 5
Details
If you want to be pampered, come to Sea Villa. In addition to its stunning common areas, you have access ... Has specials. Sea Villa is situated facing the beach with amazing unobscured ocean views

Anguilla

Beachfront | Pool | AC

from $3300/Nt
5 5+
Details
At Long Bay Villas, you can expect to be relaxed and pampered. There's a full staff, water sports, four king ... Has specials. The luxurious Sand Villa at Long Bay

Anguilla

Beachfront | Pool | AC

from $3100/Nt
5 4+
Details
Dene Court is a five-bedroom, six-bathroom villa within Barbados' famous Sandy Lane Estate. The full staff will take care of ... 3 & 4 BR rates available.
Has specials. Dene Court Villa is located in the prestigious Sandy Lane on the Old Nine Golf Course

Barbados

Pool

from $850/Nt
5 5+
Details
Guests of Kismet can enjoy both sunrise and sunset views, is surrounded by gorgeous tropical gardens. Its perfect for special ... Kismet Villa is located on Maria's Bluff overlooking Chocolate Hole and Great Cruz Bay

Chocolate Hole, St. John

Pool

from $2857/Nt
5 6+
Details
Comfort is key at Serena Villa. You can relax outside in the large pool with ocean views, the furnished gazebo, ... Serena Villa is located above Baie Rouge Beach

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $1643/Nt
5 5+
Details
If you want to be amongst nature, there's no place like Brigand Hill. Surrounded by 500 acres of a former plantation, ... Brigand Hill Villa has a very private location with a relaxing pool

Anse La Raye, St. Lucia

Near Beach | Pool

from $550/Nt
5 4
Details
Rent the Two Palms property as a five-bedroom combo, or divide the units between groups of six and four. This ... Beach Palm

Anguilla

Near Beach | Pool

from $1150/Nt
5 5+
Details
The beach is just steps away from Alizee Villa. Not just any beach, but Taylor Bay! Taylor Bay is a ... 4 BR rate available. Alizee Villa is located just a short distance away from Taylor Bay Beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1143/Nt
5 5
Details
Melissa Villa is an excellent choice for any traveler who wants privacy and luxury all at once. You'll be steps ... Has specials. Melissa Villa is located near Heron Bay in Barbados just steps away from the beach at Colony Club

Barbados

Near Beach | Pool

from $1175/Nt
5 5
Details
On the outside, Carlota Villa looks like a castle. Inside, you'll marvel at the one-of-a-kind furnishings, such as the dining ... Carlota Villa is located on a hillside overlooking Peter Bay

Peter Bay, St. John

Pool

from $2500/Nt
5 6+
Details
If you like vibrant colors and great views, you'll love Villa Amarilla. Both the interiors and exteriors are done in ... 3 & 4 BR rates available. Beautiful Anguillan sunset from the back porch at Amarilla

Anguilla

Near Beach | Pool

from $2100/Nt
5 5+
Details
Tesori has nearly 7,000 square feet of indoor and outdoor living space, with ocean views and modern amenities throughout. The villa ... 1, 2, 3 & 4 BR rates available. Tesori Villa has a beautiful pool and entertainment balcony

Rendezvous Bay, St. John

Pool

from $829/Nt
5 5+
Details
Java Bay will put you in the mood for meditation and introspection. It's a place where you can connect with ... 4 BR rate available.
Has specials. Java Bay is located in Calijanda in Westmoreland and is less than two miles from the beach

Barbados

Pool

from $1495/Nt
5 5
Details
Decaj Villa is a great retreat for a family with young children, or two families for that matter. You'll love ... 1, 2, 3 & 4 BR rates available. Decaj Villa is located in Cap Estate with views of the ocean in the distance

Cap Estate, St. Lucia

Pool

from $400/Nt
5 4+
Details
You'll think you're in an Asian palace when you arrive at Golden Pavilion. You can relax on the covered patio ... 4 BR rate available. Golden Pavilion photo

Tortola, BVI, British Virgin Islands

Pool

from $1714/Nt
5 5+
Details
Whether you're headed to Barbados for a family vacation, honeymoon, or a getaway with friends, Casuarina House is a great ... 4 BR rate available.
Has specials. Casuarina Villa has a pool right on the golf course

Barbados

Pool

from $1350/Nt
5 5+
Details
Peace Bay House is perfect for several families or a group with its ample square footage and many amenities to ... Lounge poolside on the beach at Pease Bay House

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1495/Nt
5 5+
Details
The Beach House is truly a property with something for everyone. You might want to try some rock climbing on ... The Beach House sits on Mail Bay

St. Thomas, USVI

Beachfront | AC

from $650/Nt
5 3+
Details
If you want true pampering, come to Sky Villa. Things like daily housekeeping service are par for the course. Speaking ... Has specials. Sky Villa is the most private of the Long Bay Villas located just off the beach

Anguilla

Near Beach | Pool

from $2900/Nt
5 4+
Details
Take a path down to the beach from Solitude House and enjoy the ease of access to snorkeling and the ... 1, 2, 3 & 4 BR rates available. Solitude House photo

St. Croix, USVI

Near Beach | Pool

from $457/Nt
5 4+
Details
Champagne Shores is the perfect villa rental for design lovers. The sea-facing wall is made up of huge panes of ... Champagne Shores villa sits on a secluded beach near Pelican Bay

Anguilla

Near Beach | Pool

from $1700/Nt
5 5+
Details
Cinnamon Ridge emphasizes St. John’s natural beauty and serenity through tropical gardens, scenic views, and an expansive outdoor space. ... 1, 2, 3 & 4 BR rates available. Cinnamon Ridge Villa sits on a tropical hillside above Cinnamon bay

Catherineberg, St. John

Pool

from $593/Nt
5 5
Details
Kalorama Villa is fabulously unique! This artsy villa mixes contemporary style with such items as the island's traditional, native stone. ... 1, 2, 3 & 4 BR rates available. Kalorama Villa is located in Virgin Grand Estates

Virgin Grand Estates, St. John

Pool

from $860/Nt
5 4+
Details
If you have ever dreamed about the perfect family beach vacation or getaway for several couples, St. Bernard's Hill House ... St. Bernard's Hill House sit on a tropical hillside overlooking Belmont

Tortola, BVI, British Virgin Islands

from $3643/Nt
5 6+
Details
Fushi Villa is located cliff-side of Lance Aux Epines. This family friendly villa would also be a great place for ... 3 & 4 BR rates available. The pool meets the ocean at Fushi Villa

Grenada

Pool

from $700/Nt
5 5
Details
If you are looking for a vacation villa that is just steps away from the beach with a full staff ... Bali Dreams Villa photo

Cabrera, Dominican Republic

Near Beach | Pool

from $1200/Nt
5 6
Details
Bellevue is a great choice for large families or friends. There's a great view of the sea and the hillside ... 2 & 4 BR rates available. Bellevue Villa photo

Marigot, St. Barts

Pool

from $1000/Nt
5 5
Details
Located in Punta Cana, this resort villa will spoil you with wood-paneled ceilings, your own pool and a gorgeous beach ... Villa Arrecife 25 at Tortuga Bay photo

Punta Cana, Dominican Republic

Pool

from $1720/Nt
5 5
Details
When staying at this villa, you will be privy to a one-of-a-kind island deck with deck chairs located just above ... 4 BR rate available. The pool at Palm Beach is just steps away from the beach

Lorient, St. Barts

Near Beach

from $3571/Nt
5 5
Details
Eternity Villa will make you wish you could stay there forever! Located just minutes from restaurants and stores, the villa ... 3 & 4 BR rates available. Eternity villa is tucked into at tropical hillside above Flamands

Flamands, St. Barts

Pool

from $2143/Nt
5 5
Details
Located on a private cove with a sandy beach, Arushi Villa is one of Anguilla's premier villas. With over 5,300 square ... 1, 2, 3 & 4 BR rates available. Arushi Villa is located on the western end of Rendezvous Bay

Anguilla

Beachfront | Pool | AC

from $2800/Nt
5 5+
Details
Stone House is on the Dutch side of the island, but its also near the French side's border. This five-bedroom, ... 4 BR rate available.
Has specials. Stone House Villa is located near Dawn Bay Beach overlooking Oyster Pond

Oyster Pond (Dutch side), St. Martin

Near Beach | Pool

from $640/Nt
5 4+
Details
The festive island colors used throughout this villa give it an overall cheerful ambiance that will ensure you start your ... 2, 3 & 4 BR rates available. Lush tropical greenery surrounds Sade Villa

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from $600/Nt
5 5
Details
Paprika Villa offers stately elegance on the Turks and Caicos beachfront. With five spacious bedrooms, a dining room for ten, ... Beach Villa Paprika is located on Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1682/Nt
5 5+
Details
Tamarind is perfect for two families to share, because each level has its own living area and balcony or terrace. ... 2 & 4 BR rates available. Tamarind Villa is located in Island Harbor just minutes from Shoal Bay East

Anguilla

Pool

from $500/Nt
5 5
Details
Featuring 9,000-square-feet of living space, five spacious bedrooms, and over 600 feet of the sugary sands of Grace Bay beach, Amazing ... The pool area at Amazing Grace Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $5500/Nt
5 5+
Details
Beaches Edge villa has a smart design that maximizes the ocean views. Of course there's a pool, daily maid service, ... Has specials. Lounge by the pool and enjoy amazing ocean views at Beaches Edge East Villa

Anguilla

Near Beach | Pool

from $1400/Nt
5 5+
Details
At La Danse Des Etoiles Villa in the Pointe Milou area of St. Barts, guests are invited to experience relaxation ... 3 BR rate available. La Danse Des Etoiles Villa photo

Pointe Milou, St. Barts

Pool

from $4800/Nt
5 6
Details
The Dream is a luxurious beachfront villa with ocean views, open floor plans, outdoor living areas, and a gorgeous pool. ... Has specials. Luxurious pool just steps away from the beach at The Dream Villa

Barbados

Beachfront | Pool | AC

from $3500/Nt
5 5
Details
Mahogany Villa has peace and quiet, a convenient location, and cozy interiors. The villa is only a short distance from ... 3 & 4 BR rates available. Mahogany Villa is located near Guana Bay and has an amazing view of St. Barth's from the terrace

Guana Bay (Dutch Side), St. Martin

Near Beach | Pool

from $514/Nt
5 4+
Details
Book a magical vacation unlike any other when you stay at Aja Villa. Located in the ideal spot to see ... 2, 3 & 4 BR rates available. Aja Villa photo

Tortola, BVI, British Virgin Islands

Near Beach

from $800/Nt
5 5
Details
Clear aquamarine water packed with beautiful marine animals. A secluded beach with calm water just waiting for you. It is ... Has specials. Aerial view of Coral Kai Villa on Rum Point Grand Cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $825/Nt
5 5
Details
Tradewinds is a great choice if you want to be relaxing outside as much as possible. There’s two huge ... Has specials. Tradewinds Villa is located in the Sandy Lane neighborhood

Barbados

Pool

from $2500/Nt
5 5
Details
Whether you have a large family or want to spend time with friends, Miramar Villa is the perfect escape. This ... 2, 3 & 4 BR rates available. Miramar Villa has amazing ocean views

