Caribbean Group Villas

Caribbean Group Villas

Vacation rentals that are large enough to accommodate a group are often hard to come by and renting multiple hotel rooms can break the bank. WhereToStay.com has searched all over the Caribbean to bring you a collection of villas large enough to accommodate groups on their Caribbean vacations. Unlike a hotel, villa rentals provide one cost for the entire home giving everyone their own space while still enjoying various amenities such as a private pool, chef services and housekeeping. Go on, take a look, the perfect villa for your group vacation is sure to be here!

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
Casa Bahia is luxurious, exclusive, and elegant. It has full chef services, two infinity pools, and a full home gym… ... Casa Bahia is located in Casa de Campo directly on Minitas Beach

Casa de Campo, Dominican Republic

Beachfront | Pool | AC

from $11000/Nt
12 11+
Details
Located in the Exuma Islands, Musha Cay at Copperfield Bay has five luxurious homes you can choose from, from the 10,000... 6, 7, 8, 9, 10 & 11 BR rates available. Musha Cay at Copperfield Bay photo

Musha Cay, Bahamas

Beachfront | Pool | AC

from $42000/Nt
12 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
Sanzaru is perfect for a corporate retreat, getaway with friends, or family vacation. There's easy access to the beach, shopping ... Has specials. Sanzaru photo

Barbados

Pool

from $12500/Nt
11 11
Details
This estate is the perfect place for a big group vacation. Whether you’re traveling with extended family or friends ... Palmier Royal Estate is located in Mont Jean with amazing views of Marigot Bay

Mont Jean, St. Barts

Pool

from $18571/Nt
11 11
Details
Sand Dollar Estate is the best bet for a St. Thomas wedding, family reunion, or special occasion. With a full ... 6 & 9 BR rates available. Sand Dollar Estate is located in Magen’s Bay with it's own white sandy beach

St. Thomas, USVI

Beachfront | Pool | AC

from $2679/Nt
11 11+
Details
If you've always wanted to spend a week or two in a home with interiors designed by Donna Karan including ... 3 BR rate available. Private luxury at The Sanctuary at Parrot Cay

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $14000/Nt
11 11
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
English Harbour #28 is a great family vacation villa. Six of the bedrooms can be connected to the partnering suite, and ... English Harbour #28 is located on a hillside overlooking the harbour

English Harbour, Antigua

from $3950/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
Cove Spring offers its guests every amenity they could possibly need or imagine. Guests can give their full attention to ... Has specials. Cove Spring photo

Barbados

Beachfront | Pool | AC

from $20000/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 are looking for something private, secluded, and very high-end, then Elsewhere Villa is for you. Ten bedrooms are ... 6 & 8 BR rates available.
Has specials. Elsewhere Villa is located in the prestigious Sandy Lane Club area

Barbados

Pool

from $4500/Nt
10 10
Details
If you are looking for a vacation with amazing views, an attentive staff, and plenty to do, Lazy Heart Villa ... Lazy Heart Villa is located just along the Playa Caleton Paquena

Cabrera, Dominican Republic

Near Beach | Pool

from $1500/Nt
10 10
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
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
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
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
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
Belair Great House has a gazebo where you can sit and sip on island drinks while looking over the pool ... 5 BR rate available.
Has specials. View of the villa and private pool

Barbados

Near Beach | Pool

from $625/Nt
8 6
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
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
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
Tortuga Bay C19 Good Vibes is located in Punta Cana near the La Cana golf course

Punta Cana, Dominican Republic

Pool

from $2000/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
Tucked behind the pristine sand dunes of Long Bay Beach, Triton Villa has set a new standard for luxury in ... Has specials. Beautiful stretch of Long Bay Beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $8000/Nt
7 6+
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
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
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
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
Monte Bay Villa is an attractive getaway with a master suite that will make you want to spend your entire ... 1, 2, 3, 4, 5 & 6 BR rates available. Monte Bay Villa sits atop a hillside just above Monte Bay

Klein Bay, St. John

Near Beach | Pool

from $750/Nt
7 6+
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
Set on Sandy Lane Golf course, Casablanca Villa is a golf lovers' paradise. The house has an invigorating feel with ... 5 BR rate available.
Has specials. Casablanca Villa is located in the Sandy Lane area not far from the beach

Barbados

Near Beach | Pool

from $2000/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
Villa Corales 28 is a beautiful oceanfront villa in Punta Cana

Punta Cana, Dominican Republic

Near Beach | Pool

from $5250/Nt
7 7+
Details
Lital Villa is located at the end of the road in a very quiet neighborhood. The rooms are big and ... 5 & 6 BR rates available. Lital Villa sits on a hilltop overlooking Anse des Cayes

Anse des Cayes, St. Barts

from $4857/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
Elysium is close to the beach, has a huge infinity pool, and is family friendly. What's not to love? With ... Plenty of comfortable seating under the covered patio at Elysium Villa

Barbados

Near Beach | Pool

from $1800/Nt
6 6+
Details
The Point at Maria Bluff lives up to its name. This architecturally stunning home sits on a remarkable piece of ... 1, 3, 4 & 5 BR rates available. Endless views of the Caribbean from the Point at Maria Bluff

