Caribbean Family Villas


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.


The combination of villa East and West, this large villa complex is the ultimate location for a large group. 16 BR rates available Pearls Of Long Bay Estate, Turks and Caicos villa

Pearls Of Long Bay Estate

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$16,000/Nt
Complete privacy on an island, great for large groups to get away from it all Offers Specials. Necker Island, Necker Island, BVI villa

Necker Island

Necker Island, BVI

Beachfront | Pool | AC

From
$80,000/Nt
Elegance inside and out at this 11-bedroom villa, Mes Amis - Bring your friends! 4, 5, 6, 7, 8, 9, 10, 11, 12 & 13 BR rates available Mes Amis, St. Martin villa

Mes Amis

Terres Basses (French side), St. Martin

Near Beach | Pool

From
$1,357/Nt
4 BR rates available Over Yonder Cay - A Private Island, Bahamas villa

Over Yonder Cay - A Private Island

Exuma and Cays, Bahamas

Beachfront | Pool | AC

From
$20,000/Nt
A quietly luxurious, All-Inclusive Hideaway 8 & 9 BR rates available Three Bees at Harbour Island, Bahamas villa

Three Bees at Harbour Island

Harbour Island, Bahamas

Beachfront | Pool | AC

From
$22,857/Nt
Arrecife 23/24/25 Estate at Punta Cana Resort, Dominican Republic villa

Arrecife 23/24/25 Estate at Punta Cana Resort

Punta Cana, Dominican Republic

Pool

From
$4,390/Nt
Whether you want to spend your vacation listening to your iPod and reading or play tennis or taking the time ... 5, 6, 7, 8, 9, 10 & 11 BR rates available Golden Clouds, Jamaica villa

Golden Clouds

Ocho Rios, Jamaica

Pool

From
$1,343/Nt
5 & 10 BR rates available Camp David, St. Barts villa

Camp David

Saint Jean, St. Barts

Beachfront | Pool | AC

From
$16,429/Nt
Gorgeous villa estate offers the utlimate in luxury with private beach and pools, gorgeous views, and resort amenties Offers Specials. Parrot Cay Resort- The Residence, Turks and Caicos villa

Parrot Cay Resort- The Residence

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

From
$13,500/Nt
2, 3, 4, 5, 6, 7, 8 & 9 BR rates available Valley Trunk Estate, Virgin Gorda, BVI villa

Valley Trunk Estate

The Baths, Virgin Gorda, BVI

Beachfront | Pool | AC

From
$6,000/Nt
Park yourself right on the beach in Jamaica's 10 bedroom jewel, Flor de Cabrera Villa Flor de Cabrera, Dominican Republic villa

Flor de Cabrera

Cabrera, Dominican Republic

Beachfront | Pool | AC

From
$2,900/Nt
High End Modern Elegance offers two swimming pools and two beaches on 2.5 acres Offers Specials. 5 & 8 BR rates available Le Bleu Villa, Anguilla villa

Le Bleu Villa

Anguilla

Beachfront | Pool | AC

From
$7,750/Nt
Self-contained hideaway (with its own theater) is a little chunk of paradise to make for the perfect holiday Offers Specials. 7 & 8 BR rates available Crystal Springs Villa, Barbados villa

Crystal Springs Villa

Barbados

Beachfront | Pool | AC

From
$7,245/Nt
Haystack Villa offers you outdoor living at it's best. With a grand pool, game room, pool table and verandah, this ... 5, 6, 7 & 8 BR rates available Haystack Villa at Tryall Club, Jamaica villa

Haystack Villa at Tryall Club

Montego Bay, Jamaica

Pool

From
$1,786/Nt
Huge luxury estate features 2 separate villas, a full staff, and incredible ocean views Ani Villa Estate, Anguilla villa

Ani Villa Estate

Anguilla

Pool

From
$8,600/Nt
The ultimate in luxury, this 10 bedroom estate sits on the very best part of Grace Bay beach. 5, 6 & 8 BR rates available Hawksbill Villa, Turks and Caicos villa

Hawksbill Villa

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$6,800/Nt
Lionsgate Mansion, Dominican Republic villa

Lionsgate Mansion

Cabarete, Dominican Republic

Beachfront | Pool | AC

From
$5,250/Nt
Offers Specials. Las Brisas, Dominican Republic villa

Las Brisas

Punta Cana, Dominican Republic

Beachfront | Pool | AC

From
$10,000/Nt
Villa Arrecife 24/25, Dominican Republic villa

Villa Arrecife 24/25

Punta Cana, Dominican Republic

Pool

From
$2,790/Nt
For corporate retreats, group events, or family reunions, this all-encompassing 9-bedrrom villa can provide all the amenities you'll need. 4, 5, 6, 7 & 8 BR rates available La Bella Casa , St. Martin villa

