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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.

St. Bernard's Hill House is just special. You can see the iconic purple roof on top of the hill from a distance and you know it's a special place when ...
St. Bernard's Hill House Villa is located on a tropical hillside overlooking Belmont
Specials.

St. Bernard's Hill House

5 0

Tortola, BVI, British Virgin Islands

Pool | AC

Details
You probably won't be able to tear yourself away from LaVida long enough to take advantage of the nearby shopping and dining, because there is so much to do right ...
La Vida Villa is located on a hillside overlooking Nail Bay

La Vida Villa

5 5+

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

Details
Bellevue is a great choice for large families or friends. There's a great view of the sea and the hillside from the glass balcony, and all five of the bedrooms ...
Bellevue Villa is located
2-4 BR rates.

Bellevue Villa

5 5

Marigot, St. Barts

Pool | AC

Details
Located in Punta Cana, this resort villa will spoil you with wood-paneled ceilings, your own pool and a gorgeous beach within walking distance. Enjoy golf and tennis as well as ...
Villa Arrecife 25 is located in the gated community of La Cana Resort & Club

Villa Arrecife 25 at Tortuga Bay

5 5

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
When staying at this villa, you will be privy to a one-of-a-kind island deck with deck chairs located just above the sea. What an enjoyable way to relax after playing ...
The pool at Palm Beach is just steps away from the beach
4 BR rate.

Palm Beach Villa

5 5

Lorient, St. Barts

Near Beach | AC

Details
Eternity Villa will make you wish you could stay there forever! Located just minutes from restaurants and stores, the villa has 5 large bedrooms with every amenity you could ask for. ...
Eternity villa is tucked into at tropical hillside above Flamands

Eternity Villa

5 5

Flamands, St. Barts

Pool | AC

Details
This modern, minimalist villa has gorgeous design, gorgeous views, and gorgeous amenities! Fleur De Mer is all about luxury and relaxation, with glass doors throughout and an unbelievable panoramic ocean ...
Fleur De Mer Villa is located in Colombier with amazing views

Fleur De Mer Villa

5 5

Colombier, St. Barts

Pool | AC

Details
Lantano Villa is so comfortable and scenic! Its the type of home that makes you want to take your shoes off, kick back, and relax in the sun all day. ...
Lantano Villa is located in Peter Bay Estate overlooking the Caribbean and the north shore
Specials.

Lantano Villa

5 5+

Peter Bay, St. John

Pool | AC

Details
Set on the cliffs in Terres Basses, Esprit de la Mer Villa is the ideal choice for large families or groups vacationing in St. Martin. This 5 bedroom, 5.5 bathroom has something ...
Esprit de la Mer is located on a clifftop with Caribbean vies just off Baie aux Cayes
4 BR rate.
Specials.

Esprit de la Mer Villa

5 5+

Terres Basses (French side), St. Martin

Near Beach | Pool | AC

Details
Paprika Villa offers stately elegance on the Turks and Caicos beachfront. With five spacious bedrooms, a dining room for ten, and snorkeling right outside your door, you may never want ...
Beach Villa Paprika is located on Grace Bay Beach

Paprika Villa

5 5+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Tamarind is perfect for two families to share, because each level has its own living area and balcony or terrace. Both living areas have a library and dining space. The ...
Tamarind Villa is located in Island Harbor just minutes from Shoal Bay East
2, 4 BR rates.

Tamarind Villa

5 5

Anguilla

Pool | AC

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 Grace has everything you need to experience the laid back ...
Amazing Grace Villa photo
Specials.

Amazing Grace Villa

5 5+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Beaches Edge villa has a smart design that maximizes the ocean views. Of course there's a pool, daily maid service, and a concierge, but there's also full air-conditioning, an outside ...
Lounge by the pool and enjoy amazing ocean views at Beaches Edge East Villa

Beaches Edge

5 5+

Anguilla

Near Beach | Pool | AC

Details
At La Danse Des Etoiles Villa in the Pointe Milou area of St. Barts, guests are invited to experience relaxation like never before. This spacious villa comes with 5 bedrooms with ...
La Danse Des Etoiles Villa photo
3 BR rate.

La Danse Des Etoiles Villa

5 6

Pointe Milou, St. Barts

Pool | AC

Details
At Castaway villa, you’ll find distinctive features few other holiday rentals can offer, including handmade furniture, four beachfront master suites, and a freshwater swimming pool complete with an infinity-styled ...
Castaway Villa is located beachfront on Thompson Cove

Castaway Villa

5 5

North Shore, Turks and Caicos

Beachfront | Pool | AC

Details
Clear aquamarine water packed with beautiful marine animals. A secluded beach with calm water just waiting for you. It is not just your Monday morning fantasy. It is a reality ...
Aerial view of Coral Kai Villa on Rum Point Grand Cayman
Specials.

