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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.

Jamoon is the place to be for family reunions, couples getaways, and girls trips. Kids and adults alike love the pool - it wraps around the house and comes with ...
Private resort style pool and outdoor entertainment area at Jamoon
3-6 BR rates.

Jamoon - Sandy Lane

7 6+

Barbados

Pool | AC

Details
If you want a private, oceanfront villa with a secluded beach, On The Rocks is a great choice. This villa would be great for a family vacation, because there's bedrooms ...
On the Rocks Villa is located in the Beach Bay community
Specials.

On The Rocks Villa

7 4

Grand Cayman, Cayman

Near Beach | Pool | AC

Details
If you’re looking for beachside luxury with access to exclusive activities and resort amenities, Villa Corales 28 is a great choice. This seven-bedroom villa is perfectly equipped for large families, ...
Villa Corales 28 is a beautiful oceanfront villa in Punta Cana

Villa Corales 28

7 7+

Punta Cana, Dominican Republic

Near Beach | Pool | AC | Resort Villa

Details
La Perla Estate is absolutely gorgeous. This is hands down one of my favorite estates on the island, because each villa is so thought-out and lovely. Bianca and Classic, the ...
La Perla Estate consists of the three La Perla properties - Bianca - Classic - Palais
Specials.

La Perla Estate

7 7

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

Details
Wake Up is super modern, well-equipped, and gorgeously designed. There's tons of space to relax outside by the pool or on the balcony, and the ocean is steps from the ...
Wake Up Villa is located on the beautiful Flamands Beach

Wake Up

6 6

Flamands, St. Barts

Beachfront | Pool | AC

Details
Yellow Bear Villa is great for your family's next vacation! Parents, have a babysitter watch the kids while you go golf, get massages, and workout at the fitness center. For ...
Yellow Bear Villa - Very large pool and outdoor areas

Yellow Bear Villa

6 6+

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
This villa is totally serene. There's more than enough activities - pool and beach toys, kayaks, snorkeling, and a huge pool. Laze by the ocean on the beachfront patio, or ...
Casa Barana is located on Thompson Cove and has amazing ocean views

Casa Barana

6 5+

North Shore, Turks and Caicos

Beachfront | Pool | AC

Details
There's a lot to love about Halle Rose. The whole property is surrounded by gardens, so you have a lot of privacy with a convenient location. Sandy Lane Beach is ...
Halle Rose Villa offers a beautiful pool surrounded by lush tropical landscaping
3, 4 BR rates.

Halle Rose

6 5

Barbados

Pool | AC

Details
If you want a fully-staffed villa that has activities for everyone, then Villa Corales 114 is perfect for you. There's a 72 ft. long lap pool that stretches across the property, Apple ...
Villa Corales 114 has a decadent lawn and pool area

Villa Corales 114

6 6+

Punta Cana, Dominican Republic

Near Beach | Pool | AC | Resort Villa

Details
This family-friendly villa has a private pool, gorgeous hillside views, and is in the prime location for Antigua's sailing events. There's horseback riding, scuba diving, fishing tours, boat rentals, and ...
Al fresco dining for eight
5 BR rate.

Falmouth Harbour #022

6 6

English Harbour, Antigua

Pool | AC

Details
I love Villa Blackstone for family vacations. There's two bedrooms that are connected, a super safe pool terrace with crystal clear glass balconies, and a great hillside location over Marigot ...
Villa Blackstone is nestled in the hillside above Marigot Bay
2, 4 BR rates.

Villa Blackstone

6 6

Marigot, St. Barts

Pool | AC

Details
Big Chill is perfect for big families who want to chill in paradise! Its location on the Leeward Canal is great for ocean lovers, because most of the island's best ...
Big Chill Villa has a canal front pool with great areas to relax and entertain
Specials.

Big Chill

6 6+

Leeward, Turks and Caicos

Pool | AC

Details
This villa is great for two families or several couples to share. Each suite is set up like its own retreat, and there's more than enough bikes, paddle boards, and ...
Villa Viatu in Turks and Caicos

Viatu

6 6+

Leeward, Turks and Caicos

Near Beach | Pool | AC

Details
Seaclusion will make you feel like royalty. There's more chandeliers and ocean views that I can count, and the exterior is just as luxurious as the interior. There's several living ...
Seaclusion is located just steps away from an amazing white sand beach

Seaclusion

6 5

Barbados

Beachfront | Pool | AC

Details
Mandala is a perfect Punta Cana family villa, with all the bedrooms upstairs or in the guest house and the common area downstairs. You'll love relaxing outside while the kids ...
Mandala Villa is located right on the La Cana Golf Course

Mandala

6 6+

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
These resort villas are perfect for any group that wants to vacation in style. The villas range from three to six bedrooms, and every suite has a king or two ...
The elegant Shore Club Villas feature private swimming pools
4, 5 BR rates.

