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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.

One thing everyone who stays at Akasha mentions is the gorgeous view. It’s absolutely breathtaking! The villa is well-designed for big families because four of the suites are in ...
Akasha Villa is located in Cap Estate and offers views of the Piton Mountains and Pigeon Island
1-5 BR rates.

Akasha Villa

6 6

Cap Estate, St. Lucia

Pool | AC

Details
SPECIAL RESERVE COLLECTION includes a Private Chef for up to 2 meals/day, Preferred access to Beach Club chaise lounges, VIP arrivals service, and 24/7 Personal Concierge. Located in Saline, Dunes Villa ...
Dunes Villais located on 2.5 acres in Saline

Dunes Villa

6 6

Saline, St. Barts

Near Beach | Pool | AC

Details
With three secluded villas offering accommodations for up to 12, an on-site chef, and a chapel, Little Whale Cay is a great spot for special events or family reunions. The Flamingo ...
Little Whale Cay private island retreat in the Berry Islands

Little Whale Cay

6 6

Berry Islands, Bahamas

Pool | AC

Details
Antilles Pearl is a super luxurious beachfront villa in one of the best spots on Anguilla. There's a 50-foot skywalk that makes you feel like you're floating above the sea, ...
Antilles Pearl is located on Shoal Bay Beach
5 BR rate.
Specials.

Antilles Pearl Villa at Altamer

6 6

Anguilla

Beachfront | Pool | AC

Details
Sandyline Villa is one of the most luxurious estates on St. Martin. The exterior amenities are endless, and the villa’s design blends the lines between inside and out. Kids ...
Plenty of loungers surround the swimming pool
3-5 BR rates.
Specials.

Sandyline Villa

6 7

Terres Basses (French side), St. Martin

Near Beach | Pool | AC

Details
The name says it all at Go Easy Villa. This villa enjoys water and island views, a gourmet kitchen, numerous living areas, and its own tennis court. The beach is ...
Go Easy Villa at Sugar Hill

Go Easy Villa at Sugar Hill

6 6+

Barbados

Pool | AC | Resort Villa

Details
Vistamar Villa has plenty of room for any family vacation or special event. With six bedrooms and lots of living space, you can spend time together or apart. Spend your ...
Vistamar features a poolside gazebo and an ample sundeck

Vistamar Villa

6 5

Barbados

Pool | AC

Details
Jable has gorgeous views, gorgeous design, and gorgeous amenities. Every spot in the villa is outfitted for luxury and comfort, from the interior to the exterior. Plus, the villa is ...
Tucked away on a hillside Jable Villa has a private pool that provides some amazing views
1-5 BR rates.

Jable

6 6+

Petite Saline, St. Barts

Pool | AC

Details
As one of the few six-bedroom villas on the island, Panache Villa delights with magnificent views and unforgettable sunrises and sunsets. This villa is beautiful inside and out! Traditional stone ...
Panache Villa has amazing views over Rendezvous Bay
3, 5 BR rates.
Specials.

Panache Villa

6 7

Rendezvous Bay, St. John

Pool | AC

Details
The impression one gets when walking into this villa, is simply elegant Caribbean. It features a clean white interior with beautiful modern decor. Alas the interior can only hold your ...
Amazing views of the harbor from Paradiso Villa
3-5 BR rates.
Specials.

Paradiso Villa

6 6+

Oyster Pond (Dutch side), St. Martin

Pool | AC

Details
There’s something for everyone at Sandalwood House. You can enjoy a round of golf and a romantic dinner for two in the covered gazebo, spend the night with cocktails ...
Twilight on the patio at Sandalwood Cottage
3, 4 BR rates.

Sandalwood House

6 7

Barbados

Near Beach | Pool | AC

Details
SPECIAL RESERVE COLLECTION includes a Private Chef for 3 meals/day, Preferred access to Beach Club chaise lounges, VIP arrivals service, and 24/7 Personal Concierge. Children are welcome at Silver Rainbow Villa, ...
Silver Rainbow Villa looks out into Petit Cul De Sac
3 BR rate.

Silver Rainbow Villa

6 6

Petit Cul de Sac, St. Barts

Near Beach | Pool | AC

Details
This newer 3-story beachfront villa offers ocean views and sunsets that will make your stay at Bougainvillea a lifetime memory. Surrounded by natural rock, this villa home is only minutes ...
The pool at Bougainvillea Villa has beautiful views of the Caribbean
4 BR rate.

