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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.

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

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

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
Specials.

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
Specials.

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

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

Cielo

4 5

Chalk Sound, Turks and Caicos

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
Alexambre has an amazing location in Jardin d'Orient, a gated community that overlooks Orient Bay Beach. This villa is a great option for families, because it has two king suites ...
Alexambre is located in Jardin d'Orient overlooking Orient Bay in the distance
Specials.

Alexambre

4 2

Orient Bay (French side), St. Martin

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
Bonavista Villa is located in a gated community, and is just steps away from Gibbs Beach. It has a cook, a laundress, and a housekeeper to see to your every ...
Tropical surroundings greet you at the pool at Bonavista Villa
3 BR rate.

Bonavista Villa

4 4+

Barbados

Beachfront | Pool | AC

Details
Evergreen is a luxurious garden villa with a full staff, spacious interiors, and modern amenities. You can watch movies or read a book from the owner’s library in the ...
The stunning Evergreen property, in the prestigious Sandy Lane neighborhood, from an aerial view
3 BR rate.

Evergreen Villa

4 5

Barbados

Pool | AC

Details
The modern villa of Ecume des Jours is just 15 minutes from the airport, but it is situated in a very secluded area with a beach that is literally right at ...
Ecume des Jours is located on the end of Plum Bay Beach
2, 3 BR rates.
Specials.

Ecume des Jours

4 3

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

Details
Four bedrooms and four baths make Kir Royal Villa perfect for a pair of vacationing couples or a large family. St. Jean Beach is just a few minutes away by ...
Kir Royal Villa is located in St. Jean
2, 3 BR rates.

Kir Royal Villa

4 4

Saint Jean, St. Barts

Near Beach | Pool | AC

Details
There are many villas in Terres Basses on the French side of St. Martin that can accommodate small children, but few will cater to the needs of a family with ...
Oceane Villa is located in Terres Basses on the French side of St. Martin
2, 3 BR rates.
Specials.

Oceane Villa

4 4+

Terres Basses (French side), St. Martin

Near Beach | Pool | AC

Details
With a thatched-roof outdoor dining area, hot tub, private infinity-edge pool, and beach access, you'll want Valentina Villa to become your home away from home. Located on Sapodilla Bay, you'll ...
Valentina Villa has a beautiful pool and patio and is situated just above Sapodilla Bay

Valentina Villa

4 4+

Taylor Bay-Sapodilla Bay, Turks and Caicos

Near Beach | Pool | AC

Details
Southern Breeze Villa is a warm, spacious home overlooking Fish Bay and Cocolobo Point. This fully air-conditioned beautiful four-bedroom home is the perfect getaway for friends or families traveling together. ...
Southern Breeze is located near the Battery Gut area and has amazing Caribbean views
1-3 BR rates.
Specials.

Southern Breeze

4 4

Rendezvous Bay, St. John

Pool | AC

Details
With four bedrooms, spacious living areas, and an open floor plan that combines indoor and outdoor living, High Trees Villa is a peaceful and relaxing home away from home. This ...
High Trees Villa is located on Gibbs Bay Beach

High Trees Villa

4 4

Barbados

Beachfront | Pool | AC

Details
At Le Moulin, you have instant access to St. Jean's beach, an infinity-edge pool, and air-conditioning. This 4-bedroom villa has an updated, open design so you can make the most ...
The landmark -Windmill- at Le Moulin Villa on St.Jean Beach
2, 3 BR rates.

Le Moulin Villa

4 4

Saint Jean, St. Barts

Beachfront | Pool | AC

Details
The Ushuaia Villa has four bedrooms, three queen and one with twin beds. The latter can accommodate families traveling with two older children, as it has its own bathroom, allowing ...
Ushuaia Villa has great views over Flammands

Ushuaia Villa

4 4

Flamands, St. Barts

Near Beach | Pool | AC

Details
Abrigado Villa is perfect for vacationing couples or families looking to entertain and unwind. There's plenty of room for privacy across the villa’s four bedrooms, but the common areas ...
Poolside views from the prestigious Abrigado Villa in Virgin Grand Estates
2, 3 BR rates.

Abrigado Villa

4 4+

Virgin Grand Estates, St. John

Pool | AC

Details
If you love outdoor showers, infinity pools, and a 20-second walk to the beach, stay at Alegria Villa. You'll find a spacious home with its own pool, gym, media room, ...
The beautiful pool and Caribbean views from Alegria Villa
Specials.

Alegria Villa

4 4

Anguilla

Near Beach | Pool | AC

Details
If you love design, you'll go crazy for Claridge villa. The magazine-worthy living area is all-white with exposed beams and an open design. Dark, well-polished wood cabinetry and furniture stands ...
Claridge Villa is located in the heights of Anse des Cayes overlooking St. Jean and Anse des Cayes
2, 3 BR rates.

Claridge Villa

4 4

Anse des Cayes, St. Barts

Pool | AC

Details
Vista Caribe is located in the exclusive Virgin Grande Estates and has breathtaking views of the Caribbean Sea, St. James, and St. Thomas. Overlooking the lush hillside of the island, ...
Vista Caribe is located above Great Cruz Bay in the Virgin Grand Estates
1-3 BR rates.
Specials.