Coral Kai

5 5

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Tradewinds is a great choice if you want to be relaxing outside as much as possible. There’s two huge gazebos, one for dining and one for lounging. The wet ...
Tradewinds Villa is located in the Sandy Lane neighborhood

Tradewinds Villa

5 5

Barbados

Pool | AC

Details
La Petite Sereine is definitely luxurious. The decor is beautiful, the view is beautiful, the outdoor space is beautiful. I highly recommend this villa for any luxury vacation.
Pool at La Petite Sereine overlooking the ocean

La Petite Sereine Villa

5 6

Pointe Milou, St. Barts

Pool | AC

Details
Cayman Sands is a great family vacation villa for peace and quiet. There are two children's bedrooms, two master bedrooms, and a guest cottage with kitchenette. The pool terrace is ...
Cayman Sands is located in Old Man Bay along a beautiful stretch of white sandy beach
Specials.

Cayman Sands

5 5

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Mango Manor is a great choice for your next family vacation or celebration. It's super private but still within easy reach of everything. The views are absolutely stunning and nearly ...
Mango Manor

Mango Manor

5 5

Tortola, BVI, British Virgin Islands

Pool | AC

Details
What is there not to love about Kai Conut Villa. This ocean front property is open and airy with five bedrooms and offers great amenities to help you relax. You ...
The pool at Kai Conut is just steps away from the beach
Specials.

Kai Conut Villa

5 3

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
This is the perfect location to bring the family together. The house is spacious and inviting. There are five bedrooms that have their own ensuite bathrooms and then a huge ...
Reef Romance Villa has an ideal oceanfront location on Rum Point
Specials.

Reef Romance Villa

5 5

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Expect a grand and luxurious vacation when you come to Still Fathoms. This is an exquisite and unique five bedroom home with a tasteful and modern sea life theme throughout ...
Still Fathoms is a super stylish villa just steps away from the beach
4 BR rate.

Still Fathoms

5 5+

Barbados

Beachfront | Pool | AC

Details
Windward Villa is spacious, exclusive, and totally perfect for a group of 10. It's part of the Sandy Lane Resort, so you have direct access to the private Sandy Lane Beach ...
Windward Villa in Sandy Lane offers luxurious amenities

Windward - Sandy Lane

5 5

Barbados

Pool | AC

Details
Villa Isla is not only exquisite, it feels like heaven on earth. Large palm trees line the entrance, and the cooling ocean breeze wraps around the house. Each of the ...
Amazing infinity edged pool on Long Bay Beach at Villa Isla

Villa Isla

5 5+

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Outrigger House is great for groups or families that want to have tons of space under one roof. There are four bedrooms and each has large, glass doors allowing you ...
Outrigger Villa photo

Outrigger Villa

5 5+

St. Thomas, USVI

Pool | AC

Details
The layout of Reefside ensures that everyone in your party has beautiful rooms, private bathrooms, and complete privacy. The common areas are comfortable and spacious, and the pool deck is ...
Views into Chocolate Hole Bay from Reefside Villa
1-4 BR rates.
Specials.

Reefside Villa

5 5+

Chocolate Hole, St. John

Near Beach | Pool | AC

Details
Queens Fort 10 is perfect for any group who wants to upgrade their Barbados vacation. The property is within short walking distance to St. James Beach, and with its sizable yard ...
Queens Fort #10 is located in St.James on the West coast close to St. James Beach

Queens Fort # 10

5 5+

Barbados

Near Beach | Pool | AC

Details
Sky Blue has incredible views of the water and a spacious, open floor plan that's perfect for a relaxing getaway. The outdoor area is pretty impressive, and a few of ...
Relax by the pool and enjoy the ocean view at Sky Blue
2-4 BR rates.
Specials.

Sky Blue

5 5+

Dawn Beach (Dutch side), St. Martin

Near Beach | Pool | AC

Details
When I think of Firefly Villa, two words come to mind: grand and spacious. The decor is so chic, it looks like its out of a magazine, and all the ...
View from Old Trees#6 Firefly

Old Trees #6, Firefly Villa

5 5+

Barbados

Beachfront | Pool | AC | Resort Villa

Details
Galley Bay Heights #014 is a cozy, nearly beachfront villa that would be great to share with three other couples. There's plenty of ways to stay entertained here, with two bookshelves, ...
Aerial view of Galley Bay Heights Villa #104 and the beautiful beachfront
2 BR rate.