La Bella Casa

Terres Basses (French side), St. Martin

Pool

From
$1,071/Nt
A former embassy, this sprawling property is set up for big groups. The villa has a full staff and a fantastically creative manager. Its also walkable to a beach which is hard to find in St Lucia. Offers Specials. 5, 6, 7 & 8 BR rates available Capri Villa, St. Lucia villa

Capri Villa

Cap Estate, St. Lucia

Near Beach | Pool

From
$850/Nt
Sun, sand, and swimming on Plum Bay Beach for numerous guests with the villa's 9 bedrooms. 5 BR rates available Le Chateau des Palmiers, St. Martin villa

Le Chateau des Palmiers

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

From
$6,000/Nt
Heaven is where you'll think you are when staying at the private resort of Cereulean Villa Cerulean Villa, Anguilla villa

Cerulean Villa

Anguilla

Beachfront | Pool | AC

From
$14,286/Nt
Directly on Long Bay Beach, the Casa Varnishkes Villa is an opulent, spacious gated estate with everything a large group could need, including a sport court and massive pool. 6 BR rates available Casa Varnishkes Villa, Turks and Caicos villa

Casa Varnishkes Villa

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$2,464/Nt
You'll love A La Mer's enormous pool and deck, when you're not snorkeling at Great Cruz Bay 8 BR rates available A La Mer Villa, St. John villa

A La Mer Villa

Great Cruz Bay, St. John

Near Beach | Pool

From
$5,280/Nt
6, 7 & 8 BR rates available Hanover Grange Villa, Jamaica villa

Hanover Grange Villa

Montego Bay, Jamaica

Pool

From
$2,143/Nt
6 BR rates available Casa de Campo #3613, Dominican Republic villa

Casa de Campo #3613

Casa de Campo, Dominican Republic

Pool

From
$3,500/Nt
6 BR rates available Casa de Campo #3018, Dominican Republic villa

Casa de Campo #3018

Casa de Campo, Dominican Republic

Pool

From
$2,800/Nt
6 BR rates available Casa de Campo #3022, Dominican Republic villa

Casa de Campo #3022

Casa de Campo, Dominican Republic

Pool

From
$2,000/Nt
Casa de Campo 4520, Dominican Republic villa

Casa de Campo 4520

Casa de Campo, Dominican Republic

Pool

From
$1,740/Nt
Offers Specials. 4, 5, 6 & 7 BR rates available Villa Enea, St. Barts villa

Villa Enea

Lorient, St. Barts

Near Beach | Pool

From
$2,857/Nt
Secluded villa has 6 bedrooms and access to Sandy Lane Beach, along with a large pool and staff. Offers Specials. 2 & 6 BR rates available Bluff House And Cottage - Sandy Lane, Barbados villa

Bluff House And Cottage - Sandy Lane

Barbados

Beachfront | Pool | AC

From
$500/Nt
This beachfront Anguilla villa sits on a hill overlooking Anguilla's popular Shoal Bay 2, 3, 4, 6 & 7 BR rates available Beach Court Villa, Anguilla villa

Beach Court Villa

Anguilla

Beachfront | Pool | AC

From
$1,100/Nt
Water, water everywhere at La Reve Villa with water lily and cascading ponds to greet you. 6 BR rates available Le Reve Villa, St. Martin villa

Le Reve Villa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

From
$6,143/Nt
Beach access and shopping in the exclusive Domaine du Soleil Couchant area 3, 4, 5, 6 & 7 BR rates available Fabrizia Villa, St. Barts villa

Fabrizia Villa

Gustavia, St. Barts

Near Beach | Pool

From
$2,571/Nt
Large oceanfront villa is Ideal for families with children and within walking distance of Shell Beach 2, 3, 4, 5 & 6 BR rates available La Pointe Villa, St. Barts villa

La Pointe Villa

Gustavia, St. Barts

Near Beach | Pool

From
$857/Nt
Beachfront architectural masterpiece with butler! Offers Specials. African Sapphire Villa at Altamer, Anguilla villa

African Sapphire Villa at Altamer

Anguilla

Beachfront | Pool | AC

From
$3,571/Nt
One of the Ultimate villas in Anguilla with over 20,000 square feet of enjoyment space! 2, 3, 4, 5, 6 & 7 BR rates available Ultimacy Villa, Anguilla villa

Ultimacy Villa

Anguilla

From
$1,000/Nt
Elegant luxury combines with intense privacy at Casa Kimball Casa Kimball, Dominican Republic villa

