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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.

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
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.

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
3 BR rate.
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
Hura Sea Azure puts guests right on Long Bay near several restaurants and shops. You can easily get to jet ski rentals, horseback riding, and kitesurfing within a short drive ...
Hura Sea Azure photo
Specials.

Hura Sea Azure

4 4+

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
If you’re looking for a gorgeous villa for up to four couples, Mar Azul is a great choice! Its comfortable design and modern amenities are nothing compared to how ...
Mar Azul is located on a high ridge between Maria Bluff and Blasbalg Point
1-3 BR rates.

Mar Azul

4 3+

Great Cruz Bay, St. John

Pool | AC

Details
Wind Chime is all about relaxation and luxury. The spaces are all designed to feel expansive and open, and every ounce of technology offers the latest and greatest. Every guest ...
Wind Chime Villa in Turks and Caicos
Specials.

Wind Chime

4 4+

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

Details
Turks and Caicos is well known for its beautiful beaches, and Five Turtles Villa gives you direct access to one of the finest on the island. This popular 4-bedroom villa ...
Six Turtles on Taylor Bay

Six Turtles Villa

4 4+

Taylor Bay-Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Your hunt for beauty, solitude, and affordability near one of the world's best beaches is over. Okeanos is located 150 feet above the sea rocks with spectacular views. Whether you relax ...
Villa Okeanos sits in Shoal Bay East,
3 BR rate.

Okeanos

4 3+

Anguilla

Pool | AC

Details
Cielo Villa is an unparalleled sanctuary nestled along Chalk Sound. With its awe-inspiring sea views, an inviting infinity pool lined with loungers, and a harmonious blend of contemporary design and ...
Cielo Villa on Chalk Sound
Specials.

Cielo

4 5

Chalk Sound, Turks and Caicos

Beachfront | Pool | AC

Details
Fiore villa is a beautiful, fully air-conditioned 4 bedroom villa just a short 2-3 minute walk to lovely Shoal Bay Beach. All four bedrooms have views of Shoal Bay East and 2 ...
Fiore Villa photo

Fiore Villa

4 4+

Anguilla

Near Beach | Pool | AC

Details
If you're looking for luxury, look no further than Aqua Rock in Terres Basses, St. Martin! This property is a dream come true with its 4 bedrooms, chic furnishings, and the ...
Aqua Rock Villa in Terres Basses
2 BR rate.
Specials.

Aqua Rock

4 4+

Terres Basses (French side), St. Martin

Pool | AC

Details
Hakuna Matata is a wonderful, spacious home surrounded by flowers, palm trees, and tropical landscaping. The owners have stayed true to the natural settings by including native materials like stones ...
Hakuna Matata is located in the Catherineberg Estate overlooking Cinnamon Bay
2 BR rate.
Specials.

Hakuna Matata

4 5+

Catherineberg, St. John

Pool | AC

Details
Beach Dreams is great for beach lovers and snorkelers. The beach is a few steps away from the pool, with a well-maintained lawn in between. A snorkeling reef is just ...
Wonderful beach just steps away from the pool at Beach Dreams Villa
2 BR rate.

Beach Dreams Villa

4 4+

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

Details
This villa has an ideal location far from crowds yet minutes from Grace Bay, and is a cozy choice for any family vacation. You won’t want to miss snorkeling ...
Endless ocean views
3 BR rate.

Ocean Palms Villa

4 4

Turtle Tail, Turks and Caicos

Pool | AC

Details
Situated right on the sandy beach, Thespina is one of Barbados' most unique private villas. The home itself is very contemporary, but still very comfortable. With 4 bedrooms and 5 bathrooms Thespina ...
Thespina Villa is located in Holetown right on the beach nestled in tropical foliage

Thespina Villa

4 4

Barbados

Beachfront | AC

Details
You can spend your days relaxing around the heated pool or stretched out on the white sand beaches, without a care in the world. The daily maid service ensures that ...
Euphoria Villa sits above Clarke Rock in Leverick Bay
3 BR rate.

Euphoria Villa

4 3

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool | AC

Details
Located right on the French side of St. Martin, Blue Beach Villa is a great beachfront home with tons of privacy, modern design, and ocean views. The pool and the ...
Blue Beach Villa is located right on Long Bay Beach
Specials.

Blue Beach Villa

4 4

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

Details
Villa Farina is the ultimate beachfront paradise in Anguilla! With 4 spacious bedrooms, each with interior access, and breathtaking sea views from the master bedrooms, this villa is perfect for a ...
Villa Farina in Anguilla
Specials.

Villa Farina

4 4

Anguilla

Beachfront | Pool | AC

Details

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