Caribbean Family Villas

Caribbean Family Villas

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

There's really no island quite like Calivigny. This gem was purchased in 2000 by a couple who wanted to create a ... 20 BR rate available.

Calivigny Island is located just south of Woburn Bay, Grenada

Calivigny Island - Estate

Grenada

Beachfront | Pool | AC

24 24

Details

The Pearls of Long Bay are the gems of Providenciales. Each home has a theater-style media room, two pools, tons ...

The Pearls of Long Bay Estate consist of Pearl East, Pearls West and Lidia House

Pearls Of Long Bay Estate

Long Bay, Turks and Caicos

Beachfront | Pool | AC

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

Necker Island, BVI, British Virgin Islands

Beachfront | Pool | AC

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

Thatch Caye

Belize

Near Beach

15 15

Details

Over Yonder Cay is the pinnacle of luxury. It's a private island in the Bahamas with a full staff of ...

Over Yonder Cay is a spectacular exclusive private island south of Nassau in the Bahamas

Over Yonder Cay - A Private Island

Exuma and Cays, Bahamas

Beachfront | Pool | AC

15 12

Details

ÀNI Dominican Republic is a property that doesn't skimp on luxury. There's pools with massive water slides, a private beach, ... 6, 7, 8, 9, 10, 11, 12 & 13 BR rates available.

ÀNI Dominican Republic has an amazing infinity edge pool with Caribbean views

ANI Dominican Republic

Cabrera, Dominican Republic

Pool

14 14

Details

This estate can easily accommodate large groups thanks to fourteen large bedrooms, indoor and outdoor dining areas, and sprawling patios. ... 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

Mes Amis

Terres Basses (French side), St. Martin

Pool

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

Seaclusion Estate

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

13 14+

Details

Combining the words, "Luxurious" and "All-Inclusive" can almost sound paradoxical. But at Three Bees at Harbour Island, Bahamas these two ...

Three Bees is located on Harbour Island Bahamas

Three Bees at Harbour Island

Harbour Island, Bahamas

Beachfront | Pool | AC

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

Arrecife 23/24/25 Estate at Punta Cana Resort

Punta Cana, Dominican Republic

Pool

13 13+

Details

Laughing Waters is luxurious, exclusive, and secluded without being isolated. This unbelievable resort estate has a full team of staff, ...

Laughing Waters is located in Barbados Sandy Lane

Laughing Waters

Barbados

Pool

12 12

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

La Bella Casa

Terres Basses (French side), St. Martin

Pool

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

Golden Clouds

Ocho Rios, Jamaica

Pool

12 12

Details

The Branson Estate offers a private island experience for large groups and families. The estate offers three impressive master suites ... Has specials.

Branson Estate is situated at the northeast tip of Moskito Island

The Branson Estate at Moskito Island

Moskito Island, BVI, British Virgin Islands

Beachfront | Pool | AC

11 11+

Details

Hawksbill Estate is ideal for hosting staff retreats as well as family get-togethers. The sheer magnitude of it gives the ...

The Hawksbill Estate is located on a beautiful stretch of Grace Bay Beach

Hawksbill Estate

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

11 11

Details

If you do things with an all or nothing attitude, you'll flip over Le Bleu Villa. It's hard to think ... 10 BR rate available.

Le Bleu Villa its on 2.5 acres of beachfront in Little Harbor

Le Bleu Villa

Anguilla

Beachfront | Pool | AC

11 11

Details

Villa Doma has a gorgeous location right on Babalua Beach. Hang around the beach with the villa’s stand up ... 8 & 9 BR rates available.
Has specials.

Bella Vita is a contemporary villa located near Babalua Beach

Villa Doma

Providenciales, Turks and Caicos

Beachfront | Pool | AC

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

Samsara

North Shore, Turks and Caicos

Beachfront | Pool | AC

10 7+

Details

If you're looking for luxury and elegance in St. Jean, Unik has it in spades. This ten-bedroom villa will make ... 6 & 7 BR rates available.

Unik villa is located in the heights Saint Jean overlooking St. Jean Bay

Unik

Saint Jean, St. Barts

Pool

10 10

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

Le Chateau des Palmiers

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

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

Flor de Cabrera

Cabrera, Dominican Republic

Beachfront | Pool | AC

10 9+

Details

Silent Waters Villa is a sprawling villa just outside of Montego Bay that offers everything you could possibly need for ... 3, 4, 5 & 7 BR rates available.
Has specials.

Aerial View of Silent Waters

Silent Waters Villa

Montego Bay, Jamaica

Pool

10 6

Details

The cove on which Crystal Springs Villa rests is like a clip out of a castaway movie. It is private ... 5, 7, 8 & 9 BR rates available.
Has specials.

Crystal Springs is a beautiful Estate located right on the beach

Crystal Springs Villa

Barbados

Beachfront | Pool | AC

10 11

Details

For large groups wanting extreme luxury, the oceanfront ÀNI Anguilla is a perfect choice. There are two separate villas, each ... 4, 6, 7, 8 & 9 BR rates available.
Has specials.

ÀNI Anguilla

ANI Anguilla

Anguilla

Pool

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

Casa Sunshine

Guana Bay (Dutch Side), St. Martin

Beachfront | Pool | AC

10 10

Details

Villa Arrecife 24/25 is located in the gated community of La Cana Resort & Club

Villa Arrecife 24/25

Punta Cana, Dominican Republic

Pool

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

Yarari Royale

Cap Cana, Dominican Republic

Pool

9 9+

Details

The Beach House is the biggest and most impressive accommodation on the island. If you want to vacation in style, ... 7 BR rate available.

The Beach House at Calivigny Island

Calivigny Island - The Beach House

Grenada

Beachfront | Pool | AC

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 ...

La Dolce Vita sits beachfront on a beautiful stretch of Long Bay Beach

La Dolce Vita

Long Bay, Turks and Caicos

Beachfront | Pool | AC

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

One Perfect Day

St. Thomas, USVI

Near Beach | Pool

9 9+

Details

This villa has all the luxury and amenities you'd expect in a five-star Caribbean villa. The floor plans are open ...

La Palmeraie is located on Harbour Island in the Bahamas

La Palmeraie - Villa 1

Harbour Island, Bahamas

Beachfront | Pool | AC

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 ... 6, 7 & 8 BR rates available.

Luxury pool and golf course views

Arrecife Royale

Punta Cana, Dominican Republic

Pool

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

Nevaeh Villa - Fully Staffed

Anguilla

Beachfront | Pool | AC

9 8+

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.
Has specials.

Villa Kiko is located on Payne's Bay

Kiko

Barbados

Beachfront | Pool | AC

9 9+

Details

The Oasis Estate has it all - luxury, privacy, and exclusivity. This four-story, nine-bedroom villa is on an island that ... Has specials.

The Oasis Estate is a sleek and contemporary tropical hideaway perched on the island’s peak

The Oasis Estate at Moskito Island

Moskito Island, BVI, British Virgin Islands

Pool

9 9

Details

If you're wanting to vacation in a quiet, luxurious, beachfront villa, La Palmeraie is perfect! This villa is huge - ...

La Palmeraie - Villa 2 is located in Triana Shores on Harbour Island

La Palmeraie - Villa 2

Harbour Island, Bahamas

Beachfront | AC

9 8

Details

Rip Kai is a magnificent, oceanfront estate perfect for your next Grand Cayman vacation. It's prepared to handle families celebrating ...

Rip Kai is located on Rum Point Drive with beautiful ocean views

Rip Kai - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

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

Capri Villa

Cap Estate, St. Lucia

Near Beach | Pool

9 9+

Details

"Cerulean" means "heaven," and this private resort attends to all the details of your stay to create your personal heaven. ...

Cerulean Villa is located on Barnes Bay

Cerulean Villa

Anguilla

Beachfront | Pool | AC

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.

Casa Varnishkes is located on a beautiful stretch pf Long Bay Beach

Casa Varnishkes Villa

Long Bay, Turks and Caicos

Beachfront | Pool | AC

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.

Santosha is located along a beautiful stretch of Long Bay Beach

Santosha Villa Estate

Anguilla

Beachfront | Pool | AC

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

Nevaeh Villa

Anguilla

Beachfront | Pool | AC

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

Coconut Walk

Grand Cayman, Cayman

Beachfront | Pool | AC

8 6+

Details

Impulse is honestly one of a kind. There's sculptures and statues throughout the space, waves of colored lights in the ... 4 & 7 BR rates available.

Expansive living area has endless views of the ocean

Impulse Beach Estate

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

8 8

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

La Serena

Punta Cana, Dominican Republic

Beachfront | Pool | AC

8 6+

Details

Kandara is great if you're looking for space and privacy. The villa and guest house has 10,000 square feet of space, ... 6 BR rate available.

Kandara Villa is located on Anguilla's West End

Kandara

Anguilla

Near Beach | Pool

8 8+

Details

Sea Orchard Retreat is a great choice for weddings, groups, or family vacations. Located a short drive from Seven Mile ...

Sea Orchard Retreat is a gated oceanfront boutique of cottages on the northern coast of Grand Cayman

Sea Orchard Retreat

Grand Cayman, Cayman

8 8

Details

English Harbour #048 is a hidden gem. With eight bedrooms, three pavilions and an extensive exterior, the villa is large enough ... 5 BR rate available.

English Harbour #048 is located on Windward Bay

English Harbour #048

English Harbour, Antigua

Near Beach | Pool

8 7

Details

Silver Sands is modern, luxurious, fully staffed, and beachfront. The villa has its own stainless steel pool, and Thompson Cove ... 5 BR rate available.

Silver Sands Villa is located along Thompson's Cove on the world famous Grace Bay

Silver Sands

Providenciales, Turks and Caicos

Beachfront | Pool | AC

8 7+

Details

If you're looking for luxury, Kempa Caribe is the place to be. Not only is this villa on a massive ...

Castillo Caribe is located on the southern coast of Grand Cayman

Kempa Caribe

Grand Cayman, Cayman

Beachfront | Pool | AC

8 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

Seaclusion

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

8 9+

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

Footprints Estate

Barbados

Beachfront | Pool | AC

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

Coconut Walk - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

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

Fischer's Reef - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

8 8+

Details

Kaiku is a fun choice for your next luxury beachfront vacation. The house sits right on the beach and has ... 7 BR rate available.

Kaiku is located on the Rum Point end of the island directly on Bio-luminescent Bay

Kaiku - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

8 6+

Details

If you want to breathe in the ocean air and relax, Arrecife 17 is an excellent choice for your next vacation. ...

Arrecife 17 is located in Punta Cana with beautiful Caribbean views

Arrecife 17

Punta Cana, Dominican Republic

Pool

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

Emerald Cay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

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 #46

English Harbour, Antigua

Pool

8 8+

Details

The Point Estate is an amazing option for families who want a totally luxurious private island experience. This estate offers ... Has specials.

The Point Estate Villa rests on a cliffside with scenic views

The Point Estate at Moskito Island

Moskito Island, BVI, British Virgin Islands

Pool

8 8

Details

Sun Rays Villa is located on a beautiful stretch of white sand beach on Sand Point Road

Sun Rays - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

8 8+

Details

Mango Bay is a large estate featuring seven bedrooms, a full on-site staff, and easy access to some of Barbados ... 6 & 7 BR rates available.
Has specials.

Mango Bay's patio sits right on the beach

Mango Bay

Barbados

Beachfront | Pool | AC

8 7+

Details

If you want to not only see the water from your villa but be able to step right into it, ... 2, 4, 6 & 7 BR rates available.

Beach Court Villa is settled at the western end of Shoal Bay Beach

Beach Court Villa

Anguilla

Beachfront | Pool | AC

8 8

Details

Fabrizia Villa is a great property for groups or a family with older children. This vacation rental has 8 bedrooms, several ... 3, 4, 5, 6 & 7 BR rates available.

Fabrizia Villa offers a great pool nestled on the hillside over Gustavia Harbor

Fabrizia Villa

Gustavia, St. Barts

Near Beach | Pool

8 9

Details

From the inviting front exterior to the contemporary furnishings, from the large pool to the quiet beach, Kaiku Villa is ... 7 BR rate available.

Kaiku is located on the Rum Point end of the island directly on Bio-luminescent Bay

Kaiku

Grand Cayman, Cayman

Beachfront | Pool | AC

8 6+

Details

Nelson Gay House’s design, staff, and location are all the ingredients you need for an incredible vacation. The crystal ... Has specials.

Nelson Gay House is located on Godings Beach and has beautiful gardens

Nelson Gay House

Barbados

Beachfront | Pool | AC

8 8+

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

Casa Kimball

Cabrera, Dominican Republic

Near Beach | Pool

8 8

Details

Mullins Mill is truly where the living is easy. With a full staff to anticipate your every desire, you'll have ... 4 & 6 BR rates available.
Has specials.

There is a beautiful ridge side pool at Mullins Mill

Mullins Mill

Barbados

Pool

8 8

Details

La Belle Creole is a great choice for a family vacation. There are eight bedrooms total, and seven of them ... 3, 4, 5, 6 & 7 BR rates available.

La Belle Creole photo

La Belle Creole

Saint Jean, St. Barts

Pool

8 7

Details

If you want to hear the ocean from every room, then Sunrise Villa is the perfect setting for your next ...

Sunrise Villa photo

Sunrise Villa

Cabrera, Dominican Republic

Beachfront | Pool | AC

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 ... 4, 5 & 6 BR rates available.
Has specials.

Grand views of the pool and the ocean beyond from the balcony at Plantation House

Plantation House

Barbados

Pool

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 ...

The Beach House features an amazing pool and outdoor area

The Beach House

Anguilla

Beachfront | Pool | AC

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

Sentosa Villa

Providenciales, Turks and Caicos

Beachfront | Pool | AC

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 BR rate available.
Has specials.

Prudence Villa is located in Old Queen’s Fort

Prudence Villa

Barbados

Near Beach | Pool

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 is located just a mile from the famous Rum Point Club on a white sand beach

Fischer's Reef Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

8 8+

Details

This villa is perfect for family reunions or staff retreats. The sheer size of it all makes you feel like ... 6 BR rate available.

Hawksbill Villa is located on the beautiful Grace Bay Beach

Hawksbill Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

8 9

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.

Aerial view of Pearl East

Pearl East Villa

Long Bay, Turks and Caicos

Beachfront | Pool | AC

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.

Exterior Pearl West

Pearl West Villa

Long Bay, Turks and Caicos

Beachfront | Pool | AC

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

Martello House

Barbados

Pool

8 8+

Details

Our Cayman Cottage is pretty impressive. This villa was made for family reunions, with ample space for kids and adults ...

Our Cayman Cottage sits along a beautiful stretch of beach on the north side of Grand Cayman

Our Cayman Cottage

Grand Cayman, Cayman

Beachfront | Pool | AC

7 6+

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

Evolution

Grand Cayman, Cayman

Beachfront | Pool | AC

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

Kaia Kamina

Grand Cayman, Cayman

Beachfront | Pool | AC

7 7+

Details

Sand & Sea offers tons of ways to have fun in the sun. Not only does it sit directly between Grace ...

Sand & Sea Villa sits just on the canal a short walk to the very end of Grace Bay Beach

Sand and Sea

Leeward, Turks and Caicos

Near Beach | Pool

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

Middle Cay

Harbour Island, Bahamas

Pool

7 6+

Details

Beach Enclave is unique not only because it sits on Long Bay, but also because it has a resort feel ... 6 BR rate available.
Has specials.

A boardwalk to the beach

Beach Enclave Beach Front Villa Plus 2 Bedroom Cottage at Long Bay

Long Bay, Turks and Caicos

Beachfront | Pool | AC

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

Villa Londali

Punta Cana, Dominican Republic

Pool

7 7

Details

Kempa Kai is luxurious, gorgeous, and unforgettable. Its modern design is both beautiful and practical, while the exterior is packed ... Has specials.

Kempa Kai villa is located on a nature preserve near Rum Point

Kempa Kai

Grand Cayman, Cayman

Beachfront | AC

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 ...

Casa de Suenos is located within the gated Los Suenos Resort community

Casa de Suenos

Costa Rica

Pool

7 7

Details

Blue Oasis is modern, luxurious, and expansive. Every room is spacious and well-lit, and each amenity has been handpicked for ...

