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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’re looking for an Anguilla beachfront rental, this resort villa is worth a look. It’s right on Meads Bay, one of the island’s most gorgeous beaches, ...
Tranquility Beach - Beachfront Penthouse Villa is located on Meads Bay Beach
Specials.

Tranquility Beach - Beachfront Penthouse

3 3+

Anguilla

Beachfront | AC | Resort Villa

Details
Viceroy Sugar Beach's Three Bedroom Villa Residence is the ideal rental for a luxurious beachfront experience. The beach is steps from the veranda, and the resort's endless activities are minutes ...
The Viceroy 3 Bedroom Villa Residences are set in the foothills of the Pitons and the Caribbean Sea

Viceroy Sugar Beach - Three Bedroom Villa Residence - Beachfront

3 3+

Soufriere, St. Lucia

Beachfront | Pool | AC

Details
This gorgeous villa is perfect if you want to be near Seven Mile Beach, but away from the crowds. There’s tons to do at and around the villa, so ...
Casa Luna 4 is located in the resort community along the coastline just south of Seven Mile Beach

Casa Luna 4

3 4

Grand Cayman, Cayman

Beachfront | AC | Resort Villa

Details
This spacious, beachfront villa has a convenient location within walking distance of dining, attractions, and excursions. Even though Rum Point Beach and Cayman Kai are minutes away, Les Jalousies has ...
Les Jalousies is located in Cayman Kai

Les Jalousies

3 3

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Love this sweet villa that sits just above the quaint fishing village of Corossol. It's perfect for a family with all three bedrooms located on the same level, a super ...
AKA Villa is located in Corossol with great views of Gustavia Harbor
1 BR rate.

Aka Villa

3 2

Corossol, St. Barts

Pool | AC

Details
Modern design, beach access, and three bedrooms make this penthouse the perfect rental for your next vacation. It’s right on Meads Bay, which is one of the island’s ...
Tranquility Beach Anguilla is located on Meads Bay Beach
Specials.

Tranquility Beach - Penthouse

3 3+

Anguilla

Beachfront | AC | Resort Villa

Details
Sapphire Beach 401 has easy beach access near great snorkeling, restaurants, and activities. It’s a great choice for your next family vacation, because there’s a king suite, a queen ...
Sapphire Beach 401 has views right over the beach
2 BR rate.

Sapphire Beach 401

3 3

Barbados

Beachfront | AC | Resort Villa

Details
If you want gorgeous views, interiors, and design, Infinity is a great choice. This Pointe Milou villa has a quiet location near the island's hot spots, and the views are ...
Infinity Villa is located on a hilltop in Pointe Milou overlooking Lorient Bay
2 BR rate.

Infinity

3 3

Pointe Milou, St. Barts

Pool | AC

Details
Sailrock Resort is a great part of the island to stay on if you want tranquility, convenience, and seclusion. The resort's neighborhood is low-density and off the beaten path, so ...
Sailrock Resort Oceanfront Coral Villa is located oceanfront on the Sailrock Peninsula

Sailrock Resort Oceanfront Coral Villa

3 3

South Caicos, Turks and Caicos

Pool | AC | Resort Villa

Details
Vacationing with teens? This is the perfect villa. This two-bedroom beach house and one-bedroom cottage is incredible for families who want to be near all the action without spending their ...
Beach Enclave Long Bay is located on the southeastern edge of Providenciales

BE - 2 Bedroom Beach Front Plus 1 Bedroom Cottage at Long Bay

3 3+

Long Bay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
The Cottage at Meads Bay is a quiet, peaceful retreat for any vacationer. This villa offers three spacious bedrooms, gorgeous ocean views, and direct beach access to one of the ...
The Cottage at Meads Bay is located on Meads Bay, Anguilla’s most desirable beach

The Cottage at Meads Bay

3 3+

Anguilla

Beachfront | AC

Details
No Limit is a charming villa with gorgeous ocean views and a spacious exterior with several lounging and dining areas. You’ll never want to go inside! There are two ...
No Limit is located on a hillside in Terres Basses overlooking Baie Longue
2 BR rate.
Specials.