Bougainvillea Villa

6 6

Dawn Beach (Dutch side), St. Martin

Pool | AC

Details
Tamarind Villa is located in Providencials' best neighborhood, right on Grace Bay Beach. The views from both inside and outside the villa are great, with the beach literally steps away. ...
Tamarind Villa is located on the shores of Grace Bay Beach

Tamarind Villa

6 6+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Eclipse Villa is perfect for large families or couples traveling together. The villa looks right out over the ocean, so the views are perfect. All you see are the blues ...
Eclipse Villa is located on the hillside in Vitet a few minutes away from Lorient Beach
3-5 BR rates.

Eclipse Villa

6 6

Camaruche, St. Barts

Pool | AC

Details
Royal Belize is an exclusive private island rental with seclusion, luxury, and full service. There are three villas and a bunkhouse on the island, and the full staff includes a ...
Royal Belize Private Island
5 BR rate.

Royal Belize - Private Island

6 6+

Belize

Beachfront | AC

Details
Casa Grande is totally relaxing. Its super open, has great views, and is steps from a private part of Grace Bay beach. Its great for families who want a fully-equipped ...
Casa Grande is located on a beautiful stretch of Grace Bay Beach

Casa Grande Villa

6 5+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
When you arrive at Bon Temps Villa, the first thing to do is stake out your chaise lounge. While everyone else will fight over the bedrooms, you'll have secured the ...
Bon Temps is located on the west side of Pointe Milou looking out into the Caribbean
4, 5 BR rates.

Bon Temps Villa

6 6

Pointe Milou, St. Barts

Pool | AC

Details
Le Manoir de Lurin Villa is larger than your usual villa! This six-bedroom rental offers tons of exterior space for everyone to find their own sunbathed or shaded spot to ...
Le Manoir de Lurin Villa photo
5 BR rate.

Le Manoir de Lurin Villa

6 6

Lurin, St. Barts

Pool | AC

Details
Get a gorgeous view of Dawn Beach and great access to Phillipsburg in one package at Dawn Beach Villa. Just ten minutes from Phillipsburg, here you will have access to ...
Beautiful views of the Caribbean form the pool at Dawn Beach Villa
2-5 BR rates.
Specials.

Dawn Beach Villa

6 6

Dawn Beach (Dutch side), St. Martin

Near Beach | AC

Details
Whether you are vacationing with others or having a quiet family trip, Amberley House is ready to meet your needs. With four full bedrooms in the main house and a ...
Poolside view of Amberley House
4 BR rate.

Amberley House

6 5

Barbados

Near Beach | Pool | AC

Details
Perched on the coast, Sun Salutations Villa has spacious, modern interiors and stunning views that make it an ideal spot for your next vacation getaway. This villa's large Great Room ...
The perfect image for Sun Salutations Villa
Specials.

Sun Salutations Villa

6 5+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Finding the perfect mix of oceanfront and privacy for a larger family can be difficult at times, but Coconut Villa makes it easier. The villa's freshwater pool, al fresco dining ...
Coconut Beach villa is right on the Beach near Rum Point
Specials.

Coconut Beach Villa

6 4

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Villa Susanna is a tropical paradise secluded above Marigot Bay. It's wooden exterior and lush gardens contrasts beautifully with the modern interiors and top of the line appliances. All four ...
Aerial view of Villa Susanna

Villa Susanna

6 7

Marigot Bay, St. Lucia

Near Beach | Pool | AC

Details
Villa Colibri has a sleek and modern design that belongs on a magazine cover. There's a swimming pool with different depths that any swimmer can enjoy, tons of outdoor space, ...
You'll find contemporary class at Colibri Villa.
2-5 BR rates.
Specials.

Colibri Villa

6 6

Anguilla

Pool | AC

Details
This villa offers guests luxury, starting with its view of the 13th hole of the Royal Westmoreland Resort's golf course. There's plenty of room for guests to spread out, and ...
Beautiful pool and outdoor area at Westerings
5 BR rate.

Westerings

6 6

Barbados

Pool | AC

Details
This six-bedroom Clairmont Overlook Villa is absolutely perfect for large family getaways, employee retreats, or for a group of friends looking to spend some time in St. Croix. It's right ...
Clairmont Overlook is located right on Salt River
1-5 BR rates.

Clairmont Overlook

6 6+

St. Croix, USVI

Pool | AC

Details
I love this villa's clean lines and all-white interior, and how quiet and private it is. Not only is C'est La Vie beautiful and beachside, but it also has a ...
C'est La Vie is located on the beautiful beach of Plum Bay in the Terres Basses gated community
Specials.