Blue Oasis Villa is located in a secluded area of Cap Cana

Blue Oasis

Punta Cana, Dominican Republic

Beachfront | Pool | AC

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 ... 6 BR rate available.

Royal Island is located four miles from North Eleuthera, and 40 miles northeast of Nassau

Royal Island

Eleuthera Island, Bahamas

Beachfront | Pool | AC

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 is located on incredible beach frontage on Gun Bay

Cayman Castle and Guesthouse - Platinum

Grand Cayman, Cayman

Near Beach | Pool

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

Twin Palms - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

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

Mora - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

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

Our Cayman Cottage - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

7 6+

Details

Epicure has everything guests could want for a relaxing, cozy Caribbean vacation. The villa has tons of space for 14 guests, ... 4, 5 & 6 BR rates available.

Epicure Villa is located on a hillside overlooking Marigot

Epicure

Marigot, St. Barts

Pool

7 7

Details

Zenaida offers a great experience at an exceptional value. The beach is down a short, private path, and the villa ... 3, 4, 5 & 6 BR rates available.

Zenaida Beach & Tennis Estate is located just above Sandy Hill Beach

Zenaida Beach & Tennis Estate

Anguilla

Beachfront | Pool | AC

7 7

Details

This seaside villa is 7,000 square feet and is on 3.5 acres of land with gorgeous panoramic views. Between the pool, hot ... 4 & 5 BR rates available.

Paradise Villa is located near Blowing Point

Paradise Villa

Anguilla

Pool

7 5+

Details

Note - We are currently having issues with vendors setting up on the beach right by the La Koubba beach ... 6 BR rate available.

La Koubba Villa sits on the white sands of Sapodilla Bay

La Koubba Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

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.

Vieux Caribe Villa is located near Taylor Bay Beach

Vieux Caribe Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

7 7+

Details

It is probably the short walk to Guana Bay Beach that will please you the most when you stay at ... 3, 4, 5 & 6 BR rates available.
Has specials.

Alizee Villa sits on a hillside above Guan Bay

Alizee Villa

Guana Bay (Dutch Side), St. Martin

Near Beach | Pool

7 7

Details

Tamarind Villa is an ideal choice for a family with young children. It has 7 bedrooms, with two cribs and one ... 3 BR rate available.

Tamarind Villa is located in Windward Hills views are of both the Atlantic Ocean and the Caribbean

Tamarind Villa

Cap Estate, St. Lucia

Pool

7 7

Details

SPECIAL RESERVE COLLECTION includes a Private Chef for up to 2 meals/day, Preferred access to Beach Club chaise lounges, VIP ... 4, 5 & 6 BR rates available.

Luxurious Lorient Bay beachside pool deck at La Plage

La Plage Villa

Lorient, St. Barts

Beachfront | Pool | AC

7 7

Details

A La Mer Villa is one of the most spacious, well-designed villas on St. John. Its exterior has so many ...

A La Mer sits on St. John's coastline near Grat Cruz Bay

A La Mer Villa

Great Cruz Bay, St. John

Near Beach | Pool

7 7

Details

Le Manoir de Lorient is one of the most unique properties on St. Bart's. This five-bedroom villa combines Old World ... 4, 5 & 6 BR rates available.

Le Manoir de Lorient is tucked in a sweet neighborhood just across the street from Lorient Beach

Le Manoir de Lorient

Lorient, St. Barts

Near Beach | Pool

7 6+

Details

Fustic House is a legendary vacation destination. The villa was built in the 18th century, then transformed by the famous ... Has specials.

Amazing private swimming pool at Fustic House

Fustic House

Barbados

Near Beach | Pool

7 7

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 Villa is located on Grace Bay Beach

Coral House Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

7 7+

Details

Caye Blanche is a fun choice for couples or large families with older kids. It's close to Anse Marcel's beach ... 5 & 6 BR rates available.
Has specials.

Caye Blanche photo

Caye Blanche

Anse Marcel (French side), St. Martin

Pool

7 7+

Details

Le Caprice is designed for days of sunbathing and unwinding. The large pool is surrounded by a sprawling sundeck, and ... 4, 5 & 6 BR rates available.
Has specials.

Le Caprice Villa is located on a hilltop above Baie Rouge in Terres Basses

Le Caprice Villa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

7 6

Details

Bella Vita Villa is a three-story house with a ton of privacy, luxury, and amenities. The tropical surroundings, infinity pool, ... 4 & 6 BR rates available.

Bella Vita Villa is located in the residential enclave of Pelican Key in Dutch St. Maarten

Bella Vita Villa

Pelican Key (Dutch side), St. Martin

Pool

7 8+

Details

This is a fantastic property for large families or groups that are working within a budget. There is plenty of ...

Twin Palms is located near Rum Point on a beautiful stretch of ocean

Twin Palms Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

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 ...

Villa Mora is located beachfront in South Sound

Villa Mora

Grand Cayman, Cayman

Beachfront | Pool | AC

7 7+

Details

Cayman Castle has plenty of opportunity for fun! It has access to a beach, tons of room outside to take ...

Cayman Castle is located on incredible beach frontage on Gun Bay

Cayman Castle

Grand Cayman, Cayman

Near Beach | Pool

7 7+

Details

Wake up to the soothing sounds of the ocean and fall asleep to the cooling trade winds. Huge arcs throughout ...

Conched Out is located on Long Bay Beach and offers panoramic ocean views

Conched Out

Long Bay, Turks and Caicos

Beachfront | Pool | AC

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 is located on Seven Mile Beach

Seascape Villa

Grand Cayman, Cayman

Beachfront | AC

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

Jamoon - Sandy Lane

Barbados

Pool

7 6+

Details

If you want a private, oceanfront villa with a secluded beach, On The Rocks is a great choice. This villa ...

On the Rocks Villa is located in the Beach Bay community

On The Rocks Villa

Grand Cayman, Cayman

Near Beach | Pool

7 4

Details

If you’re looking for beachside luxury with access to exclusive activities and resort amenities, Villa Corales 28 is a great ...

Villa Corales 28 is a beautiful oceanfront villa in Punta Cana

Villa Corales 28

Punta Cana, Dominican Republic

Near Beach | Pool

7 7+

Details

Grace Too is the ideal beachfront escape. With wraparound porches and room for 16, it was made for big families and ...

The beachside pool at Grace Too - main beach house

Grace Too Estate

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

6 5+

Details

Wake Up is super modern, well-equipped, and gorgeously designed. There's tons of space to relax outside by the pool or ...

Wake Up Villa is located on the beautiful Flamands Beach

Wake Up

Flamands, St. Barts

Beachfront | Pool | AC

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

Yellow Bear Villa

Punta Cana, Dominican Republic

Pool

6 6+

Details

This villa is totally serene. There's more than enough activities - pool and beach toys, kayaks, snorkeling, and a huge ...

Casa Barana is located on Thompson Cove and has amazing ocean views

Casa Barana

North Shore, Turks and Caicos

Beachfront | Pool | AC

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

Villa Corales 114

Punta Cana, Dominican Republic

Near Beach | Pool

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

Falmouth Harbour #022

English Harbour, Antigua

Pool

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

Villa Blackstone

Marigot, St. Barts

Pool

6 6

Details

Big Chill is perfect for big families who want to chill in paradise! Its location on the Leeward Canal is ... Has specials.

Big Chill Villa has a canal front pool with great areas to relax and entertain

Big Chill

Leeward, Turks and Caicos

Pool

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

Viatu

Leeward, Turks and Caicos

Near Beach | Pool

6 6+

Details

Seaclusion will make you feel like royalty. There's more chandeliers and ocean views that I can count, and the exterior ... Has specials.

Seaclusion is located just steps away from an amazing white sand beach

Seaclusion

Barbados

Beachfront | Pool | AC

6 5

Details

Salacia is a gorgeous, family-friendly choice for a luxurious vacation on Grace Bay Beach. It sits on 1.5 acres with over 200 ...

Salacia Villa in Grace Bay offers amazing amenities

Salacia

Grace Bay, Turks and Caicos

Near Beach | Pool

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

Mandala

Punta Cana, Dominican Republic

Pool

6 6+

Details

These resort villas are perfect for any group that wants to vacation in style. The villas range from three to ... 4 & 5 BR rates available.

The elegant Shore Club Villas feature private swimming pools

The Shore Club Oceanfront Villa

Long Bay, Turks and Caicos

Beachfront | Pool | AC

6 8

Details

Les Lataniers has a uniquely Caribbean charm, and I love how the owners have combined antique decor with modern amenities. ... 5 BR rate available.

Villa Les Lataniers sits at the very end of Anse des Cayes

Lataniers

Anse des Cayes, St. Barts

Pool

6 6

Details

This beachfront villa is a great choice if you want to take your family to Turks and Caicos, and you ... Has specials.

Beach Enclave Beach Front Villa Plus 1 Bedroom Cottage at Long Bay photo

Beach Enclave Beach Front Villa Plus 1 Bedroom Cottage at Long Bay

Long Bay, Turks and Caicos

Beachfront | Pool | AC

6 6+

Details

Casa Patron is a great villa if you and your guests want plenty of space in a gated community. The ...

Casa Patron Villa is located just above Colina

Casa Patron

Costa Rica

Pool

6 5+

Details

If you and your friends want to take a family vacation, Harmon Estate is perfect. Thanks to the main house ...

The Harmon Estate Villa is located in the Eco Golf Community

Harmon Estate

Costa Rica

Pool

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

Amalia

Guana Bay (Dutch Side), St. Martin

Near Beach | Pool

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

White Coral

Leeward, Turks and Caicos

Pool

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

Dei Sogni

Lorient, St. Barts

Beachfront | Pool | AC

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

Blue Dragon

Gouverneur, St. Barts

Pool

6 6

Details

CieloMar is one of the most stunning villas in the Caribbean. It has everything you could want in a vacation ... 3, 4 & 5 BR rates available.

CieloMar is perched on the hillside above Peninsula Papagayo in a gated community

CieloMar

Costa Rica

Pool

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 ... 5 BR rate available.
Has specials.

Mapai is located in Terrasse de Cul de Sac and looks out to Pinel Island

Mapai

Cul de Sac (French Side), St. Martin

Pool

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

Corales 60

Punta Cana, Dominican Republic

Pool

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

Ammonite

Punta Cana, Dominican Republic

Pool

6 6+

Details

Allegria is a great choice for your next beachfront vacation. You can kayak, swim, and sunbathe right outside the back ... 4 BR rate available.

Allegria Villa is located on a beautiful stretch of beach across from Mangrove Cay

Allegria

Leeward, Turks and Caicos

Beachfront | Pool | AC

6 6

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

Ocean Kai - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

6 5+

Details

Moon Kai is a great family vacation villa on a barefoot beach in Cayman Kai. The villa is designed for ... Has specials.

Moon Kai is located right on a white sandy beach with in walking distance to Rum Point

Moon Kai - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

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

Alta Gracia

Punta Cana, Dominican Republic

Pool

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

Villa de Agua

Punta Cana, Dominican Republic

Pool

6 6+

Details

Cabuya is one of the most gorgeous villas on Providenciales's eastern coast. This villa has it all: a beachfront location, ... 5 BR rate available.
Has specials.

Cabuya Villa is located in Leeward on a beautiful stretch of white sand beach

Cabuya

Leeward, Turks and Caicos

Beachfront | Pool | AC

6 6+

Details

Z'Abricot is a great option for your next family vacation. All of the bedrooms are interior access only, there's a ... 4 & 5 BR rates available.
Has specials.

Villa Z'Abricot is located near Orient Bay

Z'Abricot

Orient Bay (French side), St. Martin

Pool

6 4

Details

Kisiwa is an elegant, luxurious vacation rental near Grace Bay. Staying here gives you easy access to the beach and ... Has specials.

Kisiwa House is located just steps away from Grace Bay Beach

Kisiwa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

6 6+

Details

Beach Enclave gives you gorgeous ocean views, resort amenities, and modern living spaces fit for any interior design magazine. The ... Has specials.

Beach Enclave at Grace Bay is located on a beautiful stretch of Grace Bay Beach

Beach Enclave 6 Bedroom Premium Ocean View at Grace Bay

Grace Bay, Turks and Caicos

Near Beach | Pool

6 6+

Details

Blondel Cove has everything you could possibly want in a luxury vacation villa. It has its own gym, home theatre, ...

Aerial views of the area

Blondel Cove

Leeward, Turks and Caicos

Beachfront | Pool | AC

6 6+

Details

Blue Vista offers waterfront luxury, peace and quiet, and tons of room for large groups. There are two separate sleeping ... 4 BR rate available.

Blue Vista Villa is located in Turtle Tail

Blue Vista

Turtle Tail, Turks and Caicos

Pool

6 6+

Details

Hura Sea Estate is a quietly luxurious beachfront villa with access to Long Bay and proximity to several restaurants and ...

Hura Sea Estate photo

Hura Sea Estate

Long Bay, Turks and Caicos

Beachfront | Pool | AC

6 6+

Details

Find all the Caribbean luxury and beauty you could dream of at Lizard Lounge. This Grace Bay villa has two ...

Lizard Lounge is located on Grace Bay in Turtle Cove

Lizard Lounge

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

6 6+

Details

Plum Bay is a quiet, restful retreat for your family's next vacation. It's between two lovely, quiet beaches in the ... 2, 3 & 4 BR rates available.

Plum Bay Villa is located in Terre-Basses

Plum Bay

Terres Basses (French side), St. Martin

Pool

6 6

Details

Looking for luxury and tranquility on a private island? Dream Pavilion has it in spades! This six-bedroom villa puts guests ...

Dream Pavilion photo

Dream Pavilion

Ambergris Cay, Turks and Caicos

Beachfront | Pool | AC

6 6+

Details

This rental property combines two villas into a supersized vacation home. Casa Luna - Platinum is great for travelers who ...

Casa Luna

Casa Luna - Platinum

Grand Cayman, Cayman

Beachfront | AC

6 6+

Details

The Last Resort stands true to its name…it’s certainly a paradise and feels like a mini-resort. This beautiful ...

The Last Resort Villa located in Chocolate Hole

The Last Resort

Chocolate Hole, St. John

Pool

6 6+

Details

There's something for everyone at Sea Star! Kick back in the infinity pool and gaze out at the sea, walk ...

Sea Star Villa is located on Cabrita Point

Sea Star

St. Thomas, USVI

Beachfront | Pool | AC

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

Chateau Margot Villa

Bordeaux, St. John

Pool

6 5+

Details

Azzurra Castle is just the place for families or four couples to vacation together. There are six air-conditioned bedrooms, including ...

Azzurra Castle sits on the southwest shore of Greneda's L'Anse aux Epines

Azzurra Castle

Grenada

Pool

6 6+

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.
Has specials.

Loblolly Villa photo

Loblolly Villa

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

6 6

Details

This classic, luxury beachfront villa sits on Little Trunk Bay, with those amazing boulders flanking the beach. It's truly paradise! ...

Sol y Sombra Villa is located on a hillside just above Little Trunk Bay

Sol y Sombra

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

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.
Has specials.

Baraka Point photo

Baraka Point

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

6 6+

Details

Two beaches to choose from, a large private pool, gated entrance, and views of the Caribbean waters are among the ... 4 & 5 BR rates available.
Has specials.

La Salamandre is located in Terres Basses with views of Simpson Bay

La Salamandre

Terres Basses (French side), St. Martin

Near Beach | Pool

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

Encore Villa

Terres Basses (French side), St. Martin

Pool

6 6

Details

Bajacu Villa has a totally unique design that gives you the best of both worlds: hilltop views and easy ocean ...

Bajacu is located on a private hilltop in Turtle Cove

Bajacu

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

6 7+

Details

Location, location, location! Petite Plage 5 is a sprawling beachfront property sleeping up to 12 guests offering privacy, one of the largest ... Has specials.

A resort like pool and amazing ocean views

Petite Plage 5 Villa

Grand Case (French side), St. Martin

Beachfront | Pool | AC

6 6+

Details

Valentina has everything you could want for a quiet, relaxing vacation. There's fitness equipment and a lap pool so you ... 3 & 4 BR rates available.

Valentina Villa is located at the eastern end of Pointe Milou

Valentina Villa

Pointe Milou, St. Barts

Pool

6 6

Details

Inside and out, Pelican Vista offers the best of Providenciales. You can enjoy the view inside, or find a spot ... 4 BR rate available.