No Limit

3 3+

Terres Basses (French side), St. Martin

Pool | AC

Details
Casa Luna 16 has next-level benefits for anyone seeking privacy, resort amenities, and luxury. The exterior is tricked out for entertaining and dining, and the resort's pool and barefoot beach are ...
Casa Luna 16 is located in the exclusive resort at the very end of Seven Mile Beach

Casa Luna 16

3 3

Grand Cayman, Cayman

Beachfront | AC | Resort Villa

Details
Blu in Turks and Caicos is definitely the place to be! With its stunning sunsets and a mere hop, skip, and a jump to the beach, you'll be sure to ...
Villa Blu is located steps from Grace Bay beach

Blu

3 3

Grace Bay, Turks and Caicos

Pool | AC

Details
Cheemaun Beach Villa is ideal for family holidays and romantic retreats. Convenience and excitement are combined at this beachfront property on Oil Nut Bay, just steps from the resort beach ...
Cheemaun Beach Villa is located Steps from Oil Nut Bay’s white sand beach

Cheemaun Beach Villa

3 3+

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC | Resort Villa

Details
With its prime water front location, Belvedere Villa in North Caicos offers an amazing three-bedroom retreat boasting stunning ocean views, a private pool, and a sense of calm and serenity. ...
Belvedere Villa is located in North Caicos

Belvedere

3 3+

North Caicos, Turks and Caicos

Pool | AC

Details
Escape to Driftwood Villa and let yourself be captivated by the mesmerizing views of St. John. With its hillside location in Ditleff Point, this luxurious retreat offers you breathtaking vistas ...
Driftwood Villa on Ditleff Point

Driftwood

3 4+

Rendezvous Bay, St. John

Pool | AC

Details
Beachi at Coral Cove is the ultimate beachfront property in Barbados. With an amazing terrace offering breathtaking views, three bedrooms, and direct access to the beach, this is the perfect ...
Aerial view of beachfront access at Beachi - Coral Cove #9

Beachi

3 3

Barbados

Beachfront | AC

Details
Osprey villa has gorgeous sunset views and outdoor amenities perfect for a family vacation. The waterfront location is enhanced by a seaside deck, kayaks, and an oceanfront gazebo. There's a ...
Osprey is located on the ocean side of Chalk Sound

Osprey Villa

3 3

Taylor Bay-Sapodilla Bay, Turks and Caicos

Pool | AC

Details
Caribbean vacations offer much more than you might imagine, especially if you have never heard about the wonderful accommodation options. One is the beautiful Hummingbird Villa of St. Lucia. This ...
Hummingbird Villa photo

Hummingbird Villa

3 3

Cap Estate, St. Lucia

Pool

Details
The beautifully landscaped and stylish Saline Reef is a great vacation spot for families with children over 12, or adults who want an exclusive get-away location. The views from this three-bedroom ...
Saline Reef sits on the northernmost end of St. Lucia and has a beautiful pool and patio
2 BR rate.

Saline Reef Villa

3 3

Cap Estate, St. Lucia

Near Beach | Pool | AC

Details
Terres Basses is known as one of St. Martin's nicest areas, and Callisto does not disappoint. The villa consists of 3 bedrooms with en-suite bathrooms, a living room with a piano ...
Callisto Villa is located on a hillside in Terres Basses and enjoys sunset views over Baie Longue
2 BR rate.
Specials.

Callisto

3 3+

Terres Basses (French side), St. Martin

Pool | AC

Details
It's rare that the name of a vacation rental could truly summarize the benefits you will find inside, but this one says it all at Serenity. Your holiday should encompass ...
Villa Serenity has a beautiful deck and unparalleled views of Gustavia Harbour
1, 2 BR rates.

