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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.

Built on top of a small island cliff, Villa Turquesa can't help but show off a brilliant view of Sapodilla Bay. You can stare at the sea from the infinity ...
Enjoy amazing views of the Caribbean from the pool at Turquesa Villa

Turquesa Villa

4 4+

Taylor Bay-Sapodilla Bay, Turks and Caicos

Near Beach | Pool | AC

Details
Agave Azul Villa is great for friends or couples traveling together. The home is very private and sits on a hillside overlooking Grand Cul de Sac, so the ocean and ...
Agave Azul villa is located on a hillside overlooking Grand Cul de Sac
2, 3 BR rates.

Agave Azul Villa

4 4

Vitet, St. Barts

Pool | AC

Details
Agora Villa is the place to be for an unforgettable vacation. The pool and terrace are amazing, there’s tons of space to relax and dine al fresco in or ...
Amazing infinity edge pool at Agora Villa
2, 3 BR rates.
Specials.

Agora Villa

4 4+

Terres Basses (French side), St. Martin

Pool | AC

Details
LUZ Villa's best feature is its exterior. You can relax around the large living area, the outdoor dining table, the wet bar, or the L-shaped pool. The terraces, pool area, ...
LUZ Villa enjoys amazing views of Lorient Bay
2 BR rate.

LUZ Villa

4 4

Camaruche, St. Barts

Pool | AC

Details
The four-bedroom penthouse suite at Smugglers Cove comes with everything you need for the perfect island vacation. The 60-ft balcony overlooks the ocean, and the sunset views can be enjoyed ...
Smugglers Cove #7 Penthouse overlooks Paynes Bay

Smugglers Cove #7- Penthouse

4 5+

Barbados

Beachfront | Pool | AC

Details
With 4 bedrooms and 4 bathrooms, this super private cliffside villa on St. Barts is easily one of the most upscale properties on the island and is perfect for larger groups. The ...
Located on the tip of the island jetty near Lorient Bay - Cap Au Vent enjoys great ocean views
1-3 BR rates.

Cap Au Vent Villa

4 4

Pointe Milou, St. Barts

Pool | AC

Details
Few places are quite as tourist-friendly as Barbados, but thanks to the amazing weather, friendly people, and great activities, this island has become one of the premiere destinations on the ...
Capri Manor is located just across the street from Gibbs Beach

Capri Manor

4 4+

Barbados

Near Beach | Pool | AC

Details
Any holiday is better when you have an amazing view, and Villa Jasmine can provide you with that and much more. A new property, here you'll find a view of ...
Jasmine Villa is located in Gouverneur overlooking the Caribbean
1-3 BR rates.

Jasmine Villa

4 5+

Gouverneur, St. Barts

Pool | AC

Details
Atelier's architect, Alistair Downie, infused tranquility and serenity into every modern detail at this two-story villa. From the master bedroom balcony's ocean views to the gourmet kitchen, there's sleek design ...
Atelier Villa has modern architectural lines and a beautiful pool

Atelier Villa

4 3+

Barbados

Near Beach | Pool | AC

Details
Ready to go gourmet on your next holiday? You will have to demand the finer things in life, and Ariana Villa certainly fits the bill. Located just five minutes from ...
Ariana sits on a hilltop over Lower Belmont Bay
2, 3 BR rates.

Ariana Villa

4 3+

Tortola, BVI, British Virgin Islands

Near Beach | Pool | AC

Details
If you want a tropical escape, Ana Capri fits the bill. It has amazing views, gorgeous Italian design, and lush gardens all around the villa. The infinity pool and tiered ...
Ana Capri Estate photo
1-3 BR rates.

Ana Capri Estate

4 4+

Tortola, BVI, British Virgin Islands

Pool | AC

Details
Marsh Mellow has incredible views, a spacious layout, and a huge, deep pool. Since the villa is crescent-shaped, every room faces the view. It's all very open-air, too, so there's ...
Marsh Mellow Villa is located in Westmoreland in Barbados and has great views of the ocean

Marsh Mellow Villa

4 4+

Barbados

Pool | AC

Details
Many people like to stay on Seven Mile beach because that's where all the action is. Then there are others who still want to experience the beauty of Grand Cayman ...
View from above Castaway Villa - you can see the beach and the ocean

Castaway Cove

4 3+

Grand Cayman, Cayman

AC

Details
Even though this villa is set up for family vacations, it still feels like a romantic secret garden. Every room is colorful and relaxing, and there's even a hammock where ...
Edge of Paradise is located on the Southern shore of Meagan's Bay
Specials.