The pool and palapa at Pelican Vista Villa

Pelican Vista

Grace Bay, Turks and Caicos

Near Beach | Pool

6 5

Details

Colibri Cottage is ideal for a nature-centric getaway in St. Lucia. The villa has gorgeous views of Petit Piton and ... 2 BR rate available.

Colibri Cottage sits on a hill above Soufriere Bay

Colibri Cottage

Soufriere, St. Lucia

Near Beach | Pool

6 6

Details

Le Reve will have you hooked from the first glance. Palm trees, sandy beaches, and gorgeous ocean views fill the ... Has specials.

Le Reve Villa is located on a private stretch of beach in Baie Rouge

Le Reve Villa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

6 7+

Details

Located within the gated community of Sandy Lane Estate, Moon Dance Villa is ideal for couples who want a tropical ... 4 BR rate available.
Has specials.

Luxurious pool and backyard at Moon Dance Villa

Moon Dance Villa

Barbados

Pool

6 6+

Details

Always Villa, recently entirely renovated, is decorated in appealing white to showcase its clean lines, as well as gleaming polished ... 4 & 5 BR rates available.
Has specials.

Always Villa is located in Terres Basses

Always Villa

Terres Basses (French side), St. Martin

Pool

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

Maison de Reve Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

6 6+

Details

Triton Villa is nestled into its own hillside enclave above Lockrum Bay and Little Harbour. This villa shares a secluded ... 4 & 5 BR rates available.

Triton Villa is located on LockRum Bay

Triton Villa at Kamique

Anguilla

Near Beach | Pool

6 6+

Details

Spacious and colorful, Mare Blu Villa overlooking Rendezvous Bay is the ideal getaway for your St. John vacation. Up to 12 ... 3, 4 & 5 BR rates available.

Mare Blu is located hillside on the exclusive Rendezvous Bay overlooking the south shore

Mare Blu Villa

Rendezvous Bay, St. John

Pool

6 8

Details

This Happy Bay hideaway has plenty of space for everybody to relax - especially several couples traveling together. Ocean 5 is ... 4 & 5 BR rates available.
Has specials.

Ocean 5 Villa sits on a Hillside in Mt. Choisy

Ocean 5

Happy Bay (French Side), St. Martin

Near Beach | Pool

6 6+

Details

One thing everyone who stays at Akasha mentions is the gorgeous view. It’s absolutely breathtaking! The villa is well-designed ... 1, 2, 3, 4 & 5 BR rates available.

Akasha Villa is located in Cap Estate and offers views of the Piton Mountains and Pigeon Island

Akasha Villa

Cap Estate, St. Lucia

Pool

6 6

Details

SPECIAL RESERVE COLLECTION includes a Private Chef for up to 2 meals/day, Preferred access to Beach Club chaise lounges, VIP ...

Dunes Villais located on 2.5 acres in Saline

Dunes Villa

Saline, St. Barts

Near Beach | Pool

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

Little Whale Cay

Berry Islands, Bahamas

Pool

6 6

Details

Cumulus Villa is just a short walk from Lorient Beach, and was built with all the latest amenities in mind. ... 4 & 5 BR rates available.

Cumulus Villa photo

Cumulus Villa

Lorient, St. Barts

Near Beach | Pool

6 6

Details

Antilles Pearl is a super luxurious beachfront villa in one of the best spots on Anguilla. There's a 50-foot skywalk ... 5 BR rate available.
Has specials.

Antilles Pearl is located on Shoal Bay Beach

Antilles Pearl Villa at Altamer

Anguilla

Beachfront | Pool | AC

6 6

Details

Sandyline Villa is one of the most luxurious estates on St. Martin. The exterior amenities are endless, and the villa’... 3, 4 & 5 BR rates available.
Has specials.

Plenty of loungers surround the swimming pool

Sandyline Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

6 7

Details

The name says it all at Go Easy Villa. This villa enjoys water and island views, a gourmet kitchen, numerous ... Has specials.

Go Easy Villa at Sugar Hill

Go Easy Villa at Sugar Hill

Barbados

Pool

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

Vistamar Villa

Barbados

Pool

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

Jable

Petite Saline, St. Barts

Pool

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

Panache Villa

Rendezvous Bay, St. John

Pool

6 7

Details

The impression one gets when walking into this villa, is simply elegant Caribbean. It features a clean white interior with ... 3, 4 & 5 BR rates available.
Has specials.

Amazing views of the harbor from Paradiso Villa

Paradiso Villa

Oyster Pond (Dutch side), St. Martin

Pool

6 6+

Details

There’s something for everyone at Sandalwood House. You can enjoy a round of golf and a romantic dinner for ... 3 & 4 BR rates available.
Has specials.

Twilight on the patio at Sandalwood Cottage

Sandalwood House

Barbados

Near Beach | Pool

6 7

Details

SPECIAL RESERVE COLLECTION includes a Private Chef for 3 meals/day, Preferred access to Beach Club chaise lounges, VIP arrivals service, ... 3 BR rate available.

Silver Rainbow Villa looks out into Petit Cul De Sac

Silver Rainbow Villa

Petit Cul de Sac, St. Barts

Near Beach | Pool

6 6

Details

This newer 3-story beachfront villa offers ocean views and sunsets that will make your stay at Bougainvillea a lifetime memory. ... 4 BR rate available.

The pool at Bougainvillea Villa has beautiful views of the Caribbean

Bougainvillea Villa

Dawn Beach (Dutch side), St. Martin

Pool

6 6

Details

Tamarind Villa is located in Providencials' best neighborhood, right on Grace Bay Beach. The views from both inside and outside ...

Tamarind Villa is located on the shores of Grace Bay Beach

Tamarind Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

6 6+

Details

With lots of space indoors and out, a great beachfront location, and easy access to water sports and entertainment, Serenity ...

Serenity House Villa is located directly on Grace Bay Beach

Serenity House

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

6 6+

Details

Eclipse Villa is perfect for large families or couples traveling together. The villa looks right out over the ocean, so ... 3, 4 & 5 BR rates available.

Eclipse Villa is located on the hillside in Vitet a few minutes away from Lorient Beach

Eclipse Villa

Camaruche, St. Barts

Pool

6 6

Details

Royal Belize is an exclusive private island rental with seclusion, luxury, and full service. There are three villas and a ... 5 BR rate available.

Royal Belize Private Island

Royal Belize - Private Island

Belize

Beachfront | AC

6 6+

Details

Casa Grande is totally relaxing. Its super open, has great views, and is steps from a private part of Grace ...

Casa Grande is located on a beautiful stretch of Grace Bay Beach

Casa Grande Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

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

Bon Temps Villa

Pointe Milou, St. Barts

Pool

6 6

Details

Le Manoir de Lurin Villa is larger than your usual villa! This six-bedroom rental offers tons of exterior space for ... 5 BR rate available.

Le Manoir de Lurin Villa photo

Le Manoir de Lurin Villa

Lurin, St. Barts

Pool

6 6

Details

Get a gorgeous view of Dawn Beach and great access to Phillipsburg in one package at Dawn Beach Villa. Just ... 2, 3, 4 & 5 BR rates available.
Has specials.

Beautiful views of the Caribbean form the pool at Dawn Beach Villa

Dawn Beach Villa

Dawn Beach (Dutch side), St. Martin

Near Beach

6 6

Details

Whether you are vacationing with others or having a quiet family trip, Amberley House is ready to meet your needs. ... 4 BR rate available.
Has specials.

Poolside view of Amberley House

Amberley House

Barbados

Near Beach | Pool

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

Sun Salutations Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

6 5+

Details

Finding the perfect mix of oceanfront and privacy for a larger family can be difficult at times, but Coconut Villa ...

Coconut Beach villa is right on the Beach near Rum Point

Coconut Beach Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

6 4

Details

Facing the impressive coast of the Caribbean Sea in Rum Point, Moon Kai Villa has six bedrooms that provide you ... Has specials.

Moon Kai is located on the coast of the Caribbean Sea in Rum Point

Moon Kai Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

6 6

Details

Villa Susanna is a tropical paradise secluded above Marigot Bay. It's wooden exterior and lush gardens contrasts beautifully with the ... 3 BR rate available.

Aerial view of Villa Susanna

Villa Susanna

Marigot Bay, St. Lucia

Near Beach | Pool

6 7

Details

Villa Colibri has a sleek and modern design that belongs on a magazine cover. There's a swimming pool with different ... 2, 3, 4 & 5 BR rates available.
Has specials.

You'll find contemporary class at Colibri Villa.

Colibri Villa

Anguilla

Pool

6 6

Details

This villa offers guests luxury, starting with its view of the 13th hole of the Royal Westmoreland Resort's golf course. ... 4 & 5 BR rates available.
Has specials.

Beautiful pool and outdoor area at Westerings

Westerings

Barbados

Pool

6 6

Details

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

Clairmont Overlook is located right on Salt River

Clairmont Overlook

St. Croix, USVI

Pool

6 6+

Details

Jolly Harbour's Palm Point Villa is THE retreat for wedding parties, family reunions, or any group of 16 who are ready ...

Palm Point Villa is located right on Jolly Harbour

Palm Point Villa

Jolly Harbour, Antigua

Beachfront | Pool | AC

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 is located on the beautiful beach of Plum Bay in the Terres Basses gated community

C'est La Vie Villa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

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

Mandalay Villa

Long Bay, Turks and Caicos

Beachfront | Pool | AC

6 7+

Details

This villa has a great open floor plan and sits on picturesque Cayman Kai. The high ceilings, minimal design, and ...

Ocean Kai sits directly on the beach near Rum Point

Ocean Kai

Grand Cayman, Cayman

Beachfront | Pool | AC

6 5

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

Coco Rock Villa

Petit Cul de Sac, St. Barts

Pool

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.

Hidden Cove is located in Cayman Kai neighborhood

Hidden Cove Villa

Grand Cayman, Cayman

Near Beach | Pool

6 5

Details

Villa Oceania has a beautiful pool and shaded back patio

Villa Oceania

Cap Cana, Dominican Republic

Pool

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

Sirena

Punta Cana, Dominican Republic

Near Beach | Pool

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

Point of View Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

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

Maison Blanc Bleu Villa

Lurin, St. Barts

Pool

6 6

Details

I love Alta Bella because it's so peaceful. It's perfect for kids and family gatherings at a really great value. ...

Alta Bella Villa sits on a inlet just on chalk Sound

Alta Bella

Chalk Sound, Turks and Caicos

Near Beach | Pool

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 ...

A private cabana sits beachfront at Love Pumpkin

Love Pumpkin at COMO Parrot Cay

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

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

Tip of the Tail

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

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

Beach Enclave Ocean View Villas North Shore

North Shore, Turks and Caicos

Beachfront | Pool | AC

5 5

Details

Crystal Waters, formerly known as Mudslide, is the perfect villa for your next family vacation. Every room is oversized, and ...

Crystal Waters Villa sits beach front near the popular Water Cay and Kaibo Yacht Club

Crystal Waters

Grand Cayman, Cayman

Beachfront | Pool | AC

5 4

Details

This spacious, historic estate is ideal for family reunions. The large patio area and infinity pool are great for holiday ...

Langarra Estate photo

Langarra Estate

St. Thomas, USVI

Pool

5 5+

Details

Magens Hideaway is located on the Peterborg Peninsula overlooking Great Hans Lollick and the BVI's

Magens Hideaway

St. Thomas, USVI

Pool

5 4+

Details

Hesperides is one of a kind. The location couldn't be better either, because it's close to Sapodilla Bay and Las ...

Hesperides House has amazing uninterrupted ocean views

Hesperides House

Taylor Bay/Sapodilla Bay, Turks and Caicos

Pool

5 5

Details

Starfish Villa is one of the more vibrant villas in the Punta Cana Resort. The villa itself is well-equipped, but ...

Starfish Villa is located in Punta Cana on the golf course

Starfish

Punta Cana, Dominican Republic

Pool

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

The Beach House

St. Thomas, USVI

Beachfront | AC

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

Coral Pavilion

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

5 5

Details

Hilltime is perfect for any family or couples who want to relax by the sea with minimal fuss. This villa ...

Hilltime Villa is located on the north coast of Cayman in Rum Point

Hilltime

Grand Cayman, Cayman

Beachfront | Pool | AC

5 4

Details

White Cottage is a great vacation rental for anyone who loves the ocean and privacy. It's in a quiet region ... Has specials.

White Cottage is a great beachfront villa

White Cottage

Grand Cayman, Cayman

Beachfront | Pool | AC

5 3

Details

Great Bluff Estate is perfect for groups who want privacy and space. It's fully gated, and sits on the quiet, ... Has specials.

Great Bluff Estates sits along the beautiful northern coast of Grand cayman

Great Bluff Estates

Grand Cayman, Cayman

Beachfront | Pool | AC

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

Alinna

Chalk Sound, Turks and Caicos

Pool

5 6+

Details

Second Chances is a great choice for a relaxed getaway. It's 200 meters from Grace Bay, so you can go to ...

Second Chances Villa has plenty of outdoor space for relaxing and entertaining

Second Chances

Leeward, Turks and Caicos

Near Beach | Pool

5 6

Details

The Five Bedroom Beach Level residences are perfect for families or four couples to share. They're right on Grace Bay ... Has specials.

The Grace Bay Club Estate

Grace Bay Club Estate Five Bedroom Beach Level Pool Residence

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

5 4+

Details

Casa de la Playa is perfect for two families who want to vacation on St. Martin's glamorous west coast. It ... 3 & 4 BR rates available.
Has specials.

Casa de la Playa Villa is located on Baie Longue in Terres Basses

Casa de la Playa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

5 5

Details

This five-bedroom beachfront resort villa is absolutely gorgeous. It's on Long Bay, which is the quieter, windier sister to Grace ... Has specials.

Beach Enclave Beach Front Villas on Long Bay

Beach Enclave Beach Front Villa at Long Bay

Long Bay, Turks and Caicos

Beachfront | Pool | AC

5 5

Details

Nirvana is ideal for couples who want to vacation on the beach in style. The pool isn't massive, but who ... Has specials.

Nirvana's pool deck and lounges

Nirvana

Barbados

Beachfront | Pool | AC

5 5

Details

Lime Tree is a cool villa to stay in because it combines Mediterranean architecture with cushy amenities. The master bedroom ...

Lime Tree Villa sits on a tropical hillside in the Peter Bay area

Lime Tree at Peter Bay

Peter Bay, St. John

Pool

5 4+

Details

La Case Créole is a great family vacation villa. It has six bedrooms spread across two levels, and every ... 3 & 4 BR rates available.

La Case Créole is located on a hilltop above St. Jean Bay

La Case Créole

Saint Jean, St. Barts

Pool

5 5

Details

Mirabelle is ideal if you want the beauty of Turks and Caicos without the crowds of Grace Bay. Sapodilla Bay ...

Mirabelle sits on a beautiful stretch of Sapodilla Bay Beach

Mirabelle

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

5 5+

Details

This luxury rental sits right on Paynes Bay and is the only unit in the complex to have a private ... 4 BR rate available.
Has specials.

The Villa at the St. James is located beachfront on Paynes Bay Beach

The Villa at the St. James

Barbados

Beachfront | Pool | AC

5 5

Details

Three Dolphins isn't only gorgeous inside, it also has amazing sea views with St. Martin in the distance. The villa ...

Three Dolphins sits in a beautiful location with great ocean views

Three Dolphins

Anguilla

Near Beach | Pool

5 4+

Details

This waterfront villa would be great for a few couples or a large family. There's two queen suites upstairs and ...

Water's Edge Villa is located on Blowing Point

Water's Edge

Anguilla

Near Beach | Pool

5 5

Details

Windfall is an amazing family vacation destination for any age group. It has three king suites, one queen, and two ... Has specials.

Windfall Villa's open-air pool with retractable canopy

Windfall

Barbados

Pool

5 6

Details

Casa Oasis is the place to go for a family vacation in Costa Rica. The two double suites, ping pong, ...

Casa Oasis Villa is located above Los Sueños popular Eco Golf Course

Casa Oasis

Costa Rica

Pool

5 5

Details

Casa Puesta del Sol manages to be extremely chic and elegant without feeling stuffy or uncomfortable. It has high ceilings, ...

