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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.

Coconut Walk is a gorgeous choice for a group vacation. The villa is modern, elegant, and well-designed for large parties. Most of the bedrooms are on the upper level, but ...
Coconut Walk is an oceanfront estate on Seven Mile Beach

Coconut Walk - Platinum Luxury

8 7+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Fischer’s Reef is a great beachfront villa for large groups. There are four king suites, three queen suites, and a bunk room, so families can enjoy plenty of privacy ...
Fischer's Reef Villa is located in Rum Point right on the beach

Fischer's Reef - Platinum

8 8+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
If you want to breathe in the ocean air and relax, Arrecife 17 is an excellent choice for your next vacation. It’s in Punta Cana, which is a luxury resort ...
Arrecife 17 is located in Punta Cana with beautiful Caribbean views

Arrecife 17

8 8+

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
Emerald Cay combines natural beauty with state-of-the-art technology for the ideal modern getaway. The master suite is a great example of this balance: floor-to-ceiling windows frame the ocean view, while ...
Aerial views of Emerald Cay

Emerald Cay

8 8+

Taylor Bay-Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

Details
The Point Estate is an amazing option for families who want a totally luxurious private island experience. This estate offers seven gorgeous master suites and an impressive bunkroom for children, ...
The Point Estate Villa rests on a cliffside with scenic views

The Point Estate at Moskito Island

8 8

Moskito Island, BVI, British Virgin Islands

Pool | AC

Details
Sun Rays Villa in Cayman Kai

Sun Rays - Platinum

8 8+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Emara East provides a resort-like experience while maintaining the exclusivity of a villa. Whether you were a Prince fan or just seeking your own private haven, this property is ideal ...
Emara East is located on the Turtle Tail peninsula of Providenciales island

Emara East

8 8+

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

Details
If you're looking for a tropical paradise, then Sandy Estate in the Turks and Caicos should be at the top of your list! With two stunning villas, 8 bedrooms, luxurious pools, ...
Endless ocean Views at Sandy Bottom

Sandy Estate

8 8

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

Details
Bella Rocca in Cayman is the epitome of luxury. Perfect for large groups, it's even ideal for weddings. But what I really love about this villa is the sheer beauty ...
Bella Rocca villa in Cayman

Bella Rocca - Platinum

8 8+

Grand Cayman, Cayman

Pool | AC

Details
Just two minutes from the beach, Bluff House and Cottage is great for families and friends traveling together. The main house has six bedrooms while the cottage offers an additional ...
Bluff House in Sandy Lane
6 BR rate.

Bluff House - Sandy Lane

8 8

Barbados

Near Beach | Pool | AC

Details
Mango Bay is a large estate featuring seven bedrooms, a full on-site staff, and easy access to some of Barbados most popular attractions. The villa feels pretty private because it's ...
Mango Bay's patio sits right on the beach
7 BR rate.

Mango Bay

8 7+

Barbados

Beachfront | Pool | AC

Details
If you want to not only see the water from your villa but be able to step right into it, you'll love Beach Court Villa. Shoal Bay is a great ...
Beach Court Villa is settled at the western end of Shoal Bay Beach
2-7 BR rates.

Beach Court Villa

8 8

Anguilla

Beachfront | Pool | AC

Details
Fabrizia Villa is a great property for groups or a family with older children. This vacation rental has 8 bedrooms, several private terraces, and an infinity pool that juts out over ...
Fabrizia Villa offers a great pool nestled on the hillside over Gustavia Harbor
3-7 BR rates.

Fabrizia Villa

8 9

Gustavia, St. Barts

Near Beach | Pool | AC

Details
One of my favorite things about Dawn Beach Villa is how close it is to all the amenities of Turtle Cove Marina. Several restaurants, boat charters, snorkeling reefs, and dive ...
Dawn Beach on Grace Bay (photo rendering)

Dawn Beach Villa

8 8+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
From the inviting front exterior to the contemporary furnishings, from the large pool to the quiet beach, Kaiku Villa is deluxe in every way. It has the feel of a ...
Kaiku Villa is located in Rum Point on the ocean with its own beachfront
7 BR rate.

Kaiku

8 6+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Nelson Gay House’s design, staff, and location are all the ingredients you need for an incredible vacation. The crystal blue waters just outside the garden are impossible to resist, ...
Nelson Gay House is located on Godings Beach and has beautiful gardens
6, 7 BR rates.