Edge of Paradise Villa

4 4+

St. Thomas, USVI

Near Beach | Pool | AC

Details
Rose Dog is truly an eclectic gem on the island of St. Barts. It has a comfortable layout, unique design, and conveniently separate suite for anyone who wants extra privacy.
Rose Dog is located on a hillside in Dévé
1-3 BR rates.

Rose Dog Villa

4 4

Vitet, St. Barts

Pool | AC

Details
Cohoba is a large Belmont Estates villa that shows off fantastic ocean views and a location near Smuggler's Cove. Designed with classic Caribbean style, this four-bedroom rental is all about ...
Cohoba is located in Belmont Estates overlooking Lower Belmont Bay
1-3 BR rates.

Cohoba Villa

4 4

Tortola, BVI, British Virgin Islands

Near Beach | Pool | AC

Details
The pool deck and sunbathing deck at Bakea Villa are great because they leave guests plenty of room to spread out and enjoy the view. I love how close this ...
Bakea is located above of Anse des Cayes

Bakea Villa

4 4

Anse des Cayes, St. Barts

Pool | AC

Details
This villa is stunning. It has a full kitchen and beautiful architecture that's really unique to the area, and the photos don't do it justice.
Villa MOH is located in Lurin
1, 3 BR rates.

MOH Villa

4 4

Lurin, St. Barts

Pool | AC

Details
Palermo provides expansive views of Turtle Tail, and you won't be able to get enough of the infinity pool and easy access to the ocean. Walk to the platform in ...
Palermo Villa is located directly on the ocean

Palermo Villa

4 4+

Turtle Tail, Turks and Caicos

Pool | AC

Details
Monte Verde is a charming villa perfect for couples traveling together. The king suites are pretty equal so great for couples, and the outdoor area is well-sized for friends to ...
Monte Verde is located in Hope Hill and has great views of Orient Bay
3 BR rate.
Specials.

Monte Verde Villa

4 4+

Orient Bay (French side), St. Martin

Pool | AC

Details
With two separate master bedrooms and two guest bedrooms, the villa is well suited to couples traveling together, or to families with grown children. I love how spread out everything ...
W View Villa is located on the hillside above St. Jean Bay
2, 3 BR rates.

W View Villa

4 4

Saint Jean, St. Barts

Pool | AC

Details
Aqua Vue condo is spacious and well-arranged, and also really close to some of the island's best restaurants, beaches, and shops. I love all the Porto Cupecoy amenities, like the ...
Aqua Vue is located in Porto Cupecoy
2, 3 BR rates.
Specials.

Aqua Vue

4 4+

Cupecoy (Dutch side), St. Martin

Near Beach | AC

Details
Pastels Villa is the perfect countryside villa for your family's next vacation. It has a child-friendly layout, ample sitting areas with vantage points of the pool, and is 10 minutes away ...
Pastles Villa is located on a hillside in Vitet
2, 3 BR rates.

Pastels Villa

4 4

Vitet, St. Barts

Pool | AC

Details
Right on Grace Bay, Sunsara Villa will have you living in the lap of luxury. Everything about this place is modern, from the gourmet kitchen to the decor and furniture ...
Sunsara villa on Grace Bay
Specials.

Sunsara

4 4

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
In Harmony is a charming beachfront villa that would be perfect for your next family vacation. It has a private beach just beyond the deck with a rocky shoreline that ...
An aerial view of in Harmony Villa located directly on the beach

In Harmony Villa

4 4

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
I think this villa would be perfect for a family vacation-- it has three master bedrooms upstairs and a twin bedroom downstairs, and each bedroom is really well-sized. The views ...
A beachfront pool awaits you at Christmas Palms Villa
Specials.

Christmas Palms Villa

4 3+

Grand Cayman, Cayman

Pool | AC

Details
Tarasand villa is a great choice for anyone who wants to be near Rum Point and have easy access to snorkeling, water sports, and the beach. The lower level has ...
The beach set up in front of Tarasand Villa

Tarasand Villa

4 3

Grand Cayman, Cayman

Beachfront | AC

Details
If you love the ocean, you'll love Villa Caymanas. It sits on Old Man's Bay, a quiet and undeveloped region known for amazing snorkeling. I love watching the waves roll ...
Villa Caymanas is located on the North side of the island on the beach

Villa Caymanas

4 4+

Grand Cayman, Cayman

Near Beach | Pool | AC

Details
This villa is great for four couples, because each suite has a queen bed and private bathroom. There's three beaches that are within a short walk or drive, and the ...
Galley Bay Heights #007 is located on one of the highest points of the beautiful Galley Bay Heights
2 BR rate.