Casa Puestra del Sol Villa is located the neighborhood of Vista Tres Bahias in Los Suenos

Casa Puesta del Sol

Costa Rica

Pool

5 5

Details

Casa Pacifica is ideal for four couples or adult families. Four of the five bedrooms have king beds, and the ...

Casa Pacifica is located in the hills of the Los Suenos Resort

Casa Pacífica

Costa Rica

Pool

5 5

Details

Seagrace is a bright, modern villa right on the water. It has gorgeous views, tons of natural light, and a ...

Seagrace Villa is located on the Ailla Canal in the gated community of Leeward

Seagrace

Leeward, Turks and Caicos

Pool

5 4

Details

Abita Kai is a great choice for a multi-generational family vacation. With three bedrooms spread across two levels of the ... Has specials.

Abita Kai is located on a beautiful stretch of white sand beach in Cayman Kai

Abita Kai

Grand Cayman, Cayman

Beachfront | Pool | AC

5 5

Details

Westland Heights 9 is a chic choice for your next Barbados vacation. It's on the west coast, which is one of ... Has specials.

Westland Heights 9 is located in a community on the west coast

Westland Heights 9

Barbados

Pool

5 5

Details

Vision Beach is a gorgeous, luxurious villa on Turks and Caicos’s most envied location: Grace Bay Beach. Not only ...

Vision Beach Villa is located directly on Grace Bay Beach

Vision Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

5 5+

Details

Seascape is the perfect place for five couples to experience the best part of Turks and Caicos. This chic five-bedroom ... Has specials.

Seascape Villa is located on a beautiful stretch of Grace Bay Beach

Seascape

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

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

Residence 3

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

5 5+

Details

Bajan Heights is a luxurious villa with five-star amenities and daily housekeeping. The villa is in a gated community near ... 4 BR rate available.
Has specials.

Bajan Heights is located in Royal Westmoreland

Bajan Heights

Barbados

Pool

5 5

Details

Looking for luxury? Crystal Waters has it in spades. This beachfront villa has an ideal location within walking distance of ...

Crystal Waters Villa is located just across the street from the Kaibo Yacht Club

Crystal Waters - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

5 4

Details

Blue Water is the place to be for large groups. There are five bedrooms that can all accommodate couples, although ...

Blue Water Villa is located on Rum Point Drive on a beautiful stretch of white sand beach

Blue Water - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

5 4+

Details

Great Bluff Estates is a fun, gorgeous place to be on Grand Cayman’s beachfront. There are several levels to ... Has specials.

Great Bluff Estates sits along the beautiful northern coast of Grand cayman

Great Bluff Estates - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

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

Pease Bay House - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

5 5+

Details

Two Rainbows is a fantastic choice for your next family vacation if you want total relaxation. This villa is on ...

Two Rainbows is located within walking distance to the Rum Point Club

Two Rainbows - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

5 4+

Details

Tolumnia is a beautiful, spacious villa for group vacations. There’s tons of lounging space outside around the pool and ... 2, 3 & 4 BR rates available.

Tolumnia is located on an acre of national park overlooking the bay of Willoughby

Tolumnia

English Harbour, Antigua

Pool

5 4+

Details

Rotunda is a great, family-friendly villa rental with gorgeous views and privacy. It’s elevated above Peter and Trunk Bay, ...

Rotunda Villa is located above Peter Bay and Trunk Bay

Rotunda

Peter Bay, St. John

Pool

5 5+

Details

If you want the resort experience without the crowds, Beach Enclave at Grace Bay is for you. Each villa enjoys ... Has specials.

Beach Enclave at Grace Bay

Beach Enclave Beach Front at Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

5 4+

Details

Baltazar is a bohemian haven. There are tons of natural elements incorporated into the decor, and every room has a ... 3 & 4 BR rates available.
Has specials.

Villa Baltazar is located on St. Martin’s northern coastline and overlooking the island of Pinel

Baltazar

Cul de Sac (French Side), St. Martin

5 5

Details

Moonshadow combines privacy and luxury at the ocean’s edge. This villa has the most gorgeous view of the ocean, ...

Moonshadow Villa is located on the tip of Sapodilla Bay

Moonshadow

Chalk Sound, Turks and Caicos

Near Beach | Pool

5 4

Details

This five-bedroom villa is a great choice for travelers who want convenience, space, and luxury. It’s a couple minutes ... Has specials.

Beach Enclave 5 bedroom Ocean View at Grace Bay

Beach Enclave 5 Bedroom Ocean View at Grace Bay

Grace Bay, Turks and Caicos

Near Beach | Pool

5 5+

Details

Etoile Brillante is the place to be for gorgeous ocean and sunset views just outside of Gustavia’s city center. ... 3 & 4 BR rates available.

Etoile Brillante Villa with amazing views

Etoile Brillante

Lurin, St. Barts

Pool

5 5+

Details

Only You is a totally gorgeous villa with a huge sundeck, two generously sized pools, and really modern interiors. There's ...

Only You Villa is located in the gated Domaine Du Levant

Only You

Petit Cul de Sac, St. Barts

Near Beach | Pool

5 5

Details

Raku has everything a big family could want for a multi-generation family vacation. There's a guest house where the grandparents ...

Raku is located on the southern most end of Virgin Gorda on Crooks Bay

Raku

Virgin Gorda, BVI, British Virgin Islands

Pool

5 5+

Details

Embrace offers endless luxury, super modern amenities, and an unbelievable location near St. Barts' best activities. A full staff caters ...

Embrace Villa is located on a hillside in Gustavia

Embrace

Gustavia, St. Barts

Pool

5 5

Details

Vacationing will be as much fun for your kids as it is for you at Sand Castle Villa. It has ... 3 BR rate available.
Has specials.

Sand Castle Villa is located on the North Shore of Anguilla with views of the Atlantic Ocean

Sand Castle Villa

Anguilla

Beachfront | Pool | AC

5 5+

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 on a hillside beside Magen’s Bay

Pallina Villa

St. Thomas, USVI

Pool

5 3+

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

Casa Bougainvillea Villa

St. Thomas, USVI

Beachfront | Pool | AC

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 is located in Estate Mafolie with views of Charlotte Amalie's harbor

Silk Cotton Villa

St. Thomas, USVI

Pool

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

The Carib House

Antigua

Near Beach | Pool

5 4

Details

This beachfront property is made for relaxation. The patio area around the pool is surrounded by cushioned loungers, so you ... 2, 3 & 4 BR rates available.
Has specials.

Caribbean Wind Villa is located on the beach at Mahoe Bay

Caribbean Wind Villa

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

5 5

Details

Looking for luxury in St. Martin? Pamplemousse is a great choice - it’s elegant, spacious, and convenient to a ... 3 & 4 BR rates available.
Has specials.

Pamplemousse is located in Terres Basses on a cliffside with views looking toward the Caribbean

Pamplemousse Villa

Terres Basses (French side), St. Martin

Pool

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

Casa Cervo Villa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

5 5

Details

If you want to be pampered, come to Sea Villa. In addition to its stunning common areas, you have access ...

Sea Villa is situated facing the beach with amazing unobscured ocean views

Sea Villa at Long Bay Villas

Anguilla

Beachfront | Pool | AC

5 5+

Details

At Long Bay Villas, you can expect to be relaxed and pampered. There's a full staff, water sports, four king ...

The luxurious Sand Villa at Long Bay

Sand Villa at Long Bay Villas

Anguilla

Beachfront | Pool | AC

5 4+

Details

Dene Court is a five-bedroom, six-bathroom villa within Barbados' famous Sandy Lane Estate. The full staff will take care of ... 3 & 4 BR rates available.
Has specials.

Dene Court Villa is located in the prestigious Sandy Lane on the Old Nine Golf Course

Dene Court - Sandy Lane

Barbados

Pool

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

Kismet

Chocolate Hole, St. John

Pool

5 6+

Details

Comfort is key at Serena Villa. You can relax outside in the large pool with ocean views, the furnished gazebo, ... Has specials.

Serena Villa is located just above Baie Rouge Beach

Serena Villa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

5 5+

Details

If you want to be amongst nature, there's no place like Brigand Hill. Surrounded by 500 acres of a former plantation, ...

Brigand Hill Villa has a very private location with a relaxing pool

Brigand Hill

Anse La Raye, St. Lucia

Near Beach | Pool

5 4

Details

Rent the Two Palms property as a five-bedroom combo, or divide the units between groups of six and four. This ...

Beach Palm

Twin Palms Villas

Anguilla

Near Beach | Pool

5 5+

Details

Aquamare Villa 1 enjoys beachfront access, a tranquil location, and gorgeous views. Guests can snorkel, beach comb, kayak, paddle board, and ...

Aquamare Villas are located on Mahoe Bay Beach

Aquamare Villa 1

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

5 6

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 property

Alizee Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

5 5

Details

Melissa Villa is an excellent choice for any traveler who wants privacy and luxury all at once. You'll be steps ... Has specials.

Melissa Villa is on the West Coast of St. James in a gated community with a short walk to the beach

Melissa Villa

Barbados

Near Beach | Pool

5 5

Details

On the outside, Carlota Villa looks like a castle. Inside, you'll marvel at the one-of-a-kind furnishings, such as the dining ...

Carlota Villa is located on a hillside overlooking Peter Bay

Carlota Villa

Peter Bay, St. John

Pool

5 6+

Details

If you like vibrant colors and great views, you'll love Villa Amarilla. Both the interiors and exteriors are done in ... 3 & 4 BR rates available.

Beautiful Anguillan sunset from the back porch at Amarilla

Villa Amarilla

Anguilla

Near Beach | Pool

5 5+

Details

Tesori has nearly 7,000 square feet of indoor and outdoor living space, with ocean views and modern amenities throughout. The villa ... 1, 2, 3 & 4 BR rates available.

Tesori Villa has a beautiful pool and entertainment balcony

Tesori Villa

Rendezvous Bay, St. John

Pool

5 5+

Details

Java Bay will put you in the mood for meditation and introspection. It's a place where you can connect with ... 4 BR rate available.
Has specials.

Java Bay is located in Calijanda in Westmoreland and is less than two miles from the beach

Java Bay

Barbados

Pool

5 5

Details

Decaj Villa is a great retreat for a family with young children, or two families for that matter. You'll love ... 3 BR rate available.

Decaj Villa is located in Cap Estate with views of the ocean in the distance

Decaj Villa

Cap Estate, St. Lucia

Pool

5 4+

Details

You'll think you're in an Asian palace when you arrive at Golden Pavilion. You can relax on the covered patio ... 4 BR rate available.

Golden Pavilion photo

Golden Pavilion

Tortola, BVI, British Virgin Islands

Pool

5 5+

Details

Whether you're headed to Barbados for a family vacation, honeymoon, or a getaway with friends, Casuarina House is a great ... 4 BR rate available.
Has specials.

Casuarina Villa has a pool right on the golf course

Casuarina House

Barbados

Pool

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

Pease Bay House

Grand Cayman, Cayman

Beachfront | Pool | AC

5 5+

Details

Blue Diamond's beachfront luxury leaves nothing out. There's a sound system, WiFi, and air-conditioning throughout the villa, a bar, a ...

Blue Diamond Villa at Altamer is set on a prestigious location on Shoal Bay

Blue Diamond Villa at Altamer

Anguilla

Beachfront | Pool | AC

5 7

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

The Beach House

St. Thomas, USVI

Beachfront | AC

5 3+

Details

If you want true pampering, come to Sky Villa. Things like daily housekeeping service are par for the course. Speaking ...

Sky Villa is the most private of the Long Bay Villas located just off the beach

Sky Villa at Long Bay Beach Villas

Anguilla

Near Beach | Pool

5 4+

Details

Take a path down to the beach from Solitude House and enjoy the ease of access to snorkeling and the ... 1, 2, 3 & 4 BR rates available.

Solitude House is situated above the calm waters of Solitude Bay

Solitude House

St. Croix, USVI

Near Beach | Pool

5 4+

Details

Champagne Shores is the perfect villa rental for design lovers. The sea-facing wall is made up of huge panes of ...

Champagne Shores villa sits on a secluded beach near Pelican Bay

Champagne Shores

Anguilla

Near Beach | Pool

5 5+

Details

Whispering Winds is a great choice for a big family vacation. There are two suites on the main level, two ... 1, 2, 3 & 4 BR rates available.

Whispering Winds Villa is located on St. Croix’s east end

Whispering Winds Villa

St. Croix, USVI

Beachfront | Pool | AC

5 4

Details

Cinnamon Ridge emphasizes St. John’s natural beauty and serenity through tropical gardens, scenic views, and an expansive outdoor space. ...

Cinnamon Ridge Villa is located on a hillside above Cinnamon Bay

Cinnamon Ridge Villa

Catherineberg, St. John

Pool

5 5

Details

Kalorama Villa is fabulously unique! This artsy villa mixes contemporary style with such items as the island's traditional, native stone. ... 3 & 4 BR rates available.

Kalorama Villa is located in Virgin Grand Estates

Kalorama Villa

Virgin Grand Estates, St. John

Pool

5 4+

Details

If you have ever dreamed about the perfect family beach vacation or getaway for several couples, St. Bernard's Hill House ... Has specials.

St. Bernard's Hill House sit on a tropical hillside overlooking Belmont

St. Bernard's Hill House

Tortola, BVI, British Virgin Islands

Pool

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

Fushi Villa

Grenada

Pool

5 5

Details

You probably won't be able to tear yourself away from LaVida long enough to take advantage of the nearby shopping ...

La Vida Villa is located on a hillside overlooking Nail Bay

La Vida Villa

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

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, 3 & 4 BR rates available.

Bellevue Villa is located

Bellevue Villa

Marigot, St. Barts

Pool

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 is located in the gated community of La Cana Resort & Club

Villa Arrecife 25 at Tortuga Bay

Punta Cana, Dominican Republic

Pool

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

Palm Beach Villa

Lorient, St. Barts

Near Beach

5 5

Details

Eternity Villa will make you wish you could stay there forever! Located just minutes from restaurants and stores, the villa ...

Eternity villa is tucked into at tropical hillside above Flamands

Eternity Villa

Flamands, St. Barts

Pool

5 5

Details

This modern, minimalist villa has gorgeous design, gorgeous views, and gorgeous amenities! Fleur De Mer is all about luxury and ...

Fleur De Mer Villa is located in Colombier with amazing views

Fleur De Mer Villa

Colombier, St. Barts

Pool

5 5

Details

Lantano Villa is so comfortable and scenic! Its the type of home that makes you want to take your shoes ...

Lantano Villa is located in Peter Bay Estate overlooking the Caribbean and the north shore

Lantano Villa

Peter Bay, St. John

Pool

5 5+

Details

Set on the cliffs in Terres Basses, Esprit de la Mer Villa is the ideal choice for large families or ... 4 BR rate available.
Has specials.

Esprit de la Mer is located on a clifftop with Caribbean vies just off Baie aux Cayes

Esprit de la Mer Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

5 5+

Details

Paprika Villa offers stately elegance on the Turks and Caicos beachfront. With five spacious bedrooms, a dining room for ten, ...

Beach Villa Paprika is located on Grace Bay Beach

Paprika Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

5 5+

Details

Tamarind is perfect for two families to share, because each level has its own living area and balcony or terrace. ... 2 & 4 BR rates available.

Tamarind Villa is located in Island Harbor just minutes from Shoal Bay East

Tamarind Villa

Anguilla

Pool

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 ... Has specials.

Amazing Grace Villa photo

Amazing Grace Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

5 5+

Details

Beaches Edge villa has a smart design that maximizes the ocean views. Of course there's a pool, daily maid service, ...

Lounge by the pool and enjoy amazing ocean views at Beaches Edge East Villa

Beaches Edge

Anguilla

Near Beach | Pool

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

La Danse Des Etoiles Villa

Pointe Milou, St. Barts

Pool

5 6

Details

At Castaway villa, you’ll find distinctive features few other holiday rentals can offer, including handmade furniture, four beachfront master ...

Castaway Villa is located beachfront on Thompson Cove

Castaway Villa

North Shore, Turks and Caicos

Beachfront | Pool | AC

5 5

Details

Clear aquamarine water packed with beautiful marine animals. A secluded beach with calm water just waiting for you. It is ...