St. Croix, USVI

Near Beach | Pool

from $1680/Nt
5 5+
Details
La Petite Sereine is definitely luxurious. The decor is beautiful, the view is beautiful, the outdoor space is beautiful. I ... Pool at La Petite Sereine overlooking the ocean

Pointe Milou, St. Barts

Pool

from $7143/Nt
5 6
Details
Cayman Sands is a great family vacation villa for peace and quiet. There are two children's bedrooms, two master bedrooms, ... Has specials. Cayman Sands is located in Old Man Bay along a beautiful stretch of white sandy beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $625/Nt
5 5
Details
What is there not to love about Kai Conut Villa. This ocean front property is open and airy with five ... Has specials. The pool at Kai Conut is just steps away from the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $625/Nt
5 3
Details
This is the perfect location to bring the family together. The house is spacious and inviting. There are five bedrooms ... Has specials. The pool and this cabana are located right on the beach at Reef Romance Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $825/Nt
5 5
Details
Expect a grand and luxurious vacation when you come to Still Fathoms. This is an exquisite and unique five bedroom ... 4 BR rate available.
Has specials. Still Fathoms is a super stylish villa just steps away from the beach

Barbados

Beachfront | Pool | AC

from $1600/Nt
5 5+
Details
Windward Villa is spacious, exclusive, and totally perfect for a group of 10. It's part of the Sandy Lane Resort, so ... Has specials. Windward Villa in Sandy Lane offers luxurious amenities

Barbados

Pool

from $2800/Nt
5 5
Details
Love the beach, but craving privacy? Blue Water is an excellent choice. The big draws to Blue Water are its ... Blue Water is located on Rum Point with a beautiful stretch of beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $900/Nt
5 4+
Details
Blue Palm Villa is great for any group of travelers, family or friends. I love how spread out the bedrooms ... 3 & 4 BR rates available.
Has specials. Blue Palm Villa is surrounded by lush tropical greenery

Terres Basses (French side), St. Martin

Near Beach | Pool

from $786/Nt
5 6+
Details
Villa Isla is not only exquisite, it feels like heaven on earth. Large palm trees line the entrance, and the ... Amazing beachfront infinity edged pool on Long Bay Beach at Villa Isla

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1643/Nt
5 5+
Details
Outrigger House is great for groups or families that want to have tons of space under one roof. There are ... 3 & 4 BR rates available. Outrigger Villa photo

St. Thomas, USVI

Pool

from $1150/Nt
5 5+
Details
Villa Atlantis has so many leisure areas (both inside and out!) that you can enjoy a new spot every day. ... 2 BR rate available. Vill Atlantis is located on a hillside in Cap Estate

Cap Estate, St. Lucia

Pool

from $800/Nt
5 4+
Details
The layout of Reefside ensures that everyone in your party has beautiful rooms, private bathrooms, and complete privacy. The common ... 1, 2, 3 & 4 BR rates available. Views into Chocolate Hole Bay from Reefside Villa

Chocolate Hole, St. John

Near Beach | Pool

from $714/Nt
5 5+
Details
Sky Blue has incredible views of the water and a spacious, open floor plan that's perfect for a relaxing getaway. ... 2, 3 & 4 BR rates available.
Has specials. Relax by the pool and enjoy the ocean view at Sky Blue

Dawn Beach (Dutch side), St. Martin

Near Beach | Pool

from $608/Nt
5 5+
Details
Turtle Tail is for any large group that wants it all. The activities you can do are limitless inside and ... Turtle Tail Estate is located on the southern tip of Turtle Tail

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $10000/Nt
5 5+
Details
If your idea of a heavenly vacation is amazing sunset views over a glistening Caribbean Sea, then CéBlue Villas ... 3 & 4 BR rates available. CeBleu Villas are located on the northern end of crocus Bay

Anguilla

Near Beach | Pool

from $1095/Nt
5 6
Details
When I think of Firefly Villa, two words come to mind: grand and spacious. The decor is so chic, it ... 4 BR rate available.
Has specials. View from Old Trees#6 Firefly

Barbados

Beachfront | Pool | AC

from $1500/Nt
5 5+
Details
Galley Bay Heights #014 is a cozy, nearly beachfront villa that would be great to share with three other couples. There's ... 2 BR rate available. Aerial view of Galley Bay Heights Villa #104 and the beautiful beachfront

Galley Bay, Antigua

Near Beach | Pool

from $1150/Nt
5 4
Details
Viento has all the space and privacy you want in a large villa, especially with a detached honeymoon suite–it’... Viento Villa photo

St. Thomas, USVI

Pool

from $1200/Nt
5 5+
Details
Mermaid Falls Villa is a beautiful home with even more beautiful views. The ocean stretches as far as the eye ... Aerial view of the villa

Peter Bay, St. John

Pool

from $1857/Nt
5 5+
Details
Ridgemont is bright, open, and spacious as all get out–perfect for any group of 10. The pool is centered between ... 3 & 4 BR rates available. Ridgemont House photo

Tortola, BVI, British Virgin Islands

Pool

from $1000/Nt
5 6
Details
This villa is lovely and well maintained, with beautifully open views out of nearly every window. The decor is charming, ... 3 & 4 BR rates available. Turtle Villa is located in Mount Jean with ocean views

Mont Jean, St. Barts

Pool

from $1071/Nt
5 5
Details
This villa manages to be luxurious and family friendly at the same time. Four bedrooms plus a bungalow make the ... BOM Villa is located on the beach in St. Jean Bay

Saint Jean, St. Barts

Beachfront | Pool | AC

from $8421/Nt
5 5
Details
This villa is great for a family. Most of the bedrooms are upstairs, and there's terraces on both levels so ... 4 BR rate available. Saving Grace Villa is located on the far northeast end of Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2300/Nt
5 3
Details
This villa has a great open floor plan and sits on picturesque Cayman Kai. The high ceilings, minimal design, and ... Has specials. Ocean Kai sits directly on the beach near Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $925/Nt
5 5
Details
The sights both inside and out are unbelievable here. Take in the waters of Long Bay Beach from anywhere in ... Aguaribay Villa is located on a beautiful stretch of Long Bay Beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1400/Nt
5 5+
Details
This beachfront villa in Rum Point has tons of outdoor activities, from volleyball to snorkeling to swimming. For air-conditioned activities, ... Sea Grape Villa sits just on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $525/Nt
5 4
Details
Villa Corales 18 photo

Punta Cana, Dominican Republic

Beachfront | Pool | AC

from $4550/Nt
5 5+
Details
This villa's outdoor space almost reminds me of a James Bond movie. The open view is sure to induce heavy ... 3 & 4 BR rates available. Castle Rock Villa photo

Camaruche, St. Barts

Pool

from $4000/Nt
5 5
Details
This villa is amazing for entertaining family and friends alike. There are three king suites and two queen suites, so ... 3 & 4 BR rates available.
Has specials. Amandara Villa is located on a cliff side in Terres Basses

Terres Basses (French side), St. Martin

Pool

from $2143/Nt
5 5
Details
Sandy Beaches is one of the most economical rentals for a large group, especially when you consider just how close ... 3 BR rate available. Aerial Views of Sandy Beaches

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $999/Nt
5 5
Details
This villa is great if you want privacy, modern amenities, and don't mind being a short drive from the beach. ... Calypso Delight Villa overlooks Magen's Bay Beach

St. Thomas, USVI

Pool

from $695/Nt
5 5
Details
With a pool that goes on forever and panoramic views, I don't see how anyone wouldn't love Ginger Villa. I ... 3 & 4 BR rates available. Ginger Villa sits in the hills above Lorient Bay

Petite Saline, St. Barts

Pool

from $2000/Nt
5 5
Details
This resort villa is in a low traffic neighborhood just five minutes from the airport and Grace Bay, and has ... 3 & 4 BR rates available. Beach Enclave Beachfront Villas offer amazing ocean views

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $4180/Nt
5 5
Details
Ardisia is one of the best choices for a luxurious St. John vacation. It has chic decor, luxury amenities, and ... 1, 2, 3 & 4 BR rates available. Pool and backyard facing Great Cruz Bay at Ardisia Villa

Great Cruz Bay, St. John

Pool

from $1571/Nt
5 5+
Details
Sunset Close is very modern, beautifully decorated, extremely comfortable and well-stocked. The Silly Creek area is known for its peace ... Perfect patio to enjoy waterfront views at Sunset Close Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $929/Nt
4 4
Details
Frangipani Villa is luxurious through and through. I love the marble countertops and sleek decor, and every feature makes you ... Located on a stretch of white sand beach Frangipani Villa enjoys all of the resort amenities

Anguilla

Beachfront | Pool | AC

from $3500/Nt
4 4+
Details
Villa B53 at Tortuga Bay

Punta Cana, Dominican Republic

Pool

from $960/Nt
4 4+
Details
Milestone is a stunning villa that manages to strike the perfect balance between convenience and privacy. It sits on the ... A luxurious pool just steps away from the beach at Milestone Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2425/Nt
4 4
Details
Blue Papaya is the perfect villa for family vacations. One of the four bedrooms enjoys a lounge and wet bar, ... 1, 2 & 3 BR rates available. Blue Papaya photo

Virgin Grand Estates, St. John

Pool

from $593/Nt
4 4
Details
Starfish Villa is one of the more vibrant villas in the Punta Cana Resort. I like that all the bedrooms ... Starfish photo

Punta Cana, Dominican Republic

Pool

from $1080/Nt
4 4+
Details
SAX in St. Barts would be perfect for a couples' getaway or a family vacation. Two of the bedrooms are ... 3 BR rate available. SAX Villa photo

Saint Jean, St. Barts

Near Beach

from $3571/Nt
4 4
Details
Casa Bella's Spanish architecture and gardens make it stand out. I loved lounging by the pool as breezes blew through ... Has specials. Casa Bella photo

Barbados

Near Beach | Pool

from $500/Nt
4 3
Details
Sailrock Resort is great for those who want complete privacy on their vacation. South Caicos is almost totally undeveloped, but ... The four bedroom Beachfront Villas at Sailrock Resort

South Caicos, Turks and Caicos

Beachfront | Pool | AC

from $4400/Nt
4 4
Details
Turquoise is a gorgeous, modern villa that is ideal for a family vacation. Grace Bay Beach is just steps away, ... Aerial view of the Turquoise Villa property

Grace Bay, Turks and Caicos

Near Beach | Pool

from $1300/Nt
4 4
Details
Etoile de Mer has an incredible location just off Taylor Bay beach. There's a wonderful restaurant easily walkable that sits ... Etoile De Mer pool with furnished gazebo

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $714/Nt
4 4
Details
Villa Antigua - Jolly Harbour #008 is a great choice for travelers who want to experience island living at its fullest. ... Relax on the covered patio with beach and harbor views

Jolly Harbour, Antigua

Beachfront | Pool | AC

from $1350/Nt
4 4
Details
Olympus is a modern, beachfront villa with full air-conditioning and an enviable location near Rum Point Beach. Rum Point is ... An aerial view of Olympus Villa and the beautiful beachfront

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1500/Nt
4 4+
Details
If you're looking for a villa that feels like a personal slice of paradise, check out Limones 39. Its blanketed with ... Limones is located near Minitas Beach and has a great pool