Galley Bay Heights Villa - #007

4 4

Galley Bay, Antigua

Near Beach | AC

Details
The contemporary style of Bahia Blue will wow you, from the outdoor kitchen, to the bright bedrooms, to the beach location. I can't think of any better way to find ...
Bahia Blue is located in Terres Basses within walking distance to Baie Rouge Beach
3 BR rate.
Specials.

Bahia Blue

4 4

Terres Basses (French side), St. Martin

Near Beach | Pool | AC

Details
Estrella is a lovely 4 bedroom, 4 bathroom villa, located in Flamands, just a few steps away from one of the most beautiful beaches in St Barts! Even better, town and shopping ...
Estrela Villa is located in Flamands overlooking the beautiful Flamands Bay Beach
2, 3 BR rates.

Estrela Villa

4 4

Flamands, St. Barts

Near Beach | Pool | AC

Details
This house is great for two families to share. There are two king suites that each have exterior access, and two queen suites with no exterior access. Plus, the villa ...
Heritage House Villa is located on the very desirable Rum Point

Heritage House

4 4

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
I really like the living area in this villa, which is multi-leveled and has a few nooks for relaxing. The villa is just 5 minutes from everything, which is nice for ...
Yellow Bird Villa sits on a hillside in Pointe Milou overlooking Lorient Bay to Marigot
2 BR rate.

Yellow Bird Villa

4 4

Pointe Milou, St. Barts

Pool | AC

Details
Staying in Arrecife 23 is a gorgeous way to enjoy Punta Cana Resort. It has wrought iron and travertine accents, high ceilings, and spacious bedrooms that provide an oasis for every ...
Arrecife 23 is located in Punta Cana Resort on the golf course with ocean views

Arrecife 23

4 4

Punta Cana, Dominican Republic

Near Beach | Pool | AC | Resort Villa

Details
Island Girl has a really cool layout that gives everyone in your party plenty of room to kick back and relax. The four bedrooms are separated by a half-level set ...
View of Coral Bay from the villa pool area
1-3 BR rates.

Island Girl

4 4

Coral Bay, St. John

Pool | AC

Details
Gypsy is perfect for a family who wants a beachfront vacation rental with spacious rooms, a private bay, and easy access to restaurants and activities. I love that there's two ...
Gypsy Villa in Rum Point

Gypsy Villa

4 4

Grand Cayman, Cayman

Beachfront | Pool | AC

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

Villa Arrecife 24 at Tortuga Bay

4 4

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
Smugglers Cove is an excellent choice for beach lovers. You'll have direct access to Paynes Bay, and are just a short walk from Sandy Lane Hotel's restaurant and bar. This ...
Sandy Lane Beach just steps outside of Smugglers Cove

Smugglers Cove #6

4 4+

Barbados

Beachfront | AC

Details
Turks and Caicos is well-known as one of the best areas in the Caribbean for beach lovers, and the Venetian resort will put you right on one of the finest ...
Penthouse at The Venetian photo

Penthouse at The Venetian

3 3

Grace Bay, Turks and Caicos

Beachfront | AC | Resort Villa

Details
Villa Kai has water access to Sandy Hill Bay for exploring, and you can watch the waves crash onto the shore from the back door. The property is fenced in, ...
Villa Kai is located on Sandy Hill Bay
1, 2 BR rates.

Villa Kai

3 3

Anguilla

Pool | AC

Details
Clementine is beautifully decorated, super open, and spacious. I love it for families and groups of friends, because the bedrooms are all nearly equal. Plus, there's a pool, loungers, entertainment ...
Villa Clémentine photo
1, 2 BR rates.

Villa Clémentine

3 3+

Vitet, St. Barts

Pool | AC

Details
This villa has a beautiful view and plenty of lounging space on the terrace to enjoy it. The upstairs bedrooms have their own balconies, too, so you can wake up ...
Sasha photo
2 BR rate.

Sasha

3 3

Corossol, St. Barts

Pool | AC

Details
This villa has a cool Balinese vibe and outdoor showers that really elevate the luxury. It's well designed, and has a unique outdoor structure that sets it apart.
Villa Sauvage has a beautiful pool overlooking the island
2 BR rate.

Sauvage Villa

3 3

Flamands, St. Barts

Pool | AC

Details
Bikini Villa is simply cozy. An open floor plan allows you to see all your guests relaxing, and the rooms seamlessly blend with the outdoor area to really incorporate the ...
Bikini Villa photo
1, 2 BR rates.

Bikini Villa

3 3

Lorient, St. Barts

Near Beach | Pool | AC

Details
Aliza villa is chic and convenient! The decor is very minimalist and modern, and the villa is just a short walk from the beach and a few minutes from town. ...
Aliza photo
1, 2 BR rates.

