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Family Villa Collection

Family Villa Collection

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.

Three Dolphins isn't only gorgeous inside, it also has amazing sea views with St. Martin in the distance. The villa has all the modern amenities you want, like Roku TV ...
Three Dolphins sits in a beautiful location with great ocean views

Three Dolphins

5 4+

Anguilla

Near Beach | Pool | AC

Details
This waterfront villa would be great for a few couples or a large family. There's two queen suites upstairs and two twin suites downstairs, so adults can relax in solitude ...
Water's Edge Villa is located on Blowing Point
2, 4 BR rates.

Water's Edge

5 5

Anguilla

Near Beach | Pool | AC

Details
Windfall is an amazing family vacation destination for any age group. It has three king suites, one queen, and two twin beds, so you could stay here with young children ...
Windfall Villa's open-air pool with retractable canopy

Windfall

5 6

Barbados

Pool | AC

Details
Casa Oasis is the place to go for a family vacation in Costa Rica. The two double suites, ping pong, foosball table, pool, and resort amenities will keep any teen ...
Casa Oasis Villa is located above Los Sueños popular Eco Golf Course

Casa Oasis

5 5

Costa Rica

Pool | AC

Details
Casa Puesta del Sol manages to be extremely chic and elegant without feeling stuffy or uncomfortable. It has high ceilings, gleaming surfaces, an open design, and wrought iron accents. There's ...
Casa Puestra del Sol Villa is located the neighborhood of Vista Tres Bahias in Los Suenos

Casa Puesta del Sol

5 5

Costa Rica

Pool | AC

Details
Seagrace is a bright, modern villa right on the water. It has gorgeous views, tons of natural light, and a wide selection of activities. The villa provides bicycles, kayaks, and ...
Seagrace Villa is located on the Ailla Canal in the gated community of Leeward

Seagrace

5 4

Leeward, Turks and Caicos

Pool | AC

Details
Abita Kai is a great choice for a multi-generational family vacation. With three bedrooms spread across two levels of the main house and two bedrooms in the guest cottage, there's ...
Abita Kai is located on a beautiful stretch of white sand beach in Cayman Kai
Specials.

Abita Kai

5 5

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Westland Heights 9 is a chic choice for your next Barbados vacation. It's on the west coast, which is one of the most envied locations on the island, and it's well-designed ...
Westland Heights 9 is located in a community on the west coast

Westland Heights 9

5 5

Barbados

Pool | AC

Details
Vision Beach is a gorgeous, luxurious villa on Turks and Caicos’s most envied location: Grace Bay Beach. Not only does it have a full staff, it also enjoys 240 feet ...
Vision Beach Villa is located directly on Grace Bay Beach

Vision Beach

5 5+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Seascape is the perfect place for five couples to experience the best part of Turks and Caicos. This chic five-bedroom villa offers first-class amenities, unobstructed ocean views, and direct beach ...
Seascape Villa is located on a beautiful stretch of Grace Bay Beach
Specials.

Seascape

5 5+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Portofino enjoys luxurious design inside and out, from the open exterior to the elegant living area. The kitchen is well-designed for any home cook. Grace Bay Beach is steps away, ...
Portofino sits directly on Grace Bay Beachfront and each have private infinity pools
Specials.

Portofino

5 5+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
Bajan Heights is a luxurious villa with five-star amenities and daily housekeeping. The villa is in a gated community near golf, tennis, and dining.
Bajan Heights is located in Royal Westmoreland
4 BR rate.

Bajan Heights

5 5

Barbados

Pool | AC

Details
Tolumnia is a beautiful, spacious villa for group vacations. There’s tons of lounging space outside around the pool and veranda, and the ocean views are unbelievable. If you all ...
Tolumnia is located on an acre of national park overlooking the bay of Willoughby
2-4 BR rates.

Tolumnia

5 4+

English Harbour, Antigua

Pool | AC

Details
Rotunda is a great, family-friendly villa rental with gorgeous views and privacy. It’s elevated above Peter and Trunk Bay, so you can easily get to the beach but also ...
Rotunda Villa is located above Peter Bay and Trunk Bay

Rotunda

5 5+

Peter Bay, St. John

Pool | AC

Details
If you want the resort experience without the crowds, Beach Enclave at Grace Bay is for you. Each villa enjoys full-service butlers, an acre of property with beachfront, sleek architecture, ...
Beach Enclave at Grace Bay
Specials.

BE - Beach Front at Grace Bay

5 4+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
Baltazar is a bohemian haven. There are tons of natural elements incorporated into the decor, and every room has a comfortable, warm layout perfect for families or a few couples. ...
Villa Baltazar is located on St. Martin’s northern coastline and overlooking the island of Pinel
3, 4 BR rates.
Specials.