Casa de Campo, Dominican Republic

Near Beach | Pool

from $1220/Nt
4 4+
Details
The Penthouse Suite in the Villas at Grace Bay Club is perfect for travelers who want to be as close ... Has specials. Grace Bay Club Resort pool

Grace Bay, Turks and Caicos

Beachfront | AC

from $4800/Nt
4 4
Details
Villa Islander is an architect's dream. Its surrounded by greenery, has floor-to-ceiling windows in every room, and uses only the ... Villa Islander is located just off the famous Grace Bay Beach

Grace Bay, Turks and Caicos

Near Beach | Pool

from $1880/Nt
4 4
Details
Imagine certainly fits my ideal vacation rental. It's right on the beach, still has privacy, and has modern interiors. There's ... Has specials. Imagine photo

Barbados

Beachfront | Pool | AC

from $850/Nt
4 4+
Details
Mirador is a great villa for a family or four couples who want to be as close to the beach ... Has specials. Mirador is located in Fitts Village - right on the beach

Barbados

Beachfront | Pool | AC

from $1500/Nt
4 4+
Details
This villa is great for four couples who want privacy and convenience. The exterior is multi-leveled and three of the ... 1, 2 & 3 BR rates available. EauSea sits atop a hillside overlooking Great Cruz Bay

Great Cruz Bay, St. John

Pool

from $857/Nt
4 4
Details
Sand Castle is the perfect choice for a beach vacation. It's open-air design brings the sea, sand and sun right ... Sand Castle Villa is located directly on Lorient Bay Beach

Lorient, St. Barts

Beachfront | AC

from $1429/Nt
4 3
Details
Since Spero sits steps away from Punta Cana's golf course, it's surrounded by perfectly manicured lawns and upscale gardens. The ... Spero Villa sits directly on Puna Cana's beautiful Hacienda Golf Course

Punta Cana, Dominican Republic

Pool

from $1000/Nt
4 4
Details
Alainn is sleek and modern with practical well thought out design. Its a great villa if you want to be ... Alainn Villa is located right on the water on Chalk Sound

Chalk Sound, Turks and Caicos

Pool

from $857/Nt
4 3
Details
If you're traveling to Costa Rica with your friends or extended family, you'll love La Perla. There's three suites in ... Has specials. La Perla Villa is located in Altamira, just above the Marina in Los Suenos

Costa Rica

Pool

from $1600/Nt
4 4
Details
Sandcastle Beach House is an action-packed choice for your next family vacation, anniversary, or celebration. With kayaks, paddle boards, bikes, ... Has specials. The Sandcastle Beach House is located on a beautiful beach in Limestone Bay

Anguilla

Beachfront | Pool | AC

from $1850/Nt
4 4+
Details
Albacore is a great villa for friends and family to share. The common area is spacious and modern, and each ... 2 & 3 BR rates available.
Has specials. Albacore Villa is located on the heights of Orient Bay

Orient Bay (French side), St. Martin

Pool

from $643/Nt
4 4
Details
Coco de Mer is a gorgeous luxury villa with tons of lounging space, lots of privacy, and four king suites. ... Has specials. Coco de Mer sits on top of the Sandy Lane Estate

Barbados

Pool

from $2500/Nt
4 4+
Details
Windchaser Grand is a bright, modern villa with a welcoming design and plenty of lounge space. I love how you ... Windchaser Grand is located beachfront on the beautiful Long Bay Beach

Long Bay, Turks and Caicos

Near Beach | Pool

from $1199/Nt
4 4
Details
Bahia Mar is ideal for a family or four couples who want to vacation on Taylor Bay. The beach is ... Bahia Mar Villa is located on Taylor Bay

Chalk Sound, Turks and Caicos

Beachfront | Pool | AC

from $1200/Nt
4 4
Details
Pelican Bay would be a great choice for a multi-generational family vacation. Three bedrooms are in the main house with ... Pelican Bay Villa in Anguilla

Anguilla

Pool

from $995/Nt
4 4+
Details
Bristol Bliss is the perfect villa for a quiet vacation with your favorite couples. It's on Turtle Tail, which is ... The pool at Bristol Bliss sits beachside overlooking the azure waters so famous in Turks and Caicos

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $2100/Nt
4 4
Details
Gustavia Views is a gorgeous choice for your next family vacation. Whether you're traveling with teenagers, infants, or adults, you'll ... 2 & 3 BR rates available. Gustavia Views Villa lives up to its name and more - also boasting a private pool

Gustavia, St. Barts

Pool

from $1714/Nt
4 3
Details
Residence 2 lets you enjoy the convenience of a resort community and the comforts of home, in one villa. The villa ... Has specials. The Residences are located directly on Grace Bay Beachfront and each have private infinity pools

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4100/Nt
4 5+
Details
At Glacier Moreno, it’s all about the sea. The ocean pours into every room, and the rooftop pool enjoys ... 2 & 3 BR rates available.
Has specials. Glacier Moreno Villa is located in Oyster Pond Estates overlooking nearby Dawn Beach and beyond

Oyster Pond (Dutch side), St. Martin

Pool

from $986/Nt
4 3
Details
Emeraude feels like a private resort, it’s so gorgeous. The pool deck is super luxurious, and there’s so ... 3 BR rate available.
Has specials. Villa Emeraude is located in Indigo Bay

Indigo Bay (Dutch Side), St. Martin

Pool

from $929/Nt
4 4
Details
Beach House is all about location, location, location. It’s on Taylor Bay, which is one of my absolute favorites ... The Beach House Villa is located within walking distance of Taylor Bay Beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1575/Nt
4 4+
Details
Gypsy is the place to be for a relaxing beachfront vacation. It’s right by the water in Rum Point, ... Gypsy is located in Rum Point right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $725/Nt
4 4
Details
Kai Vista is a charming beachfront villa for couples or families with older kids. It’s a short walk to ... Kai Vista is located in Rum Point along the north coast

Grand Cayman, Cayman

Beachfront | Pool | AC

from $745/Nt
4 4
Details
Olympus has it all: a beachfront location, modern design, and tons of space to lounge. Whether you want to relax ... Olympus is located on the beach front in Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1500/Nt
4 4+
Details
Tarasand Villa is a great choice for anyone who wants to be near Rum Point and have easy access to ... Tarasand sits on the waterfront in Cayman Kai, a short distance from Rum Point

Grand Cayman, Cayman

Beachfront | AC

from $950/Nt
4 3
Details
Rosso Di Sera has one of the best locations on the island, equidistant between Taylor Bay, Sapodilla Bay, and Chalk ... Rosso di Sera Villa is located on Chalk Sound

Chalk Sound, Turks and Caicos

Near Beach | Pool

from $643/Nt
4 4
Details
Rainbow Beach House has a perfect layout for relaxation. The beachfront location is great, because you can swim in the ... 1, 2 & 3 BR rates available. Rainbow Beach House Villa is located on Coral Bay

Coral Bay, St. John

Beachfront | Pool | AC

from $379/Nt
4 4
Details
Madison at Sandy Lane is a tranquil villa with resort amenities, golf course access, and elegant design. Whether you want ... Madison Villa is located on a hilltop in the Sandy Lane Estate with panoramic 180 degree views

Barbados

Pool

from $1200/Nt
4 4
Details
Turks and Caicos is well known for its beautiful beaches, and Five Turtles Villa gives you direct access to one ... Five Turtles Villa is just steps away from Taylor Bay Beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1214/Nt
4 3+
Details
A stay at Mille Fleurs is undeniably relaxing. This Terres Basses beauty has chic, elegant design, spacious common areas, and ... 1, 2 & 3 BR rates available. Mille Fleurs Villa is located in Terres Basses and overlooks Plum Bay Beach

Terres Basses (French side), St. Martin

Near Beach | Pool

from $714/Nt
4 4+
Details
Pallina Villa is a place you can bring your family and feel completely at home. There is a comfortable ambience ... Pallina Villa is located perched slightly beside Magen’s Bay

St. Thomas, USVI

Pool

from $950/Nt
4 3+
Details
Hakuna Matata is a wonderful, spacious home surrounded by flowers, palm trees, and tropical landscaping. The owners have stayed true ... 2 BR rate available. Hakuna Matata is located in the Catherineberg Estate overlooking Cinnamon Bay

Catherineberg, St. John

Pool

from $893/Nt
4 5+
Details
Villa On The Beach is a family-friendly villa that can easily accommodate three couples. There are four bedrooms, three of ... 2 BR rate available. Villa on the Beach is located beachfront on Mahoe Bay

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from $886/Nt
4 5
Details
Beach Dreams is great for beach lovers and snorkelers. The beach is a few steps away from the pool, with ... 2 BR rate available. Wonderful beach just steps away from the pool at Beach Dreams Villa

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from $886/Nt
4 4+
Details
This villa has an ideal location far from crowds yet minutes from Grace Bay, and is a cozy choice for ... 3 BR rate available. Endless ocean views

Turtle Tail, Turks and Caicos

Pool

from $786/Nt
4 4
Details
Situated right on the sandy beach, Thespina is one of Barbados' most unique private villas. The home itself is very ... 2 & 3 BR rates available.
Has specials. Thespina Villa is located in Holetown right on the beach nestled in tropical foliage

Barbados

Beachfront | AC

from $600/Nt
4 4
Details
You can spend your days relaxing around the heated pool or stretched out on the white sand beaches, without a ... 2 & 3 BR rates available. Euphoria Villa looks out over Leverick Bay

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

from $514/Nt
4 3
Details
Located right on the French side of St. Martin, Blue Beach Villa is a great beachfront home with tons of ... 2 & 3 BR rates available.
Has specials. Lounge by the pool with amazing ocean views

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $929/Nt
4 4
Details
The Tamarind House is a large villa surrounded by gorgeous gardens and tropical views. The house is filled with intricate ... 3 BR rate available. Uninterrupted views of the Pitons

Soufriere, St. Lucia

Pool

from $500/Nt
4 4
Details
Bonavista Villa is located in a gated community, and is just steps away from Gibbs Beach. It has a cook, ... 3 BR rate available.
Has specials. Tropical surroundings greet you at the pool at Bonavista Villa

Barbados

Beachfront | Pool | AC

from $1280/Nt
4 4+
Details
Evergreen is a luxurious garden villa with a full staff, spacious interiors, and modern amenities. You can watch movies or ... 3 BR rate available.
Has specials. The stunning Evergreen property, in the prestigious Sandy Lane neighborhood, from an aerial view

Barbados

Pool

from $1100/Nt
4 5
Details
The modern villa of Ecume des Jours is just 15 minutes from the airport, but it is situated in a very ... 2 & 3 BR rates available.
Has specials. Ecume des Jours is located on the end of Plum Bay Beach

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $829/Nt
4 3
Details
Four bedrooms and four baths make Kir Royal Villa perfect for a pair of vacationing couples or a large family. ... 2 & 3 BR rates available. Kir Royal Villa is located in St. Jean

Saint Jean, St. Barts

Near Beach | Pool

from $786/Nt
4 4
Details
There are many villas in Terres Basses on the French side of St. Martin that can accommodate small children, but ... 2 & 3 BR rates available.
Has specials. Oceane Villa is located in Terres Basses on the French side of St. Martin

Terres Basses (French side), St. Martin

Near Beach | Pool

from $629/Nt
4 4+
Details
With a thatched-roof outdoor dining area, hot tub, private infinity-edge pool, and beach access, you'll want Valentina Villa to become ... Has specials. Valentina Villa has a beautiful pool and patio and is situated just above Sapodilla Bay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1485/Nt
4 4+
Details
Southern Breeze Villa is a warm, spacious home overlooking Fish Bay and Cocolobo Point. This beautiful four-bedroom home is the ... 1, 2 & 3 BR rates available. Southern Breeze is located near the Battery Gut area and has amazing Caribbean views

Rendezvous Bay, St. John

Pool

from $414/Nt
4 4
Details
Built in 2009, Ocean Villa is a 4-bedroom, 3.5-bathroom accommodation located within the Wyndham Rio Mar Beach Resort, making this great ... View to the ocean and pool from the 4 bedroom ocean villa!