Serenity Villa

3 3

Gustavia, St. Barts

Near Beach | Pool | AC

Details
Anchorage Villa is a warm, sun-drenched property with a spacious living room and an open-concept dining area. The housekeeper prepares breakfast and lunch every day, so you can explore the ...
Anchorage Villa is on the western end of the Sandy Lane Estate

Anchorage Villa

3 3

Barbados

Pool | AC

Details
Guests will be immediately taken with the sleek, peaceful influence of Japan when they enter Plein Ciel Villa. The high vaulted ceilings and tile floors keep the villa cool on ...
Plein Ciel Villa photo
2 BR rate.

Plein Ciel Villa

3 2

Marigot, St. Barts

Pool | AC

Details
You're bound to enjoy the gardens, but there are many other features in this estate to make you feel at home. The high vaulted ceilings and tile floors keep the ...
Canefield house sits on a lovely hillside in the heart of Tortola
2 BR rate.

Canefield House

3 3+

Tortola, BVI, British Virgin Islands

Pool | AC

Details
Abby Villa is the perfect St. Barts getaway for three couples who want a cozy, peaceful location near multiple beaches. This hillside beauty has chic, white interiors, top-notch appliances, and ...
Abby Villa photo
2 BR rate.

Abby Villa

3 3

Vitet, St. Barts

Pool | AC

Details
At Rocky Point, you have the opportunity for privacy and excitement, as well as spectacular ocean views. This three-bedroom villa offers two acres of sand and beach, tropical vegetation, and ...
The pool at Rocky Point villa!

Rocky Point at COMO Parrot Cay

3 3

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
Terres Basses in St. Martin is known for fine beaches and great scenery, and La Magnolia Villa is situated to enjoy these. The home overlooks the ocean, so the water ...
La Magnolia sits on a hilltop over Baie Longue with a great view of the ocean
1, 2 BR rates.
Specials.

La Magnolia Villa

3 3

Terres Basses (French side), St. Martin

Pool | AC

Details
This villa is great for a few couples or a family. All three bedrooms have ensuite bathrooms, and two are kings while the third has two twins. There's a common ...
Sweet Return Villa is located near the golf course and Rendezvous Bay
2 BR rate.

Sweet Return Villa

3 3

Anguilla

Pool | AC

Details
If you're ready for a Caribbean escape with views galore, then Eaglesnest is the place for you. It's location on Contant Point gives you panoramic views of Great Cruz Bay, ...
Eaglesnest is located on a hillside overlooking Great Cruz Bay
1, 2 BR rates.

Eaglesnest Villa

3 3

Great Cruz Bay, St. John

Pool | AC

Details
Casawapa is great for couples traveling together or family vacations. The rooms are equal in size and separated by the living area, which gives your guests plenty of privacy. Outside, ...
The One Villa sits on the Colombier hillside overlooking the Caribbean
2 BR rate.

The One

3 3

Colombier, St. Barts

Pool | AC

Details
Located on a hillside in Marigot, Au Couer du Rocher is an open home. It is stylishly furnished and also includes partial air-conditioning, a fully equipped kitchen, a large living ...
Au Coeur du Rocher is located on a on a hillside in Marigot
1, 2 BR rates.

Au Coeur du Rocher

3 3+

Marigot, St. Barts

Pool | AC

Details
Dasha Villa is quickly building a roster of loyal fans. A recent visitor summed up her stay at the villa by saying, 'It was just what we needed! Perfect, relaxing, ...
Dasha Villa is located on a hillside overlooking Views of Gouverneur
1, 2 BR rates.

Dasha Villa

3 3

Lurin, St. Barts

Pool | AC

Details
Whether you want to relax by the pool for your entire vacation, or you're an adventurer who wants a lot of action, Victoria Villa is the place to stay. In ...
Victoria Villa is located in the Oyster Pond neighborhood on a hillside overlooking Orient Bay
Specials.

Victoria Villa

3 3+

Oyster Pond (Dutch side), St. Martin

Pool | AC

Details
Mer Soleil is a contemporary villa located in Gouverneur just a five minute drive to the pristine beach. Stop and have a long lunch at the Santa Fe restaurant, then ...
Amazing views from the deck
2 BR rate.