C'est La Vie Villa

6 6+

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

Details
Mandalay Villa’s design, features, and amenities will make you feel like royalty the instant you arrive. This 5-bedroom beach house was made for social gatherings with more than 12,000 sq. ...
The palatial pool area

Mandalay Villa

6 7+

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
This villa has a great open floor plan and sits on picturesque Cayman Kai. The high ceilings, minimal design, and walls of glass windows bring the sea in, and the ...
Ocean Kai sits directly on the beach near Rum Point

Ocean Kai

6 5

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
This villa is unique because of the four-level design. The bedrooms are really spread out, so guests have privacy that can't be found in other villas. The pool provides a ...
Villa Coco Rock is located on a secluded Petit Cul de Sac hillside
2-5 BR rates.

Coco Rock Villa

6 6

Petit Cul de Sac, St. Barts

Pool | AC

Details
Hidden Cove is perfect if you love being on the water and want a bit of privacy. It's near great snorkeling reefs, the bioluminescent bay, and Rum Point Beach, so ...
Hidden Cove is located in Cayman Kai neighborhood
Specials.

Hidden Cove Villa

6 5

Grand Cayman, Cayman

Near Beach | Pool | AC

Details
Villa Oceania has a beautiful pool and shaded back patio

Villa Oceania

6 6+

Cap Cana, Dominican Republic

Pool | AC | Resort Villa

Details
Sirena is a great choice for families who want to soak up the island. Punta Cana is a resort community with golf courses, beaches, and five-star staff, so you can ...
Villa Sirena is located in Punta Cana on the La Cana golf course

Sirena

6 6

Punta Cana, Dominican Republic

Near Beach | Pool | AC | Resort Villa

Details
Point of View is a great villa rental for large groups of travelers who want to be near the beach without sacrificing comfort. There's too many notable features to list, ...
Point of View Villa is located on a picturesque Caribbean beachfront
Specials.

Point of View Villa

6 6+

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Maison Blanc Bleu is breathtaking. The pool is huge, and the deck leaves plenty of room if you use the villa's full capacity for 12 guests. I love that the master ...
Maison Blanc Bleu Villa photo
4, 5 BR rates.

Maison Blanc Bleu Villa

6 6

Lurin, St. Barts

Pool | AC

Details
I love Alta Bella because it's so peaceful. It's perfect for kids and family gatherings at a really great value. We can help you rent kayaks to make the most ...
Alta Bella Villa sits on a inlet just on chalk Sound

Alta Bella

6 6

Chalk Sound, Turks and Caicos

Near Beach | Pool | AC

Details
If you want a luxurious resort experience with zen-inducing Balinese design and nonstop ocean views, then you'll fall in love with Love Pumpkin at COMO Parrot Cay. This villa sits ...
A private cabana sits beachfront at Love Pumpkin

Love Pumpkin at COMO Parrot Cay

5 5

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
Eos is sleek, modern, and innovative. One of my favorite features is the retractable wall in each of the bedrooms that opens up the gorgeous surroundings. The design of this ...
Eos photo

Eos

5 5+

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Helios is very sleek, so your vacation feels swanky and relaxing all at once. One of my favorite features is the retractable wall in each of the bedrooms and the ...
Helios Villa Long bay

Helios

5 5+

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
This villa is equidistant from Turks and Caicos Islands Tennis Club, Turtle Cove, and Smiths Reef. Not only is the villa gorgeous, but the location is perfect for your family ...
Hyperion Villa at Long Bay Estates

Hyperion

5 5+

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Tip of the Tail is so private, you'll feel like you have the island all to yourself. It has an amazing view over the ocean, and has its own stretch ...
Tip of the Tail Villa sits on the peninsula for which it is named

Tip of the Tail

5 6

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

Details
Beach Enclave Ocean View Villas are stunning beachfront villas perfect for travelers who appreciate elegant design and want to spend time on the water. These resort villas have direct access ...
The pool and view of the ocean from Beach Enclave Ocean View Villas
3, 4 BR rates.
Specials.