Northeast Coast, Puerto Rico

Beachfront | AC

from $536/Nt
4 3+
Details
With four bedrooms, spacious living areas, and an open floor plan that combines indoor and outdoor living, High Trees Villa ... Has specials. High Trees Villa is located on Gibbs Bay Beach

Barbados

Beachfront | Pool | AC

from $1180/Nt
4 4
Details
The Ushuaia Villa has four bedrooms, three queen and one with twin beds. The latter can accommodate families traveling with ... 2 BR rate available. Ushuaia Villa has great views over Flammands

Flamands, St. Barts

Near Beach | Pool

from $936/Nt
4 4
Details
Alamandra Villa is a spacious luxury villa with the best waterfront views in Silly Creek. There's a 20 x 35 infinity edge ... Alamandra is located in Silly Creek with great waterfront views

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1129/Nt
4 4+
Details
Abrigado Villa is perfect for vacationing couples or families looking to entertain and unwind. There's plenty of room for privacy ... 2 & 3 BR rates available. Relax and enjoy the amazing view poolside from Abrigado Villa

Virgin Grand Estates, St. John

Pool

from $643/Nt
4 4+
Details
If you love outdoor showers, infinity pools, and a 20-second walk to the beach, stay at Alegria Villa. You'll find ... The beautiful pool and Caribbean views from Alegria Villa

Anguilla

Near Beach | Pool

from $1500/Nt
4 4
Details
If you love design, you'll go crazy for Claridge villa. The magazine-worthy living area is all-white with exposed beams and ... 2 & 3 BR rates available. Lounge poolside and enjoy amazing ocean views from Claridge Villa

Anse des Cayes, St. Barts

Beachfront | Pool | AC

from $1429/Nt
4 4
Details
Vista Caribe is located in the exclusive Virgin Grande Estates and has breathtaking views of the Caribbean Sea, St. James, ... 1, 2 & 3 BR rates available. Vista Caribe Villa photo

Virgin Grand Estates, St. John

Pool

from $643/Nt
4 4+
Details
This spacious villa is perfect if you are looking for an active beach vacation. With a billiards table, private pool, ... Lounges over look the pool and out into the sound

Chalk Sound, Turks and Caicos

Pool

from $643/Nt
4 3+
Details
Great Turtle sits nestled within the hills and enjoys wonderful views of Coral Bay, the Caribbean Sea, and the Bordeaux ... 2 & 3 BR rates available. Great Turtle Villa is nestled on a tropical hillside above Coral Bay

Coral Bay, St. John

Pool

from $473/Nt
4 4+
Details
One of my favorite things about Dawn Beach Villa is how close it is to all the amenities of Turtle ... 3 BR rate available. Dawn Beach Villa has a beautiful pool and a hot tub

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1129/Nt
4 4
Details
Once you stay at West Bay Club, you'll be planning your return before you even leave. You'll love sitting on ... Has specials. The West Bay Club by night

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2020/Nt
4 4
Details
Summer Breeze Villa, also known as Villa Minou, is one of the top choices in a vacation location for families ... 2 & 3 BR rates available. The infinity edge pool and patio deck overlook Grand-cul-de-sac

Grand Cul de Sac, St. Barts

Near Beach | Pool

from $986/Nt
4 4
Details
Located in the peaceful Turtle Tail area, Sandy Shore has direct beach access, a private onsite swimming pool, a kayak, ... Sandy Shore Villa is located on the beach of the beautiful Taylor Bay

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $857/Nt
4 4
Details
With four ensuite bedrooms, its own private infinity-edge swimming pool, and quick access to the sea and snorkeling, Breezy Villa ... Breezy Villa sits directly on the ocean

Long Bay, Turks and Caicos

Pool

from $1143/Nt
4 4
Details
This secluded villa is great for guests who want to relax with a good book or adventure on the water. ... 2 & 3 BR rates available. Bright Idea has great views of Chalk Sound

Chalk Sound, Turks and Caicos

Beachfront | Pool | AC

from $800/Nt
4 4+
Details
If you know what Poggenpohl and Miele are, you know you want them in your kitchen. Not only do guests ... Sandcastle Pointe Villa is located on the waterfront on Shoal Bay

Anguilla

Pool

from $1200/Nt
4 4
Details
Great Escape is a great villa rental for a family vacation or special event. Everyone will have plenty of space, ... Has specials. Great Escape Villa is very close to the beautiful beach

Grand Cayman, Cayman

Near Beach | Pool

from $645/Nt
4 3
Details
Our readers agree that staying at Lime Hill Villa will provide you with the vacation memories that you want to ... Lime Hill Villa photo

English Harbour, Antigua

Near Beach | Pool

from $716/Nt
4 4
Details
Because vacations are supposed to be relaxing and stress-free, it is often counterproductive to take a trip that involves renting ... 2 & 3 BR rates available.
Has specials. Villa Mango sits on the hillside above Orient Bay

Orient Bay (French side), St. Martin

Near Beach | Pool

from $600/Nt
4 4
Details
Ambiance is all that the name implies - a villa with a special atmosphere that will positively impact your entire ... Has specials. Ambiance is located in the heart of Terres Basses with access to beautiful beaches nearby

Terres Basses (French side), St. Martin

Pool

from $1000/Nt
4 4+
Details
La Percha is ideal for any group of travelers. It has everything you could want in a tropical getaway- four ... Has specials. La Percha Villa photo

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1485/Nt
4 4+
Details
Rapture Villa is 5000 sq. feet of Caribbean luxury and style. Elegant turtle statues float above the pool overlooking the sea ... 1, 2 & 3 BR rates available. Rapture Villa photo

Virgin Grand Estates, St. John

Pool

from $749/Nt
4 4
Details
With a private pool, onsite restaurants and activities, and a beachfront location, you and your family will never want to ... Has specials. Turtle Villa is located in Jolly Harbour on the beautiful Lignum Vitae Bay

Jolly Harbour, Antigua

Beachfront | Pool | AC

from $1843/Nt
4 4+
Details
Reef Beach House truly is a tropical haven. Located right on Grace Bay Beach, this villa offers four air-conditioned bedrooms ... 2 BR rate available. Reef Beach House is located near Smith Reef along Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $686/Nt
4 3
Details
If you like both contemporary and Caribbean styles, you'll love the beautiful browns, blues and whites at Seabird Villa. This ... 2 & 3 BR rates available. Seabird Villa has beautiful sunset views

Anguilla

Near Beach | Pool

from $650/Nt
4 4+
Details
Caprice Villa has everything you need to enjoy a carefree vacation in Barbados. Spend your mornings playing golf or tennis, ... Has specials. Caprice Villa sits in it's stately location on the Gold Coast Beachfront

Barbados

Beachfront | Pool | AC

from $1800/Nt
4 4+
Details
What a wonderful place for a large family or several friends and families to take a beach vacation. This large, ... 2 & 3 BR rates available. Amarillo Villa is located in True Blue Grenada

Grenada

Pool

from $500/Nt
4 4
Details
Jessamine Villa is located on the West Coast of Barbados, near Gibbs Bay Beach, golf and tennis, and an assortment ... 3 BR rate available.
Has specials. Set amid lush tropical greenery Jessamine offers a beautiful private pool

Barbados

Near Beach | Pool

from $510/Nt
4 4
Details
This villa has some of the most beautiful ocean views on the island. It's a few steps from the water, ... Has specials. Hemingway House is tucked in a cove between Gibbs Beach and Mullins Beach

Barbados

Beachfront | Pool | AC

from $2150/Nt
4 4+
Details
Mahogany trees, tropical plants, fruit trees, and a multitude of green foliage make Shangri La a little slice of heaven. ... Has specials. Shangri La Villa is located in the Holders Hill area right on the Barbados Polo Club

Barbados

Pool

from $1235/Nt
4 4
Details
Hacienda has plenty of space for a large group, and has a great location for exploring the island. It's private, ... 2 & 3 BR rates available.
Has specials. La Hacienda Villa sits on the Terres Basses hillside

Terres Basses (French side), St. Martin

Pool

from $636/Nt
4 3
Details
Sea Breeze Villa has a full wall of windows that bring the outdoors in, and an infinity-edge pool amidst a ... Sea Breeze Villa has a beautiful private pool

Providenciales, Turks and Caicos

Near Beach | Pool

from $1095/Nt
4 4
Details
Westshore Beach House is ideal for two couples or families who are traveling together. Both levels have two bedrooms, seating ... Westshore Beach House is located right on the beach between Alleyne's Bay and Reeds Bay

Barbados

Beachfront | Pool | AC

from $950/Nt
4 4+
Details
Lantano Villa is so comfortable and scenic! Its the type of home that makes you want to take your shoes ... Lantano Villa is located in Peter Bay Estate overlooking the Caribbean and the north shore

Peter Bay, St. John

Pool

from $1571/Nt
4 4+
Details
Island Sun’s North Shore views are the most beautiful in the world. There’s plenty of sun around the ... 2 & 3 BR rates available. Island Sun sits on a hillside above Cinnamon Bay

Catherineberg, St. John

Pool

from $771/Nt
4 5
Details
When ISLANDS magazine names you 'One of the Top 20 villas in the World', it's always a good sign. It has ... 1, 2 & 3 BR rates available. The beautiful Bird of Paradise Villa

Anguilla

Near Beach | Pool

from $1850/Nt
4 4+
Details
Imagine waking up to a perfect ocean view every morning, walking into a gourmet kitchen for breakfast, and enjoying a ... 2 & 3 BR rates available.
Has specials. Happy Bay Villa is located on the northern coast of the island within walking distance of Friars Bay

Happy Bay (French Side), St. Martin

Near Beach | Pool

from $700/Nt
4 4+
Details
2B at Peter Bay Villa is known for its spacious design, high end furnishings, and waterfront location. This spectacular home ... 2B at peter Bay is perched on a tropical hillside above the west end of Peter Bay

North Shore, St. John

Near Beach | Pool

from $1857/Nt
4 4+
Details
Angelina Villa works quite nicely for a family with older children or a group, and because of its modern amenities, ... 1 & 3 BR rates available. Angelina villa has great views of the harbor

Gustavia, St. Barts

Near Beach | Pool

from $1357/Nt
4 4
Details
Illusion Villa is perfect for a larger family with older children. An on-site tennis court, putting green, and art-decor inspired ... Has specials. Beautiful views from the balcony at Illusion Villa