Great Cruz Bay, St. John

Pool

from $729/Nt
6 5+
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
This villa is literally right on the beach, with the most gorgeous view from the back patio. Kids can swim ... 4 & 5 BR rates available. Loungers by the beachfront pool at Aqua Villa

Grand Cul de Sac, St. Barts

Beachfront | Pool | AC

from $4714/Nt
6 6
Details
Bleu's pool runs the length of the house, and sits right on the beach. 6 bedrooms leaves room for every family ... 4 & 5 BR rates available. The beachfront lap pool at Bleu Villa

Grand Cul de Sac, St. Barts

Beachfront | Pool | AC

from $4714/Nt
6 6
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
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
Crescent Beach Estate has tons of space for large groups, with two separate villas to offer. Each villa has three ... Stunning beach and ocean views from Crescent Beach Villa

Bequia, St. Vincent & Grenadines

Pool

from $786/Nt
6 6
Details
Do you love modern design and ocean views? Then pack your bags and book a stay at NEO Villa! This ... NEO Villa has amazing views of the ocean below

Saint Jean, St. Barts

Pool

from $12143/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
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
This villa is great for two families or several couples to share. Each suite is set up like its own ... Viatu is just a very short distance to Grace Bay Beach

Leeward, Turks and Caicos

Near Beach | Pool

from $1820/Nt
6 6+
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
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
June is super bright and breezy, so it's perfect for travelers seeking Caribbean sunshine. I love how the infinity pool ... 4 & 5 BR rates available. Covered outdoor seating area

Corossol, St. Barts

Pool

from $4000/Nt
6 6
Details
Limin' da Coconut is perfect for anyone who wants a quiet, laidback vacation. It sits on the beachfront of Little ... 3, 4 & 5 BR rates available. Limin da Coconut is located on a private stretch of coastline on Little Harbor

Anguilla

Near Beach | Pool

from $2500/Nt
6 5
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
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
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
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
My ALL enjoys amazing views from almost every point of the three-acre property. There’s tons of space to take ... 2, 3, 4 & 5 BR rates available. My All Villa is located on the western point of Trunk Bay beach

Tortola, BVI, British Virgin Islands

Pool

from $875/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
Paradis Sur Mer is an inarguably beautiful villa, but the real advantage is its beachfront location. The beach has sugar ... Paradis Sur Mer is located on a quiet residential road in Cayman Kai

Grand Cayman, Cayman

Beachfront | Pool | AC

from $4150/Nt
6 6+
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
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
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
This luxurious, beachfront villa has everything you need for an unforgettable vacation. L’Oasis gives guests instant access to the ... 4 & 5 BR rates available.
Has specials. L'Oasis Villa photo

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $3143/Nt
6 7
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
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
With fantastic sweeping water and hillside views, Amancaya is a private and beautifully landscaped villa near Anse des Cayes and ... 1, 2, 3, 4 & 5 BR rates available. Amancaya Villa photo

Anse des Cayes, St. Barts

Pool

from $2429/Nt
6 6
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
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
Turtle Breeze Villa is one of the most striking villas you will ever see. This beachfront villa features a freeform ... 5 BR rate available. Turtle Breeze is a beachfront getaway like no other on Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4000/Nt
6 6
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
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
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
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
With a billiards table, fitness area, an outdoor covered terrace, a heated swimming pool, and nearby tennis courts, this property ... 4 BR rate available. Tropical ambiance surrounds Casa del Mar Villa

Petit Cul de Sac, St. Barts

Near Beach | Pool

from $4286/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
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
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
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
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
Deja View is perfect for any special event. With five master suites and a bunk room, there's no shortage of ... 5 BR rate available. Deja View is located above Rendezvous Bay on the southern side of St. John

Gift Hill, St. John

from $1221/Nt
6 6+
Details
Kishti Villa on Meads East is a spacious and extravagant beachfront property on one of the best beaches in the ... 4 BR rate available. Kishti Villa East on Meads Bay offers relaxing outdoor spaces

Anguilla

Beachfront | Pool | AC

from $4200/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
Las Hamacas Villa is the perfect destination for a beachfront luxury vacation. It has an open-air, Balinese design with hammocks ... Las Hamacas Villa photo

Cap Cana, Dominican Republic

Beachfront | AC

from $5870/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
Cayuco 9 is luxuriously situated with a golf course view and beach proximity. The open common areas are great for enjoying ... Cayuco 9 is located right on the golf course in Cap Cana

Cap Cana, Dominican Republic

Pool

from $1600/Nt
6 6
Details
Tortuga Bay C-17 photo

Punta Cana, Dominican Republic

Near Beach | Pool

from $2000/Nt
6 6+
Details
Trou Rolland has everything you could want in a Caribbean villa: amazing views, beach proximity, and a great location. You’... 2, 3 & 4 BR rates available. Trou Rolland is located on a hillside overlooking Marigot Bay