Aerial view of Coral Kai Villa on Rum Point Grand Cayman

Coral Kai

Grand Cayman, Cayman

Beachfront | Pool | AC

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

Tradewinds Villa

Barbados

Pool

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

La Petite Sereine Villa

Pointe Milou, St. Barts

Pool

5 6

Details

Cayman Sands is a great family vacation villa for peace and quiet. There are two children's bedrooms, two master bedrooms, ... Has specials.

Cayman Sands is located in Old Man Bay along a beautiful stretch of white sandy beach

Cayman Sands

Grand Cayman, Cayman

Beachfront | Pool | AC

5 5

Details

Mango Manor is a great choice for your next family vacation or celebration. It's super private but still within easy ...

Mango Manor

Mango Manor

Tortola, BVI, British Virgin Islands

Pool

5 5

Details

What is there not to love about Kai Conut Villa. This ocean front property is open and airy with five ...

The pool at Kai Conut is just steps away from the beach

Kai Conut Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

5 3

Details

This is the perfect location to bring the family together. The house is spacious and inviting. There are five bedrooms ... Has specials.

Reef Romance Villa has an ideal oceanfront location on Rum Point

Reef Romance Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

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

Still Fathoms

Barbados

Beachfront | Pool | AC

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

Windward - Sandy Lane

Barbados

Pool

5 5

Details

Love the beach, but craving privacy? Blue Water is an excellent choice. The big draws to Blue Water are its ...

Blue Water has a great beach front location in Rum Point

Blue Water

Grand Cayman, Cayman

Beachfront | Pool | AC

5 4+

Details

Blue Palm Villa is great for any group of travelers, family or friends. I love how spread out the bedrooms ... 3 & 4 BR rates available.
Has specials.

Blue Palm Villa is surrounded by lush tropical greenery

Blue Palm Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

5 6+

Details

Villa Isla is not only exquisite, it feels like heaven on earth. Large palm trees line the entrance, and the ...

Amazing infinity edged pool on Long Bay Beach at Villa Isla

Villa Isla

Long Bay, Turks and Caicos

Beachfront | Pool | AC

5 5+

Details

Outrigger House is great for groups or families that want to have tons of space under one roof. There are ...

Outrigger Villa photo

Outrigger Villa

St. Thomas, USVI

Pool

5 5+

Details

Villa Atlantis has so many leisure areas (both inside and out!) that you can enjoy a new spot every day. ... 2 BR rate available.

Vill Atlantis is located on a hillside in Cap Estate

Villa Atlantis

Cap Estate, St. Lucia

Pool

5 4+

Details

The layout of Reefside ensures that everyone in your party has beautiful rooms, private bathrooms, and complete privacy. The common ... 1, 2, 3 & 4 BR rates available.

Views into Chocolate Hole Bay from Reefside Villa

Reefside Villa

Chocolate Hole, St. John

Near Beach | Pool

5 5+

Details

Queens Fort 10 is perfect for any group who wants to upgrade their Barbados vacation. The property is within short walking ... Has specials.

Queens Fort #10 is located in St.James on the West coast close to St. James Beach

Queens Fort # 10

Barbados

Near Beach | Pool

5 5+

Details

Sky Blue has incredible views of the water and a spacious, open floor plan that's perfect for a relaxing getaway. ... 2, 3 & 4 BR rates available.
Has specials.

Relax by the pool and enjoy the ocean view at Sky Blue

Sky Blue

Dawn Beach (Dutch side), St. Martin

Near Beach | Pool

5 5+

Details

When I think of Firefly Villa, two words come to mind: grand and spacious. The decor is so chic, it ... 4 BR rate available.
Has specials.

View from Old Trees#6 Firefly

Old Trees #6, Firefly Villa

Barbados

Beachfront | Pool | AC

5 5+

Details

Galley Bay Heights #014 is a cozy, nearly beachfront villa that would be great to share with three other couples. There's ... 2 BR rate available.

Aerial view of Galley Bay Heights Villa #104 and the beautiful beachfront

Galley Bay Heights Villa- #014

Galley Bay, Antigua

Near Beach | Pool

5 4

Details

Viento has all the space and privacy you want in a large villa, especially with a detached honeymoon suite–it’...

Viento Villa photo

Viento Villa

St. Thomas, USVI

Pool

5 5+

Details

Mermaid Falls Villa is a beautiful home with even more beautiful views. The ocean stretches as far as the eye ...

Aerial view of the villa

Mermaid Falls Villa

Peter Bay, St. John

Pool

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 sits on a hillside at the divide between Long Bay and the Sir Francis Drake Channel

Ridgemont House

Tortola, BVI, British Virgin Islands

Pool

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

Turtle Villa

Mont Jean, St. Barts

Pool

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

BOM Villa

Saint Jean, St. Barts

Beachfront | Pool | AC

5 5

Details

This villa is great for a family. Most of the bedrooms are upstairs, and there's terraces on both levels so ... 4 BR rate available.

Saving Grace Villa is located on the far northeast end of Grace Bay

Saving Grace Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

5 3

Details

The sights both inside and out are unbelievable here. Take in the waters of Long Bay Beach from anywhere in ...

Aguaribay Villa is located on a beautiful stretch of Long Bay Beach

Aguaribay Villa

Long Bay, Turks and Caicos

Beachfront | Pool | AC

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

Sea Grape Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

5 4

Details

Villa Corales 18 is located in Punta Cana with a private beach

Villa Corales 18

Punta Cana, Dominican Republic

Beachfront | Pool | AC

5 5+

Details

This villa's outdoor space almost reminds me of a James Bond movie. The open view is sure to induce heavy ... 2, 3 & 4 BR rates available.

Castle Rock Villa photo

Castle Rock Villa

Camaruche, St. Barts

Pool

5 5

Details

This villa is amazing for entertaining family and friends alike. There are three king suites and two queen suites, so ... 4 BR rate available.
Has specials.

Amandara Villa is located on a cliff side in Terres Basses

Amandara Villa

Terres Basses (French side), St. Martin

Pool

5 5

Details

Sandy Beaches is one of the most economical rentals for a large group, especially when you consider just how close ... 3 BR rate available.

Sandy Beaches Villa is located directly on Long Bay Beach

Sandy Beaches Villa

Long Bay, Turks and Caicos

Beachfront | Pool | AC

5 5

Details

This villa is great if you want privacy, modern amenities, and don't mind being a short drive from the beach. ...

Calypso Delight Villa overlooks Magen's Bay Beach

Calypso Delight

St. Thomas, USVI

Pool

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

Ginger

Petite Saline, St. Barts

Pool

5 5

Details

Aquamare Villa 2 is a perfect place to soak up the island’s adventure. This beachfront villa has an ideal location ...

Aquamare Villas are located on Mahoe Bay Beach

Aquamare Villa 2

Virgin Gorda, BVI, British Virgin Islands

Beachfront | AC

5 6

Details

Aquamare is the ideal setting for beachfront vacations. There are three villas in total, each with identical layouts and amenities. ...

Aquamare is Villas are located on Mahoe Bay Beach

Aquamare Villa 3

Virgin Gorda, BVI, British Virgin Islands

Beachfront | AC

5 6

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.
Has specials.

Beach Enclave Beachfront Villas offer amazing ocean views

Beach Enclave Beach Front Villas North Shore

North Shore, Turks and Caicos

Beachfront | Pool | AC

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.

Ardisia Villa is located on Great Cruz Bay

Ardisia Villa

Great Cruz Bay, St. John

Pool

5 5+

Details

Sunset Close is very modern, beautifully decorated, extremely comfortable and well-stocked. The Silly Creek area is known for its peace ...

Perfect patio to enjoy waterfront views at Sunset Close Villa

Sunset Close

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

4 4

Details

Frangipani Villa is luxurious through and through. I love the marble countertops and sleek decor, and every feature makes you ...

Located on a stretch of white sand beach Frangipani Villa enjoys all of the resort amenities

Frangipani Villa

Anguilla

Beachfront | Pool | AC

4 4+

Details

Villa B53 at Tortuga Bay

Villa B53 at Tortuga Bay

Punta Cana, Dominican Republic

Pool

4 4+

Details

Milestone is a stunning villa that manages to strike the perfect balance between convenience and privacy. It sits on the ...

A luxurious pool just steps away from the beach at Milestone Villa

Milestone

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

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

Blue Papaya

Virgin Grand Estates, St. John

Pool

4 4

Details

SAX in St. Barts would be perfect for a couples' getaway or a family vacation. Two of the bedrooms are ... 2 & 3 BR rates available.

SAX Villa photo

SAX Villa

Saint Jean, St. Barts

Near Beach

4 4

Details

Casa Bella's Spanish architecture and gardens make it stand out. I loved lounging by the pool as breezes blew through ... Has specials.

Casa Bella photo

Casa Bella

Barbados

Near Beach | Pool

4 3

Details

Terre Azure is a dream! I'd recommend this villa for family vacations and getaways with friends, because the bedrooms are ... 2 & 3 BR rates available.
Has specials.

Terre Azure Villa is located in Terres Basses with great views of Simpson Bay

Terre Azure

Terres Basses (French side), St. Martin

Pool

4 4+

Details

Turquoise is a gorgeous, modern villa that is ideal for a family vacation. Grace Bay Beach is just steps away, ...

Aerial view of the Turquoise Villa property

Turquoise

Grace Bay, Turks and Caicos

Near Beach | Pool

4 4

Details

Etoile de Mer has an incredible location just off Taylor Bay beach. There's a wonderful restaurant easily walkable that sits ...

Etoile De Mer pool with furnished gazebo

Etoile De Mer

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

4 4

Details

Absolute Beach Villa is a great choice for travelers who want to experience island living at its fullest. It's within ...

Relax on the covered patio with beach and harbor views

Jolly Harbour #008 - Absolute Beach

Jolly Harbour, Antigua

Beachfront | Pool | AC

4 4

Details

Olympus is a modern, beachfront villa with full air-conditioning and an enviable location near Rum Point Beach. Rum Point is ...

An aerial view of Olympus Villa and the beautiful beachfront

Olympus

Grand Cayman, Cayman

Beachfront | Pool | AC

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 Club Penthouse Suite in the Villas

Grace Bay, Turks and Caicos

Beachfront | AC

4 4

Details

Villa Islander is an architect's dream. Its surrounded by greenery, has floor-to-ceiling windows in every room, and uses only the ...

Villa Islander is located just off the famous Grace Bay Beach

Villa Islander

Grace Bay, Turks and Caicos

Near Beach | Pool

4 4

Details

Imagine certainly fits my ideal vacation rental. It's right on the beach, still has privacy, and has modern interiors. There's ... Has specials.

Imagine photo

Imagine

Barbados

Beachfront | Pool | AC

4 4+

Details

Mirador is a great villa for a family or four couples who want to be as close to the beach ... Has specials.

Mirador photo

Mirador

Barbados

Beachfront | Pool | AC

4 4+

Details

This villa is great for four couples who want privacy and convenience. The exterior is multi-leveled and three of the ... 1, 2 & 3 BR rates available.

EauSea sits atop a hillside overlooking Great Cruz Bay

EauSea

Great Cruz Bay, St. John

Pool

4 4

Details

Sand Castle is the perfect choice for a beach vacation. It's open-air design brings the sea, sand and sun right ... 3 BR rate available.

Sand Castle Villa is located directly on Lorient Bay Beach

Sand Castle

Lorient, St. Barts

Beachfront | AC

4 3

Details

Since Spero sits steps away from Punta Cana's golf course, it's surrounded by perfectly manicured lawns and upscale gardens. The ...

Spero Villa sits directly on Puna Cana's beautiful Hacienda Golf Course

Spero

Punta Cana, Dominican Republic

Pool

4 4

Details

If you're traveling to Costa Rica with your friends or extended family, you'll love La Perla. There's three suites in ...

La Perla Villa is located in Altamira, just above the Marina in Los Suenos

La Perla

Costa Rica

Pool

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.

Sandcastle Beach House is located on on Limestone Bay

Sandcastle Beach House

Anguilla

Beachfront | Pool | AC

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

Albacore

Orient Bay (French side), St. Martin

Pool

4 4

Details

Coco de Mer is a gorgeous luxury villa with tons of lounging space, lots of privacy, and four king suites. ... Has specials.

Coco de Mer sits on top of the Sandy Lane Estate

Coco de Mer

Barbados

Pool

4 4+

Details

Pelican Bay would be a great choice for a multi-generational family vacation. Three bedrooms are in the main house with ... 1, 2 & 3 BR rates available.

Pelican Bay Villa has an ideal location in between Blowing Point and Pelican Bay

Pelican Bay

Anguilla

Pool

4 4+

Details

Bristol Bliss is the perfect villa for a quiet vacation with your favorite couples. It's on Turtle Tail, which is ...

The pool at Bristol Bliss sits beachside overlooking the azure waters so famous in Turks and Caicos

Bristol Bliss

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

4 4

Details

Gustavia Views is a gorgeous choice for your next family vacation. Whether you're traveling with teenagers, infants, or adults, you'll ... 2 & 3 BR rates available.

Gustavia Views Villa lives up to its name and more - also boasting a private pool

Gustavia Views

Gustavia, St. Barts

Pool

4 3

Details

Residence 2 lets you enjoy the convenience of a resort community and the comforts of home, in one villa. The villa ... Has specials.

The Residences are located directly on Grace Bay Beachfront and each have private infinity pools

Residence 2

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

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

Glacier Moreno

Oyster Pond (Dutch side), St. Martin

Pool

4 3

Details

Emeraude feels like a private resort, it’s so gorgeous. The pool deck is super luxurious, and there’s so ... 3 BR rate available.
Has specials.

Villa Emeraude is located in Indigo Bay

Emeraude

Indigo Bay (Dutch Side), St. Martin

Pool

4 4

Details

Beach House is all about location, location, location. It’s on Taylor Bay, which is one of my absolute favorites ...

The Beach House Villa is located within walking distance of Taylor Bay Beach

Beach House

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

4 4+

Details

Kai Vista is a charming beachfront villa for couples or families with older kids. It’s a short walk to ...

Kai Vista is located in Rum Point along the north coast

Kai Vista - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

4 4

Details

Olympus has it all: a beachfront location, modern design, and tons of space to lounge. Whether you want to relax ...

Olympus is located on the beach front in Rum Point

Olympus - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

4 4+

Details

Tarasand Villa is a great choice for anyone who wants to be near Rum Point and have easy access to ...

Tarasand sits on the waterfront in Cayman Kai, a short distance from Rum Point

Tarasand - Platinum

Grand Cayman, Cayman

Beachfront | AC

4 3

Details

Madison at Sandy Lane is a tranquil villa with resort amenities, golf course access, and elegant design. Whether you want ... Has specials.

Madison Villa is located on a hilltop in the Sandy Lane Estate with panoramic 180 degree views

Madison Villa at Sandy Lane

Barbados

Pool

4 4

Details

Beach Enclave takes family vacations to the next level. With endless amenities, activities for all ages, and a convenient location ... Has specials.

Beach Enclave 4 bedroom Ocean View at Grace Bay

Beach Enclave 4 bedroom Ocean View at Grace Bay

Grace Bay, Turks and Caicos

Near Beach | Pool

4 4+

Details

Looking for privacy, convenience, and tranquility? Beach Enclave Long Bay may be the perfect fit for your family. With a ... Has specials.

Beach Enclave Long Bay is located on the southeastern edge of Providenciales

Beach Enclave - 2 Bedroom Beach Front Plus 2 Bedroom Cottage at Long Bay

Long Bay, Turks and Caicos

Beachfront | Pool | AC

4 4+

Details

Hura Sea Azure puts guests right on Long Bay near several restaurants and shops. You can easily get to jet ...

Hura Sea Azure photo

Hura Sea Azure

Long Bay, Turks and Caicos

Beachfront | Pool | AC

4 4+

Details

If you’re looking for a gorgeous villa for up to four couples, Mar Azul is a great choice! Its ... 1, 2 & 3 BR rates available.

Mar Azul is located on a high ridge between Maria Bluff and Blasbalg Point

Mar Azul

Cruz Bay, St. John

Pool

4 3+

Details

Wind Chime is all about relaxation and luxury. The spaces are all designed to feel expansive and open, and every ... Has specials.

Wind Chime Villa is located on the coastal community of Turtle Tail

Wind Chime

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

4 4+

Details

Turks and Caicos is well known for its beautiful beaches, and Five Turtles Villa gives you direct access to one ...