Baltazar

5 5

Cul de Sac (French Side), St. Martin

AC

Details
Moonshadow combines privacy and luxury at the ocean’s edge. This villa has the most gorgeous view of the ocean, sunsets, and adjacent bays. You can get to the beach ...
Moonshadow Villa is located on the tip of Sapodilla Bay

Moonshadow

5 4

Chalk Sound, Turks and Caicos

Near Beach | Pool | AC

Details
This five-bedroom villa is a great choice for travelers who want convenience, space, and luxury. It’s a couple minutes from Grace Bay Beach, but has a whole acre of ...
Beach Enclave 5 bedroom Ocean View at Grace Bay
Specials.

BE - 5 Bedroom Ocean View at Grace Bay

5 5+

Grace Bay, Turks and Caicos

Near Beach | Pool | AC | Resort Villa

Details
Etoile Brillante is the place to be for gorgeous ocean and sunset views just outside of Gustavia’s city center. The beach, shops, and restaurants are all within a 10-minute ...
Etoile Brillante Villa with amazing views
3, 4 BR rates.

Etoile Brillante

5 5+

Lurin, St. Barts

Pool | AC

Details
Only You is a totally gorgeous villa with a huge sundeck, two generously sized pools, and really modern interiors. There's tons of space inside and out to relax and eat, ...
Only You Villa is located in the gated Domaine Du Levant

Only You

5 5

Petit Cul de Sac, St. Barts

Near Beach | Pool | AC

Details
Raku has everything a big family could want for a multi-generation family vacation. There's a guest house where the grandparents or kids could sleep, two suites for younger families, and ...
Raku is located on the southern most end of Virgin Gorda on Crooks Bay

Raku

5 5+

Virgin Gorda, BVI, British Virgin Islands

Pool | AC

Details
Embrace offers endless luxury, super modern amenities, and an unbelievable location near St. Barts' best activities. A full staff caters to your every need, and the villa's amazing theater, game ...
Embrace Villa is located on a hillside in Gustavia

Embrace

5 5

Gustavia, St. Barts

Pool | AC

Details
Vacationing will be as much fun for your kids as it is for you at Sand Castle Villa. It has everything you could possibly think of to keep the children ...
Sand Castle Villa is located on the North Shore of Anguilla with views of the Atlantic Ocean
3 BR rate.
Specials.

Sand Castle Villa

5 5+

Anguilla

Beachfront | Pool | AC

Details
La Mer West, located on the shores of Sapodilla Bay in Chalk Sound, is a stunning, family-friendly option for an amazing holiday. This modern home with water frontage features outdoor ...
Le Mer Villa South is located on Sapodilla Bay in Chalk Sound

La Mer Villa West

5 5

Taylor Bay-Sapodilla Bay, Turks and Caicos

AC

Details
Envision is ideal for any family looking to unwind by the sea. This delightful beachfront villa is modern, with ample space inside and outdoors to relax. Guests may lounge by ...
Envision Villa is located beachfront on Cayman's North Side

Envision

5 3+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
If you want to have a peaceful relaxing holiday, Ocean Breeze villa is perfect. You and your family will have all the elements for extreme fun in the sun with ...
Ocean Breeze is located directly on Chalk Sound

Ocean Breeze

5 5

Chalk Sound, Turks and Caicos

Pool | AC

Details
If you're looking for a place to kick back and relax, you won't find anywhere better than Hidden Treasure in Cayman! With 5 bedrooms, a beachfront location, and 100 feet of sandy ...
Hidden Treasure Villa is centrally located on the southern coast

Hidden Treasure

5 4+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Nestled in the pristine beauty of Tortola, British Virgin Islands, Cooper Bay is a captivating haven that offers discerning travelers the ultimate escape. Seamlessly blending luxury, comfort, and breathtaking vistas, ...
Views from Cooper Bay Villa

Cooper Bay villa

5 5+

Tortola, BVI, British Virgin Islands

Pool | AC

Details
Cornucopia is a special place where you will feel welcomed and immediately relaxed. The adults-only (age 15+) luxury property includes daily chef-cooked breakfasts and its location near Little Trunk Bay makes ...
Cornucopia Villa photo
2-4 BR rates.