Marigot Bay, St. Lucia

Near Beach | Pool

from $517/Nt
6 6+
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
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
If you're looking for an oceanfront honeymoon or group vacay villa, Sea's Edge is perfect. It has easy ocean access ... 2, 3 & 4 BR rates available. Sea’s Edge sits above Rendezvous Bay with amazing ocean views

Rendezvous Bay, St. John

Pool

from $1071/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
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
At High Breeze, the decor is luxurious, the floor plan is luxurious, the outdoor space is luxurious... see a trend? ... 3 & 4 BR rates available.
Has specials. High Breeze Villa overlooks Barbados' west coast on Holders Polo Ridge in St. James

Barbados

Pool

from $1215/Nt
5 5+
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
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
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
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
If you need a place to go for a wedding or special event, Alicia is perfect. Its exterior space is ... 2, 3 & 4 BR rates available. Alicia photo

Tortola, BVI, British Virgin Islands

Pool

from $550/Nt
5 6+
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 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
Dunes 2 by Grace Bay Resorts is an easy, breezy way to relax in luxury in Turks and Caicos. This villa ... Has specials. Dunes 2 on Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $3900/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 owners of La Vita are long-time St. Johnians, and you can tell they love the island. The villa is ... La Vita Villa is located on a hillside above Peter Bay Beach

Peter Bay, St. John

Pool

from $2571/Nt
5 5+
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
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
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
Tre Vista is a super tranquil, comfortable villa perfect for you and your closest friends. There's a separate suite for ... 1, 2, 3 & 4 BR rates available. Tre Vista Estate sits on a hillside overlooking Great Cruz Bay

Chocolate Hole, St. John

Pool

from $857/Nt
5 5+
Details
Le Chant de la Mer has access to the edge of the sea, natural pools along the hillside, and lush, ... 1, 2, 3 & 4 BR rates available. Le Chant de la Mer Villa is located on a hillside on Point Milou

Pointe Milou, St. Barts

Pool

from $3571/Nt
5 6
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
Caribe Villa is a comfortable, family-friendly villa perfect for large groups. Its huge deck, living room, and kitchen are well ... 2, 3 & 4 BR rates available. At Caribe Villa you can lounge on the sundeck and enjoy views of Rendezvous Bay

Rendezvous Bay, St. John

Pool

from $700/Nt
5 5+
Details
La Dacha is a cliffside getaway with an amazing location near shops, restaurants, and nightlife. The whole villa has a ... La Dacha Villa is located on a cliffside at Falaise des Oiseaux

Terres Basses (French side), St. Martin

Near Beach | Pool

from $1000/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
You can easily share Mer Soleil with up to four other couples or the whole family, with five king-sized beds ... 3 & 4 BR rates available.
Has specials. Mer Soleil sits on a hillside in Terres Basses

Terres Basses (French side), St. Martin

Pool

from $743/Nt
5 5
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
If you must work, Giselle Villa will make it painless. The villa has open interiors that will accommodate working in ... 3 & 4 BR rates available.
Has specials. Beautiful views pool side at Giselle Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

from $821/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
Panoramic View Villa has something for everyone. Spend your days swimming in the pool, lounging on one of the padded ... 3 & 4 BR rates available. Panoramic View is located in Lurin overlooking the Gustavia Harbour

Lurin, St. Barts

Pool

from $2571/Nt
5 5
Details
If you're looking for a large villa estate with privacy, ocean views, and a location close to the action, Lagon ... 3 & 4 BR rates available. Lagon Bleu is located in prestigious Domaine du Levant overlooking Petite cul de Sac

Petit Cul de Sac, St. Barts

Near Beach | Pool

from $1143/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
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
Looking straight over the sea to St. Thomas and beyond, Rhapsody St. John is a home filled with classic island ... 2, 3 & 4 BR rates available. Rhapsody Villa sits above Turner Bay looking out to the Island of St. Thomas

Great Cruz Bay, St. John

Pool

from $929/Nt
5 5+
Details
Coco de Mer is a great choice for big groups who want to soak up St. John’s beaches and ... 2, 3 & 4 BR rates available. Coco de Mer at Peter Bay photo

Peter Bay, St. John

Near Beach | Pool

from $1400/Nt
5 6+
Details
Great for a family, Indian Song Villa is in a private gated community, with beachfront access and plenty of space ... 2, 3 & 4 BR rates available. Beautiful infinity edge pool over looking Petit cul de sac

Petit Cul de Sac, St. Barts

Beachfront | Pool | AC

from $2429/Nt
5 5+
Details
Petite Plage 4 is named for a white sandy beach in Grand Case, and the beach is close enough to touch ... Petite Plage 4 is located on the French side of St. Martin in Grand Case

Grand Case (French side), St. Martin

Beachfront | Pool | AC

from $2357/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
Bliss Villa is a good choice for 3 or 4 couples looking to share in getting away from it all, or families ... 2, 3 & 4 BR rates available. Amazing views of the ocean from the pool and patio at Bliss Villa

Cap Estate, St. Lucia

Near Beach | Pool

from $300/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
Mystic Villa is located on a St. Jean hillside and is ideal for a family with older children, four couples, ... 2, 3 & 4 BR rates available. Mystic Villa overlooks the beautiful St. Jean Bay and the famous Eden Rock hotel