Five Turtles Villa is just steps away from Taylor Bay Beach

Five Turtles Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

4 3+

Details

A stay at Mille Fleurs is undeniably relaxing. This Terres Basses beauty has chic, elegant design, spacious common areas, and ... 1, 2 & 3 BR rates available.
Has specials.

Mille Fleurs Villa is located in Terres Basses and overlooks Plum Bay Beach

Mille Fleurs Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

4 4+

Details

Hakuna Matata is a wonderful, spacious home surrounded by flowers, palm trees, and tropical landscaping. The owners have stayed true ... 2 BR rate available.

Hakuna Matata is located in the Catherineberg Estate overlooking Cinnamon Bay

Hakuna Matata

Catherineberg, St. John

Pool

4 5+

Details

Beach Dreams is great for beach lovers and snorkelers. The beach is a few steps away from the pool, with ... 2 BR rate available.

Wonderful beach just steps away from the pool at Beach Dreams Villa

Beach Dreams Villa

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

4 4+

Details

Alexambre has an amazing location in Jardin d'Orient, a gated community that overlooks Orient Bay Beach. This villa is a ...

Alexambre is located in Jardin d'Orient overlooking Orient Bay in the distance

Alexambre

Orient Bay (French side), St. Martin

Pool

4 2

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

Ocean Palms Villa

Turtle Tail, Turks and Caicos

Pool

4 4

Details

Situated right on the sandy beach, Thespina is one of Barbados' most unique private villas. The home itself is very ... Has specials.

Thespina Villa is located in Holetown right on the beach nestled in tropical foliage

Thespina Villa

Barbados

Beachfront | AC

4 4

Details

Located right on the French side of St. Martin, Blue Beach Villa is a great beachfront home with tons of ... Has specials.

Blue Beach Villa is located right on Long Bay Beach

Blue Beach Villa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

4 4

Details

Bonavista Villa is located in a gated community, and is just steps away from Gibbs Beach. It has a cook, ... 3 BR rate available.
Has specials.

Tropical surroundings greet you at the pool at Bonavista Villa

Bonavista Villa

Barbados

Beachfront | Pool | AC

4 4+

Details

Evergreen is a luxurious garden villa with a full staff, spacious interiors, and modern amenities. You can watch movies or ... 3 BR rate available.
Has specials.

The stunning Evergreen property, in the prestigious Sandy Lane neighborhood, from an aerial view

Evergreen Villa

Barbados

Pool

4 5

Details

The modern villa of Ecume des Jours is just 15 minutes from the airport, but it is situated in a very ... 2 & 3 BR rates available.
Has specials.

Ecume des Jours is located on the end of Plum Bay Beach

Ecume des Jours

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

4 3

Details

Four bedrooms and four baths make Kir Royal Villa perfect for a pair of vacationing couples or a large family. ... 2 & 3 BR rates available.

Kir Royal Villa is located in St. Jean

Kir Royal Villa

Saint Jean, St. Barts

Near Beach | Pool

4 4

Details

There are many villas in Terres Basses on the French side of St. Martin that can accommodate small children, but ... 2 & 3 BR rates available.
Has specials.

Oceane Villa is located in Terres Basses on the French side of St. Martin

Oceane Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

4 4+

Details

With a thatched-roof outdoor dining area, hot tub, private infinity-edge pool, and beach access, you'll want Valentina Villa to become ...

Valentina Villa has a beautiful pool and patio and is situated just above Sapodilla Bay

Valentina Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

4 4+

Details

Southern Breeze Villa is a warm, spacious home overlooking Fish Bay and Cocolobo Point. This fully air-conditioned beautiful four-bedroom home ... 1, 2 & 3 BR rates available.

Southern Breeze is located near the Battery Gut area and has amazing Caribbean views

Southern Breeze

Rendezvous Bay, St. John

Pool

4 4

Details

With four bedrooms, spacious living areas, and an open floor plan that combines indoor and outdoor living, High Trees Villa ... Has specials.

High Trees Villa is located on Gibbs Bay Beach

High Trees Villa

Barbados

Beachfront | Pool | AC

4 4

Details

The Ushuaia Villa has four bedrooms, three queen and one with twin beds. The latter can accommodate families traveling with ... 2 BR rate available.

Ushuaia Villa has great views over Flammands

Ushuaia Villa

Flamands, St. Barts

Near Beach | Pool

4 4

Details

Abrigado Villa is perfect for vacationing couples or families looking to entertain and unwind. There's plenty of room for privacy ... 2 & 3 BR rates available.

Relax and enjoy the amazing view poolside from Abrigado Villa

Abrigado Villa

Virgin Grand Estates, St. John

Pool

4 4+

Details

If you love outdoor showers, infinity pools, and a 20-second walk to the beach, stay at Alegria Villa. You'll find ...

The beautiful pool and Caribbean views from Alegria Villa

Alegria Villa

Anguilla

Near Beach | Pool

4 4

Details

If you love design, you'll go crazy for Claridge villa. The magazine-worthy living area is all-white with exposed beams and ... 2 & 3 BR rates available.

Claridge Villa is located in the heights of Anse des Cayes overlooking St. Jean and Anse des Cayes

Claridge Villa

Anse des Cayes, St. Barts

Pool

4 4

Details

Vista Caribe is located in the exclusive Virgin Grande Estates and has breathtaking views of the Caribbean Sea, St. James, ... 1, 2 & 3 BR rates available.

Vista Caribe is located above Great Cruz Bay in the Virgin Grand Estates

Vista Caribe Villa

Virgin Grand Estates, St. John

Pool

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

Breezy Palms

Chalk Sound, Turks and Caicos

Pool

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

Great Turtle Villa

Coral Bay, St. John

Pool

4 4+

Details

One of my favorite things about Dawn Beach Villa is how close it is to all the amenities of Turtle ...

Dawn Beach Villa has a beautiful pool and a hot tub

Dawn Beach Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

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

West Bay Club - Oceanfront Luxury 4 Bedroom

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

4 4

Details

Summer Breeze Villa, also known as Villa Minou, is one of the top choices in a vacation location for families ... 2 & 3 BR rates available.

The infinity edge pool and patio deck overlook Grand-cul-de-sac

Summer Breeze

Grand Cul de Sac, St. Barts

Near Beach | Pool

4 4

Details

Located in the peaceful Turtle Tail area, Sandy Shore has direct beach access, a private onsite swimming pool, a kayak, ...

Sandy Shore Villa is located on the beach of the beautiful Taylor Bay

Sandy Shore Villa

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

4 4

Details

With four ensuite bedrooms, its own private infinity-edge swimming pool, and quick access to the sea and snorkeling, Breezy Villa ...

Breezy Villa sits directly on the ocean

Breezy Villa

Long Bay, Turks and Caicos

Pool

4 4

Details

This secluded villa is great for guests who want to relax with a good book or adventure on the water. ...

Bright Idea has great views of Chalk Sound

Bright Idea Villa

Chalk Sound, Turks and Caicos

Beachfront | Pool | AC

4 4+

Details

Guests at Sandcastle Pointe get access to jaw-dropping ocean views, modern amenities, and luxurious design. Dive into the private infinity ...

Sandcastle Pointe Villa is located just west of Shoal Bay Beach

Sandcastle Pointe at Shoal Bay

Anguilla

Pool

4 4

Details

Great Escape is a great villa rental for a family vacation or special event. Everyone will have plenty of space, ...

Great Escape Villa is located on the Rum Point end of the island with a beautiful stretch of beach

Great Escape Villa

Grand Cayman, Cayman

Near Beach | Pool

4 3

Details

Our readers agree that staying at Lime Hill Villa will provide you with the vacation memories that you want to ...

Lime Hill Villa photo

Lime Hill Villa

English Harbour, Antigua

Near Beach | Pool

4 4

Details

Because vacations are supposed to be relaxing and stress-free, it is often counterproductive to take a trip that involves renting ... 3 BR rate available.
Has specials.

Villa Mango sits on the hillside above Orient Bay

Mango Villa

Orient Bay (French side), St. Martin

Near Beach | Pool

4 4

Details

Ambiance is all that the name implies - a villa with a special atmosphere that will positively impact your entire ... 2 & 3 BR rates available.
Has specials.

Ambiance is located in the heart of Terres Basses with access to beautiful beaches nearby

Ambiance Villa

Terres Basses (French side), St. Martin

Pool

4 4+

Details

La Percha is ideal for any group of travelers. It has everything you could want in a tropical getaway- four ...

La Percha Villa is ideally located on the beautiful Taylor Bay

La Percha Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

4 4+

Details

Rapture Villa is 5000 sq. feet of Caribbean luxury and style. Elegant turtle statues float above the pool overlooking the sea ...

Rapture villa is located in Virgin Grand Estates

Rapture Villa

Virgin Grand Estates, St. John

Pool

4 4

Details

With a private pool, onsite restaurants and activities, and a beachfront location, you and your family will never want to ...

Turtle Villa is located in Jolly Harbour on the beautiful Lignum Vitae Bay

Turtle Villa

Jolly Harbour, Antigua

Beachfront | Pool | AC

4 4+

Details

Reef Beach House truly is a tropical haven. Located right on Grace Bay Beach, this villa offers four air-conditioned bedrooms ... 2 BR rate available.

Reef Beach House is located on the very desirable, Grace Bay Beach

Reef Beach House

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

4 3

Details

If you like both contemporary and Caribbean styles, you'll love the beautiful browns, blues and whites at Seabird Villa. This ... 2 & 3 BR rates available.

Seabird Villa has beautiful sunset views

Seabird Villa

Anguilla

Near Beach | Pool

4 4+

Details

Jessamine Villa is located on the West Coast of Barbados, near Gibbs Bay Beach, golf and tennis, and an assortment ... 3 BR rate available.
Has specials.

Set amid lush tropical greenery Jessamine offers a beautiful private pool

Jessamine Villa

Barbados

Near Beach | Pool

4 4

Details

This villa has some of the most beautiful ocean views on the island. It's a few steps from the water, ... Has specials.

Hemingway House is tucked in a cove between Gibbs Beach and Mullins Beach

Hemingway House

Barbados

Beachfront | Pool | AC

4 4+

Details

Mahogany trees, tropical plants, fruit trees, and a multitude of green foliage make Shangri La a little slice of heaven. ... Has specials.

Shangri La Villa is located in the Holders Hill area right on the Barbados Polo Club

Shangri La - Villa

Barbados

Pool

4 4

Details

Phebus Villa overlooks St. Jean Bay and is within a short walking distance from St. Jean Beach, Nikki Beach, and ... 2 BR rate available.

Phebus Villa is located in St. Jean with views of St. Jean Bay

Phebus Villa

Saint Jean, St. Barts

Near Beach

4 4

Details

Hacienda has plenty of space for a large group, and has a great location for exploring the island. It's private, ... 2 & 3 BR rates available.
Has specials.

La Hacienda Villa sits on the Terres Basses hillside

La Hacienda Villa

Terres Basses (French side), St. Martin

Pool

4 3

Details

Westshore Beach House is ideal for two couples or families who are traveling together. Both levels have two bedrooms, seating ... Has specials.

Westshore Beach House is located right on the beach just north of Holetown

Westshore Beach House

Barbados

Beachfront | Pool | AC

4 4+

Details

When ISLANDS magazine names you 'One of the Top 20 villas in the World', it's always a good sign. It has ... 1, 2 & 3 BR rates available.

The beautiful Bird of Paradise Villa

Bird of Paradise Villa

Anguilla

Near Beach | Pool

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 Villa

Happy Bay (French Side), St. Martin

Near Beach | Pool

4 4+

Details

2B at Peter Bay Villa is known for its spacious design, high end furnishings, and waterfront location. This spectacular home ...

2B at peter Bay is perched on a tropical hillside above the west end of Peter Bay

2B at Peter Bay Villa

Peter Bay, St. John

Near Beach | Pool

4 4+

Details

Angelina Villa works quite nicely for a family with older children or a group, and because of its modern amenities, ... 2 & 3 BR rates available.

Angelina villa has great views of the harbor

Angelina Villa

Gustavia, St. Barts

Near Beach | Pool

4 4

Details

Illusion Villa is perfect for a larger family with older children. An on-site tennis court, putting green, and art-decor inspired ... Has specials.

Beautiful views from the balcony at Illusion Villa

Illusion Villa At Sugar Hill

Barbados

Pool

4 4+

Details

Recently remodeled, Rising Star Villa has a contemporary flair that still manages to be comfortable, allowing guests to feel right ... 2 & 3 BR rates available.
Has specials.

Rising Star Villa photo

Rising Star Villa

Tamarind Hill (Dutch Side), St. Martin

Pool

4 4

Details

Situated at the water's edge on the south end of Anguilla, Anani Villa takes advantage of its location to offer ... 3 BR rate available.

Anani Villa Kamique is one of three villas on Kamique Estate, situated directly on the Caribbean Sea

Anani Villa at Kamique

Anguilla

Beachfront | Pool | AC

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

Globe Trotter Villa

Lurin, St. Barts

Pool

4 4

Details

Built on top of a small island cliff, Villa Turquesa can't help but show off a brilliant view of Sapodilla ...

Enjoy amazing views of the Caribbean from the pool at Turquesa Villa

Turquesa Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

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

Casa Azul Villa

Vitet, St. Barts

Pool

4 4

Details

Agora Villa is the place to be for an unforgettable vacation. The pool and terrace are amazing, there’s tons ... 2 & 3 BR rates available.

Amazing infinity edge pool at Agora Villa

Agora Villa

Terres Basses (French side), St. Martin

Pool

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

LUZ Villa

Camaruche, St. Barts

Pool

4 4

Details

The four-bedroom penthouse suite at Smugglers Cove comes with everything you need for the perfect island vacation. The 60-ft balcony ... Has specials.

Smugglers Cove #7 Penthouse overlooks Paynes Bay

Smugglers Cove #7- Penthouse

Barbados

Beachfront | Pool | AC

4 5+

Details

With 4 bedrooms and 4 bathrooms, this super private cliffside villa on St. Barts is easily one of the most upscale properties ... 1, 2 & 3 BR rates available.

Located on the tip of the island jetty near Lorient Bay - Cap Au Vent enjoys great ocean views

Cap Au Vent Villa

Pointe Milou, St. Barts

Pool

4 4

Details

Few places are quite as tourist-friendly as Barbados, but thanks to the amazing weather, friendly people, and great activities, this ... Has specials.

Capri Manor is located just across the street from Gibbs Beach

Capri Manor

Barbados

Near Beach | Pool

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

Jasmine Villa

Gouverneur, St. Barts

Pool

4 5+

Details

Atelier's architect, Alistair Downie, infused tranquility and serenity into every modern detail at this two-story villa. From the master bedroom ... Has specials.

Atelier Villa has modern architectural lines and a beautiful pool

Atelier Villa

Barbados

Near Beach | Pool

4 3+

Details

Ready to go gourmet on your next holiday? You will have to demand the finer things in life, and Ariana ... 2 & 3 BR rates available.

Ariana sits on a hilltop over Lower Belmont Bay

Ariana Villa

Tortola, BVI, British Virgin Islands

Near Beach | Pool

4 3+

Details

If you want a tropical escape, Ana Capri fits the bill. It has amazing views, gorgeous Italian design, and lush ... 1, 2 & 3 BR rates available.

Ana Capri Estate photo

Ana Capri Estate

Tortola, BVI, British Virgin Islands

Pool

4 4+

Details

Right on the coastline, the Bora Bora Lower Villa provides easy access to the water sports and beaches that make ... 2 BR rate available.
Has specials.

Dining

Bora Bora Lower Villa

Barbados

Beachfront | AC

4 4

Details

Looking out over the waters of Paynes Bay Beach, the Bora Bora Upper Villa is the complete mix of privacy ... 2 BR rate available.
Has specials.

Bora Bora Upper Villa photo

Bora Bora Upper Villa

Barbados

Beachfront | AC

4 4

Details

Marsh Mellow has incredible views, a spacious layout, and a huge, deep pool. Since the villa is crescent-shaped, every room ... Has specials.

Marsh Mellow Villa is located in Westmoreland in Barbados and has great views of the ocean

Marsh Mellow Villa

Barbados

Pool

4 4+

Details

Many people like to stay on Seven Mile beach because that's where all the action is. Then there are others ...