The Shore Club Oceanfront Villa

6 8

Long Bay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
Les Lataniers has a uniquely Caribbean charm, and I love how the owners have combined antique decor with modern amenities. The lava stone infinity pool is awesome, and the cabana ...
Villa Les Lataniers sits at the very end of Anse des Cayes
5 BR rate.

Lataniers

6 6

Anse des Cayes, St. Barts

Pool | AC

Details
This beachfront villa is a great choice if you want to take your family to Turks and Caicos, and you want a bit more of a resort feel but still ...
BE - Beach Front Villa Plus 1 Bedroom Cottage at Long Bay photo
Specials.

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

6 6+

Long Bay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
Casa Patron is a great villa if you and your guests want plenty of space in a gated community. The bedrooms are spread throughout the home, but a couple are ...
Casa Patron Villa is located just above Colina

Casa Patron

6 5+

Costa Rica

Pool | AC

Details
If you and your friends want to take a family vacation, Harmon Estate is perfect. Thanks to the main house and two guest houses, five couples or two families could ...
The Harmon Estate Villa is located in the Eco Golf Community

Harmon Estate

6 6

Costa Rica

Pool | AC

Details
Amalia is a gorgeous villa for a luxurious St. Martin vacation. I love how its architecture frames the views and creates open spaces for making memories. The bedrooms are all ...
Amalia Villa is located on a hillside overlooking Guana Bay
5 BR rate.
Specials.

Amalia

6 7

Guana Bay (Dutch Side), St. Martin

Near Beach | Pool | AC

Details
Blue Dragon is dramatic, luxurious, and spacious. It's minutes from Gouverneur's shops and activities, and a short hike from the beach. The villa's six bedrooms sleep 12 (or more with the ...
Blue Dragon sits on the hillside above Gouverneur

Blue Dragon

6 6

Gouverneur, St. Barts

Pool | AC

Details
CieloMar is one of the most stunning villas in the Caribbean. It has everything you could want in a vacation rental, like an infinity pool, lounging space, a gourmet kitchen, ...
CieloMar is perched on the hillside above Peninsula Papagayo in a gated community
3-5 BR rates.

CieloMar

6 7+

Costa Rica

Pool | AC

Details
This gorgeous family-friendly villa is perfect if you have older children. Each of the bedrooms has exterior access, and there's a studio suite on the lower level where you can ...
Mapai is located in Terrasse de Cul de Sac and looks out to Pinel Island
5 BR rate.
Specials.

Mapai

6 6+

Cul de Sac (French Side), St. Martin

Pool | AC

Details
Corales 60 is the place to be for an elegant, tranquil vacation. This luxury villa would be perfect for couples and friends, with six independent cottage suites, open interiors, and a ...
Corales 60 Villa is located on the Golf Course in the Punta Cana Resort & Club

Corales 60

6 6+

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
Allegria is a great choice for your next beachfront vacation. You can kayak, swim, and sunbathe right outside the back door on the most gorgeous beach in the world: Emerald ...
Allegria Villa is located on a beautiful stretch of beach across from Mangrove Cay

Allegria

6 6

Leeward, Turks and Caicos

Beachfront | Pool | AC

Details
Moon Kai is a great family vacation villa on a barefoot beach in Cayman Kai. The villa is designed for comfort, from the soft sand and calm water to the ...
Moon Kai is located right on a white sandy beach with in walking distance to Rum Point

Moon Kai - Platinum

6 6

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Alta Gracia pulls out all the stops. This villa is part of Punta Cana Resort, but it feels like a resort in and of itself. Every single detail inside and ...
Alta Gracia Villa is located in Punta Cana near a beautiful golf course

Alta Gracia

6 6

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
Villa de Agua has all the amenities of a classic Caribbean rental, and the design is magazine-worthy. If you love to cook, the kitchen’s luxury appliances and massive counter ...
Villa de Agua is located in Punta Cana on the ocean ans just moments from Corales Beach

Villa de Agua

6 6+

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
Cabuya is one of the most gorgeous villas on Providenciales's eastern coast. This villa has it all: a beachfront location, gorgeous design, an infinity pool, and a location near tons ...
Cabuya Villa is located in Leeward on a beautiful stretch of white sand beach
5 BR rate.
Specials.

Cabuya

6 6+

Leeward, Turks and Caicos

Beachfront | Pool | AC

Details
Z'Abricot is a great option for your next family vacation. All of the bedrooms are interior access only, there's a loft with room for four kids, and the villa is ...
Villa Z'Abricot is located near Orient Bay
4, 5 BR rates.
Specials.