Saint Jean, St. Barts

Pool

from $2136/Nt
5 5+
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
Large enough for five couples or a small business retreat, Tom Tom Villa is the perfect home away from home ... Has specials. Tom Tom Villa is located in the heart of Royal Westmoreland and features an infinity edge pool

Barbados

Pool

from $1700/Nt
5 5+
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
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
Mezel Villa is warm, open, and very Caribbean. There's panoramic ocean views, a spacious terrace and infinity pool, and tons ... 3 & 4 BR rates available.
Has specials. Mezel Villa is located in Terres Basses overlooking the Caribbean

Terres Basses (French side), St. Martin

Pool

from $800/Nt
5 5
Details
This is the perfect villa for anyone who loves the sun and sea. Between the beaches and Francis Bay Estate’... 3 BR rate available. Francis Bay Estate Villa overlooks Francis Bay and is with in walking distance to Francis Bay Beach

North Shore, St. John

Near Beach | Pool

from $957/Nt
5 5+
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
Located in Peter Bay, Delfina is a five-star villa with an entire floor dedicated to entertainment. With an open view ... 3 BR rate available. Villa Delfina is located on a hillside overlooking Peter Bay

Peter Bay, St. John

Near Beach | Pool

from $1686/Nt
5 6+
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
Arc En Ciel is set in an exotic wonderland with volcanos, waterfalls, and the Piton mountain range. Its near diving, ... 3 BR rate available. Arc En Ciel Villa photo

Soufriere, St. Lucia

Near Beach | Pool

from $1900/Nt
5 5
Details
Turtle Beach Villa fits the bill for a Caribbean getaway: private pool, beautiful beach, ocean views, and easy water sport ... Aerial views of the Turtle Beach property

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1357/Nt
5 5
Details
Danse du Soleil is great for any family or group of couples who want plenty of peace and quiet. The ... 1 & 3 BR rates available. Danse du Soleil is located on the heights of Deve overlooking the sea and the Toiny hillside

Deve, St. Barts

Pool

from $1807/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
Calypso villa is gorgeous, and you'll probably be spending much of your time outdoors. Great ocean views, a private swim ... Has specials. Aerial view of Calypso and Sapodilla Bay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1440/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
Vue De Reve Villa is a uniquely designed private estate with upscale furnishings and tons of privacy. The main house ... Amazing views of the bay and the Caribbean beyond

Saint Jean, St. Barts

Pool

from $7071/Nt
5 5
Details
Om Villa has pretty-as-a-postcard sea views, a solar-heated pool, and a home theater. It offers five bedrooms for groups of ... 3 & 4 BR rates available. OM Villa is located on a hillside overlooking Marigot Bay

Mont Jean, St. Barts

Pool

from $2000/Nt
5 5
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
The sunsets at Kishti Villa on Blackgarden are truly incomparable. In fact, the sunset-obsessed owner of the villa gave his ... Kishti Villa on Blackgarden is situated to enjoy amazing ocean views

Anguilla

Near Beach | Pool

from $3500/Nt
5 5+
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
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
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
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
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
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
Whatever you’re looking for in an island getaway, Nandana’s got it. You have ultimate privacy, luxurious everything, and ... 3 BR rate available. Nandana Villa in the Bahamas

Grand Bahama Island, Bahamas

Pool

from $10500/Nt
5 6
Details
If you want an oceanfront property that is as deluxe as it is spacious, then Kishti Villa on Meads Bay ... 4 BR rate available. Relax in the pool and hot tub during your stay at Kishti Villa West

Anguilla

Beachfront | Pool | AC

from $4200/Nt
5 6+
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
This villa's name and decor was inspired by Sinatra's "I Did It My Way", and the luxurious, unique design certainly ... 3 & 4 BR rates available. My Way Villa sits on a hillside looking over the Flamands Bay

Flamands, St. Barts

Pool

from $3571/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 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
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
The Dunes 1 is perfect for any traveler who wants five-star resort amenities on picturesque Grace Bay. Stroll along the beach ... Has specials. The interior pool and dining palapa at the Dunes 1 Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $3900/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
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
I can't get over this villa's decor and layout. It feels like a zen retreat, but is still fairly convenient ... 3 BR rate available. Ixfalia photo

Saint Jean, St. Barts

Pool

from $3571/Nt
4 4+
Details
Axel Rocks is great for many reasons, and one of those is its location. A short drive will take you ... 2 & 3 BR rates available. Amazing Caribbean views from Axel Rocks Villa

Gustavia, St. Barts

Pool

from $3571/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
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
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
This villa is a great choice for any group of travelers. The villa is only a few minutes from Flamands ... 3 BR rate available. Alpaka Villa has beautiful views from its hillside location over Flamands Beach

Flamands, St. Barts

Pool

from $1000/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
Seagrass is ideal for four couples who want to have a relaxing St. John vacation. Each bedroom is a master ... 1, 2 & 3 BR rates available. Seagrass Villa is in Virgin Grande Estates, near Great Cruz Bay