Cornucopia Villa

5 6

Virgin Gorda, BVI, British Virgin Islands

Near Beach | AC

Details
Pallina Villa is a place you can bring your family and feel completely at home. There is a comfortable ambience here that won't leave you on pins and needles worrying ...
Pallina Villa is located perched on a hillside beside Magen’s Bay

Pallina Villa

5 3+

St. Thomas, USVI

Pool | AC

Details
Casa Bougainvillea is the ideal spot for guests who love water sports and beach combing. Situated right on the water's edge, this property lets you enjoy the waves, snorkeling, and ...
Casa Bougainvillea Villa has a beautiful private pool

Casa Bougainvillea Villa

5 4

St. Thomas, USVI

Beachfront | Pool | AC

Details
The open floor plan and high vaulted ceilings throughout this villa, coupled with the stone and tile work, keep the house cool on the warmest days. If you're a sun ...
Silk Cotton Villa is located in Estate Mafolie with views of Charlotte Amalie's harbor
2-4 BR rates.

Silk Cotton Villa

5 5

St. Thomas, USVI

Pool | AC

Details
Paraiso Azul is a comfortable, family-friendly villa perfect for large groups. Its huge deck, living room, and kitchen are well designed for parties and gatherings of all types. Each bedroom ...
Paraiso Azul is located in Monte and overlooks Rendezvous Bay

Paraiso Azul

5 5+

Rendezvous Bay, St. John

Pool | AC

Details
The Carib House is located on the south coast of Antigua, and is perfect for your next getaway, honeymoon or vacation with friends. With space for entertaining up to eighty ...
The Carib House photo
2-4 BR rates.

The Carib House

5 4

Antigua

Near Beach | Pool | AC

Details
This beachfront property is made for relaxation. The patio area around the pool is surrounded by cushioned loungers, so you can nap or read while you soak up the warm ...
Caribbean Wind Villa is located on the beach at Mahoe Bay
2-4 BR rates.

Caribbean Wind Villa

5 5

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool | AC

Details
Casa Cervo is just steps away from the white sands of Baie Rouge with its secluded beaches, blue skies, and gentle trade winds. You can go beachcombing in the early ...
Casa Cervo is an idyllic beach front villa - located directly on Baie Rouge
3, 4 BR rates.
Specials.

Casa Cervo Villa

5 5

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

Details
If you want to be pampered, come to Sea Villa. In addition to its stunning common areas, you have access to an infinity pool, a Jacuzzi, outdoor space, and a ...
Sea Villa is situated facing the beach with amazing unobscured ocean views

Sea Villa at Long Bay Villas

5 5+

Anguilla

Beachfront | Pool | AC

Details
At Long Bay Villas, you can expect to be relaxed and pampered. There's a full staff, water sports, four king suites, and a bunk room, so everyone you travel with ...
The luxurious Sand Villa at Long Bay

Sand Villa at Long Bay Villas

5 4+

Anguilla

Beachfront | Pool | AC

Details
Dene Court is a five-bedroom, six-bathroom villa within Barbados' famous Sandy Lane Estate. The full staff will take care of every need, from cooking to cleaning to everything in between. ...
Dene Court Villa is located in the prestigious Sandy Lane on the Old Nine Golf Course
3, 4 BR rates.

Dene Court - Sandy Lane

5 5+

Barbados

Pool | AC

Details
Comfort is key at Serena Villa. You can relax outside in the large pool with ocean views, the furnished gazebo, or take a few steps to sunbathe on Baie Longue ...
Serena Villa is located just above Baie Rouge Beach
Specials.

Serena Villa

5 5+

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

Details
If you want to be amongst nature, there's no place like Brigand Hill. Surrounded by 500 acres of a former plantation, this villa enjoys gorgeous, unobstructed views and easy ocean access. ...
Brigand Hill Villa has a very private location with a relaxing pool

Brigand Hill

5 4

Anse La Raye, St. Lucia

Near Beach | Pool

Details
Rent the Two Palms property as a five-bedroom combo, or divide the units between groups of six and four. This rental is just off the waters of Meads Bay, and ...
Beach Palm

Twin Palms Villas

5 5+

Anguilla

Near Beach | Pool | AC

Details
Aquamare Villa 1 enjoys beachfront access, a tranquil location, and gorgeous views. Guests can snorkel, beach comb, kayak, paddle board, and dive into the sea all steps from their back door. ...
Aquamare Villas are located on Mahoe Bay Beach

Aquamare Villa 1

5 5+

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

Details
The beach is just steps away from Alizee Villa. Not just any beach, but Taylor Bay! Taylor Bay is a great choice for families, since the water is clear, shallow, ...
Alizee Villa in Chalk Sound

Alizee Villa

5 5

Taylor Bay-Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Melissa Villa is an excellent choice for any traveler who wants privacy and luxury all at once. You'll be steps from the beach, minutes from activities and shops, and a ...
Melissa Villa is on the West Coast of St. James in a gated community with a short walk to the beach

Melissa Villa

5 5

Barbados

Near Beach | Pool | AC

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 room table made from a Balinese monastery door. Art enthusiasts ...
Carlota Villa is located on a hillside overlooking Peter Bay

Carlota Villa

5 6+

Peter Bay, St. John

Pool | AC

Details
If you like vibrant colors and great views, you'll love Villa Amarilla. Both the interiors and exteriors are done in a Caribbean style with an Italian vibe and Moroccan influences. ...
Beautiful Anguillan sunset from the back porch at Amarilla
3, 4 BR rates.