Barbados

Pool

from $2250/Nt
4 4+
Details
Recently remodeled, Rising Star Villa has a contemporary flair that still manages to be comfortable, allowing guests to feel right ... 2 & 3 BR rates available.
Has specials. Rising Star Villa photo

Tamarind Hill (Dutch Side), St. Martin

Pool

from $358/Nt
4 4
Details
Situated at the water's edge on the south end of Anguilla, Anani Villa takes advantage of its location to offer ... 3 BR rate available. Lounge by the pool at Anani and enjoy views of the Caribbean and the mountains of St. Maarten beyond

Anguilla

Beachfront | Pool | AC

from $1500/Nt
4 4
Details
An "extraordinary villa for extraordinary people", Globe Trotter Villa is a fantastic place to sit back, relax and take in ... 2 & 3 BR rates available. From the pool deck at Globe Trotter Villa you will enjoy beautiful views of the Caribbean

Lurin, St. Barts

Pool

from $1414/Nt
4 4
Details
Built on top of a small island cliff, Villa Turquesa can't help but show off a brilliant view of Sapodilla ... Has specials. Enjoy amazing views of the Caribbean from the pool at Turquesa Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1305/Nt
4 4+
Details
Four bedrooms and four bathrooms provide plenty of space and privacy for up to 8 guests staying at OUI Villa. This ... 2 & 3 BR rates available. OUI Villa is located in Petit Cul de Sac in the Domaine du Levant

Petit Cul de Sac, St. Barts

Near Beach | Pool

from $1429/Nt
4 4
Details
Casa Azul Villa is great for friends or couples traveling together. The home is very private and sits on a ... 2 & 3 BR rates available. Casa Azul villa is located on a hillside overlooking Grand Cul de Sac

Vitet, St. Barts

Pool

from $886/Nt
4 4
Details
Located on a St. Jean hillside, ISA Villa enjoys a fantastic location that allows for great views over the surrounding ... 2 & 3 BR rates available. Lounge pool side and enjoy views of St. Jean Bay

Saint Jean, St. Barts

Pool

from $1757/Nt
4 4
Details
LUZ Villa's best feature is its exterior. You can relax around the large living area, the outdoor dining table, the ... 1, 2 & 3 BR rates available. LUZ Villa enjoys amazing views of Lorient Bay

Camaruche, St. Barts

Pool

from $629/Nt
4 4
Details
From the gardens to the infinity pool to the villa itself, you'll never want to leave Venusville! The views of ... 3 BR rate available. Venusville Villa has a beautiful pool and deck for entertaining

Petite Saline, St. Barts

Pool

from $3286/Nt
4 4
Details
The four-bedroom penthouse suite at Smugglers Cove comes with everything you need for the perfect island vacation. The 60-ft balcony ... Has specials. Smugglers Cove #7 Penthouse overlooks Paynes Bay

Barbados

Beachfront | Pool | AC

from $2500/Nt
4 5+
Details
With 4 bedrooms and 4 bathrooms, this super private cliffside villa on St. Barts is easily one of the most upscale properties ... 1, 2 & 3 BR rates available. Located on the tip of the island jetty near Lorient Bay - Cap Au Vent enjoys great ocean views

Pointe Milou, St. Barts

Pool

from $1700/Nt
4 4
Details
Few places are quite as tourist-friendly as Barbados, but thanks to the amazing weather, friendly people, and great activities, this ... Has specials. Capri Manor is located just across the street from Gibbs Beach

Barbados

Near Beach | Pool

from $550/Nt
4 4+
Details
Any holiday is better when you have an amazing view, and Villa Jasmine can provide you with that and much ... 1, 2 & 3 BR rates available. Jasmine Villa is located in Gouverneur overlooking the Caribbean

Gouverneur, St. Barts

Pool

from $2000/Nt
4 5+
Details
Sitting beachfront, Aquazure offers all of the necessities for an ideal Caribbean experience. It has a clean modern look and ... Beachfront Villa Aquazure is located in Leeward along a beautiful stretch of white sandy beach

Leeward, Turks and Caicos

Beachfront | Pool | AC

from $848/Nt
4 4
Details
Atelier's architect, Alistair Downie, infused tranquility and serenity into every modern detail at this two-story villa. From the master bedroom ... Has specials. Atelier Villa has modern architectural lines and a beautiful pool

Barbados

Near Beach | Pool

from $1500/Nt
4 3+
Details
Ready to go gourmet on your next holiday? You will have to demand the finer things in life, and Ariana ... 2 & 3 BR rates available. Ariana sits on a hilltop over Lower Belmont Bay

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from $575/Nt
4 3+
Details
If you want a tropical escape, Ana Capri fits the bill. It has amazing views, gorgeous Italian design, and lush ... 1, 2 & 3 BR rates available. Ana Capri Estate photo

Tortola, BVI, British Virgin Islands

Pool

from $1047/Nt
4 4+
Details
Designed to help you relax whether you are indoors or outdoors, the four-bedroom Bord De Mer Villa has a large ... 1, 2 & 3 BR rates available. Private pool at Bord de Mer Villa

Saint Jean, St. Barts

Beachfront | Pool | AC

from $943/Nt
4 4
Details
With beautifully clear ocean views from every room, Cocoa at Pelican’s Nest is ideal for any family or group ... 3 BR rate available. Pelican's Nest Villas - Cocoa is located near Grace Bay Beach

Grace Bay, Turks and Caicos

Near Beach | Pool

from $857/Nt
4 3+
Details
Right on the coastline, the Bora Bora Lower Villa provides easy access to the water sports and beaches that make ... 2 BR rate available.
Has specials. Dining

Barbados

Beachfront | AC

from $350/Nt
4 4
Details
Looking out over the waters of Paynes Bay Beach, the Bora Bora Upper Villa is the complete mix of privacy ... 2 BR rate available.
Has specials. Bora Bora Upper Villa photo

Barbados

Beachfront | AC

from $335/Nt
4 4
Details
Marsh Mellow has incredible views, a spacious layout, and a huge, deep pool. Since the villa is crescent-shaped, every room ... Has specials. Marsh Mellow Villa is located in Westmoreland in Barbados and has great views of the ocean

Barbados

Pool

from $965/Nt
4 4+
Details
Many people like to stay on Seven Mile beach because that's where all the action is. Then there are others ... View from above Castaway Villa - you can see the beach and the ocean

Grand Cayman, Cayman

from $415/Nt
4 3+
Details
This villa is perfect if you want to travel with friends and family but also enjoy your own space. The ... Has specials. Resort style luxury awaits at Greentails Residence One Villa

Barbados

Pool

from $1000/Nt
4 4+
Details
Kai Vista is a colorful oceanfront villa that encompasses all that an idyllic, tropical getaway destination should. After long evening ... Kai Vista photo

Grand Cayman, Cayman

Beachfront | Pool | AC

from $745/Nt
4 4
Details
Sea La Vie Villa is truly an amazing place to come taste the island life. This home is great for ... 1, 2 & 3 BR rates available.
Has specials. Lounge in the Caribbean sun at Sea La Vie Villa

Tamarind Hill (Dutch Side), St. Martin

Pool

from $400/Nt
4 5
Details
Even though this villa is set up for family vacations, it still feels like a romantic secret garden. Every room ... Has specials. Edge of Paradise is located on the Southern shore of Meagan's Bay

St. Thomas, USVI

Near Beach | Pool

from $1429/Nt
4 4+
Details
Rose Dog is truly an eclectic gem on the island of St. Barts. It has a comfortable layout, unique design, ... 2 & 3 BR rates available. Rose Dog is located on a hillside in Dévé

Vitet, St. Barts

Pool

from $1095/Nt
4 4
Details
This island getaway is located near Marigot Beach where only swimming and snorkeling are allowed because of the protected natural ... 2 & 3 BR rates available. Black Pearl Villa photo

Marigot, St. Barts

Pool

from $1143/Nt
4 4
Details
Ocean Dream is a great option for families. Everything you could possibly need is within five minutes of the villa, ... 2 & 3 BR rates available. Ocean Dream is located in Gustavia and is just a short walk to the beach

Gustavia, St. Barts

Near Beach | Pool

from $1000/Nt
4 3+
Details
Cohoba is a large Belmont Estates villa that shows off fantastic ocean views and a location near Smuggler's Cove. Designed ... 2 & 3 BR rates available. Cohoba is located in Belmont Estates overlooking Lower Belmont Bay

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from $700/Nt
4 4
Details
The views from this villa are incredible, not to mention the ample deck space and open floor plan. I love ... 2 & 3 BR rates available. Villa Aurea sits just above Lorient Beach

Lorient, St. Barts

Pool

from $1143/Nt
4 4
Details
The pool deck and sunbathing deck at Bakea Villa are great because they leave guests plenty of room to spread ... 1, 2 & 3 BR rates available. Bakea Villa photo

Anse des Cayes, St. Barts

Pool

from $1429/Nt
4 4
Details
Villa Rosa has a breathtaking view of the ocean that's only enhanced by the free form swimming pool. I love ... 2 & 3 BR rates available.
Has specials. Villa Rosa has amazing views out into the Caribbean and across the St. Barthelemy channel

Guana Bay (Dutch Side), St. Martin

Near Beach | Pool

from $429/Nt
4 4
Details
Palermo provides expansive views of Turtle Tail, and you won't be able to get enough of the infinity pool and ... Palermo Villa is located directly on the ocean

Turtle Tail, Turks and Caicos

Pool

from $1143/Nt
4 4+
Details
Monte Verde is a charming villa perfect for couples traveling together. The king suites are pretty equal so great for ... 2 & 3 BR rates available.
Has specials. Monte Verde is located in Hope Hill and has great views of Orient Bay

Orient Bay (French side), St. Martin

Pool

from $600/Nt
4 4+
Details
This villa is comfortable, chic, and well equipped. The view is amazing, but the al fresco dining area is my ... 2 & 3 BR rates available. Bibi Villa photo

Vitet, St. Barts

Pool

from $817/Nt
4 4
Details
With two separate master bedrooms and two guest bedrooms, the villa is well suited to couples traveling together, or to ... 1, 2 & 3 BR rates available. W View Villa is located on the hillside above St. Jean Bay

Saint Jean, St. Barts

Pool

from $1714/Nt
4 4
Details
Aqua Vue condo is spacious and well-arranged, and also really close to some of the island's best restaurants, beaches, and ... 2 & 3 BR rates available.
Has specials. Aqua Vue photo

Cupecoy (Dutch side), St. Martin

Near Beach

from $336/Nt
4 4+
Details
Pastels Villa is the perfect countryside villa for your family's next vacation. It has a child-friendly layout, ample sitting areas ... 1, 2 & 3 BR rates available. Pastles Villa is located on a hillside in Vitet

Vitet, St. Barts

Pool

from $700/Nt
4 4
Details
In Harmony is a charming beachfront villa that would be perfect for your next family vacation. It has a private ... An aerial view of in Harmony Villa located directly on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $645/Nt
4 4
Details
If you love the ocean, you'll love vacationing at Serenity Now. The villa is a minute from Seven Mile Beach, ... Serenity Now Villa is located in the West Bay area and is steps away from Seven Mile Beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1139/Nt
4 3
Details
Vista Villa is a family vacation dream. The bedrooms are spread out over two levels of the house, and the ... 3 BR rate available.
Has specials. Vista Villa is located in the gated community of Almond Grove Estates