Z'Abricot

6 4

Orient Bay (French side), St. Martin

Pool | AC

Details
Kisiwa is an elegant, luxurious vacation rental near Grace Bay. Staying here gives you easy access to the beach and modern amenities. The majority of the villa is set outside ...
Kisiwa House is located just steps away from Grace Bay Beach
Specials.

Kisiwa

6 6+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
Beach Enclave gives you gorgeous ocean views, resort amenities, and modern living spaces fit for any interior design magazine. The villa is a short walk from picturesque Sunset Beach and ...
Beach Enclave at Grace Bay is located on a beautiful stretch of Grace Bay Beach
Specials.

BE - 6 Bedroom Premium Ocean View at Grace Bay

6 6+

Grace Bay, Turks and Caicos

Near Beach | Pool | AC | Resort Villa

Details
Blondel Cove has everything you could possibly want in a luxury vacation villa. It has its own gym, home theatre, and wine room; but it’s also close to the ...
Aerial views of the area

Blondel Cove

6 6+

Leeward, Turks and Caicos

Beachfront | Pool | AC

Details
Blue Vista offers waterfront luxury, peace and quiet, and tons of room for large groups. There are two separate sleeping quarters, so two families could enjoy the villa in privacy. ...
Blue Vista Villa is located in Turtle Tail
4 BR rate.

Blue Vista

6 6+

Turtle Tail, Turks and Caicos

Pool | AC

Details
Hura Sea Estate is a quietly luxurious beachfront villa with access to Long Bay and proximity to several restaurants and shops. The estate offers two houses with their own bedrooms ...
Hura Sea Estate photo

Hura Sea Estate

6 6+

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Find all the Caribbean luxury and beauty you could dream of at Azzurra. This Grace Bay villa has two stories of interior and exterior lounges, a chef-worthy kitchen, and tons ...
Aerial views of the property

Azzurra

6 6+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Plum Bay is a quiet, restful retreat for your family's next vacation. It's between two lovely, quiet beaches in the gated Terres Basses community. There's tons of room inside and ...
Plum Bay Villa is located in Terre-Basses
2-4 BR rates.
Specials.

Plum Bay

6 6

Terres Basses (French side), St. Martin

Pool | AC

Details
This rental property combines two villas into a supersized vacation home. Casa Luna is great for travelers who want the privacy of a villa without losing resort amenities and vacationers ...
Casa Luna

Casa Luna

6 6+

Grand Cayman, Cayman

Beachfront | AC | Resort Villa

Details
The Last Resort stands true to its name…it’s certainly a paradise and feels like a mini-resort. This beautiful estate sits elevated between Chocolate Hold and Hart Bay with ...
The Last Resort Villa located in Chocolate Hole

The Last Resort

6 6+

Chocolate Hole, St. John

Pool | AC

Details
If you're looking for a lavish getaway, Legasea in Turks and Caicos is the place to be! Whether you're after some rest and relaxation, or something a bit more active, ...
Legasea Villa on Long Bay
Specials.

Legasea

6 6+

Long Bay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
There's something for everyone at Sea Star! Kick back in the infinity pool and gaze out at the sea, walk down the stairs to the coral and sand beach, or ...
Sea Star Villa is located on Cabrita Point

Sea Star

6 6+

St. Thomas, USVI

Beachfront | Pool | AC

Details
This villa is easily large enough for five couples traveling together or a family vacation. There's tons of space, and every bedroom has its own patio, which is so nice ...
Loblolly Villa photo
2, 4 BR rates.

Loblolly Villa

6 6

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool | AC

Details
This classic, luxury beachfront villa sits on Little Trunk Bay, with those amazing boulders flanking the beach. It's truly paradise! There's every amenity you could want, from a fully equipped ...
Sol y Sombra Villa is located on a hillside just above Little Trunk Bay

Sol y Sombra

6 6+

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

Details
Looking for luxury in St. Martin? Pamplemousse is a great choice - it’s elegant, spacious, and convenient to a ton of the island’s amenities. There are multiple areas ...
Pamplemousse is located in Terres Basses on a cliffside with views looking toward the Caribbean
3, 4 BR rates.
Specials.

Pamplemousse Villa

6 6+

Terres Basses (French side), St. Martin

Pool | AC

Details
Baraka Point has a so much privacy and great beach access. You can snorkel around the reef right outside the villa, watch movies on the massive flat screen TV, do ...
Baraka Point is located on the point between Mountain Trunk and Nail Bay
3 BR rate.