Casa Kimball

Cabrera, Dominican Republic

Near Beach | Pool

From
$3,000/Nt
Exciting extras like a private cabana and a Mastercraft make this converted sugar mill a real treasure for discerning guests Offers Specials. 4 & 6 BR rates available Mullins Mill, Barbados villa

Mullins Mill

Barbados

Pool

From
$1,825/Nt
Sunrise Villa: Privacy and luxury for large groups on a two acre, beachfront tropical haven Sunrise Villa, Dominican Republic villa

Sunrise Villa

Cabrera, Dominican Republic

Beachfront | Pool | AC

From
$2,000/Nt
Sprawling estate has a panoramic view and is perfect for weddings, corporate retreats, and other group events 1 & 5 BR rates available Eco Serendib Villa, St. John villa

Eco Serendib Villa

Rendezvous Bay, St. John

Pool

From
$2,200/Nt
Ultra modern and fully staffed, the Beach House's amenities will have you living like 21st century kings Offers Specials. The Beach House, Anguilla villa

The Beach House

Anguilla

Beachfront | Pool | AC

From
$10,714/Nt
Sugar Hill at Tryall Club, Jamaica villa

Sugar Hill at Tryall Club

Montego Bay, Jamaica

From
$3,143/Nt
Offers Specials. 5, 6 & 7 BR rates available Prudence Villa , Barbados villa

Prudence Villa

Barbados

Near Beach | Pool

From
$1,435/Nt
Tropical Dream Villa, Dominican Republic villa

Tropical Dream Villa

Cap Cana, Dominican Republic

Pool

From
$3,500/Nt
Wonderful sunrises and plenty of privacy! 6 BR rates available Fischer's Reef Villa, Cayman villa

Fischer's Reef Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$1,600/Nt
Tropically high-tech, this 8-bedroom villa offers guests a multilevel pool, waterfall, golf simulator, tennis/basketball court, and signing privileges at nearby resorts Offers Specials. 5 BR rates available Nevaeh Villa, Anguilla villa

Nevaeh Villa

Anguilla

Beachfront | Pool | AC

From
$4,830/Nt
Darsena 20 Villa, Dominican Republic villa

Darsena 20 Villa

Casa de Campo, Dominican Republic

Pool

From
$2,540/Nt
Mariposa Villa, Antigua villa

Mariposa Villa

Jumby Bay Resort, Antigua

From
$18,000/Nt
4, 5, 6 & 7 BR rates available Ty Molineux, Antigua villa

Ty Molineux

Jumby Bay Resort, Antigua

Beachfront | Pool | AC

From
$10,500/Nt
Ultimate modern luxury set on Long Bay Beach. 5, 6 & 7 BR rates available Pearl East Villa, Turks and Caicos villa

Pearl East Villa

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$6,500/Nt
Large and spacious with modern design, right on Long Bay Beach. 5, 6 & 7 BR rates available Pearl West Villa, Turks and Caicos villa

Pearl West Villa

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$6,500/Nt
Offers Specials. 6 BR rates available Martello House, Barbados villa

Martello House

Barbados

Pool

From
$1,750/Nt
Offers Specials. Coconut Walk, Cayman villa

Coconut Walk

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$4,000/Nt
Bring your laptop if you must; Sea Star has a wireless connection that will allow you to hop online from any place on the property 4, 5 & 6 BR rates available Sea Star, St. Thomas, USVI villa

Sea Star

St. Thomas, USVI

Beachfront | Pool | AC

From
$900/Nt
Sunrises AND Sunsets are the main attraction of this villa where avid snorkelers will have their fill 1, 2, 3, 4, 5 & 6 BR rates available Great Expectations, St. John villa

Great Expectations

Hart Bay, St. John

Near Beach | Pool

From
$607/Nt
Stunning oceanfront estate offers the most in luxury and privacy, as well as a full staff to accommodate every need. Offers Specials. 6 BR rates available Mango Bay, Barbados villa

Mango Bay

Barbados

Beachfront | Pool | AC

From
$4,500/Nt
Deluxe villa great for families and groups! Coral Reef Villa, Cayman villa

Coral Reef Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$2,600/Nt
Offers Specials. 3 & 5 BR rates available Coralita House, Barbados villa

Coralita House

Barbados

Pool

From
$1,200/Nt
Private Tennis Court is just the beginning of this stunning estate perched right above the beach Offers Specials. 3, 4, 5 & 6 BR rates available Zenaida Beach & Tennis Estate, Anguilla villa