Virgin Grand Estates, St. John

Pool

from $586/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
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
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
Gorgeous sunsets, modern interiors, and resort amenities make this villa special. Elysium is right on the beach, so the views ... Elysium is located in the Jolly Harbour community

Jolly Harbour, Antigua

Beachfront | Pool | AC

from $3500/Nt
4 4
Details
Plumbago is great for groups of couples who want to totally relax on vacation. The design and decor is absolutely ... 2 BR rate available. Plumbago is located in Colombier with ocean views and a great pool

Colombier, St. Barts

Pool

from $3500/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
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
Ocean, ocean, ocean is all around you in this fun, contemporary house filled with windows. All four bedrooms utilize large, ... 3 BR rate available.
Has specials. Turquoze Villa is located on a hilltop above Orient Bay

Orient Bay (French side), St. Martin

Pool

from $693/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
The many nooks and crannies that crop up along the garden paths at Bellamare are ideal for reading, meditating, or ... 2 & 3 BR rates available. Bellamare is located o a hilltop overlooking Mahoe Bay

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

from $514/Nt
4 8+
Details
Altagracia is a spacious four-bedroom villa on Constant Point in Cruz Bay. If you stay here, you can relax in ... 1, 2 & 3 BR rates available. Altagracia is on Constant Point in Cruz Bay with views all the way to St.Thomas

Great Cruz Bay, St. John

Pool

from $571/Nt
4 4
Details
Mirabelle's location puts you just minutes from great shops and restaurants on the island. Its super modern and chic, and ... 3 BR rate available.
Has specials. Mirabelle Villa is located on the edge of Simpson Bay Lagoon

Terres Basses (French side), St. Martin

Near Beach | Pool

from $857/Nt
4 4
Details
This villa offers views from nearly every corner, including a clear shot of the waters below from the large, private ... 2 & 3 BR rates available. Milonga is perched on the hillside above Marigot

Marigot, St. Barts

Pool

from $971/Nt
4 4
Details
La Pergola is a favorite of visitors to St. Martin. One recent guest wrote, "The villa and location were beautiful. ... 2 & 3 BR rates available.
Has specials. La Pergola is located in Terres Basses overlooking the Caribbean and Long Bay

Terres Basses (French side), St. Martin

Pool

from $560/Nt
4 4+
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
The Sous La Falaise has four bedrooms, four bathrooms, and can accommodate two to four couples. It has partial air ... 2 & 3 BR rates available. Sous La Falaise Villa sits above the edge of beautiful St. Jean Bay

Saint Jean, St. Barts

Near Beach | Pool

from $1143/Nt
4 4
Details
Whether you’re coming down for a getaway with friends or a big family reunion, Ami La Vita is perfect. ... 1, 2 & 3 BR rates available. Ami La Vita Villa is a located on Klein Bay overlooking the Caribbean

Klein Bay, St. John

Near Beach | Pool

from $571/Nt
4 3+
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
On the Rocks Villa is impressive to say the least. The master bedroom is positioned so that you can lie ... 2 & 3 BR rates available. On the Rocks Villa is nestled along the hillside providing amazing views

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

from $929/Nt
4 4
Details
Aqua Pulchra is one of the most amazing villas on Chalk Sound. It’s spacious, gorgeous, and totally luxurious. It’... Aqua Pulchra sits above the water on Chalk Sound

Chalk Sound, Turks and Caicos

Pool

from $1071/Nt
4 3
Details
Antique furniture and an open-air atmosphere provide a tranquil setting for all guests ten years or older. Daily maid service ... 2 & 3 BR rates available. The infinity pool blends into the views of St. Jean Bay

Saint Jean, St. Barts

Near Beach | Pool

from $1329/Nt
4 4
Details
A serene setting and lots of natural beauty greet you at Peace & Plenty Villa. This roomy, architectural haven is perfect ... 2 & 3 BR rates available. Peace & Plenty Villa photo

Catherineberg, St. John

Pool

from $750/Nt
4 4+
Details
Chateau La Tete Rouge’s outdoor space is phenomenal. The villa enjoys beautiful views, an open floor plan, and spacious ... 1, 2 & 3 BR rates available. Chateau La Tete Rouge Villa overlooks the south shore of St. John

Rendezvous Bay, St. John

Pool

from $571/Nt
4 3+
Details
Dreamin’ Blue is a great option for families with small children or four couples. The villa has two pools and ... 2 & 3 BR rates available.
Has specials. Dreamin’ Blue is located on a hillside between Happy Bay Beach and Friar’s Bay

Happy Bay (French Side), St. Martin

Near Beach | Pool

from $714/Nt
4 4+
Details
Pasha Villa is close (three minutes) to several beaches, as well as Gustavia harbor. It is an ideal vacation rental ... 2 & 3 BR rates available. Pasha Villa is located on a hillside overlooking the stunning St. Jean Bay

Lurin, St. Barts

Pool

from $1271/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
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
This villa is gorgeously decorated, and I love the long living and dining space that completely opens up to the ... 2 & 3 BR rates available. Angelique Villa photo