Baraka Point

6 6+

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

Details
Two beaches to choose from, a large private pool, gated entrance, and views of the Caribbean waters are among the many features that will make it difficult to leave La ...
La Salamandre is located in Terres Basses with views of Simpson Bay
4, 5 BR rates.
Specials.

La Salamandre

6 6

Terres Basses (French side), St. Martin

Near Beach | Pool | AC

Details
Only minutes from the beach, tennis, and shopping, Encore has spacious living areas both inside and out. The gazebo and outside dining area are great places to gather with family ...
Encore Villa is located in Terres Basses and is nestled amongst beautiful tropical foliage
4, 5 BR rates.
Specials.

Encore Villa

6 6

Terres Basses (French side), St. Martin

Pool | AC

Details
Bajacu Villa has a totally unique design that gives you the best of both worlds: hilltop views and easy ocean access. This sprawling retreat has two infinity pools and tons ...
Bajacu is located on a private hilltop in Turtle Cove

Bajacu

6 7+

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

Details
Guests of Kismet can enjoy both sunrise and sunset views, is surrounded by gorgeous tropical gardens. Its perfect for special events like weddings and receptions. There's three separate bedroom pavilions, ...
Kismet Villa Estate is located on a hilltop over Maria Bluff

Kismet

6 6+

Chocolate Hole, St. John

Pool | AC

Details
Location, location, location! Petite Plage 5 is a sprawling beachfront property sleeping up to 12 guests offering privacy, one of the largest pools on the island and quick access to the shops ...
A resort like pool and amazing ocean views
Specials.

Petite Plage 5 Villa

6 6+

Grand Case (French side), St. Martin

Beachfront | Pool | AC

Details
Valentina has everything you could want for a quiet, relaxing vacation. There's fitness equipment and a lap pool so you can get your workout in, and there's plenty of loungers ...
Valentina Villa is located at the eastern end of Pointe Milou
3, 4 BR rates.

Valentina Villa

6 6

Pointe Milou, St. Barts

Pool | AC

Details
Inside and out, Pelican Vista offers the best of Providenciales. You can enjoy the view inside, or find a spot on the terrace or balcony to look out over the ...
The pool and palapa at Pelican Vista Villa

Pelican Vista

6 5

Grace Bay, Turks and Caicos

Near Beach | Pool | AC

Details
Colibri Cottage is ideal for a nature-centric getaway in St. Lucia. The villa has gorgeous views of Petit Piton and the sea, plus its minutes away from water excursions and ...
Colibri Cottage sits on a hill above Soufriere Bay
2 BR rate.

Colibri Cottage

6 6

Soufriere, St. Lucia

Near Beach | Pool

Details
Le Reve will have you hooked from the first glance. Palm trees, sandy beaches, and gorgeous ocean views fill the exterior, and you can soak it all in from the ...
Le Reve Villa is located on a private stretch of beach in Baie Rouge
Specials.

Le Reve Villa

6 7+

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

Details
Located within the gated community of Sandy Lane Estate, Moon Dance Villa is ideal for couples who want a tropical getaway with regal charm. The villa is surrounded by thick ...
Luxurious pool and backyard at Moon Dance Villa
4 BR rate.

Moon Dance Villa

6 6+

Barbados

Pool | AC

Details
Always Villa, recently entirely renovated, is decorated in appealing white to showcase its clean lines, as well as gleaming polished floors. It has plenty of space for large families or ...
Always Villa is located in Terres Basses
4, 5 BR rates.
Specials.

Always Villa

6 6

Terres Basses (French side), St. Martin

Pool | AC

Details
Views of tropical greenery, Caribbean waters, and the hills beyond can be enjoyed firsthand at Maison de Reve Villa. Six large bedrooms with ensuite baths make this resort villa accommodating ...
Maison de Reve is located on a hillside in the Terres Basses area
4, 5 BR rates.
Specials.

Maison de Reve Villa

6 6+

Terres Basses (French side), St. Martin

Near Beach | Pool | AC

Details
Triton Villa is nestled into its own hillside enclave above Lockrum Bay and Little Harbour. This villa shares a secluded cove and amazing snorkeling spots with two other villas in ...
Triton Villa is located on LockRum Bay
4, 5 BR rates.

Triton Villa at Kamique

6 6+

Anguilla

Near Beach | Pool | AC

Details
Spacious and colorful, Mare Blu Villa overlooking Rendezvous Bay is the ideal getaway for your St. John vacation. Up to 12 people can call this villa their home, and there's plenty ...
Mare Blu is located hillside on the exclusive Rendezvous Bay overlooking the south shore
3-5 BR rates.

Mare Blu Villa

6 8

Rendezvous Bay, St. John

Pool | AC

Details

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