View from above Castaway Villa - you can see the beach and the ocean

Castaway Cove

Grand Cayman, Cayman

4 3+

Details

Kai Vista is a colorful oceanfront villa that encompasses all that an idyllic, tropical getaway destination should. After long evening ...

Kai Vista photo

Kai Vista

Grand Cayman, Cayman

Beachfront | Pool | AC

4 4

Details

Sea La Vie Villa is truly an amazing place to come taste the island life. This home is great for ... 1, 2 & 3 BR rates available.
Has specials.

Lounge in the Caribbean sun at Sea La Vie Villa

Sea La Vie Villa

Tamarind Hill (Dutch Side), St. Martin

Pool

4 5

Details

Even though this villa is set up for family vacations, it still feels like a romantic secret garden. Every room ... Has specials.

Edge of Paradise is located on the Southern shore of Meagan's Bay

Edge of Paradise Villa

St. Thomas, USVI

Near Beach | Pool

4 4+

Details

Rose Dog is truly an eclectic gem on the island of St. Barts. It has a comfortable layout, unique design, ... 2 & 3 BR rates available.
Has specials.

Rose Dog is located on a hillside in Dévé

Rose Dog Villa

Vitet, St. Barts

Pool

4 4

Details

This island getaway is located near Marigot Beach where only swimming and snorkeling are allowed because of the protected natural ... 2 & 3 BR rates available.

Black Pearl Villa is located near Marigot Beach

Black Pearl Villa

Marigot, St. Barts

Pool

4 4

Details

The views from this villa are incredible, not to mention the ample deck space and open floor plan. I love ... 2 & 3 BR rates available.

Villa Aurea sits just above Lorient Beach

Villa View Point

Lorient, St. Barts

Pool

4 4

Details

The pool deck and sunbathing deck at Bakea Villa are great because they leave guests plenty of room to spread ...

Bakea is located above of Anse des Cayes

Bakea Villa

Anse des Cayes, St. Barts

Pool

4 4

Details

This villa is stunning. It has a full kitchen and beautiful architecture that's really unique to the area, and the ... 3 BR rate available.

Villa MOH is located in Lurin

MOH Villa

Lurin, St. Barts

Pool

4 4

Details

Villa Rosa has a breathtaking view of the ocean that's only enhanced by the free form swimming pool. I love ... 2 & 3 BR rates available.
Has specials.

Villa Rosa has amazing views out into the Caribbean and across the St. Barthelemy channel

Villa Rosa

Guana Bay (Dutch Side), St. Martin

Near Beach | Pool

4 4

Details

Palermo provides expansive views of Turtle Tail, and you won't be able to get enough of the infinity pool and ...

Palermo Villa is located directly on the ocean

Palermo Villa

Turtle Tail, Turks and Caicos

Pool

4 4+

Details

Monte Verde is a charming villa perfect for couples traveling together. The king suites are pretty equal so great for ... 3 BR rate available.
Has specials.

Monte Verde is located in Hope Hill and has great views of Orient Bay

Monte Verde Villa

Orient Bay (French side), St. Martin

Pool

4 4+

Details

This villa is comfortable, chic, and well equipped. The view is amazing, but the al fresco dining area is my ... 3 BR rate available.

Bibi Villa photo

Bibi Villa

Vitet, St. Barts

Pool

4 4

Details

With two separate master bedrooms and two guest bedrooms, the villa is well suited to couples traveling together, or to ... 2 & 3 BR rates available.

W View Villa is located on the hillside above St. Jean Bay

W View Villa

Saint Jean, St. Barts

Pool

4 4

Details

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

Aqua Vue is located in Porto Cupecoy

Aqua Vue

Cupecoy (Dutch side), St. Martin

Near Beach

4 4+

Details

Pastels Villa is the perfect countryside villa for your family's next vacation. It has a child-friendly layout, ample sitting areas ... 2 & 3 BR rates available.

Pastles Villa is located on a hillside in Vitet

Pastels Villa

Vitet, St. Barts

Pool

4 4

Details

In Harmony is a charming beachfront villa that would be perfect for your next family vacation. It has a private ... Has specials.

An aerial view of in Harmony Villa located directly on the beach

In Harmony Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

4 4

Details

I think this villa would be perfect for a family vacation-- it has three master bedrooms upstairs and a twin ...

A beachfront pool awaits you at Christmas Palms Villa

Christmas Palms Villa

Grand Cayman, Cayman

Pool

4 3+

Details

Tarasand villa is a great choice for anyone who wants to be near Rum Point and have easy access to ...

The beach set up in front of Tarasand Villa

Tarasand Villa

Grand Cayman, Cayman

Beachfront | AC

4 3

Details

If you love the ocean, you'll love Villa Caymanas. It sits on Old Man's Bay, a quiet and undeveloped region ...

Villa Caymanas is located on the North side of the island on the beach

Villa Caymanas

Grand Cayman, Cayman

Near Beach | Pool

4 4+

Details

This villa is great for four couples, because each suite has a queen bed and private bathroom. There's three beaches ... 2 BR rate available.

Galley Bay Heights #007 is located on one of the highest points of the beautiful Galley Bay Heights

Galley Bay Heights Villa - #007

Galley Bay, Antigua

Near Beach

4 4

Details

The contemporary style of Bahia Blue will wow you, from the outdoor kitchen, to the bright bedrooms, to the beach ... 3 BR rate available.

Bahia Blue is located in Terres Basses with in walking distance to Baie Rouge Beach

Bahia Blue

Terres Basses (French side), St. Martin

Near Beach | Pool

4 4

Details

Estrella is a lovely 4 bedroom, 4 bathroom villa, located in Flamands, just a few steps away from one of the most ... 2 & 3 BR rates available.

Estrela Villa is located in Flamands overlooking the beautiful Flamands Bay Beach

Estrela Villa

Flamands, St. Barts

Near Beach | Pool

4 4

Details

This house is great for two families to share. There are two king suites that each have exterior access, and ...

Heritage House Villa is located on the very desirable Rum Point

Heritage House

Grand Cayman, Cayman

Beachfront | Pool | AC

4 4

Details

I really like the living area in this villa, which is multi-leveled and has a few nooks for relaxing. The ... 2 & 3 BR rates available.

Yellow Bird Villa sits on a hillside in Pointe Milou overlooking Lorient Bay to Marigot

Yellow Bird Villa

Pointe Milou, St. Barts

Pool

4 4

Details

Staying in Arrecife 23 is a gorgeous way to enjoy Punta Cana Resort. It has wrought iron and travertine accents, high ...

Arrecife 23 is located in Punta Cana Resort on the golf course with ocean views

Arrecife 23

Punta Cana, Dominican Republic

Near Beach | Pool

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

Island Girl

Coral Bay, St. John

Pool

4 4

Details

Villa Arrecife 24 is located in the gated community of La Cana Resort & Club

Villa Arrecife 24 at Tortuga Bay

Punta Cana, Dominican Republic

Pool

4 4

Details

Smugglers Cove is an excellent choice for beach lovers. You'll have direct access to Paynes Bay, and are just a ... Has specials.

Sandy Lane Beach just steps outside of Smugglers Cove

Smugglers Cove #6

Barbados

Beachfront | AC

4 4+

Details

Turks and Caicos is well-known as one of the best areas in the Caribbean for beach lovers, and the Venetian ... Has specials.

Penthouse at The Venetian photo

Penthouse at The Venetian

Grace Bay, Turks and Caicos

Beachfront | AC

3 3

Details

Villa Kai has water access to Sandy Hill Bay for exploring, and you can watch the waves crash onto the ... 1 & 2 BR rates available.

Villa Kai is located on Sandy Hill Bay

Villa Kai

Anguilla

Pool

3 3

Details

Clementine is beautifully decorated, super open, and spacious. I love it for families and groups of friends, because the bedrooms ... 1 & 2 BR rates available.

Villa Clémentine photo

Villa Clémentine

Vitet, St. Barts

Pool

3 3+

Details

This villa has a beautiful view and plenty of lounging space on the terrace to enjoy it. The upstairs bedrooms ... 2 BR rate available.

Sasha photo

Sasha

Corossol, St. Barts

Pool

3 3

Details

This villa has a cool Balinese vibe and outdoor showers that really elevate the luxury. It's well designed, and has ... 2 BR rate available.

Villa Sauvage has a beautiful pool overlooking the island

Sauvage Villa

Flamands, St. Barts

Pool

3 3

Details

Bikini Villa is simply cozy. An open floor plan allows you to see all your guests relaxing, and the rooms ... 1 & 2 BR rates available.

Bikini Villa photo

Bikini Villa

Lorient, St. Barts

Near Beach | Pool

3 3

Details

Aliza is chic and convenient! The decor is very minimalist and modern, and the villa is just a short walk ... 1 & 2 BR rates available.

Aliza photo

Aliza

Saint Jean, St. Barts

Near Beach | Pool

3 3

Details

This villa is great for any family who wants stunning views for an affordable price. There are tons of beaches ... 1 & 2 BR rates available.

Ballena Blue is located on a hilltop over Rendezvous Bay

Ballena Blue

Rendezvous Bay, St. John

Pool

3 3

Details

One of my favorite things about Javacanou is the waterfront access to Marigot Beach. This area is great for snorkeling, ...

Javacanou villa overlooks the beautiful protected waters of Marigot Bay

Javacanou Villa

Deve, St. Barts

Near Beach | Pool

3 3

Details

Babylon Reef feels like a classic beach house, with every amenity you could ask for. It's oceanfront, with a great ...

The private pool at Babylon Reef has a man made -beach- surrounding it

Babylon Reef

Grand Cayman, Cayman

Beachfront | Pool | AC

3 2+

Details

Sienna has a gorgeous terrace and views of the golf course. The terrace can be closed off to the pool ... Has specials.

Sienna Villa

Sienna Villa

Barbados

Pool

3 3

Details

Smugglers Cove is great for beach lovers, because the guests have direct access to Paynes Bay. The villa is spacious ... Has specials.

Paynes Bay Beach is just below the balcony at Smugglers Cove #4

Smugglers Cove #4

Barbados

Beachfront | AC

3 3

Details

Crescent Beach villa sits in beautiful, peaceful Bequia, with a view of the beach below. You’ll love listening to ... 1 BR rate available.

Crescent Beach Villa is located above Crescent Beach and has amazing ocean views

Crescent Beach Villa

Bequia, St. Vincent & Grenadines

Pool

3 3

Details

Casa Luna 17 is great for families who want a bit of privacy at a great price. Kids can stay on ... Has specials.

There is an amazing beach cove at Casa Luna Villas

Casa Luna 17

Grand Cayman, Cayman

Beachfront | AC

3 4

Details

Edge of Paradise is a great choice for three couples who want to relax by Grace Bay. The villa comes ...

Edge of Paradise is located just a few minutes from Grace Bay Beach

Edge of Paradise

Leeward, Turks and Caicos

Near Beach | Pool

3 3

Details

La Corniche is a stunning, spacious oceanfront villa with gorgeous views and an airy design. I love how the interior ...

La Corniche has a beautiful pool deck area with spectacular views of the Caribbean

La Corniche

Pointe Milou, St. Barts

Pool

3 3+

Details

If you love Grace Bay and Smith's Reef, you'll love Sandpebble. Its right by the sea, near Turks and Caicos' ...

Aerial view of the Sandpebble property

Sandpebble

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

3 3+

Details

Infinite Horizon is a gorgeous family vacation villa. It has WiFi, SONOS, a media room, a pool, and the beach ...

Infinite Horizon Villa is located on the beach just minutes from Seven Mile Beach Corridor

Infinite Horizon

Grand Cayman, Cayman

Beachfront | Pool | AC

3 3

Details

Tradewinds is ideal for three couples who want to vacation on Grace Bay without sacrificing privacy. The villa is surrounded ...

Tradewinds Villa is located near Grace Bay Beach

Tradewinds

Providenciales, Turks and Caicos

Near Beach | Pool

3 3

Details

Seashells is a great choice for a beachfront family vacation. It's steps away from the sea, has three-stories of space, ... Has specials.

Seashells Villa is set on a beautiful stretch of beach

Seashells

Barbados

Beachfront | Pool | AC

3 3+

Details

Porters is a family-friendly villa with a great location, elegant design, and gorgeous gardens. The villa's three bedrooms are all ... Has specials.

Porters Villa is located in St. James

Porters

Barbados

Near Beach | Pool

3 3

Details

On The Rocks has a classic, beach house vibe in one of Turks and Caicos's most underrated areas. Chalk Sound ...

On the Rocks is located in Silly Creek on Chalk Sound

On the Rocks

Chalk Sound, Turks and Caicos

Pool

3 3

Details

This three-bedroom resort villa has everything you need for an easy family vacation. Everything has been thought of for you, ...

Seafire Resort

The Residences at Seafire 3 Bedroom South

Grand Cayman, Cayman

Beachfront | AC

3 3+

Details

If you’re looking for an Anguilla beachfront rental, this resort villa is worth a look. It’s right on ... Has specials.

Tranquility Beach - Beachfront Penthouse Villa is located on Meads Bay Beach

Tranquility Beach - Beachfront Penthouse

Anguilla

Beachfront | AC

3 3+

Details

Viceroy Sugar Beach's Three Bedroom Villa Residence is the ideal rental for a luxurious beachfront experience. The beach is steps ...

The Viceroy 3 Bedroom Villa Residences are set in the foothills of the Pitons and the Caribbean Sea

Viceroy Sugar Beach - Three Bedroom Villa Residence - Beachfront

Soufriere, St. Lucia

Beachfront | Pool | AC

3 3+

Details

This gorgeous villa is perfect if you want to be near Seven Mile Beach, but away from the crowds. There’...

Casa Luna 4 is located in the resort community along the coastline just south of Seven Mile Beach

Casa Luna 4 - Platinum

Grand Cayman, Cayman

Beachfront | AC

3 4

Details

This spacious, beachfront villa has a convenient location within walking distance of dining, attractions, and excursions. Even though Rum Point ...

Les Jalousies is located in Cayman Kai

Les Jalousies

Grand Cayman, Cayman

Beachfront | Pool | AC

3 3

Details

1 BR rate available.

AKA Villa is located in Corossol with great views of Gustavia Harbor

Aka Villa

Corossol, St. Barts

Pool

3 2

Details

Modern design, beach access, and three bedrooms make this penthouse the perfect rental for your next vacation. It’s right ... Has specials.

Tranquility Beach Anguilla is located on Meads Bay Beach

Tranquility Beach - Penthouse

Anguilla

Beachfront | AC

3 3+

Details

Sapphire Beach 401 has easy beach access near great snorkeling, restaurants, and activities. It’s a great choice for your next ... 2 BR rate available.
Has specials.

Sapphire Beach 401 has views right over the beach

Sapphire Beach 401

Barbados

Beachfront | AC

3 3

Details

If you want gorgeous views, interiors, and design, Infinity is a great choice. This Pointe Milou villa has a quiet ... 2 BR rate available.

Infinity Villa is located on a hilltop in Pointe Milou overlooking Lorient Bay

Infinity

Pointe Milou, St. Barts

Pool

3 3

Details

Sailrock Resort is a great part of the island to stay on if you want tranquility, convenience, and seclusion. The ...

Sailrock Resort Oceanfront Coral Villa is located oceanfront on the Sailrock Peninsula

Sailrock Resort Oceanfront Coral Villa

South Caicos, Turks and Caicos

Pool

3 3

Details

Vacationing with teens? This is the perfect villa. This two-bedroom beach house and one-bedroom cottage is incredible for families who ... Has specials.

Beach Enclave Long Bay is located on the southeastern edge of Providenciales

Beach Enclave - 2 Bedroom Beach Front Plus 1 Bedroom Cottage at Long Bay

Long Bay, Turks and Caicos

Beachfront | Pool | AC

3 3+

Details

The Cottage at Meads Bay is a quiet, peaceful retreat for any vacationer. This villa offers three spacious bedrooms, gorgeous ...

The Cottage at Meads Bay is located on Meads Bay, Anguilla’s most desirable beach

The Cottage at Meads Bay

Anguilla

Beachfront | AC

3 3+

Details

No Limit is a charming villa with gorgeous ocean views and a spacious exterior with several lounging and dining areas. ... 2 BR rate available.
Has specials.