Nelson Gay House

8 8+

Barbados

Beachfront | Pool | AC

Details
Your trip to the Dominican Republic should be nothing short of quiet and relaxing, and Casa Kimball will help redefine the word vacation for you. Offering the seclusion you crave ...
Casa Kimball is located on the north coast of the island of the Dominican Republic

Casa Kimball

8 8

Cabrera, Dominican Republic

Near Beach | Pool | AC

Details
Mullins Mill is truly where the living is easy. With a full staff to anticipate your every desire, you'll have little to do but relax and have fun. Just exploring ...
There is a beautiful ridge side pool at Mullins Mill
4, 6 BR rates.

Mullins Mill

8 8

Barbados

Pool | AC

Details
La Belle Creole is a great choice for a family vacation. There are eight bedrooms total, and seven of them have king beds. One bedroom has a connected twin suite ...
La Belle Creole photo
4-7 BR rates.

La Belle Creole

8 7

Saint Jean, St. Barts

Pool | AC

Details
If you want to hear the ocean from every room, then Sunrise Villa is the perfect setting for your next vacation. With delicious food, an accommodating staff, private pool and ...
Sunrise Villa photo

Sunrise Villa

8 8

Cabrera, Dominican Republic

Beachfront | Pool | AC

Details
The Beach House's high-class architecture and contemporary style is enough to make you want to stay forever, but that's not even close to where its amazingness ends. In fact it's ...
The Beach House features an amazing pool and outdoor area
Specials.

The Beach House

8 9+

Anguilla

Beachfront | Pool | AC

Details
Sentosa Villa is the perfect vacation rental if you want a luxurious getaway on Grace Bay Beach with resort amenities. There's a gorgeous heated pool and Jacuzzi to enjoy along ...
Sentosa is located along a beautiful stretch of Grace Bay Beach

Sentosa Villa

8 8

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Jolly Harbour's Palm Point Villa is THE retreat for wedding parties, family reunions, or any group of 16 who are ready for paradise. Every angle shows off exceptional views, and the ...
Palm Point Villa is located right on Jolly Harbour
6 BR rate.
Specials.

Palm Point Villa

8 8+

Jolly Harbour, Antigua

Beachfront | Pool | AC

Details
This villa is perfect for family reunions or staff retreats. The sheer size of it all makes you feel like you're renting your very own hotel! The decor looks straight ...
Hawksbill Villa is located on the beautiful Grace Bay Beach
6 BR rate.

Hawksbill Villa

8 9

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Pearl East will make you feel like royalty. I love this villa for large family reunions and get-togethers with all your friends, because there's space for everyone inside and out. ...
Aerial view of Pearl East
5-7 BR rates.

Pearl East Villa

8 8+

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Pearl West is incredible. This villa is right on Long Bay, which is one of the most private beaches on the island and has constant waves that are perfect for ...
Exterior Pearl West
5-7 BR rates.

Pearl West Villa

8 8+

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Martello House is pretty spectacular. It has two pools, a game room, and a media room to entertain your guests, while being a short drive from all of St. James' ...
Stunning views from the infinity edged swimming pool
6 BR rate.

Martello House

8 8+

Barbados

Pool | AC

Details
Our Cayman Cottage is pretty impressive. This villa was made for family reunions, with ample space for kids and adults to spread out and let loose. I love how the ...
Our Cayman Cottage sits along a beautiful stretch of beach on the north side of Grand Cayman
Specials.

Our Cayman Cottage

7 6+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Evolution is going to revolutionize your next family vacation. Not only is there a specific children's bedroom, but there's also games and activities throughout the house that kids will love. ...
Evolution Vill offers it all - right on the beach

Evolution - Platinum

7 7+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
This luxury villa is absolutely beautiful and has plenty of room for any group. The outdoor space is amazing, with water sports equipment, an outdoor kitchen, and beach access. There’...
The pool and beautiful beach at Kaia Kamina

Kaia Kamina - Platinum

7 7+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Sand & Sea offers tons of ways to have fun in the sun. Not only does it sit directly between Grace Bay and Blue Haven Marina, it also has its own ...
Sand and Sea Villa

Sand and Sea

7 7+

Leeward, Turks and Caicos

Near Beach | Pool | AC

Details
Middle Cay is the perfect-sized, perfectly stocked private island for two families to share for a tropical getaway. The location is easy to get to and is close to Harbour ...
Middle Cay photo

Middle Cay

7 6+

Harbour Island, Bahamas

Pool | AC

Details
Beach Enclave is unique not only because it sits on Long Bay, but also because it has a resort feel and partnership with KiteProvo to offer guests the best Turks ...
A boardwalk to the beach
6 BR rate.
Specials.

