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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.

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
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.
Specials.

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
If you want a modern villa that will leave you and your friends speechless, book Cascade. The pools here come together to make an aquatic masterpiece that almost steals the ...
Cascade Villa in Turks and Caicos

Cascade Villa

5 5+

North Shore, 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
3, 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.

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

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

Mirador

4 4+

Barbados

Beachfront | Pool | AC

Details
This villa is great for four couples who want privacy and convenience. The exterior is multi-leveled and three of the suites have outdoor showers. I love how this villa is ...
EauSea sits atop a hillside overlooking Great Cruz Bay
1-3 BR rates.

EauSea

4 4

Great Cruz Bay, St. John

Pool | AC

Details
Sand Castle is the perfect choice for a beach vacation. It's open-air design brings the sea, sand and sun right to your doorstep. Lorient bay is perfect for surfing (the ...
Sand Castle Villa is located directly on Lorient Bay Beach
1-3 BR rates.

Sand Castle

4 3

Lorient, St. Barts

Beachfront | AC

Details
Since Spero sits steps away from Punta Cana's golf course, it's surrounded by perfectly manicured lawns and upscale gardens. The interior is just as aesthetically pleasing, but in a totally ...
Spero Villa sits directly on Puna Cana's beautiful Hacienda Golf Course

Spero

4 4

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
If you're traveling to Costa Rica with your friends or extended family, you'll love La Perla. There's three suites in the main house and a king suite in the guest ...
La Perla Villa is located in Altamira, just above the Marina in Los Suenos

La Perla

4 4

Costa Rica

Pool | AC

Details
Sandcastle Beach House is an action-packed choice for your next family vacation, anniversary, or celebration. With kayaks, paddle boards, bikes, and direct beach access, there's no shortage of things to ...
Sandcastle Beach House is located on on Limestone Bay
Specials.

Sandcastle Beach House

4 4+

Anguilla

Beachfront | Pool | AC

Details
Pelican Bay would be a great choice for a multi-generational family vacation. Three bedrooms are in the main house with exterior access, and the entire interior is extremely open and ...
Pelican Bay Villa has an ideal location in between Blowing Point and Pelican Bay
1-3 BR rates.

Pelican Bay

4 4+

Anguilla

Pool | AC

Details
Bristol Bliss is the perfect villa for a quiet vacation with your favorite couples. It's on Turtle Tail, which is along the southern shore of Providenciales near the marina and ...
The pool at Bristol Bliss sits beachside overlooking the azure waters so famous in Turks and Caicos
Specials.

Bristol Bliss

4 4

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

Details
Gustavia Views is a gorgeous choice for your next family vacation. Whether you're traveling with teenagers, infants, or adults, you'll love the privacy and convenience of this villa. Every bedroom ...
Gustavia Views Villa lives up to its name and more - also boasting a private pool
2, 3 BR rates.

Gustavia Views

4 3

Gustavia, St. Barts

Pool | AC

Details
Frangipani lets you enjoy the convenience of a resort community and the comforts of home, in one villa. The villa itself is gorgeous, there are amazing ocean views, and the ...
Frangipani sits directly on Grace Bay Beachfront and each have private infinity pools
Specials.

Frangipani

4 5+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
Emeraude feels like a private resort, it’s so gorgeous. The pool deck is super luxurious, and there’s so many places to relax. You’ll want to stay outside ...
Villa Emeraude is located in Indigo Bay
3 BR rate.
Specials.

Emeraude

4 4

Indigo Bay (Dutch Side), St. Martin

Pool | AC

Details
Beach House is all about location, location, location. It’s on Taylor Bay, which is one of my absolute favorites on Turks and Caicos. This quiet slice of beach is ...
The Beach House Villa is located within walking distance of Taylor Bay Beach

Beach House

4 4+

Taylor Bay-Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Olympus has it all: a beachfront location, modern design, and tons of space to lounge. Whether you want to relax inside or out, there’s plenty of space for all ...
Olympus is located on the beach front in Rum Point

Olympus - Platinum

4 4+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Madison at Sandy Lane is a tranquil villa with resort amenities, golf course access, and elegant design. Whether you want to swim in the pool, sunbathe on the deck, or ...
Madison Villa is located on a hilltop in the Sandy Lane Estate with panoramic 180 degree views

Madison Villa at Sandy Lane

4 4

Barbados

Pool | AC

Details
Beach Enclave takes family vacations to the next level. With endless amenities, activities for all ages, and a convenient location near Grace Bay, this four-bedroom villa is the perfect choice ...
Beach Enclave 4 bedroom Ocean View at Grace Bay

BE - 4 bedroom Ocean View at Grace Bay

4 4+

Grace Bay, Turks and Caicos

Near Beach | Pool | AC | Resort Villa

Details
Looking for privacy, convenience, and tranquility? Beach Enclave Long Bay may be the perfect fit for your family. With a two-bedroom main house and a two-bedroom cottage, there’s more ...
Beach Enclave Long Bay is located on the southeastern edge of Providenciales

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

4 4+

Long Bay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details

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