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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.

Eos is sleek, modern, and innovative. One of my favorite features is the retractable wall in each of the bedrooms that opens up the gorgeous surroundings. The design of this ...
Eos photo
Specials.

Eos

5 5+

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Helios is very sleek, so your vacation feels swanky and relaxing all at once. One of my favorite features is the retractable wall in each of the bedrooms and the ...
Helios Villa Long bay
Specials.

Helios

5 5+

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
This villa is equidistant from Turks and Caicos Islands Tennis Club, Turtle Cove, and Smiths Reef. Not only is the villa gorgeous, but the location is perfect for your family ...
Hyperion photo
Specials.

Hyperion

5 5+

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Tip of the Tail is so private, you'll feel like you have the island all to yourself. It has an amazing view over the ocean, and has its own stretch ...
Tip of the Tail Villa sits on the peninsula for which it is named

Tip of the Tail

5 6

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

Details
Beach Enclave Ocean View Villas are stunning beachfront villas perfect for travelers who appreciate elegant design and want to spend time on the water. These resort villas have direct access ...
The pool and view of the ocean from Beach Enclave Ocean View Villas
3, 4 BR rates.

BE - Ocean View Villas North Shore

5 5

North Shore, Turks and Caicos

Beachfront | Pool | AC

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

Magens Hideaway

5 4+

St. Thomas, USVI

Pool | AC

Details
Hesperides is one of a kind. The location couldn't be better either, because it's close to Sapodilla Bay and Las Brisas Restaurant. The sunset views are so beautiful that there's ...
Hesperides House has amazing uninterrupted ocean views

Hesperides House

5 5

Taylor Bay-Sapodilla Bay, Turks and Caicos

Pool | AC

Details
Starfish Villa is one of the more vibrant villas in the Punta Cana Resort. The villa itself is well-equipped, but the resort's amenities are even better. Drop your kids off ...
Starfish Villa is located in Punta Cana on the golf course

Starfish

5 5+

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
Coral Pavilion is chic and elegant, the perfect vacation rental if you want to feel like royalty. You’ll love staring at the ocean right outside the French doors, and ...
The luxury pool at Coral Pavilion Villa sits just a few yard from the beautiful Grace Bay Beach

Coral Pavilion

5 5

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Hilltime is perfect for any family or couples who want to relax by the sea with minimal fuss. This villa is clean and simple, with plenty of space to relax ...
Hilltime Villa is located on the north coast of Cayman in Rum Point

Hilltime

5 4

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
White Cottage is a great vacation rental for anyone who loves the ocean and privacy. It's in a quiet region of Grand Cayman, and sits steps away from the beach. ...
White Cottage is a great beachfront villa

White Cottage

5 3

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Great Bluff Estate is perfect for groups who want privacy and space. It's fully gated, and sits on the quiet, residential East End. The beach is practically deserted, and there's ...
Great Bluff Estates sits along the beautiful northern coast of Grand cayman
Specials.

Great Bluff Estates

5 7

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Alinna is a gorgeous one-level villa with views of Chalk Sound. I love it for family vacations or couples' getaways, since there's a kids' room and four equal Master Suites. ...
Alinna sits just along Chalk Sound with beautiful water views
Specials.

Alinna

5 6+

Chalk Sound, Turks and Caicos

Pool | AC

Details
Second Chances is a great choice for a relaxed getaway. It's 200 meters from Grace Bay, so you can go to the beach whenever you want, and its pool terrace is ...
Second Chances Villa has plenty of outdoor space for relaxing and entertaining

Second Chances

5 6

Leeward, Turks and Caicos

Near Beach | Pool | AC

Details
The Five Bedroom Beach Level residences are perfect for families or four couples to share. They're right on Grace Bay and have exclusive access to a superior level of service ...
The Grace Bay Club Estate
Specials.

Grace Bay Club Estate Five Bedroom Beach Level Pool Residence

5 4+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
Casa de la Playa is perfect for two families who want to vacation on St. Martin's glamorous west coast. It has four suites for adults and one children's suite with ...
Casa de la Playa Villa is located on Baie Longue in Terres Basses
3, 4 BR rates.
Specials.

Casa de la Playa

5 5

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

Details
This five-bedroom beachfront resort villa is absolutely gorgeous. It's on Long Bay, which is the quieter, windier sister to Grace Bay, and it's in a gated community with fitness facilities, ...
Beach Enclave Beach Front Villas on Long Bay
Specials.

BE - Beach Front Villa at Long Bay

5 5

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Nirvana is ideal for couples who want to vacation on the beach in style. The pool isn't massive, but who cares when the ocean is steps away? Four of the ...
Nirvana's pool deck and lounges

Nirvana

5 5

Barbados

Beachfront | Pool | AC

Details
Lime Tree is a cool villa to stay in because it combines Mediterranean architecture with cushy amenities. The master bedroom is like its own oasis, with a private bathroom and ...
Lime Tree Villa sits on a tropical hillside in the Peter Bay area
Specials.

Lime Tree at Peter Bay

5 4+

Peter Bay, St. John

Pool | AC

Details
La Case Créole is a great family vacation villa. It has six bedrooms spread across two levels, and every suite has its own bathroom and patio. The home feels ...
La Case Créole is located on a hilltop above St. Jean Bay
3, 4 BR rates.

La Case Créole

5 5

Saint Jean, St. Barts

Pool | AC

Details
Mirabelle is ideal if you want the beauty of Turks and Caicos without the crowds of Grace Bay. Sapodilla Bay is one of the less-populated beaches on Provo, but its ...
Mirabelle sits on a beautiful stretch of Sapodilla Bay Beach

Mirabelle

5 5+

Taylor Bay-Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

Details
This luxury rental sits right on Paynes Bay and is the only unit in the complex to have a private pool. It has super chic interiors and bedrooms that are ...
The Villa at the St. James is located beachfront on Paynes Bay Beach
4 BR rate.

The Villa at the St. James

5 5

Barbados

Beachfront | Pool | AC

Details
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

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

Tolumnia

5 4+

English Harbour, Antigua

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

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

BE - 5 Bedroom Ocean View at Grace Bay

5 5+

Grace Bay, Turks and Caicos

Near Beach | Pool | AC | Resort Villa

Details
Eternity Villa Estate in St. Thomas, USVI is a top-notch, luxurious vacation spot that offers a stunning, modern home with unbeatable views of the Caribbean coastline and Magens Bay. It ...
Eternity Villa Estate is located in a gated community overlooking Magens Bay Beach

Eternity Villa Estate

5 0

St. Thomas, USVI

Pool | AC

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
Specials.

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, M & M Cooper is a captivating haven that offers discerning travelers the ultimate escape. Seamlessly blending luxury, comfort, and breathtaking ...
Views from M & M Cooper Villa

M & M Cooper

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

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+

St. John

Pool | AC

Details
Aphrodite Mansion epitomizes contemporary elegance intertwined with Cycladic charm. Its infinity pool merges with the sea, offering a mesmerizing backdrop. Inside, a fully equipped kitchen flows into spacious living and ...
Aphrodite Mansion photo

Aphrodite Mansion

5 5

Mykonos, Greece

Pool | AC

Details
Discover Mas de l'Etoile in enchanting Provence. This stunning villa boasts renovated luxury, a sparkling pool, and a lit tennis court for endless fun. Perfect for family adventures or romantic ...
Mas de l'Etoile photo

Mas de l'Etoile

5 5

France

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

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