Almond Grove Estate, St. Martin

Pool

from $500/Nt
4 4
Details
I think this villa would be perfect for a family vacation-- it has three master bedrooms upstairs and a twin ... Has specials. A beachfront pool awaits you at Christmas Palms Villa

Grand Cayman, Cayman

Pool

from $525/Nt
4 3+
Details
Tarasand villa is a great choice for anyone who wants to be near Rum Point and have easy access to ... The beach set up in front of Tarasand Villa

Grand Cayman, Cayman

Beachfront | AC

from $950/Nt
4 3
Details
If you love the ocean, you'll love Villa Caymanas. It sits on Old Man's Bay, a quiet and undeveloped region ... Has specials. Villa Caymanas is located on the North side of the island on the beach

Grand Cayman, Cayman

Near Beach | Pool

from $525/Nt
4 4+
Details
This villa is great for four couples, because each suite has a queen bed and private bathroom. There's three beaches ... 2 BR rate available. Galley Bay Heights #007 is located on one of the highest points of the beautiful Galley Bay Heights

Galley Bay, Antigua

Near Beach

from $1300/Nt
4 4
Details
Picture Perfect has a great location for travelers who want to be near Seven Mile Beach and George Town. Snorkeling ... Picture Perfect Villa has many options for a fun holiday

Grand Cayman, Cayman

Beachfront | Pool | AC

from $625/Nt
4 3+
Details
Estrella is a lovely 4 bedroom, 4 bathroom villa, located in Flamands, just a few steps away from one of the most ... 2 & 3 BR rates available. Estrela Villa is located in Flamands overlooking the beautiful Flamands Bay Beach

Flamands, St. Barts

Near Beach | Pool

from $571/Nt
4 4
Details
This house is great for two families to share. There are two king suites that each have exterior access, and ... Heritage House Villa is located on the very desirable Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $525/Nt
4 4
Details
I really like the living area in this villa, which is multi-leveled and has a few nooks for relaxing. The ... 2 & 3 BR rates available. Yellow Bird Villa sits on a hillside in Pointe Milou overlooking Lorient Bay to Marigot

Pointe Milou, St. Barts

Pool

from $1000/Nt
4 4
Details
Staying in Arrecife 23 is a gorgeous way to enjoy Punta Cana Resort. It has wrought iron and travertine accents, high ... Pool

Punta Cana, Dominican Republic

Near Beach | Pool

from $1290/Nt
4 4
Details
Gypsy is perfect for a family who wants a beachfront vacation rental with spacious rooms, a private bay, and easy ... Gypsy Villa has a beautiful beach front private pool

Grand Cayman, Cayman

Beachfront | Pool | AC

from $725/Nt
4 4
Details
Villa Arrecife 24 at Tortuga Bay photo

Punta Cana, Dominican Republic

Pool

from $1080/Nt
4 4
Details
Smugglers Cove is an excellent choice for beach lovers. You'll have direct access to Paynes Bay, and are just a ... Has specials. Sandy Lane Beach just steps outside of Smugglers Cove

Barbados

Beachfront | AC

from $1400/Nt
4 4+
Details
Turks and Caicos is well-known as one of the best areas in the Caribbean for beach lovers, and the Venetian ... Has specials. Penthouse at The Venetian photo

Grace Bay, Turks and Caicos

Beachfront | AC

from $1425/Nt
3 3
Details
Villa Kai has water access to Sandy Hill Bay for exploring, and you can watch the waves crash onto the ... 1 & 2 BR rates available. Villa Kai is located on Sandy Hill Bay

Anguilla

Pool

from $500/Nt
3 3
Details
This villa has a beautiful view and plenty of lounging space on the terrace to enjoy it. The upstairs bedrooms ... 2 BR rate available. Sasha photo

Corossol, St. Barts

Pool

from $1357/Nt
3 3
Details
This villa has a cool Balinese vibe and outdoor showers that really elevate the luxury. It's well designed, and has ... 2 BR rate available. Villa Sauvage has a beautiful pool overlooking the island

Flamands, St. Barts

Pool

from $857/Nt
3 3
Details
Bikini Villa is simply cozy. An open floor plan allows you to see all your guests relaxing, and the rooms ... 1 & 2 BR rates available. Bikini Villa photo

Lorient, St. Barts

Near Beach | Pool

from $526/Nt
3 3
Details
Alaia is chic and convenient! The decor is very minimalist and modern, and the villa is just a short walk ... 2 BR rate available. Alaia photo

Saint Jean, St. Barts

Near Beach | Pool

from $1071/Nt
3 3
Details
This villa's best quality is undoubtedly its location. Long Bay Beach is a few minutes' walk away, and its so ... 2 BR rate available. The White Villas are located very close to the beautiful Long Bay Beach

Long Bay, Turks and Caicos

Near Beach | Pool

from $565/Nt
3 4
Details
This villa is great for any family who wants stunning views for an affordable price. There are tons of beaches ... 1 & 2 BR rates available. Ballena Blue is located on a hilltop over Rendezvous Bay

Rendezvous Bay, St. John

Pool

from $557/Nt
3 3
Details
Sailrock has all the best parts of a resort vacation: activities, excursions, fine dining, and a spa, all without the ... The three bedroom Beachfront Villas at Sailrock Resort

South Caicos, Turks and Caicos

Beachfront | Pool | AC

from $3880/Nt
3 3
Details
If you want a private villa with direct water access and modern amenities, Cassis is for you. It sits right ... Cassis is located along the canal and has a beautiful pool and backyard area

Leeward, Turks and Caicos

Pool

from $770/Nt
3 3
Details
One of my favorite things about Javacanou is the waterfront access to Marigot Beach. This area is great for snorkeling, ... Javacanou villa overlooks the beautiful protected waters of Marigot Bay

Deve, St. Barts

Near Beach | Pool

from $2143/Nt
3 3
Details
Babylon Reef feels like a classic beach house, with every amenity you could ask for. It's oceanfront, with a great ... The private pool at Babylon Reef has a man made -beach- surrounding it

Grand Cayman, Cayman

Beachfront | Pool | AC

from $495/Nt
3 2+
Details
Sienna has a gorgeous terrace and views of the golf course. The terrace can be closed off to the pool ... Has specials. Sienna Villa

Barbados

Pool

from $950/Nt
3 3
Details
Smugglers Cove is great for beach lovers, because the guests have direct access to Paynes Bay. The villa is spacious ... Has specials. Paynes Bay Beach is just below the balcony at Smugglers Cove #4

Barbados

Beachfront | AC

from $995/Nt
3 3
Details
Crescent Beach villa sits in beautiful, peaceful Bequia, with a view of the beach below. You’ll love listening to ... 1 BR rate available. Crescent Beach Villa is located above Crescent Beach and has amazing ocean views

Bequia, St. Vincent & Grenadines

Pool

from $321/Nt
3 3
Details
Edge of Paradise is a great choice for three couples who want to relax by Grace Bay. The villa comes ... Edge of Paradise is located just a few minutes from Grace Bay Beach

Leeward, Turks and Caicos

Near Beach | Pool

from $850/Nt
3 3
Details
La Corniche is a stunning, spacious oceanfront villa with gorgeous views and an airy design. I love how the interior ... 1 & 2 BR rates available. La Corniche has a beautiful pool deck area with spectacular views of the Caribbean

Pointe Milou, St. Barts

Pool

from $857/Nt
3 3+
Details
If you love Grace Bay and Smith's Reef, you'll love Sandpebble. Its right by the sea, near Turks and Caicos' ... Aerial view of the Sandpebble property

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $786/Nt
3 3+
Details
Ocean Eleven has daily housekeeping and a rooftop deck. I love how the marina and the ocean surround the villa, ... Ocean Eleven is located in the marina at Cap Cana

Cap Cana, Dominican Republic

Pool

from $2150/Nt
3 3+
Details
Infinite Horizon is a gorgeous family vacation villa. It has WiFi, SONOS, a media room, a pool, and the beach ... Infinite Horizon Villa is located on the beach just minutes from Seven Mile Beach Corridor

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1139/Nt
3 3
Details
Tradewinds is ideal for three couples who want to vacation on Grace Bay without sacrificing privacy. The villa is surrounded ... Tradewinds Villa is located near Grace Bay Beach

Providenciales, Turks and Caicos

Near Beach | Pool

from $571/Nt
3 3
Details
Seashells is a great choice for a beachfront family vacation. It's steps away from the sea, has three-stories of space, ... Has specials. Seashells Villa is set on a beautiful stretch of beach

Barbados

Beachfront | Pool | AC

from $495/Nt
3 3+
Details
Discovery is a lovely choice for a small family or two couples who want to vacation near Orient Bay. You ... 1 & 2 BR rates available.
Has specials. Discovery is located on a hillside in a gated area near Orient Bay

Orient Bay (French side), St. Martin

Pool

from $500/Nt
3 3
Details
Blue Mountain is a great choice for three couples who want a quiet vacation. It's near Babalua Beach, which is ... Located on a beautiful stretch of beach Blue Mountain has an excellent oceanfront location

Providenciales, Turks and Caicos

Pool

from $600/Nt
3 2+
Details
Porters is a family-friendly villa with a great location, elegant design, and gorgeous gardens. The villa's three bedrooms are all ... Has specials. Porters Villa is located in St. James

Barbados

Near Beach | Pool

from $750/Nt
3 3
Details
On The Rocks has a classic, beach house vibe in one of Turks and Caicos's most underrated areas. Chalk Sound ... On the Rocks is located in Silly Creek on Chalk Sound

Chalk Sound, Turks and Caicos

Pool

from $993/Nt
3 3
Details
Sandy Cove #301 has the best of both worlds: a convenient location and resort amenities. This three-bedroom villa is part of ... Has specials. Sandy Cove Resort

Barbados

Beachfront | AC

from $850/Nt
3 3+
Details
Aqueous would be a fantastic choice for a couples' getaway on Grace Bay. The villa is a two-minute walk from ... Aqueous is located inside the Leeward Community

Leeward, Turks and Caicos

Near Beach | Pool

from $950/Nt
3 3
Details
This three-bedroom resort villa has everything you need for an easy family vacation. Everything has been thought of for you, ... Seafire Resort

Grand Cayman, Cayman

Beachfront | AC

from $1500/Nt
3 3+
Details
If you’re looking for an Anguilla beachfront rental, this resort villa is worth a look. It’s right on ... Tranquility Beach - Beachfront Penthouse Villa is located on Meads Bay Beach

Anguilla

Beachfront | AC

from $1500/Nt
3 3+
Details
Viceroy Sugar Beach's Three Bedroom Villa Residence is the ideal rental for a luxurious beachfront experience. The beach is steps ... The Viceroy 3 Bedroom Villa Residences are set in the foothills of the Pitons and the Caribbean Sea

Soufriere, St. Lucia

Beachfront | Pool | AC

from $3915/Nt
3 3+
Details
Sandy Cove #204 has something for couples and families alike. Whether you’re traveling with your best friends, siblings, or children, ... Has specials. Sandy Cove #204 is located in the resort complex on Paynes Bay