Mer Soleil

3 3

Gouverneur, St. Barts

Pool | AC

Details
Harmony House is an elegantly furnished, fully-equipped, three-bedroom villa with everything you need for a relaxing Barbados getaway. The bedrooms are spacious and come with ensuite bathrooms and private balconies. ...
Harmony House is just steps away from Gibbes Beach

Harmony House

3 3+

Barbados

Beachfront | Pool | AC

Details
Reef Pearl Villa, with it's private swimming pool, relaxing hammock, and perfect beachfront location is the ideal getaway spot for family or group of friends. Located a quick minutes' walk ...
Ocean kayaks - Ask for availability
2 BR rate.

Reef Pearl Villa

3 3

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Conch Beach has everything you could possibly want in a family vacation rental, from the bedrooms to the design to the location. For starters, the Master Suite is huge and ...
Conch Beach Villa is located on the beautiful Grace Bay Beach

Conch Beach Villa

3 3

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
You can see the ocean from every room in this beachfront villa, and natural light enhances the tropical vibe. You can sunbathes on a cushioned lounger, dangle your feet in ...
Fathom's End - Mahogany Bay is located right on the beach at Mahogany Bay

Fathom's End - Mahogany Bay

3 3+

Barbados

Beachfront | Pool | AC

Details
Sunset Reach has the benefit of being directly on Mullins Beach, a crowd-favorite for snorkeling, water sports, and its famed beach bar. The villa features 3 bedrooms, making it perfect for ...
Sunset Reach sits a few feet from the sea on Mullins Beach
2 BR rate.

Sunset Reach Villa

3 3

Barbados

Beachfront | AC

Details
Blue Lagoon Villa is a family friendly, wheelchair accessible villa that can easily sleep up to ten people. With a classic master bedroom and unique guest suites, everyone in your ...
Blue Lagoon Villa photo
2 BR rate.

Blue Lagoon Villa

3 3

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool | AC

Details
If you have an extended family, Bambooshay Villa has the extra room that avoids what a cramped hotel would have to offer. A hammock allows for lounging time, and the ...
Relax and enjoy yourself while in the pool or hang'n in the hammock at Bambooshay

Bambooshay Villa

3 3+

St. Croix, USVI

Pool | AC

Details
This villa would be so fun for your next family vacation. Kids will love the pool, teens will love the home entertainment system and tanning chairs, and you'll love the ...
Bel'Ombre photo
1, 2 BR rates.

Bel'Ombre

3 3

Marigot, St. Barts

Pool | AC

Details
Experience the ultimate island getaway at Maxi Cooper in the British Virgin Islands. Revel in the stunning 180 degree ocean views while lounging on ample outdoor space with your favorite cocktail ...
Maxi Cooper Villa in Tortola

Maxi Cooper

3 3+

Tortola, BVI, British Virgin Islands

Pool | AC

Details
Sol e Luna is very private with gardens that surround the house giving guests the option of dressing or not. The large, open interiors also make it an ideal spot ...
Sol e Luna is located in the desirable Terres Basses
1, 2 BR rates.
Specials.

Sol e Luna Villa

3 3

Terres Basses (French side), St. Martin

Pool | AC

Details
Panarea Villa is truly beautiful, with a great housekeeper and lush gardens all around. I think this villa is ideal for a casual, laid-back Caribbean vacation, especially for young families ...
Panarea is located in Anguilla's West End, just minutes away from the island's most beautiful beache
1, 2 BR rates.

Panarea Villa

3 3

Anguilla

Near Beach | Pool | AC

Details
At just the right vantage point to see the rolling hills, town, and ocean, Villa Rivendell provides seclusion without cutting you off from all the beauty of Flamands, St. Barts. ...
Amazing view of Flamands Bay from the infinity edge pool
1, 2 BR rates.