Villa Amarilla

5 5+

Anguilla

Near Beach | Pool | AC

Details
Aprés Sea Villa has nearly 7,000 square feet of indoor and outdoor living space, with ocean views and modern amenities throughout. The villa is fully air-conditioned, which is always a ...
Aprés Sea Villa in St. John

Aprés Sea

5 5+

Rendezvous Bay, St. John

Pool | AC

Details
Java Bay will put you in the mood for meditation and introspection. It's a place where you can connect with the sea, the sky, and the locals. Located just minutes ...
Java Bay is located in Calijanda in Westmoreland and is less than two miles from the beach
4 BR rate.

Java Bay

5 5

Barbados

Pool | AC

Details
Decaj Villa is a great retreat for a family with young children, or two families for that matter. You'll love the views of both the Cas En Bas beach and ...
Decaj Villa is located in Cap Estate with views of the ocean in the distance
3 BR rate.

Decaj Villa

5 4+

Cap Estate, St. Lucia

Pool | AC

Details
You'll think you're in an Asian palace when you arrive at Golden Pavilion. You can relax on the covered patio or workout in the fully-equipped gym. A short trip down ...
Golden Pavilion photo
4 BR rate.

Golden Pavilion

5 5+

Tortola, BVI, British Virgin Islands

Pool | AC

Details
Whether you're headed to Barbados for a family vacation, honeymoon, or a getaway with friends, Casuarina House is a great choice. The laundress, cook, and housekeeper are there to serve, ...
Casuarina Villa has a pool right on the golf course
4 BR rate.

Casuarina House

5 5+

Barbados

Pool | AC

Details
Blue Diamond's beachfront luxury leaves nothing out. There's a sound system, WiFi, and air-conditioning throughout the villa, a bar, a media room, a gym, a grand piano, and a huge ...
Blue Diamond Villa at Altamer is set on a prestigious location on Shoal Bay

Blue Diamond Villa at Altamer

5 7

Anguilla

Beachfront | Pool | AC

Details
The Beach House is truly a property with something for everyone. You might want to try some rock climbing on the cliffs that descend from the house to the water's ...
The Beach House sits on Mail Bay

The Beach House

5 3+

St. Thomas, USVI

Beachfront | AC

Details
If you want true pampering, come to Sky Villa. Things like daily housekeeping service are par for the course. Speaking of the course, this villa is very close to the ...
Sky Villa is the most private of the Long Bay Villas located just off the beach

Sky Villa at Long Bay Beach Villas

5 4+

Anguilla

Near Beach | Pool | AC

Details
Take a path down to the beach from Solitude House and enjoy the ease of access to snorkeling and the Caribbean weather. The villa has a book library for those ...
Solitude House is situated above the calm waters of Solitude Bay
1-4 BR rates.

Solitude House

5 4+

St. Croix, USVI

Near Beach | Pool | AC

Details
Champagne Shores is the perfect villa rental for design lovers. The sea-facing wall is made up of huge panes of glass from top to bottom, and the terrace is made ...
Champagne Shores villa sits on a secluded beach near Pelican Bay

Champagne Shores

5 5+

Anguilla

Near Beach | Pool | AC

Details
Whispering Winds is a great choice for a big family vacation. There are two suites on the main level, two on the lower level, and a separate guest cottage with ...
Whispering Winds Villa is located on St. Croix’s east end
1-4 BR rates.

Whispering Winds Villa

5 4

St. Croix, USVI

Beachfront | Pool | AC

Details
Cinnamon Ridge emphasizes St. John’s natural beauty and serenity through tropical gardens, scenic views, and an expansive outdoor space. The house’s sleek lines contrast the rolling hills, tiny ...
Cinnamon Ridge Villa is located on a hillside above Cinnamon Bay

Cinnamon Ridge Villa

5 5

Catherineberg, St. John

Pool | AC

Details
Kalorama Villa is fabulously unique! This artsy villa mixes contemporary style with such items as the island's traditional, native stone. And with the panoramic views, it's no wonder this villa ...
Kalorama Villa is located in Virgin Grand Estates
3, 4 BR rates.

Kalorama Villa

5 4+

Virgin Grand Estates, St. John

Pool | AC

Details

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