Barbados

Beachfront | Pool | AC

from $950/Nt
3 3
Details
This gorgeous villa is perfect if you want to be near Seven Mile Beach, but away from the crowds. There’... Casa Luna 4 is located in the resort community along the coastline just south of Seven Mile Beach

Grand Cayman, Cayman

Beachfront | AC

from $650/Nt
3 4
Details
This spacious, beachfront villa has a convenient location within walking distance of dining, attractions, and excursions. Even though Rum Point ... Has specials. Les Jalousies is located in Cayman Kai

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1100/Nt
3 3
Details
1 BR rate available. Loungers with views of Gustavia Harbor

Corossol, St. Barts

Pool

from $857/Nt
3 2
Details
Modern design, beach access, and three bedrooms make this penthouse the perfect rental for your next vacation. It’s right ... Tranquility Beach Anguilla is located on Meads Bay Beach

Anguilla

Beachfront | AC

from $1050/Nt
3 3+
Details
Sapphire Beach 401 has easy beach access near great snorkeling, restaurants, and activities. It’s a great choice for your next ... 2 BR rate available. Sapphire Beach 401 has views right over the beach

Barbados

Beachfront | AC

from $335/Nt
3 3
Details
If you want gorgeous views, interiors, and design, Infinity is a great choice. This Pointe Milou villa has a quiet ... 2 BR rate available. Infinity Villa is located on a hilltop in Pointe Milou overlooking Lorient Bay

Pointe Milou, St. Barts

Pool

from $1143/Nt
3 3
Details
White Villa 5 is a great choice for a carefree Turks and Caicos vacation. It’s minutes from kiteboarding and paddle ... 2 BR rate available. The White Villas are located very close to the beautiful Long Bay Beach

Long Bay, Turks and Caicos

Near Beach | Pool

from $565/Nt
3 3
Details
Cotton House combines privacy, convenience, and panoramic ocean views. It’s minutes away from dining and beaches, but the villa ... Cotton House in Sugar Ridge is located on a hilltop overlooking Jolly Harbour

Sugar Ridge, Antigua

Pool

from $643/Nt
3 3
Details
Sailrock Resort is a great part of the island to stay on if you want tranquility, convenience, and seclusion. The ... Sailrock Resort Oceanfront Coral Villa is located oceanfront on the Sailrock Peninsula

South Caicos, Turks and Caicos

Pool

from $3750/Nt
3 3
Details
No Limit is a charming villa with gorgeous ocean views and a spacious exterior with several lounging and dining areas. ... 2 BR rate available. No Limit photo

Terres Basses (French side), St. Martin

Pool

from $557/Nt
3 3+
Details
Osprey villa has gorgeous sunset views and outdoor amenities perfect for a family vacation. The waterfront location is enhanced by ... Has specials. Osprey is located on the ocean side of Chalk Sound

Taylor Bay/Sapodilla Bay, Turks and Caicos

Pool

from $1125/Nt
3 3
Details
Hibiscus is one of eight villas within the Merlin Bay complex. There are three bedrooms, each with their own ensuite ... Has specials. Hibiscus has a private plunge pool as well as access to the Merlin Bay common pool

Barbados

Beachfront | Pool | AC

from $485/Nt
3 3
Details
Caribbean vacations offer much more than you might imagine, especially if you have never heard about the wonderful accommodation options. ... 1 BR rate available. Hummingbird Villa photo

Cap Estate, St. Lucia

Pool

from $200/Nt
3 3
Details
The beautifully landscaped and stylish Saline Reef is a great vacation spot for families with children over 12, or adults who ... 2 BR rate available. Saline Reef sits on the northernmost end of St. Lucia and has a beautiful pool and patio

Cap Estate, St. Lucia

Near Beach | Pool

from $580/Nt
3 3
Details
Tequila Sunrise is a beachfront villa perfect for anyone who wants to have a truly relaxing vacation. It's extremely private, ... 1 & 2 BR rates available. Lounge poolside with amazing views of the ocean

Anguilla

Near Beach | Pool

from $990/Nt
3 3
Details
Terres Basses is known as one of St. Martin's nicest areas, and Callisto does not disappoint. The villa consists of 3 ... 2 BR rate available.
Has specials. Callisto Villa is located on a hillside in Terres Basses and enjoys sunset views over Baie Longue

Terres Basses (French side), St. Martin

Pool

from $471/Nt
3 3+
Details
It's rare that the name of a vacation rental could truly summarize the benefits you will find inside, but this ... 1 & 2 BR rates available. Villa Serenity has a beautiful deck and unparalleled views of Gustavia Harbour

Gustavia, St. Barts

Near Beach | Pool

from $1143/Nt
3 3
Details
Anchorage Villa is a warm, sun-drenched property with a spacious living room and an open-concept dining area. The housekeeper prepares ... Has specials. Anchorage Villa is on the western end of the Sandy Lane Estate

Barbados

Pool

from $725/Nt
3 3
Details
When you need to get away from it all, you can't go wrong with Armor Villa. This is just the ... 1 & 2 BR rates available. Armor Villa is located in a gated community of Mont Jean

Mont Jean, St. Barts

Pool

from $714/Nt
3 3+
Details
Maison Villa is ideal for those who want to be within walking distance to all that St. Jean has to ... 1 & 2 BR rates available. Maison Villa is located in St. Jean overlooking the beach

Saint Jean, St. Barts

Near Beach | Pool

from $711/Nt
3 3
Details
Guests will be immediately taken with the sleek, peaceful influence of Japan when they enter Plein Ciel Villa. The high ... 2 BR rate available. Plein Ciel Villa photo

Marigot, St. Barts

Pool

from $629/Nt
3 2
Details
You're bound to enjoy the gardens, but there are many other features in this estate to make you feel at ... 1 & 2 BR rates available. Canefield house sits on a lovely hillside in the heart of Tortola

Tortola, BVI, British Virgin Islands

Pool

from $541/Nt
3 3+
Details
Abby Villa is the perfect St. Barts getaway for three couples who want a cozy, peaceful location near multiple beaches. ... 2 BR rate available. Abby Villa photo

Vitet, St. Barts

Pool

from $857/Nt
3 3
Details
At Rocky Point, you have the opportunity for privacy and excitement, as well as spectacular ocean views. This three-bedroom villa ... The pool at Rocky Point villa!

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $6000/Nt
3 3
Details
Angelina Villa is secluded enough to afford you the privacy, peace, and quiet you might hope for in an exotic ... 1 & 2 BR rates available.
Has specials. Angelina Villa is located on the Dutch hillside of Oyster Pond

Oyster Pond (Dutch side), St. Martin

Pool

from $271/Nt
3 2+
Details
Terres Basses in St. Martin is known for fine beaches and great scenery, and La Magnolia Villa is situated to ... 1 & 2 BR rates available.
Has specials. La Magnolia sits on a hilltop over Baie Longue with a great view of the ocean

Terres Basses (French side), St. Martin

Pool

from $457/Nt
3 3
Details
This villa is great for a few couples or a family. All three bedrooms have ensuite bathrooms, and two are ... 2 BR rate available. Sweet Return Villa is located near the golf course and Rendezvous Bay

Anguilla

Pool

from $492/Nt
3 3
Details
Cinnamon at Pelican's Nest is a perfect villa for guests who want breathtaking views, great value, and an enviable location. ... Pelican's Nest Villas - Cinnamon is located near Grace Bay Beach

Grace Bay, Turks and Caicos

Near Beach | Pool

from $857/Nt
3 3+
Details
If you're ready for a Caribbean escape with views galore, then Eaglesnest is the place for you. It's location on ... 1 & 2 BR rates available. Overlooking Great Cruz Bay Eaglesnest definitely has amazing views

Great Cruz Bay, St. John

Pool

from $379/Nt
3 3
Details
Furnished in contemporary Italian style, Sandy Cove #201 perfectly combines both comfort and luxury. This fully air-conditioned 3-bedroom, 3.5-bath condominium is ... Has specials. Sandy Cove Resort

Barbados

Beachfront | Pool | AC

from $950/Nt
3 3+
Details
Casawapa is great for couples traveling together or family vacations. The rooms are equal in size and separated by the ... 2 BR rate available. Casawapa Villa sits on the Colombier hillside

Colombier, St. Barts

Pool

from $757/Nt
3 3
Details
Dasha Villa is quickly building a roster of loyal fans. A recent visitor summed up her stay at the villa ... 1 & 2 BR rates available. Dasha Villa sits on a hillside overlooking Gouverneur

Lurin, St. Barts

Pool

from $943/Nt
3 3
Details
Escape Villa is perfect for families, and sits almost right on top of Lorient Beach, which is one of the ... 1 & 2 BR rates available. Tropical retreat at Escape Villa

Lorient, St. Barts

Near Beach | Pool

from $416/Nt
3 2
Details
Whether you want to relax by the pool for your entire vacation, or you're an adventurer who wants a lot ... 2 BR rate available.
Has specials. Victoria Villa is located in the Oyster Pond neighborhood on a hillside overlooking Orient Bay

Oyster Pond (Dutch side), St. Martin

Pool

from $395/Nt
3 3+
Details
For the tennis or golf aficionado, Mer Soleil offers conveniently located access to both courses and courts, but for those ... 2 BR rate available. Amazing views from the deck

Gouverneur, St. Barts

Pool

from $1857/Nt
3 3
Details
Mariposa is just a few paces from Taylor Bay beach, one of the most stunning, quiet beaches on the island. ... 1 & 2 BR rates available. Mariposa Villa is located at the very end of Sapodilla Bay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $586/Nt
3 3
Details
Surrounded by mature tropical plants, Monchal Villa on St. Martin has a very private and secluded feel about it. Step ... 1 & 2 BR rates available.
Has specials. Monchal Villa is located just a short distance from Plum Bay Beach

Terres Basses (French side), St. Martin

Near Beach | Pool

from $293/Nt
3 3
Details
The joy of renting this 3-bedroom condo at the Ritz Carlton Club is that you know your expectations will be ... The Ritz Carlton Club Condo photo

St. Thomas, USVI

Beachfront | AC

from Call for rates
3 3+
Details
Coral Cove #11 is a modern apartment right at the water's edge. You can take lunch down to the beach and ... 2 BR rate available.
Has specials. Paynes Bay Beach just a short walk from Coral Cove

Barbados

Beachfront | AC

from $495/Nt
3 3
Details
Harmony House is an elegantly furnished, fully-equipped, three-bedroom villa with everything you need for a relaxing Barbados getaway. The bedrooms ... Has specials. Harmony House is just steps away from Gibbes Beach

Barbados

Beachfront | Pool | AC

from $975/Nt
3 3+
Details
Reef Pearl Villa, with it's private swimming pool, relaxing hammock, and perfect beachfront location is the ideal getaway spot for ... 2 BR rate available. Ocean kayaks - Ask for availability

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $686/Nt
3 3
Details
Conch Beach has everything you could possibly want in a family vacation rental, from the bedrooms to the design to ... Conch Beach Villa is located on the beautiful Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $840/Nt
3 3
Details
This non-smoking villa has an open floor plan in the living areas that invites socializing and togetherness; but when you ... 2 BR rate available.
Has specials. On Island Time photo