Zenaida Beach & Tennis Estate

Anguilla

Beachfront | Pool | AC

From
$1,300/Nt
Private motorboat with boatman are part of this property that's fit for royalty (who have actually stayed here) 3, 4 & 5 BR rates available Paradise Villa, Anguilla villa

Paradise Villa

Anguilla

Pool

From
$1,200/Nt
Sapodilla bay beachfront luxury, yet the villa itself and the outside space are completely private. 6 BR rates available La Koubba Villa, Turks and Caicos villa

La Koubba Villa

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$1,786/Nt
Take full advantage of the large pool overlooking the blue ocean waters at the beautiful Alizee Villa. Offers Specials. 3, 4, 5 & 6 BR rates available Alizee Villa , St. Martin villa

Alizee Villa

Guana Bay (Dutch Side), St. Martin

Near Beach | Pool

From
$714/Nt
This gorgeous Lorient Beach estate has lots of dining and activity options for the active vacationer 3, 4, 5 & 6 BR rates available La Plage Villa, St. Barts villa

La Plage Villa

Lorient, St. Barts

Beachfront | Pool | AC

From
$3,429/Nt
Modern elegance and old Caribbean personality intersect at the Moonraker Villa on Anguilla 1, 2, 3, 4, 5 & 6 BR rates available Moonraker Villa, Anguilla villa

Moonraker Villa

Anguilla

Pool

From
$875/Nt
Little Whale Cay offers three secluded villas for maximum privacy and pleasure, accommodating up to 12 persons. 3 & 6 BR rates available Little Whale Cay, Bahamas villa

Little Whale Cay

Berry Islands, Bahamas

Pool

From
$14,760/Nt
Brand new villa with fully equipped exercise gym and close to Lorient Beach Offers Specials. 3, 4, 5 & 6 BR rates available Cumulus Villa, St. Barts villa

Cumulus Villa

Lorient, St. Barts

Near Beach | Pool

From
$1,707/Nt
Sitting poolside takes on a whole new meaning at Sandyline Villa-the ultimate vacation getaway! 3, 4 & 5 BR rates available Sandyline Villa, St. Martin villa

Sandyline Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

From
$4,214/Nt
Huge luxury villa in prestigious Royal Westmoreland features 8 bedrooms, ocean views, and lots of extras Offers Specials. 6 BR rates available Plantation House, Barbados villa

Plantation House

Barbados

Pool

From
$3,000/Nt
Enjoy spacious, cool interiors, stunning ocean views, dazzling water, and unparalleled luxury with this 7-bedroom beachfront villa 5 BR rates available Mothershouse, Turks and Caicos villa

Mothershouse

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$2,800/Nt
Antigua luxury at its finest! Kairos Beach Villa offers space, privacy, beach access, and so much more Kairos Beach Villa, Antigua villa

Kairos Beach Villa

Jumby Bay Resort, Antigua

Beachfront | Pool | AC

From
$11,995/Nt
Six bedroom oceanfront property with a protective coral reef 6 BR rates available Twin Palms Villa, Cayman villa

Twin Palms Villa

Grand Cayman, Cayman

Beachfront | AC

From
$1,275/Nt
Breathtaking ocean view from the pool, with private secluded beach just steps away 4, 5 & 6 BR rates available Crystal Blue Villa, Cayman villa

Crystal Blue Villa

Grand Cayman, Cayman

Pool

From
$700/Nt
Simple luxury in this seven bedroom beachfront home on Long Bay. 4 & 5 BR rates available Conched Out, Turks and Caicos villa

Conched Out

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$1,557/Nt
Large beachfront estate with 2 pools that's ideal for family and friends alike 5 & 6 BR rates available Casa Sunshine, St. Martin villa

Casa Sunshine

Guana Bay (Dutch Side), St. Martin

Beachfront | Pool | AC

From
$1,000/Nt
2 & 4 BR rates available Villa Susanna, St. Lucia villa

Villa Susanna

Marigot Bay, St. Lucia

Near Beach | Pool

From
$1,700/Nt
Majestic oceanfront villa right on Seven Mile Beach. Seascape Villa, Cayman villa

Seascape Villa

Grand Cayman, Cayman

Beachfront | AC

From
$1,920/Nt
A bright, two-story house, comfortable for up to 14 guests, that comes with a remarkable pool, wonderful hangout spaces, and Sandy Lane Beach Club access Offers Specials. 3, 4, 5 & 6 BR rates available Jamoon - Sandy Lane, Barbados villa

Jamoon - Sandy Lane

Barbados

Pool

From
$1,200/Nt
Luxury on Long Bay Beach! 4 BR rates available Santosha Villa, Anguilla villa