Vista Caribe Villa

4 4+

Virgin Grand Estates, St. John

Pool | AC

Details
This spacious villa is perfect if you are looking for an active beach vacation. With a billiards table, private pool, and snorkeling right outside your door, you'll have more fun ...
Lounges over look the pool and out into the sound

Breezy Palms

4 3+

Chalk Sound, Turks and Caicos

Pool | AC

Details
Great Turtle sits nestled within the hills and enjoys wonderful views of Coral Bay, the Caribbean Sea, and the Bordeaux Mountains from nearly every vantage point on the property. With ...
Great Turtle Villa is nestled on a tropical hillside above Coral Bay
2, 3 BR rates.

Great Turtle Villa

4 4+

Coral Bay, St. John

Pool | AC

Details
Summer Breeze Villa, also known as Villa Minou, is one of the top choices in a vacation location for families with children of all ages. It offers more than simply ...
The infinity edge pool and patio deck overlook Grand-cul-de-sac
2, 3 BR rates.

Summer Breeze

4 4

Grand Cul de Sac, St. Barts

Near Beach | Pool | AC

Details
Located in the peaceful Turtle Tail area, Sandy Shore has direct beach access, a private onsite swimming pool, a kayak, and numerous water sports nearby. There are five little islands ...
Sandy Shore Villa

Sandy Shore Villa

4 4

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

Details
With four ensuite bedrooms, its own private infinity-edge swimming pool, and quick access to the sea and snorkeling, Breezy Villa is the perfect getaway for a family or friends traveling ...
Breezy Villa sits directly on the ocean

Breezy Villa

4 4

Long Bay, Turks and Caicos

Pool | AC

Details
This secluded villa is great for guests who want to relax with a good book or adventure on the water. Its just across the street from Sapodilla Bay, and guests ...
Bright Idea has great views of Chalk Sound

Bright Idea Villa

4 4+

Chalk Sound, Turks and Caicos

Beachfront | Pool | AC

Details
Guests at Sandcastle Pointe get access to jaw-dropping ocean views, modern amenities, and luxurious design. Dive into the private infinity pool or take a shot on the manicured putting/croquet ...
Sandcastle Pointe Villa is located just west of Shoal Bay Beach
Specials.

Sandcastle Pointe at Shoal Bay

4 4+

Anguilla

Pool | AC

Details
Great Escape is a great villa rental for a family vacation or special event. Everyone will have plenty of space, between the guest cottage and three bedrooms on opposite sides ...
Great Escape Villa is located on the Rum Point end of the island with a beautiful stretch of beach
Specials.

Great Escape Villa

4 3

Grand Cayman, Cayman

Near Beach | Pool | AC

Details
Because vacations are supposed to be relaxing and stress-free, it is often counterproductive to take a trip that involves renting a car and doing a lot of driving, especially in ...
Villa Mango sits on the hillside above Orient Bay
Specials.

Mango Villa

4 4

Orient Bay (French side), St. Martin

Near Beach | Pool | AC

Details
Ambiance is all that the name implies - a villa with a special atmosphere that will positively impact your entire vacation. The living spaces flow into one another, so there's ...
Ambiance is located in the heart of Terres Basses with access to beautiful beaches nearby
2, 3 BR rates.
Specials.

Ambiance Villa

4 4+

Terres Basses (French side), St. Martin

Pool | AC

Details
La Percha is ideal for any group of travelers. It has everything you could want in a tropical getaway- four Master Suites, direct beach access, privacy, and modern design. Its ...
La Percha Villa is ideally located on the beautiful Taylor Bay

La Percha Villa

4 4+

Taylor Bay-Sapodilla Bay, Turks and Caicos

Near Beach | Pool | AC

Details
Rapture Villa is 5000 sq. feet of Caribbean luxury and style. Elegant turtle statues float above the pool overlooking the sea and the Virgin Islands. The National Park Beach is only 15 ...
Rapture villa is located in Virgin Grand Estates

Rapture Villa

4 4

Virgin Grand Estates, St. John

Pool | AC

Details
With a private pool, onsite restaurants and activities, and a beachfront location, you and your family will never want to leave Turtle Villa. There's tons of outdoor space and gorgeous ...
Turtle Villa is located in Jolly Harbour on the beautiful Lignum Vitae Bay

Turtle Villa

4 4+

Jolly Harbour, Antigua

Beachfront | Pool | AC

Details
Reef Beach House truly is a tropical haven. Located right on Grace Bay Beach, this villa offers four air-conditioned bedrooms and tons of outdoor space. With three al fresco dining ...
Reef Beach House is located on the very desirable, Grace Bay Beach
2 BR rate.

Reef Beach House

4 3

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
If you like both contemporary and Caribbean styles, you'll love the beautiful browns, blues and whites at Seabird Villa. This villa is both soothing and classy, with a modern kitchen ...
Seabird Villa has beautiful sunset views
2, 3 BR rates.

Seabird Villa

4 4+

Anguilla

Near Beach | Pool | AC

Details
Martangie Villa has everything you need to enjoy a carefree vacation in Barbados. Spend your mornings playing golf or tennis, and come home to relax and watch the sun cast ...
Martangie Villa sits in it's stately location on the Gold Coast

Martangie

4 4+

Barbados

Beachfront | Pool | AC

Details

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