BE - Ocean View Villas North Shore

5 5

North Shore, Turks and Caicos

Beachfront | Pool | AC

Details
Magens Hideaway is located on the Peterborg Peninsula overlooking Great Hans Lollick and the BVI's

Magens Hideaway

5 4+

St. Thomas, USVI

Pool | AC

Details
Hesperides is one of a kind. The location couldn't be better either, because it's close to Sapodilla Bay and Las Brisas Restaurant. The sunset views are so beautiful that there's ...
Hesperides House has amazing uninterrupted ocean views

Hesperides House

5 5

Taylor Bay-Sapodilla Bay, Turks and Caicos

Pool | AC

Details
Starfish Villa is one of the more vibrant villas in the Punta Cana Resort. The villa itself is well-equipped, but the resort's amenities are even better. Drop your kids off ...
Starfish Villa is located in Punta Cana on the golf course

Starfish

5 5+

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
Coral Pavilion is chic and elegant, the perfect vacation rental if you want to feel like royalty. You’ll love staring at the ocean right outside the French doors, and ...
The luxury pool at Coral Pavilion Villa sits just a few yard from the beautiful Grace Bay Beach

Coral Pavilion

5 5

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Hilltime is perfect for any family or couples who want to relax by the sea with minimal fuss. This villa is clean and simple, with plenty of space to relax ...
Hilltime Villa is located on the north coast of Cayman in Rum Point

Hilltime

5 4

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
White Cottage is a great vacation rental for anyone who loves the ocean and privacy. It's in a quiet region of Grand Cayman, and sits steps away from the beach. ...
White Cottage is a great beachfront villa

White Cottage

5 3

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Great Bluff Estate is perfect for groups who want privacy and space. It's fully gated, and sits on the quiet, residential East End. The beach is practically deserted, and there's ...
Great Bluff Estates sits along the beautiful northern coast of Grand cayman
Specials.

Great Bluff Estates

5 7

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Alinna is a gorgeous one-level villa with views of Chalk Sound. I love it for family vacations or couples' getaways, since there's a kids' room and four equal Master Suites. ...
Alinna sits just along Chalk Sound with beautiful water views
Specials.

Alinna

5 6+

Chalk Sound, Turks and Caicos

Pool | AC

Details
Second Chances is a great choice for a relaxed getaway. It's 200 meters from Grace Bay, so you can go to the beach whenever you want, and its pool terrace is ...
Second Chances Villa has plenty of outdoor space for relaxing and entertaining

Second Chances

5 6

Leeward, Turks and Caicos

Near Beach | Pool | AC

Details
The Five Bedroom Beach Level residences are perfect for families or four couples to share. They're right on Grace Bay and have exclusive access to a superior level of service ...
The Grace Bay Club Estate
Specials.

Grace Bay Club Estate Five Bedroom Beach Level Pool Residence

5 4+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
Casa de la Playa is perfect for two families who want to vacation on St. Martin's glamorous west coast. It has four suites for adults and one children's suite with ...
Casa de la Playa Villa is located on Baie Longue in Terres Basses
3, 4 BR rates.
Specials.

Casa de la Playa

5 5

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

Details
This five-bedroom beachfront resort villa is absolutely gorgeous. It's on Long Bay, which is the quieter, windier sister to Grace Bay, and it's in a gated community with fitness facilities, ...
Beach Enclave Beach Front Villas on Long Bay
Specials.

BE - Beach Front Villa at Long Bay

5 5

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Nirvana is ideal for couples who want to vacation on the beach in style. The pool isn't massive, but who cares when the ocean is steps away? Four of the ...
Nirvana's pool deck and lounges
Specials.

Nirvana

5 5

Barbados

Beachfront | Pool | AC

Details
Lime Tree is a cool villa to stay in because it combines Mediterranean architecture with cushy amenities. The master bedroom is like its own oasis, with a private bathroom and ...
Lime Tree Villa sits on a tropical hillside in the Peter Bay area
Specials.

Lime Tree at Peter Bay

5 4+

Peter Bay, St. John

Pool | AC

Details
La Case Créole is a great family vacation villa. It has six bedrooms spread across two levels, and every suite has its own bathroom and patio. The home feels ...
La Case Créole is located on a hilltop above St. Jean Bay
3, 4 BR rates.

La Case Créole

5 5

Saint Jean, St. Barts

Pool | AC

Details
Mirabelle is ideal if you want the beauty of Turks and Caicos without the crowds of Grace Bay. Sapodilla Bay is one of the less-populated beaches on Provo, but its ...
Mirabelle sits on a beautiful stretch of Sapodilla Bay Beach

Mirabelle

5 5+

Taylor Bay-Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

Details
This luxury rental sits right on Paynes Bay and is the only unit in the complex to have a private pool. It has super chic interiors and bedrooms that are ...
The Villa at the St. James is located beachfront on Paynes Bay Beach
4 BR rate.

The Villa at the St. James

5 5

Barbados

Beachfront | Pool | AC

Details

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