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

7 6+

Long Bay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
Villa Londali is a great family villa, thanks to its location, bedrooms, and amenities. It's in Punta Cana Resort, which has its own spa, golf, beach, and tennis courts. Two ...
Villa Londali is located in the Punta Cana Resort and has amazing lake and golf course views

Villa Londali

7 7

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
Kempa Kai is luxurious, gorgeous, and unforgettable. Its modern design is both beautiful and practical, while the exterior is packed for fun and relaxation. The beach is steps away, and ...
Kempa Kai villa is located on a nature preserve near Rum Point

Kempa Kai

7 7

Grand Cayman, Cayman

Beachfront | AC

Details
This wedding-friendly villa is within walking distance to amazing resort amenities, restaurants, and an 18-hole golf course in a gated community. The villa itself has a tropical back terrace with ...
Casa de Suenos is located within the gated Los Suenos Resort community

Casa de Suenos

7 7

Costa Rica

Pool | AC

Details
If you've been dreaming of a five-star luxury vacation, Royal Island is hard to beat. This private island retreat has everything you need for an unforgettable trip: a sailing fleet, ...
Royal Island is located four miles from North Eleuthera, and 40 miles northeast of Nassau
6 BR rate.

Royal Island

7 6+

Eleuthera Island, Bahamas

Beachfront | Pool | AC

Details
If you're looking for luxury, Kempa Caribe is the place to be. Not only is this villa on a massive beachfront estate, it's also decked out with five-star amenities for ...
Castillo Caribe is located on the southern coast of Grand Cayman

Kempa Caribe

7 7+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
If you love the sea, Cayman Castle and Guesthouse is the place to be. This expansive villa enjoys an oceanfront location on Gun Bay near snorkeling reefs, the Wreck of ...
Cayman Castle is located on incredible beach frontage on Gun Bay

Cayman Castle and Guesthouse

7 7+

Grand Cayman, Cayman

Near Beach | Pool | AC

Details
If you want a beachfront villa with private bedrooms, a generous lap pool, and amazing snorkeling, Mora is a great choice. There are seven bedrooms spread between the two-story main ...
Villa Mora is located on a beautiful beachfront in South Sound

Mora

7 7

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Epicure has everything guests could want for a relaxing, cozy Caribbean vacation. The villa has tons of space for 14 guests, both in the seven king suites and in the expansive ...
Epicure Villa is located on a hillside overlooking Marigot
4-6 BR rates.

Epicure

7 7

Marigot, St. Barts

Pool | AC

Details
Emerald Bay is one of the most gorgeous villas on Providenciales' south end. This chic, elegant estate offers lodging for up to 16 guests, a full fitness center, and butler, chef, ...
Emerald Bay is located in Turtle Tail on the south side of Providenciales

Emerald Bay

7 7

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

Details
Zenaida offers a great experience at an exceptional value. The beach is down a short, private path, and the villa has a private, night-lit tennis court with a soft Har-Tru ...
Zenaida Beach & Tennis Estate is located just above Sandy Hill Beach
3-6 BR rates.

Zenaida Beach & Tennis Estate

7 7

Anguilla

Beachfront | Pool | AC

Details
This seaside villa is 7,000 square feet and is on 3.5 acres of land with gorgeous panoramic views. Between the pool, hot tub, two hammocks, and snorkeling equipment, there's little reason to ...
Paradise Villa is located near Blowing Point
4, 5 BR rates.

Paradise Villa

7 5+

Anguilla

Pool | AC

Details
If you are looking for a waterfront villa with the ultimate location, Vieux Caribe is the perfect choice. This island home is steps from Taylor Bay, with kayaks to explore ...
Vieux Caribe Villa is located near Taylor Bay Beach
5 BR rate.

Vieux Caribe Villa

7 7+

Taylor Bay-Sapodilla Bay, Turks and Caicos

Near Beach | Pool | AC

Details
It is probably the short walk to Guana Bay Beach that will please you the most when you stay at Alizee villa, but the seven-bedroom villa has much more to ...
Alizee Villa sits on a hillside above Guan Bay
3-6 BR rates.
Specials.