Galley Bay Heights Villa- #014

5 4

Galley Bay, Antigua

Near Beach | Pool | AC

Details
Viento has all the space and privacy you want in a large villa, especially with a detached honeymoon suite–it’s fantastic for families with older kids. The villa shows ...
Viento Villa photo

Viento Villa

5 5+

St. Thomas, USVI

Pool | AC

Details
Outer Banks is an ideal villa for large groups, families, or couples traveling together. Overlooking Brewers Bay Beach, guests will have breathtaking views of the turquoise waters. Whether you keep ...
Outer Banks Villa situated above Brewers Beach
2-4 BR rates.

Outer Banks

5 5

Tortola, BVI, British Virgin Islands

Near Beach | Pool | AC

Details
Mermaid Falls Villa is a beautiful home with even more beautiful views. The ocean stretches as far as the eye can see in either direction, with mountains on the horizon. ...
Aerial view of the villa

Mermaid Falls Villa

5 5+

Peter Bay, St. John

Pool | AC

Details
Ridgemont is bright, open, and spacious as all get out–perfect for any group of 10. The pool is centered between the main house and guesthouse and is THE place to ...
Ridgemont House sits on a hillside at the divide between Long Bay and the Sir Francis Drake Channel
3, 4 BR rates.

Ridgemont House

5 6

Tortola, BVI, British Virgin Islands

Pool | AC

Details
This villa manages to be luxurious and family friendly at the same time. Four bedrooms plus a bungalow make the space a great retreat for a family reunion. It's easy ...
BOM Villa is located on the beach in St. Jean Bay

BOM Villa

5 5

Saint Jean, St. Barts

Beachfront | Pool | AC

Details
This villa is great for a family. Most of the bedrooms are upstairs, and there's terraces on both levels so everyone can take in the view. Plus, Grace Bay is ...
Saving Grace Villa is located on the far northeast end of Grace Bay
4 BR rate.

Saving Grace Villa

5 3

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
This villa is comfortable, chic, and well equipped. The view is amazing, but the al fresco dining area is my favorite aspect. Nothing is within walking distance, which lends to ...
Bibi is located on a hillside overlooking Grand-Cul-de-Sac
2-4 BR rates.

Bibi Villa

5 5

Vitet, St. Barts

Pool | AC

Details
The sights both inside and out are unbelievable here. Take in the waters of Long Bay Beach from anywhere in the villa, or hop the set of stairs to the ...
Aguaribay Villa is located on a beautiful stretch of Long Bay Beach

Aguaribay Villa

5 5+

Long Bay, Turks and Caicos

Beachfront | Pool | AC

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

Villa Corales 18

5 5+

Punta Cana, Dominican Republic

Beachfront | Pool | AC | Resort Villa

Details
This villa's outdoor space almost reminds me of a James Bond movie. The open view is sure to induce heavy daydreaming and relaxation, and the outdoor bar certainly helps! This ...
Castle Rock Villa photo
2-4 BR rates.

Castle Rock Villa

5 5

Camaruche, St. Barts

Pool | AC

Details
This villa is amazing for entertaining family and friends alike. There are three king suites and two queen suites, so couples can relax in peace. The exterior is absolutely gorgeous, ...
Amandara Villa is located on a cliff side in Terres Basses
4 BR rate.
Specials.

Amandara Villa

5 5

Terres Basses (French side), St. Martin

Pool | AC

Details
Sandy Beaches is one of the most economical rentals for a large group, especially when you consider just how close it is to Long Bay Beach– you’re right on ...
Sandy Beaches Villa is located directly on Long Bay Beach
3 BR rate.

Sandy Beaches Villa

5 5

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
This villa is great if you want privacy, modern amenities, and don't mind being a short drive from the beach. Calypso Delight has a cozy terrace with great views, and ...
Calypso Delight Villa overlooks Magen's Bay Beach

Calypso Delight

5 5

St. Thomas, USVI

Pool | AC

Details
With a pool that goes on forever and panoramic views, I don't see how anyone wouldn't love Ginger Villa. I really love the decor, and the year-round sunset view doesn't ...
Ginger Villa sits in the hills above Lorient Bay
2-4 BR rates.