Oyster Pond (Dutch side), St. Martin

Pool

from $379/Nt
3 3+
Details
Aquamarine is a great holiday rental for families or groups of friends looking for cheerful ambiance and lots of beach! ... Has specials. Aquamarine is located just steps away from Mullins Beach

Barbados

Beachfront | AC

from $410/Nt
3 2
Details
You can see the ocean from every room in this beachfront villa, and natural light enhances the tropical vibe. You ... Has specials. Fathom's End - Mahogany Bay is located right on the beach at Mahogany Bay

Barbados

Beachfront | Pool | AC

from $575/Nt
3 3+
Details
Blue Lagoon Villa is a family friendly, wheelchair accessible villa that can easily sleep up to ten people. With a ... 2 BR rate available. Blue Lagoon Villa photo

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

from $557/Nt
3 3
Details
If you have an extended family, Bambooshay Villa has the extra room that avoids what a cramped hotel would have ... 1 & 2 BR rates available. Relax and enjoy yourself while in the pool or hang'n in the hammock at Bambooshay

St. Croix, USVI

Pool

from $343/Nt
3 3+
Details
When it comes to Brimstage estate, you are getting the modern side of a vacation. Bold colors greet you upon ... 1 & 2 BR rates available. Brimstage Estate photo

St. Croix, USVI

Pool

from $286/Nt
3 2+
Details
This villa would be so fun for your next family vacation. Kids will love the pool, teens will love the ... 1 & 2 BR rates available. Bel'Ombre photo

Marigot, St. Barts

Pool

from $643/Nt
3 3
Details
The Dutch side of St. Martin is known for its great beaches and exciting night life, and La Casita Villa ... 1 & 2 BR rates available.
Has specials. La Casita Villa is located in the Simpson Bay area on the beach overlooking Burgeaux Bay

Beacon Hill (Dutch side), St. Martin

Near Beach | Pool

from $371/Nt
3 3
Details
Sol e Luna is very private with gardens that surround the house giving guests the option of dressing or not. ... 1 & 2 BR rates available.
Has specials. Sol e Luna is located in the desirable Terres Basses

Terres Basses (French side), St. Martin

Pool

from $521/Nt
3 3
Details
Escapade Villa is situated on a hillside overlooking Marigot Bay in the French Caribbean. Designed for comfort, Escapade offers ocean ... 1 & 2 BR rates available. Views of Marigot Bay from the pool and the large deck at Escapade Villa

Marigot, St. Barts

Near Beach | Pool

from $500/Nt
3 3
Details
Panarea Villa is truly beautiful, with a great housekeeper and lush gardens all around. I think this villa is ideal ... 2 BR rate available. Panarea is located in Anguilla's West End, just minutes away from the island's most beautiful beache

Anguilla

Near Beach | Pool

from $525/Nt
3 3
Details
At just the right vantage point to see the rolling hills, town, and ocean, Villa Rivendell provides seclusion without cutting ... 1 & 2 BR rates available. Amazing view of Flamands Bay from the infinity edge pool

Flamands, St. Barts

Pool

from $714/Nt
3 3
Details
Tuscany Resort is one of my favorite properties on Turks and Caicos. At WhereToStay.com, we only list resorts that ... 1 & 2 BR rates available.
Has specials. The Tuscany Resort is located on East Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $775/Nt
3 3
Details
A stay at Villa Gardenia will make you feel like you're a world away from the stress of everyday life. ... 1 & 2 BR rates available. Villa Gardenia is surrounded by beautiful tropical foliage

St. Thomas, USVI

Pool

from $495/Nt
3 3+
Details
Located within walking distance to a grocery store and restaurants, Ecoute les Vagues sits right on Flamands Beach, giving guests ... 1 & 2 BR rates available. Private waterfront pool at Ecoute les Vagues

Flamands, St. Barts

Beachfront | Pool | AC

from $600/Nt
3 2
Details
Sea Bird is a one-of-a-kind villa in Mont Jean, St. Bart's, with 3 bedrooms, a full kitchen, and large living areas ... 1 & 2 BR rates available. Sea Bird Villa is located on a hilltop in Mont Jean overlooking the Caribbean

Mont Jean, St. Barts

Pool

from $857/Nt
3 3
Details
Your family will love staying at The Harbour #17. This brightly colored home is right on the harbor and nestled in ... 1 & 2 BR rates available. The Harbour #17 is located in the Harbour Townhomes overlooking the harbour on Rodney Bay

Rodney Bay, St. Lucia

Near Beach

from $275/Nt
3 3+
Details
Situated on a hillside, Lataniers Villa has a great view of St. Jean Bay and the surrounding island greenery. Guests ... 1 & 2 BR rates available. Beautiful views from Lataniers Villa

Saint Jean, St. Barts

Pool

from $571/Nt
3 2
Details
You will want to schedule your time wisely to take in as much of this Caribbean beauty as possible. With ... 1 & 2 BR rates available.
Has specials. Roc Flamands 11 is located just above Flamand Beach

Flamands, St. Barts

Near Beach

from $571/Nt
3 2
Details
There is no mistaking that you are on island time when you step foot in Hurakan Villa. Each room has ... 1 & 2 BR rates available. Perched on the hillside of Colombier - Hurakan provides beautiful views of Gustavia Harbour

Colombier, St. Barts

from $543/Nt
3 3
Details
Turks and Caicos is well-known as one of the best areas in the Caribbean for beach lovers, and the Venetian ... 1 & 2 BR rates available.
Has specials. The Venetian photo

Grace Bay, Turks and Caicos

Beachfront | AC

from $875/Nt
3 3+
Details
Latitude Villa is an excellent choice for three couples. Two bedrooms are upstairs and one is downstairs, so everyone will ... Has specials. Latitude Villa photo

Barbados

Beachfront | Pool | AC

from $1150/Nt
3 3
Details
Anakao Villa, located in the Saint Jean area, is ideally located for those seeking the ultimate in peace and quiet. ... 1 BR rate available. Anakao Villa photo

Saint Jean, St. Barts

Pool

from $557/Nt
3 2
Details
Coco villa has an outdoor living area with comfy furnishings and ocean views. The infinity pool has a plateau where ... Coco Villa sits above Lorient Bay Beach looking toward St. Jean

Lorient, St. Barts

Pool

from $2000/Nt
3 3
Details
Just 2 minutes away from one of St. Martin's nicest beaches, Les Zephyrs is a private, 3-bedroom villa that comes with ... 2 BR rate available.
Has specials. The private pool at Les Zephyrs offers your own tropical getaway

Terres Basses (French side), St. Martin

Pool

from $414/Nt
3 3
Details
Dream Come True Villa delivers not only privacy, but magnificent ocean views. Just steps above Devers Bay, this three-bedroom villa ... 1 & 2 BR rates available. A Dream Come True Villa has amazing ocean views and a fun pool area

Devers Bay, St. John

Beachfront | AC

from $400/Nt
3 3+
Details
If you want a Caribbean escape with Secret Garden vibes, check out Kessi Villa. Its surrounded by gorgeous gardens and ... 1 & 2 BR rates available. Kessi Villa photo

Cap Estate, St. Lucia

Pool

from $430/Nt
3 3
Details
Cheyenne Villa is perfectly located for your next vacation. It is just 10 minutes from the beach and area shops, and ... 1 & 2 BR rates available. Villa Cheyenne is located on a hillside in Vitet

Vitet, St. Barts

Pool

from $414/Nt
3 3
Details
Tainos Villa enjoys some of the best views on the island from its location in Pointe Milou. Everything is open ... 2 BR rate available. Tainos Villa located in Pointe Milou

Pointe Milou, St. Barts

Pool

from $2143/Nt
3 3
Details
Any traveler review will tell you that the West Bay Club in Turks and Caicos is one of the best ... Has specials. The West Bay Club from Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1680/Nt
3 3
Details
Ti Moun Villa has one of the best locations in St. Barts! Situated on a hillside in Lurin, this villa ... 2 BR rate available. Ti Moun Villa sits on a hillside just above Gustavia Harbor

Lurin, St. Barts

from $1357/Nt
3 3
Details
Crowsnest at Coral Cove is designed for those who want to relax by one of the island's most beautiful beaches. ... Has specials. Coral Cove complex

Barbados

Beachfront | AC

from $850/Nt
3 3
Details
Sapphire Beach #209 is a modern and comfortable 3-bedroom condo located on the second floor of the Sapphire Beach condo community. ... Has specials. The pool and view of the ocean from Sapphire Beach

Barbados

Beachfront | AC

from $440/Nt
3 3
Details
With 3 bedrooms and 3 bathrooms, Sapphire Beach #205 is a great rental for couples or friends traveling together. This oceanfront apartment has ... 2 BR rate available.
Has specials. Sapphire Beach #205 photo

Barbados

Beachfront | AC

from $335/Nt
3 3
Details
Acamar Villa maximizes ocean views. Nearly every room has sea-facing windows, and the exterior is designed to eliminate any barrier ... 1 & 2 BR rates available. Acamar Villa is located near Toiny Beach

Toiny, St. Barts

Pool

from $1929/Nt
3 3
Details
Your next holiday should help you unwind like never before, and at Les Amis du Vent Villa, you will find ... 1 & 2 BR rates available. Les Amis du Vent Villa is located near Anse de Marigot overlooking the Caribbean

Mont Jean, St. Barts

Pool

from $1714/Nt
3 6
Details
This gorgeous property is a mini paradise of luxury and relaxation. This home has an airy and dreamy feel, with ... 2 BR rate available.
Has specials. Greystone Villa is located in Terres Basses and it is just a short drive to Baie Rouge Beach

Terres Basses (French side), St. Martin

Pool

from $370/Nt
3 3
Details
There are few things quite as fun as a vacation with friends, and Ocean View Villa has the perfect design ... Has specials. Ocean View sits on a neighborhood hillside overlooking Orient Bay and to Tintamarre and St. Barth

Orient Bay (French side), St. Martin

Near Beach | Pool

from $572/Nt
3 3+
Details
Ideally situated on Dover Beach on the south coast of Barbados and enjoying ocean views, Sapphire Beach #213 is a beachfront ... Has specials. Sapphire Beach #213 photo

Barbados

Beachfront | Pool | AC

from $440/Nt
3 3
Details
With 3 bedrooms and 3 bathrooms, Sapphire Beach #407 is a great rental for couples or friends traveling together. This oceanfront apartment has ... Has specials. The Sapphire Beach community

Barbados

Beachfront | Pool | AC

from $440/Nt
3 3
Details
Simple elegance is at your fingertips when you reserve space at Palisades in Barbados. The fully air-conditioned unit, #6A, can ... Has specials. Palisades 6A is located near Freight's Bay in Barbados

Barbados

Near Beach | Pool

from $290/Nt
3 3+
Details
L'Agua Villa puts a stylish, modern spin on the typical Caribbean villa. The massive master bedroom opens directly to a ... 1 & 2 BR rates available.
Has specials. L'Agua Villa is located above Dawn Beach

Oyster Pond (Dutch side), St. Martin

Pool

from $465/Nt
3 3
Details
<