Saint Jean, St. Barts

Pool

from $1429/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
A villa ideal for two or three couples, Captain Cook is located in the private estate of Pointe Milou, with ... 1, 2 & 3 BR rates available. A private pool and hot tub area the perfect place to vacation at Captain Cook Villa

Pointe Milou, St. Barts

Pool

from $1143/Nt
4 4
Details
If you love a beautiful sunset view, come to BP Villa. This villa offers a heated pool, covered porches, and ... 1, 2 & 3 BR rates available. BP Villa is located near Shoal Bay Beach

Anguilla

Near Beach | Pool

from $1000/Nt
4 4+
Details
High in the hills of Colombier, the fountain entrance and sunset views of Belle Bague add to the exotic feel ... 2 & 3 BR rates available. Belle Bague Villa is located in Colombier an has amazing ocean views

Colombier, St. Barts

Pool

from $1714/Nt
4 6
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
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
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
Sunspot Villa manages to combine modern architecture with island charm. It can be used for a family gathering or for ... 2 & 3 BR rates available. Sunspot Villa photo

Peter Bay, St. John

Near Beach | Pool

from $1453/Nt
4 4+
Details
Kaya has everything guests need, including four air-conditioned bedrooms, U.S. satellite TV, and WiFi. This villa is a short ... 2 & 3 BR rates available. Kaya Villa located in Vitet and overlooks Lorient Bay

Vitet, St. Barts

from $1000/Nt
4 4
Details
If you're looking for something super modern, you've come to the right place. Ani Villa North is a 4-bedroom, 4-bath ... Ani Villa North is a beautiful location for a Caribbean getaway

Anguilla

Pool

from $5225/Nt
4 4+
Details
Island Rider overlooks some of the clearest Caribbean water you've ever seen. You can spend hours just relaxing on the ... 1, 2 & 3 BR rates available. Impressive views of the Caribbean from the pool and deck area at Island Rider Villa

Rendezvous Bay, St. John

Pool

from $886/Nt
4 4+
Details
Capturing as much sunshine as possible is easy at Terrasse de Mer. Whether you want to do that on the ... 2 & 3 BR rates available.
Has specials. Terrasse de Mer Villa photo

Terres Basses (French side), St. Martin

Pool

from $814/Nt
4 4
Details
Even with a house full of people, finding peace and quiet within Mango Bay Villa is a piece of cake. ... 2 & 3 BR rates available. Mango Bay Villa offers amazing views of the Caribbean to the BVI's

Catherineberg, St. John

Pool

from $714/Nt
4 4+
Details
Every room in this villa has breathtaking water views! Whether you're relaxing on the covered deck or creating a light ... 1, 2 & 3 BR rates available. Pool at La Bella Vita

Virgin Grand Estates, St. John

Pool

from $643/Nt
4 4+
Details
Avalon Villa, located right on the world-famous Grace Bay Beach, is where fun meets relaxation. This lush, tropical island getaway ... Beautiful resort-like pool and landscaping at Avalon Villa located near Smith's Reef

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2500/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
Open rooms and modern furnishing offer the beginnings of a nice vacation. With screened doors and ceiling fans, you can ... Mango Hill is located on the eastern end of St. Croix

St. Croix, USVI

Pool

from $843/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
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
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
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
For vacationers who value privacy, but still want to be within range of beaches, restaurants, markets, and town, Casa Tigre ... 1 & 3 BR rates available. Casa Tigre Villa has beautiful Caribbean views

Vitet, St. Barts

from $1714/Nt
4 4
Details
This villa has great kayak and snorkel access, and is close to some great restaurants. On the island, there's horseback ... Amazing Caribbean views at Roi Soleil

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $1421/Nt
4 4
Details
You'll feel like you're touching the sky at Croix Vista Villa! This villa is elevated 400 feet above Fish Bay, and ... 2 BR rate available. Croix Vista Villa sits on a hilltop overlooking Fish Bay

Fish Bay, St. John

Pool

from $629/Nt
4 4+
Details
Good News Villa has much to offer potential guests. This 4-bedroom property not only has the vast, quiet spaces that ... Good News Villa is located in Petit Cul De Sac overlooking Petites Anses into the Caribbean

Petit Cul de Sac, St. Barts

Pool

from $2714/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
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
This villa is definitely striking! Two steel wings cap the roof, and the pool flows over the top deck to ... 2 & 3 BR rates available. Enjoy your private pool perched hillside in St. Jean with views of St. Jean Bay

Saint Jean, St. Barts

Pool

from $2286/Nt
4 4
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
Located off the white sands of Malcolm beach, the Amanyara Resort is great for the nature-focused traveler who wants to ... Amanyara Beach Villa photo

Providenciales, Turks and Caicos

Beachfront | Pool | AC

from Call for rates
4 4
Details
Amanyara is all about stepping out of the rush of every day and letting nature take over. This villa's pavilion ... Amanyara Oceanfront Villa photo

Providenciales, Turks and Caicos

Pool

from Call for rates
4 4
Details
Casa Del Sol is perfect for four couples or two families who want to relax and unwind on one of ... 1, 2 & 3 BR rates available. View from pool (no longer a hot tub)