Ginger

5 5

Petite Saline, St. Barts

Pool | AC

Details
This resort villa is in a low traffic neighborhood just five minutes from the airport and Grace Bay, and has a modern, bohemian vibe. You can walk down your own ...
Beach Enclave Beachfront Villas offer amazing ocean views
3, 4 BR rates.
Specials.

BE - Beach Front Villas North Shore

5 5

North Shore, Turks and Caicos

Beachfront | Pool | AC

Details
Ardisia is one of the best choices for a luxurious St. John vacation. It has chic decor, luxury amenities, and five spacious bedrooms with tons of privacy and ocean views. ...
Ardisia Villa is located on Great Cruz Bay
1-4 BR rates.

Ardisia Villa

5 5+

Great Cruz Bay, St. John

Pool | AC

Details
Sunset Close is very modern, beautifully decorated, extremely comfortable and well-stocked. The Silly Creek area is known for its peace and quiet, and only minutes from stunning Chalk Sound and ...
Perfect patio to enjoy waterfront views at Sunset Close Villa

Sunset Close

4 4

Taylor Bay-Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Villa B53 at Tortuga Bay

Villa B53 at Tortuga Bay

4 4+

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
Blue Papaya is the perfect villa for family vacations. One of the four bedrooms enjoys a lounge and wet bar, and each suite has exterior access, gorgeous views, and an ...
Blue Papaya photo
1-3 BR rates.

Blue Papaya

4 4

Virgin Grand Estates, St. John

Pool | AC

Details
SAX in St. Barts would be perfect for a couples' getaway or a family vacation. Two of the bedrooms are connected, and the fourth bedroom is in its own bungalow. ...
SAX Villa photo
2, 3 BR rates.

SAX Villa

4 4

Saint Jean, St. Barts

Near Beach | AC

Details
Casa Bella's Spanish architecture and gardens make it stand out. I loved lounging by the pool as breezes blew through the palm leaves above me. The al fresco dining area ...
Casa Bella photo
Specials.

Casa Bella

4 3

Barbados

Near Beach | Pool | AC

Details
Terre Azure is a dream! I'd recommend this villa for family vacations and getaways with friends, because the bedrooms are private and spacious, yet under the same roof. I love ...
Terre Azure Villa is located in Terres Basses with great views of Simpson Bay
2, 3 BR rates.
Specials.

Terre Azure

4 4+

Terres Basses (French side), St. Martin

Pool | AC

Details
Turquoise is a gorgeous, modern villa that is ideal for a family vacation. Grace Bay Beach is just steps away, which is one of the biggest draws to Turquoise villa. ...
Aerial view of the Turquoise Villa property

Turquoise

4 4

Grace Bay, Turks and Caicos

Near Beach | Pool | AC

Details
Etoile de Mer has an incredible location just off Taylor Bay beach. There's a wonderful restaurant easily walkable that sits on Chalk Sound and Sapodilla Beach is just a couple ...
Etoile De Mer pool with furnished gazebo

Etoile De Mer

4 4

Taylor Bay-Sapodilla Bay, Turks and Caicos

Near Beach | Pool | AC

Details
Absolute Beach Villa is a great choice for travelers who want to experience island living at its fullest. It's within walking distance to restaurants, the grocery store, and bars, and ...
Relax on the covered patio with beach and harbor views

Jolly Harbour #008 - Absolute Beach

4 4

Jolly Harbour, Antigua

Beachfront | Pool | AC

Details
The Penthouse Suite in the Villas at Grace Bay Club is perfect for travelers who want to be as close to Grace Bay as possible without sacrificing resort amenities. The ...
Grace Bay Club Resort pool
Specials.

Grace Bay Club Penthouse Suite in the Villas

4 4

Grace Bay, Turks and Caicos

Beachfront | AC | Resort Villa

Details
Villa Islander is an architect's dream. Its surrounded by greenery, has floor-to-ceiling windows in every room, and uses only the most modern finishes. If you care more about location than ...
Villa Islander is located just off the famous Grace Bay Beach

Villa Islander

4 4

Grace Bay, Turks and Caicos

Near Beach | Pool | AC

Details
Imagine certainly fits my ideal vacation rental. It's right on the beach, still has privacy, and has modern interiors. There's a private chef and a housekeeper so no one has ...
Imagine photo

Imagine

4 4+

Barbados

Beachfront | Pool | AC

Details
Mirador is a great villa for a family or four couples who want to be as close to the beach as possible. It has tons of outdoor space, lounging and ...
Mirador photo
Specials.

Mirador

4 4+

Barbados

Beachfront | Pool | AC

Details

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