Santosha Villa

Anguilla

Beachfront | Pool | AC

From
$8,857/Nt
Live like kings and queens for the duration of your vacation at Tryall Club's Round House Villa Round House Villa at Tryall Club, Jamaica villa

Round House Villa at Tryall Club

Montego Bay, Jamaica

Pool

From
$2,143/Nt
A luxuriously modern 5-bedroom beachfront villa that will raise all your island vacation standards Mandalay Villa, Turks and Caicos villa

Mandalay Villa

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$7,000/Nt
Fratelli Cresta, St. Thomas, USVI villa

Fratelli Cresta

St. Thomas, USVI

Pool

From
$1,342/Nt
Hummingbird House, Jamaica villa

Hummingbird House

Montego Bay, Jamaica

Pool

From
$3,143/Nt
4 & 5 BR rates available Joy, St. Barts villa

Joy

Marigot, St. Barts

Pool

From
$4,286/Nt
Casa de Campo #2306, Dominican Republic villa

Casa de Campo #2306

Casa de Campo, Dominican Republic

Pool

From
$2,700/Nt
Casa de Campo #2305, Dominican Republic villa

Casa de Campo #2305

Casa de Campo, Dominican Republic

Pool

From
$3,500/Nt
Each bedroom at Summer Heights has a private balcony that faces the sea, making it an ideal getaway for couples traveling together. 2, 3, 4 & 5 BR rates available Summer Heights, Tortola, BVI villa

Summer Heights

Tortola, BVI

Pool

From
$500/Nt
Centrally located in the Mahoe Bay community, Loblolly offers seclusion while remaining close to activities and restaurants. 2, 3 & 4 BR rates available Loblolly Villa, Virgin Gorda, BVI villa

Loblolly Villa

Mahoe Bay, Virgin Gorda, BVI

Near Beach | Pool

From
$486/Nt
Mexican style decor and rich appointments set this 2 story villa apart from the others Offers Specials. 2, 3, 4 & 5 BR rates available La Paloma Villa, St. Lucia villa

La Paloma Villa

Vigie, St. Lucia

Near Beach | Pool

From
$375/Nt
Enjoy the complete decadence of showering au natural in one of the alfresco showers with a view. 2, 4 & 5 BR rates available Caribbean Wind Villa, Virgin Gorda, BVI villa

Caribbean Wind Villa

Mahoe Bay, Virgin Gorda, BVI

Near Beach | Pool

From
$929/Nt
Choose between two beaches and a large private pool for your stay in paradise, or, have them all. Offers Specials. 4 & 5 BR rates available La Salamandre, St. Martin villa

La Salamandre

Terres Basses (French side), St. Martin

Near Beach | Pool

From
$1,414/Nt
Wonderful architectural design suited for anyone with an artist's tastes, this property dates back to 1791 3, 4 & 5 BR rates available Estate Belvedere, St. Croix, USVI villa

Estate Belvedere

St. Croix, USVI

Pool

From
$860/Nt
Encore Villa will have you wanting to visit over and over, and over, again. Offers Specials. 4 & 5 BR rates available Encore Villa, St. Martin villa

Encore Villa

Terres Basses (French side), St. Martin

Pool

From
$979/Nt
Luxury abounds at the gorgeous Bajacu Villa, a sprawling private retreat on the island of Providencialies. 2, 3 & 4 BR rates available Bajacu, Turks and Caicos villa

Bajacu

Providenciales, Turks and Caicos

Pool

From
$3,000/Nt
Beachfront villa with private pool that our readers rave about Offers Specials. 4 & 5 BR rates available Calypso Blue, Cayman villa

Calypso Blue

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$700/Nt
Wrap-around pool near to Grand Case beach is great for families and children Petite Plage 5 Villa, St. Martin villa

Petite Plage 5 Villa

Grand Case (French side), St. Martin

Beachfront | Pool | AC

From
$2,829/Nt
VI Friendship Villa:A coveted locale with a well-appointed interior that will do its best to keep you indoors 3, 4 & 5 BR rates available VI Friendship Villa, St. John villa

VI Friendship Villa

Great Cruz Bay, St. John

Pool

From
$1,443/Nt
Located in the exclusive Leeward community on the eastern end of Grace Bay, just a couple of minutes walk down a quiet lane takes you to the best part of the beach. The outside space and pool area are fantastic at this modern villa. 4 & 5 BR rates available Pelican Vista, Turks and Caicos villa

Pelican Vista

Providenciales, Turks and Caicos

Near Beach | Pool

From
$1,220/Nt
2, 3 & 4 BR rates available Colibri Cottage, St. Lucia villa

Colibri Cottage

Soufriere, St. Lucia

Near Beach | Pool

From
$415/Nt