Klein Bay, St. John

from $564/Nt
4 4
Details
This three-story villa is perfect for families and friends alike. I love the beautiful design and convenience to 6 different beaches. 2 BR rate available. What Else Villa photo

Pointe Milou, St. Barts

Pool

from $1171/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
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
Madras Villa is within walking distance of beautiful Plum Bay, and has a charming pool area with a view. There's ... 2 & 3 BR rates available.
Has specials. Madras Villa is located in Terres Basses just a short walk from Plum Bay

Terres Basses (French side), St. Martin

Near Beach | Pool

from $429/Nt
4 4+
Details
This villa has a great view of St. Jean from the pool, and you can watch the boats go by ... 2 & 3 BR rates available. Xanadu Villa photo

Saint Jean, St. Barts

Near Beach

from $1357/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
Island Girl has a really cool layout that gives everyone in your party plenty of room to kick back and ... 1, 2 & 3 BR rates available. View of Coral Bay from the villa pool area

Coral Bay, St. John

Pool

from $714/Nt
4 4
Details
Villa Arrecife 24 at Tortuga Bay photo

Punta Cana, Dominican Republic

Pool

from $1080/Nt
4 4
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 an amazing private beach that's perfectly set up for parties and al fresco feasts. The bedrooms are ... The private pool at Kai Zen is tucked away to the side of the villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $645/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
D'Zir is a great choice if you and your friends need a vacation. There's unbelievable views and a relaxing breeze ... 2 BR rate available. D'Zir Villa offers amazing views over Gustavia Harbor

Colombier, St. Barts

Pool

from $1714/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
Kai Zen covers my top priorities for a Caribbean villa: gorgeous design and a beachfront location. This villa has up-close-and-personal ... Kia Zen is located right on the beach close to Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $645/Nt
3 3+
Details
Mamiami is everything you could want in a quiet Caribbean vacation. The villa is luxurious, but understated, and every room ... 1 & 2 BR rates available. Mamiami is located in Vitet and overlooks the ocean

Vitet, St. Barts

Pool

from $1143/Nt
3 4
Details
With its contemporary West Indian design, Baie Longue Beach House provides a much-needed relaxing getaway for couples, friends, or families ... 1 & 2 BR rates available.
Has specials. Baie Longue Beach House Villa overlooks the beautiful Beach and Bay

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $771/Nt
3 3
Details
Bell'mare is a unique property located right on Dawn Beach; in fact, it's the only home in the area with ... 1 BR rate available.
Has specials. Bell'mare photo

Dawn Beach (Dutch side), St. Martin

Near Beach | Pool

from $412/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
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
You could spend your entire vacation without ever leaving Maracuja Villa and have the best time of your life. Spend ... 2 BR rate available. Maracuja Villa photo

Vitet, St. Barts

Pool

from $743/Nt
3 3
Details
Carnival Beach House is perfect for three couples to share. Two of the bedrooms have their own kitchenette, bathroom, living ... 1 & 2 BR rates available. Perched above Klein Bay Carnival Beach House has amazing ocen views

Klein Bay, St. John

Beachfront | Pool | AC

from $445/Nt
3 3
Details
Every detail at Lucky House is designed to maximize the views. Whether you're enjoying a cocktail by the beach fire ... Private pool at Lucky House

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $6000/Nt
3 3
Details
La Favorita Villa stands up to its name; it will be a favorite place to go after you experience all ... 1 & 2 BR rates available.
Has specials. La Favorita sits in the heart of Terres Basses and overlook Baie Longue

Terres Basses (French side), St. Martin

Pool

from $614/Nt
3 3+
Details
At Le Moulin, you have instant access to St. Jean's beach, onsite tennis, an infinity-edge pool, and air-conditioned bedrooms. This ... 1 & 2 BR rates available. The landmark -Windmill- at Le Moulin Villa on St.Jean Beach

Saint Jean, St. Barts

Beachfront | Pool | AC

from $1714/Nt
3 3
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
Located on a hillside in Marigot, Au Couer du Rocher is an open home. It is stylishly furnished and also ... 1 & 2 BR rates available. Au Coeur du Rocher photo

Marigot, St. Barts

Pool

from $543/Nt
3 3
Details
The large pool is a focal point for this light-filled, 3-bedroom villa. Kids can play without getting in each others ... 1 & 2 BR rates available. Cactus Villa has amazing views of Gustavia Harbor wether it be by day or by night

Colombier, St. Barts

Pool

from $714/Nt
3 3
Details
With panoramic ocean views from the pool terrace, Ker Anna Villa is a great place for friends and family on ... 2 BR rate available. Ker Anna Villa enjoys unique views of St. Jean Bay and across to the Gustaf III runway

Saint Jean, St. Barts

Pool

from $714/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
COMO Villa is perfect if you want ocean views and lots of privacy. With a staff that’s delighted to ... Has specials. Como Villa has a private location in Parrot Cay among the sand dunes and lush vegetation

