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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.

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
An exquisite retreat in Agios Lazaros, Mykonos. Enjoy uninterrupted views of the Aegean Sea and easy access to Psarou Beach. Relax in the outdoor pool or spacious seating area with ...
Villa Lazaros photo

Villa Lazaros

5 5

Mykonos, Greece

Near Beach | 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
Mas Daudet, a Provencal dream! Impeccable gardens, stunning renovations—perfect for families and friends. Modern comforts meet traditional charm, with a spacious kitchen, vibrant living areas, and seamless indoor-outdoor living. ...
Mas Daudet photo
4 BR rate.

Mas Daudet

5 5

Provence, France

Pool | AC

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
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
2 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
Peace Bay House is perfect for several families or a group with its ample square footage and many amenities to indulge in. An infinity pool and large deck that overlooks ...
Pease Bay House in Cayman

Pease Bay House - Platinum

5 5+

Grand Cayman, Cayman

Beachfront | 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
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 5+

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
Villa Mavi offers a luxurious island lifestyle with spacious open-plan living areas and stunning Aegean Sea views. Enjoy the expansive outdoor space with a large "Beach Entry" pool, BBQ, Jacuzzi, ...
Villa Mavi photo

Villa Mavi

5 5

Mykonos, Greece

Near Beach | Pool | 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
With direct beach access, it's ideal for sun-seekers. Enjoy the infinity pool's panoramic views. The traditional Mykonos-style villa boasts ample outdoor entertaining spaces and chic interiors. With five bedrooms, it ...
Barbarossa photo

Barbarossa

5 5

Mykonos, Greece

Near Beach | Pool | AC

Details
Indulge in sophisticated luxury amidst Ibiza's stunning countryside at Lujo Supremo. This contemporary retreat offers a seamless blend of modern comforts and a back-to-nature ambience. With breathtaking views of the ...
Lujo Supremo photo

Lujo Supremo

5 5

Ibiza, Spain

Pool | AC

Details
Bakkero Villa is a luxury villa that will wow you! With stunning ocean views and luxurious accommodations, you'll feel like a celebrity on vacation. Plus it can sleep up to 20 ...
Bakkero Villa in St. Thomas

Bakkero Villa

5 5+

St. Thomas, USVI

Pool | AC

Details
Uncover the magic of Le Mas d'Eygalières, just a stone's throw from Saint-Rémy-de-Provençe and Les Baux-de-Provence, this retreat is a symphony of luxury and location. With lavender ...
Le Mas d'Eygalieres photo

Le Mas d'Eygalieres

5 5+

France

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
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
Sitting beachfront, Aquazure offers all of the necessities for an ideal Caribbean experience. It has a clean modern look and proximity to not only the beach, but to local shops ...
Beachfront Villa Aquazure in Leeward

Beachfront Villa Aquazure

5 5

Leeward, Turks and Caicos

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
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

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