No Limit is located on a hillside in Terres Basses overlooking Baie Longue

No Limit

Terres Basses (French side), St. Martin

Pool

3 3+

Details

Casa Luna 16 - Platinum has next-level benefits for anyone seeking privacy, resort amenities, and luxury. The exterior is tricked out ...

Casa Luna 16 - Platinum is located in the exclusive resort at the very end of Seven Mile Beach

Casa Luna 16 - Platinum

Grand Cayman, Cayman

Beachfront | AC

3 3

Details

Casa Luna has something for everyone! It has all the privacy of an independent villa, but all the amenities of ... Has specials.

Casa Luna 17 is located along the coastline just south of Seven Mile Beach

Casa Luna 17 - Platinum

Grand Cayman, Cayman

Beachfront | AC

3 4

Details

Osprey villa has gorgeous sunset views and outdoor amenities perfect for a family vacation. The waterfront location is enhanced by ...

Osprey is located on the ocean side of Chalk Sound

Osprey Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Pool

3 3

Details

Caribbean vacations offer much more than you might imagine, especially if you have never heard about the wonderful accommodation options. ...

Hummingbird Villa photo

Hummingbird Villa

Cap Estate, St. Lucia

Pool

3 3

Details

The beautifully landscaped and stylish Saline Reef is a great vacation spot for families with children over 12, or adults who ... 2 BR rate available.

Saline Reef sits on the northernmost end of St. Lucia and has a beautiful pool and patio

Saline Reef Villa

Cap Estate, St. Lucia

Near Beach | Pool

3 3

Details

Terres Basses is known as one of St. Martin's nicest areas, and Callisto does not disappoint. The villa consists of 3 ... 2 BR rate available.
Has specials.

Callisto Villa is located on a hillside in Terres Basses and enjoys sunset views over Baie Longue

Callisto

Terres Basses (French side), St. Martin

Pool

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

Serenity Villa

Gustavia, St. Barts

Near Beach | Pool

3 3

Details

Anchorage Villa is a warm, sun-drenched property with a spacious living room and an open-concept dining area. The housekeeper prepares ... Has specials.

Anchorage Villa is on the western end of the Sandy Lane Estate

Anchorage Villa

Barbados

Pool

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

Armor Villa

Mont Jean, St. Barts

Pool

3 3+

Details

Guests will be immediately taken with the sleek, peaceful influence of Japan when they enter Plein Ciel Villa. The high ... 2 BR rate available.

Plein Ciel Villa photo

Plein Ciel Villa

Marigot, St. Barts

Pool

3 2

Details

You're bound to enjoy the gardens, but there are many other features in this estate to make you feel at ... 2 BR rate available.

Canefield house sits on a lovely hillside in the heart of Tortola

Canefield House

Tortola, BVI, British Virgin Islands

Pool

3 3+

Details

Abby Villa is the perfect St. Barts getaway for three couples who want a cozy, peaceful location near multiple beaches. ... 2 BR rate available.

Abby Villa photo

Abby Villa

Vitet, St. Barts

Pool

3 3

Details

At Rocky Point, you have the opportunity for privacy and excitement, as well as spectacular ocean views. This three-bedroom villa ...

The pool at Rocky Point villa!

Rocky Point at COMO Parrot Cay

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

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

La Magnolia Villa

Terres Basses (French side), St. Martin

Pool

3 3

Details

This villa is great for a few couples or a family. All three bedrooms have ensuite bathrooms, and two are ... 2 BR rate available.

Sweet Return Villa is located near the golf course and Rendezvous Bay

Sweet Return Villa

Anguilla

Pool

3 3

Details

If you're ready for a Caribbean escape with views galore, then Eaglesnest is the place for you. It's location on ... 1 & 2 BR rates available.

Overlooking Great Cruz Bay Eaglesnest definitely has amazing views

Eaglesnest Villa

Great Cruz Bay, St. John

Pool

3 3

Details

Casawapa is great for couples traveling together or family vacations. The rooms are equal in size and separated by the ... 2 BR rate available.

The One Villa sits on the Colombier hillside overlooking the Caribbean

The One

Colombier, St. Barts

Pool

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 is located on a on a hillside in Marigot

Au Coeur du Rocher

Marigot, St. Barts

Pool

3 3+

Details

Dasha Villa is quickly building a roster of loyal fans. A recent visitor summed up her stay at the villa ... 1 & 2 BR rates available.

Dasha Villa is located on a hillside overlooking Views of Gouverneur

Dasha Villa

Lurin, St. Barts

Pool

3 3

Details

Escape Villa is perfect for families, and sits almost right on top of Lorient Beach, which is one of the ... 1 & 2 BR rates available.

Tropical retreat at Escape Villa

Escape Villa

Lorient, St. Barts

Near Beach | Pool

3 2

Details

Whether you want to relax by the pool for your entire vacation, or you're an adventurer who wants a lot ... 2 BR rate available.
Has specials.

Victoria Villa is located in the Oyster Pond neighborhood on a hillside overlooking Orient Bay

Victoria Villa

Oyster Pond (Dutch side), St. Martin

Pool

3 3+

Details

Mer Soleil is a contemporary villa located in Gouverneur just a five minute drive to the pristine beach. Stop and ... 2 BR rate available.

Amazing views from the deck

Mer Soleil

Gouverneur, St. Barts

Pool

3 3

Details

Mariposa is just a few paces from Taylor Bay beach, one of the most stunning, quiet beaches on the island. ...

Mariposa Villa is located at the very end of Sapodilla Bay

Mariposa Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

3 3

Details

Harmony House is an elegantly furnished, fully-equipped, three-bedroom villa with everything you need for a relaxing Barbados getaway. The bedrooms ... Has specials.

Harmony House is just steps away from Gibbes Beach

Harmony House

Barbados

Beachfront | Pool | AC

3 3+

Details

Reef Pearl Villa, with it's private swimming pool, relaxing hammock, and perfect beachfront location is the ideal getaway spot for ... 2 BR rate available.

Ocean kayaks - Ask for availability

Reef Pearl Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

3 3

Details

Conch Beach has everything you could possibly want in a family vacation rental, from the bedrooms to the design to ...

Conch Beach Villa is located on the beautiful Grace Bay Beach

Conch Beach Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

3 3

Details

This non-smoking villa has an open floor plan in the living areas that invites socializing and togetherness; but when you ... 2 BR rate available.
Has specials.

On Island Time photo

On Island Time

Oyster Pond (Dutch side), St. Martin

Pool

3 3+

Details

You can see the ocean from every room in this beachfront villa, and natural light enhances the tropical vibe. You ... Has specials.

Fathom's End - Mahogany Bay is located right on the beach at Mahogany Bay

Fathom's End - Mahogany Bay

Barbados

Beachfront | Pool | AC

3 3+

Details

Sunset Reach has the benefit of being directly on Mullins Beach, a crowd-favorite for snorkeling, water sports, and its famed ... 2 BR rate available.
Has specials.

Sunset Reach sits a few feet from the sea on Mullins Beach

Sunset Reach Villa

Barbados

Beachfront | AC

3 3

Details

Blue Lagoon Villa is a family friendly, wheelchair accessible villa that can easily sleep up to ten people. With a ... 2 BR rate available.
Has specials.

Blue Lagoon Villa photo

Blue Lagoon Villa

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

3 3

Details

Kiwi Villa is a 3-bedroom contemporary-style home that is situated to enjoy the views of the ocean and the surrounding ... 1 & 2 BR rates available.

Lounge by the private pool while enjoying views of the Caribbean from the deck at Kiwi Villa

Kiwi Villa

Terres Basses (French side), St. Martin

Pool

3 3+

Details

If you have an extended family, Bambooshay Villa has the extra room that avoids what a cramped hotel would have ... 1 & 2 BR rates available.

Relax and enjoy yourself while in the pool or hang'n in the hammock at Bambooshay

Bambooshay Villa

St. Croix, USVI

Pool

3 3+

Details

This villa would be so fun for your next family vacation. Kids will love the pool, teens will love the ... 1 & 2 BR rates available.

Bel'Ombre photo

Bel'Ombre

Marigot, St. Barts

Pool

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

Sol e Luna Villa

Terres Basses (French side), St. Martin

Pool

3 3

Details

Escapade Villa is situated on a hillside overlooking Marigot Bay in the French Caribbean. Designed for comfort, Escapade offers ocean ... 1 & 2 BR rates available.

Views of Marigot Bay from the pool and the large deck at Escapade Villa

Escapade Villa

Marigot, St. Barts

Near Beach | Pool

3 3

Details

Panarea Villa is truly beautiful, with a great housekeeper and lush gardens all around. I think this villa is ideal ... 1 & 2 BR rates available.

Panarea is located in Anguilla's West End, just minutes away from the island's most beautiful beache

Panarea Villa

Anguilla

Near Beach | Pool

3 3

Details

At just the right vantage point to see the rolling hills, town, and ocean, Villa Rivendell provides seclusion without cutting ... 1 & 2 BR rates available.

Amazing view of Flamands Bay from the infinity edge pool

Rivendell Villa

Flamands, St. Barts

Pool

3 3

Details

Tuscany Resort is one of my favorite properties on Turks and Caicos. At WhereToStay.com, we only list resorts that ... 1 & 2 BR rates available.
Has specials.

The Tuscany Resort is located on East Grace Bay Beach

Tuscany

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

3 3

Details

Located within walking distance to a grocery store and restaurants, Ecoute les Vagues sits right on Flamands Beach, giving guests ...

Ecoute les Vagues is located right on the beach in Flamands Bay

Ecoute les Vagues

Flamands, St. Barts

Beachfront | Pool | AC

3 2

Details

Sea Bird is a one-of-a-kind villa in Mont Jean, St. Bart's, with 3 bedrooms, a full kitchen, and large living areas ... 1 & 2 BR rates available.
Has specials.

Sea Bird Villa is located on a hilltop in Mont Jean overlooking the Caribbean

Sea Bird Villa

Mont Jean, St. Barts

Pool

3 3

Details

Your family will love staying at The Harbour #17. This brightly colored home is right on the harbor and nestled in ... 2 BR rate available.

The Harbour #17 is located in the Harbour Townhomes overlooking the harbour on Rodney Bay

The Harbour #17

Rodney Bay, St. Lucia

Near Beach

3 3+

Details

Situated on a hillside, Lataniers Villa has a great view of St. Jean Bay and the surrounding island greenery. Guests ... 2 BR rate available.

Beautiful views from Lataniers Villa

Lataniers Villa

Saint Jean, St. Barts

Pool

3 2

Details

You will want to schedule your time wisely to take in as much of this Caribbean beauty as possible. With ... 1 & 2 BR rates available.

Roc Flamands 11 is located just above Flamand Beach

Roc Flamands 11 Villa

Flamands, St. Barts

Near Beach

3 2

Details

There is no mistaking that you are on island time when you step foot in Hurakan Villa. Each room has ... 1 & 2 BR rates available.

Perched on the hillside of Colombier - Hurakan provides beautiful views of Gustavia Harbour

Hurakan Villa

Colombier, St. Barts

3 3

Details

Turks and Caicos is well-known as one of the best areas in the Caribbean for beach lovers, and the Venetian ... 1 & 2 BR rates available.
Has specials.

The Venetian photo

The Venetian

Grace Bay, Turks and Caicos

Beachfront | AC

3 3+

Details

Latitude Villa is an excellent choice for three couples. Two bedrooms are upstairs and one is downstairs, so everyone will ... Has specials.

Latitude Villa photo

Latitude Villa

Barbados

Beachfront | Pool | AC

3 3

Details

Anakao Villa, located in the Saint Jean area, is ideally located for those seeking the ultimate in peace and quiet. ... 1 & 2 BR rates available.

Anakao Villa is located in St. Jean just minutes from St. Jean Beach

Anakao Villa

Saint Jean, St. Barts

Pool

3 2

Details

Coco villa has an outdoor living area with comfy furnishings and ocean views. The infinity pool has a plateau where ...

Coco Villa sits above Lorient Bay Beach looking toward St. Jean

Coco Villa

Lorient, St. Barts

Pool

3 3

Details

Just 2 minutes away from one of St. Martin's nicest beaches, Les Zephyrs is a private, 3-bedroom villa that comes with ... 2 BR rate available.
Has specials.

The private pool at Les Zephyrs offers your own tropical getaway

Les Zephyrs Villa

Terres Basses (French side), St. Martin

Pool

3 3

Details

Dream Come True Villa delivers not only privacy, but magnificent ocean views. Just steps above Devers Bay, this three-bedroom villa ... 1 & 2 BR rates available.

A Dream Come True Villa has amazing ocean views and a fun pool area

Dream Come True Villa

Devers Bay, St. John

Beachfront | AC

3 3+

Details

If you want a Caribbean escape with Secret Garden vibes, check out Kessi Villa. Its surrounded by gorgeous gardens and ... 2 BR rate available.

Kessi Villa photo

Kessi Villa

Cap Estate, St. Lucia

Pool

3 3

Details

Tainos Villa enjoys some of the best views on the island from its location in Pointe Milou. Everything is open ...

Tainos Villa located in Pointe Milou

Tainos

Pointe Milou, St. Barts

Pool

3 3

Details

West Bay Club has one of the best locations on Turks and Caicos, just behind Grace Bay Beach. A short, ...

The West Bay Club from Grace Bay Beach

West Bay Club - Oceanfront Premier 3 Bedroom

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

3 3

Details

Ti Moun Villa has one of the best locations in St. Barts! Situated on a hillside in Lurin, this villa ... 1 & 2 BR rates available.

Ti Moun Villa sits on a hillside just above Gustavia Harbor

Ti Moun Villa

Lurin, St. Barts

3 3

Details

Crowsnest at Coral Cove is designed for those who want to relax by one of the island's most beautiful beaches. ... Has specials.

Coral Cove complex

Coral Cove #14 - Crows Nest

Barbados

Beachfront | AC

3 3

Details

Sapphire Beach #209 is a modern and comfortable 3-bedroom condo located on the second floor of the Sapphire Beach condo community. ... Has specials.

The pool and view of the ocean from Sapphire Beach

Sapphire Beach #209

Barbados

Beachfront | AC

3 3

Details

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

Sapphire Beach #205 photo

Sapphire Beach #205

Barbados

Beachfront | AC

3 3

Details

Acamar Villa maximizes ocean views. Nearly every room has sea-facing windows, and the exterior is designed to eliminate any barrier ... 2 BR rate available.

Acamar Villa is located near Toiny Beach

Acamar Villa

Toiny, St. Barts

Pool

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

Les Amis du Vent Villa

Mont Jean, St. Barts

Pool

3 6

Details

There are few things quite as fun as a vacation with friends, and Ocean View Villa has the perfect design ... Has specials.

Ocean View sits on a neighborhood hillside overlooking Orient Bay and to Tintamarre and St. Barth

Ocean View Villa

Orient Bay (French side), St. Martin

Near Beach | Pool

3 3+

Details

Simple elegance is at your fingertips when you reserve space at Palisades in Barbados. The fully air-conditioned unit, #6A, can ... Has specials.

Palisades 6A is located near Freight's Bay in Barbados

Palisades 6A

Barbados

Near Beach | Pool

3 3+

Details

L'Agua Villa puts a stylish, modern spin on the typical Caribbean villa. The massive master bedroom opens directly to a ... 1 & 2 BR rates available.
Has specials.

L'Agua Villa is located above Dawn Beach

L'Agua Villa

Oyster Pond (Dutch side), St. Martin

Pool

3 3

Details

This modern, three bedroom home has a chic and sleek design. All of the rooms have large, wall size windows ... 1 & 2 BR rates available.

Upside Villa is perched over Pointe Milou overlooking Lorient Bay and out to St. Martin

Upside Villa

Pointe Milou, St. Barts

3 3

Details

Luxury, beauty, and a walk on the wild side of Grand Fond await when you reserve La Roche Dans L'eau ... 1 & 2 BR rates available.

A beautiful beach entry pool at La Roche dans l’Eau

La Roche Dans L'Eau Villa

Grand Fond, St. Barts

Pool

3 3

Details

The best thing about Soleil Villa is the location. You get a stunning view of Trunk Bay, and you can ... 2 BR rate available.

Infinity edge pool with amazing views of Trunk Bay Beach at Soleil villa

Soleil Villa

Tortola, BVI, British Virgin Islands

Near Beach | Pool