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $5850/Nt
3 3
Details
Domingue Villa is near Marigot Beach and has stunning ocean and sunset views. This villa is near several restaurants and ... 2 BR rate available. Domingue Villa is located near Marigot Beach with stunning ocean and sunset views

Pointe Milou, St. Barts

Pool

from $1329/Nt
3 3
Details
Carolina Villa is perfect for any traveler who loves ocean views and lots of privacy. The home is comfortably furnished ... 1 & 2 BR rates available. Carolina Villa photo

Coral Bay, St. John

from $514/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
La Baleine Villa has a lot going for it: a hillside location, gorgeous ocean views, an open floor plan, and ... 1 & 2 BR rates available. An aerial shot from above La Baleine Villa shows off views of Gustavia Harbor

Colombier, St. Barts

Pool

from $371/Nt
3 3
Details
With its cool, white decor amid splashes of color, Super Sky Villa provides a relaxing and comfortable atmosphere for travelers ... 1 & 2 BR rates available. Villa Super Sky is located in St. Jean

Saint Jean, St. Barts

Pool

from $750/Nt
3 3
Details
Nikki Villa's stunning ocean view, with a blue sky, green hills, and tropical plants galore, makes it one of the ... 1 & 2 BR rates available. Nikki Villa has great views right into St. Jean Bay

Saint Jean, St. Barts

Near Beach | Pool

from $1143/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
Whether you want the gorgeous view of La Samanna or the beautiful sunset over Plum Bay Beach, Just in Paradise ... 1 & 2 BR rates available.
Has specials. Just in Paradise Villa is located in Terres-Basses overlooking Plum Bay

Terres Basses (French side), St. Martin

Pool

from $743/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
Meli Melo manages to be ultra modern and cozy at the same time. The villa has an open floor plan ... 1 & 2 BR rates available. Meli Melo Villa is located on a hillside above St. Jean Bay

Saint Jean, St. Barts

Pool

from $1714/Nt
3 3+
Details
This villa is stunning. It has a full kitchen and beautiful architecture that's really unique to the area, and the ... Villa MOH is located in Lurin

Lurin, St. Barts

Pool

from $1257/Nt
3 3
Details
Emvie is super modern and crisp, which I love because it only makes the view better. The master bedroom is ... 1 BR rate available.
Has specials. Emvie Villa photo

Orient Bay (French side), St. Martin

Pool

from $557/Nt
3 3
Details
This villa is great if you're traveling with two other couples. It's on a hill near Rendezvous Bay, Ditleff Point, ... 1 & 2 BR rates available. Spectacular views from the pool and veranda at Caribbean Palm Villa

Rendezvous Bay, St. John

from $643/Nt
3 3+
Details
You will love the personalized service that COMO Parrot Cay has to offer. With a staff that is delighted to ... Has specials. Como Parrot Cay Two Bedroom Beach Villa has a great beach front swimming pool

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $4500/Nt
2 3
Details
The Captain's House is a perfect getaway for celebrating anniversaries or to just be together on beautiful Tortola. With 2 pavilions-a ... 1 BR rate available. Captain's House villa is located on a hillside in Belmont Estates on the Northwest end of Tortola

Tortola, BVI, British Virgin Islands

Pool

from $310/Nt
2 2
Details
Terrahawk offers a lot in terms of privacy, views, easy access to National Park lands, secluded beaches, and in-town action. ... Views of Hawksnest Bay from the deck at Terrahawk

North Shore, St. John

Near Beach

from $400/Nt
2 2
Details
Overlooking the Caribbean Sea, Byzance Villa in Colombier is the ideal getaway for one or two couples. Outside, there is ... 1 BR rate available. Byzance Villa is located in Colombier overlooking the Flamands Bay

Colombier, St. Barts

Pool

from $857/Nt
2 2
Details
There are plenty of modern amenities that make Sky Vista a simple vacation destination that can easily accommodate a relaxation ... A beautiful view from the pool and deck at Sky Vista Villa

Gustavia, St. Barts

Near Beach | Pool

from $857/Nt
2 2
Details
Petit Lagon is a great place for a honeymoon, a family with older children, or two couples who want to ... 1 BR rate available. Petit Lagon is perched on a tropical hillside in Petit Cul de Sac

Petit Cul de Sac, St. Barts

Near Beach | Pool

from $571/Nt
2 2
Details
Alizee d'Eden is a great choice for couples who want gorgeous views and beach proximity. Every space enjoys panoramic ocean ... 1 BR rate available. Alizee d' Eden is located on a hillside in Pointe Milou

Pointe Milou, St. Barts

Pool

from $414/Nt
2 2
Details
With 2 king bedrooms and 2.5 bathrooms, Bonjour Villa in St. Jean is a private home that is available for rent by ... 1 BR rate available. Bonjour Villa is located on a hillside in St. Jean overlooking St Jean Bay

Saint Jean, St. Barts

Near Beach | Pool

from $439/Nt
2 2+
Details
A new space, Diamond Villa has much to offer those on holiday including intense seclusion, beautiful views, and spacious accommodations. ... 1 BR rate available. Diamond Villa offers great views over Gustavia

Saint Jean, St. Barts

Pool

from $929/Nt
2 2
Details