Alizee Villa

7 7

Guana Bay (Dutch Side), St. Martin

Near Beach | Pool | AC

Details
Tamarind Villa is an ideal choice for a family with young children. It has 7 bedrooms, with two cribs and one crib with a pack n' play. A wood patio runs ...
Tamarind Villa is located in Windward Hills views are of both the Atlantic Ocean and the Caribbean
3 BR rate.

Tamarind Villa

7 7

Cap Estate, St. Lucia

Pool | AC

Details
Seven bedroom La Plage Villa is located right on Lorient Beach. Offering modern amenities such as flat-screen TVs, US satellite service, and internet access, the property is great for couples ...
Luxurious Lorient Bay beachside pool deck at La Plage
1-6 BR rates.

La Plage Villa

7 7

Lorient, St. Barts

Beachfront | Pool | AC

Details
A La Mer Villa is one of the most spacious, well-designed villas on St. John. Its exterior has so many places to relax and lounge, you may never want to ...
A La Mer sits on St. John's coastline near Grat Cruz Bay

A La Mer Villa

7 7

Great Cruz Bay, St. John

Near Beach | Pool | AC

Details
Le Manoir de Lorient is one of the most unique properties on St. Bart's. This five-bedroom villa combines Old World charm with modern amenities into one luxurious vacation rental. The ...
Le Manoir de Lorient is tucked in a sweet neighborhood just across the street from Lorient Beach
4-6 BR rates.

Le Manoir de Lorient

7 6+

Lorient, St. Barts

Near Beach | Pool | AC

Details
Fustic House is a legendary vacation destination. The villa was built in the 18th century, then transformed by the famous theatrical designer Oliver Messel in the 1970s. Fustic House offers ...
Amazing private swimming pool at Fustic House

Fustic House

7 7

Barbados

Near Beach | Pool | AC

Details
If you are looking for a completely stunning location for your family getaway, Coral House might just be it. With a private staff, yoga studio, personal chef, and an outdoor ...
Coral House Villa is located on Grace Bay Beach
5 BR rate.

Coral House Villa

7 7+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Caye Blanche is a fun choice for couples or large families with older kids. It's close to Anse Marcel's beach and several restaurants, but the villa still feels hidden on ...
Caye Blanche photo
5, 6 BR rates.
Specials.

Caye Blanche

7 7+

Anse Marcel (French side), St. Martin

Pool | AC

Details
Le Caprice is designed for days of sunbathing and unwinding. The large pool is surrounded by a sprawling sundeck, and the outdoor kitchen has everything you need to enjoy every ...
Le Caprice Villa is located on a hilltop above Baie Rouge in Terres Basses
4-6 BR rates.
Specials.

Le Caprice Villa

7 6

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

Details
Bella Vita Villa is a three-story house with a ton of privacy, luxury, and amenities. The tropical surroundings, infinity pool, and rooftop kitchen give guests plenty to stay entertained with ...
Bella Vita Villa is located in the residential enclave of Pelican Key in Dutch St. Maarten
4, 6 BR rates.
Specials.

Bella Vita Villa

7 8+

Pelican Key (Dutch side), St. Martin

Pool | AC

Details
This is a fantastic property for large families or groups that are working within a budget. There is plenty of space in this six/seven bedroom home for all to ...
Twin Palms is located near Rum Point on a beautiful stretch of ocean

Twin Palms Villa

7 4

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Villa Mora balances luxury, access, and spaciousness. With 8,000 square feet and beachfront access, everyone in your party will have plenty of room to spread out and relax. In addition to ...
Villa Mora is located beachfront in South Sound

Villa Mora

7 7+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Cayman Castle has plenty of opportunity for fun! It has access to a beach, tons of room outside to take in the view, and is close to some of the ...
Cayman Castle is located on incredible beach frontage on Gun Bay

Cayman Castle

7 7+

Grand Cayman, Cayman

Near Beach | Pool | AC

Details
Wake up to the soothing sounds of the ocean and fall asleep to the cooling trade winds. Huge arcs throughout the house make you feel as if you are looking ...
Aerial views of Long Bay
4 BR rate.

Conched Out

7 7

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
If you want your own private beachfront home with plenty of room for all 17 of your guests, Seascape is for you. A large wall of windows on every floor allows ...
Seascape is located on Seven Mile Beach

Seascape Villa

7 5

Grand Cayman, Cayman

Beachfront | AC

Details

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