Aliza

3 3

Saint Jean, St. Barts

Near Beach | Pool | AC

Details
This villa is great for any family who wants stunning views for an affordable price. There are tons of beaches nearby, and the wraparound deck has front row seats to ...
Ballena Blue is located on a hilltop over Rendezvous Bay
1, 2 BR rates.
Specials.

Ballena Blue

3 3

Rendezvous Bay, St. John

Pool | AC

Details
One of my favorite things about Javacanou is the waterfront access to Marigot Beach. This area is great for snorkeling, and the turtles will swim right next to you! Obviously, ...
Javacanou villa overlooks the beautiful protected waters of Marigot Bay

Javacanou Villa

3 3

Deve, St. Barts

Near Beach | Pool | AC

Details
Babylon Reef feels like a classic beach house, with every amenity you could ask for. It's oceanfront, with a great view of the Caribbean framed by palm fronds. A hammock ...
The private pool at Babylon Reef has a man made -beach- surrounding it

Babylon Reef

3 2+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Sienna has a gorgeous terrace and views of the golf course. The terrace can be closed off to the pool and view for more privacy, since the villa sits steps ...
Sienna Villa

Sienna Villa

3 3

Barbados

Pool | AC

Details
Smugglers Cove is great for beach lovers, because the guests have direct access to Paynes Bay. The villa is spacious and beautifully decorated, and has a friendly staff. There's several ...
Paynes Bay Beach is just below the balcony at Smugglers Cove #4

Smugglers Cove #4

3 3

Barbados

Beachfront | AC

Details
Crescent Beach villa sits in beautiful, peaceful Bequia, with a view of the beach below. You’ll love listening to the gentle waves and breeze blowing through, and the hillside ...
Crescent Beach Villa is located above Crescent Beach and has amazing ocean views
1 BR rate.

Crescent Beach Villa

3 3

Bequia, St. Vincent & Grenadines

Pool | AC

Details
Casa Luna 17 is great for families who want a bit of privacy at a great price. Kids can stay on the lower level in two suites, and the basement-level bathroom ...
There is an amazing beach cove at Casa Luna Villas

Casa Luna 17

3 4

Grand Cayman, Cayman

Beachfront | AC | Resort Villa

Details
Edge of Paradise is a great choice for three couples who want to relax by Grace Bay. The villa comes with a cooler, and an electric golf cart so you ...
Edge of Paradise is located just a few minutes from Grace Bay Beach

Edge of Paradise

3 3

Leeward, Turks and Caicos

Near Beach | Pool | AC

Details
La Corniche is a stunning, spacious oceanfront villa with gorgeous views and an airy design. I love how the interior is so chic and simple, because it doesn't distract from ...
La Corniche has a beautiful pool deck area with spectacular views of the Caribbean
2 BR rate.

La Corniche

3 3+

Pointe Milou, St. Barts

Pool | AC

Details
If you love Grace Bay and Smith's Reef, you'll love Sandpebble. Its right by the sea, near Turks and Caicos' best snorkeling, and has gorgeous ocean views. There's a good ...
Aerial view of the Sandpebble property

Sandpebble

3 3+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Tradewinds is ideal for three couples who want to vacation on Grace Bay without sacrificing privacy. The villa is surrounded by thick gardens and has a private path to the ...
Tradewinds Villa is located near Grace Bay Beach

Tradewinds

3 3

Providenciales, Turks and Caicos

Near Beach | Pool | AC

Details
Seashells is a great choice for a beachfront family vacation. It's steps away from the sea, has three-stories of space, and offers tons of outdoor space. The pool isn't that ...
Seashells Villa is set on a beautiful stretch of beach

Seashells

3 3+

Barbados

Beachfront | Pool | AC

Details
Porters is a family-friendly villa with a great location, elegant design, and gorgeous gardens. The villa's three bedrooms are all kings or twins that can be made up as kings, ...
Porters Villa is located in St. James

Porters

3 3

Barbados

Near Beach | Pool | AC

Details
On The Rocks has a classic, beach house vibe in one of Turks and Caicos's most underrated areas. Chalk Sound is absolutely gorgeous, well-developed, and famous solely with locals and ...
On the Rocks is located in Silly Creek on Chalk Sound

On the Rocks

3 3

Chalk Sound, Turks and Caicos

Pool | AC

Details
This three-bedroom resort villa has everything you need for an easy family vacation. Everything has been thought of for you, from the kitchen gadgets to the complimentary cribs to the ...
Seafire Resort

The Residences at Seafire 3 Bedroom South

3 3+

Grand Cayman, Cayman

Beachfront | AC

Details

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