Rivendell Villa

3 3

Flamands, St. Barts

Pool | AC

Details
Tuscany Resort is one of my favorite properties on Turks and Caicos. At WhereToStay.com, we only list resorts that feel like a private villa. Tuscany made our list because ...
The Tuscany Resort is located on East Grace Bay Beach
1, 2 BR rates.

Tuscany

3 3

Grace Bay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
Located within walking distance to a grocery store and restaurants, Ecoute les Vagues sits right on Flamands Beach, giving guests easy access to swimming, snorkeling, and sunbathing galore. The villa ...
Ecoute les Vagues is located right on the beach in Flamands Bay

Ecoute les Vagues

3 2

Flamands, St. Barts

Beachfront | Pool | AC

Details
Sea Bird is a one-of-a-kind villa in Mont Jean, St. Bart's, with 3 bedrooms, a full kitchen, and large living areas for lounging, watching TV, or enjoying meals. The master bedroom ...
Sea Bird Villa is located on a hilltop in Mont Jean overlooking the Caribbean
1, 2 BR rates.

Sea Bird Villa

3 3

Mont Jean, St. Barts

Pool

Details
Your family will love staying at The Harbour #17. This brightly colored home is right on the harbor and nestled in the island's most happening bay. You can walk to everything, ...
The Harbour #17 is located in the Harbour Townhomes overlooking the harbour on Rodney Bay
2 BR rate.

The Harbour #17

3 3+

Rodney Bay, St. Lucia

Near Beach | AC | Resort Villa

Details
Situated on a hillside, Lataniers Villa has a great view of St. Jean Bay and the surrounding island greenery. Guests of this home will enjoy lots of little perks, like ...
Beautiful views from Lataniers Villa
2 BR rate.

Lataniers Villa

3 2

Saint Jean, St. Barts

Pool | AC

Details
There is no mistaking that you are on island time when you step foot in Hurakan Villa. Each room has large, wooden beam cathedral ceilings that give the rooms their ...
Perched on the hillside of Colombier - Hurakan provides beautiful views of Gustavia Harbour
1, 2 BR rates.

Hurakan Villa

3 3

Colombier, St. Barts

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 ...
The Venetian photo
1, 2 BR rates.

The Venetian

3 3+

Grace Bay, Turks and Caicos

Beachfront | AC | Resort Villa

Details
Latitude Villa is an excellent choice for three couples. Two bedrooms are upstairs and one is downstairs, so everyone will feel like they have their own space. None of the ...
Latitude Villa photo

Latitude Villa

3 3

Barbados

Beachfront | Pool | AC

Details
Anakao Villa, located in the Saint Jean area, is ideally located for those seeking the ultimate in peace and quiet. Perched on a hillside overlooking tropical plants and other villas, ...
Anakao Villa is located in St. Jean just minutes from St. Jean Beach
1, 2 BR rates.

Anakao Villa

3 2

Saint Jean, St. Barts

Pool | AC

Details
Coco villa has an outdoor living area with comfy furnishings and ocean views. The infinity pool has a plateau where you can enjoy an afternoon cocktail, and there’s no ...
Coco Villa sits above Lorient Bay Beach looking toward St. Jean

Coco Villa

3 3

Lorient, St. Barts

Pool | AC

Details
Just 2 minutes away from one of St. Martin's nicest beaches, Les Zephyrs is a private, 3-bedroom villa that comes with all the space and privacy you need during your Caribbean ...
Les Zephyrs Villa in Terres Basses
2 BR rate.
Specials.

Les Zephyrs Villa

3 3

Terres Basses (French side), St. Martin

Pool | AC

Details
Dream Come True Villa delivers not only privacy, but magnificent ocean views. Just steps above Devers Bay, this three-bedroom villa is ideal for couples or families who want to step ...
A Dream Come True Villa has amazing ocean views and a fun pool area
1, 2 BR rates.

Dream Come True Villa

3 3+

Devers Bay, St. John

Beachfront | AC

Details

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