Caribbean Group Villas


Vacation rentals that are large enough to accommodate a group are often hard to come by and renting multiple hotel rooms can break the bank. WhereToStay.com has searched all over the Caribbean to bring you a collection of villas large enough to accommodate groups on their Caribbean vacations. Unlike a hotel, villa rentals provide one cost for the entire home giving everyone their own space while still enjoying various amenities such as a private pool, chef services and housekeeping. Go on, take a look, the perfect villa for your group vacation is sure to be here!


The combination of villa East and West, this large villa complex is the ultimate location for a large group. 16 & 18 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! Offers Specials. 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
$1,358/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
Three Dolphins Villa: Amazing beachfront views on the popular Long Bay Beach. 4, 6, 7, 8, 9, 10 & 11 BR rates available Three Dolphins, Turks and Caicos villa

Three Dolphins

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$1,446/Nt
Combine business with pleasure at Musha Cay at Copperfield Bay, where there are five houses to choose from and a host of sporting activities. 6, 7, 8, 9, 10 & 11 BR rates available Musha Cay at Copperfield Bay, Bahamas villa

Musha Cay at Copperfield Bay

Musha Cay, Bahamas

Beachfront | Pool | AC

From
$39,000/Nt
Whether you want to spend your vacation listening to your iPod and reading or play tennis or taking the time ... 4, 5, 6, 7, 8, 9, 10 & 11 BR rates available Golden Clouds, Jamaica villa

Golden Clouds

Ocho Rios, Jamaica

Pool

From
$1,143/Nt
Camp David, St. Barts villa

Camp David

Saint Jean, St. Barts

Beachfront | Pool | AC

From
$16,429/Nt
Spoil yourself with luxury amenities, beach access, and gorgeous views inside and out at this private island villa estate Offers Specials. Parrot Cay Resort- The Sanctuary, Turks and Caicos villa

Parrot Cay Resort- The Sanctuary

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

From
$25,000/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

Leverick Bay, Virgin Gorda, BVI

Beachfront | Pool | AC

From
$6,000/Nt
A fully equipped gym, a staff of 12, and a theater that seats 20 sets this island estate apart from the usual vacation villa Offers Specials. 9 BR rates available Cove Spring, Barbados villa

Cove Spring

Barbados

Beachfront | Pool | AC

From
$15,000/Nt
A horseback ride on a semi-private beach is just one of the suprises at this 10 acre, nine cottage oasis in Jamaica 4 BR rates available Lazy Heart Villa, Dominican Republic villa

Lazy Heart Villa

Cabrera, Dominican Republic

Pool

From
$1,250/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
Huge luxury estate features 2 separate villas, a full staff, and incredible ocean views Offers Specials. 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. Fully staffed. 5, 6 & 8 BR rates available Hawksbill, Turks and Caicos villa

Hawksbill

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$6,725/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
6 BR rates available Sand Dollar Villa, St. Thomas, USVI villa

Sand Dollar Villa

St. Thomas, USVI

Beachfront | Pool | AC

From
$2,464/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
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
Villa Castellamonte del Mare: Tuscan living on the northern coast of the Dominican Republic. Villa Castellamonte del Mare, Dominican Republic villa

Villa Castellamonte del Mare

Cabrera, Dominican Republic

Near Beach | Pool

From
$2,000/Nt
Large, newly renovated beachfront home can accommodate up to 16 and the gated pool makes it child-friendly. Updated tennis court. Offers Specials. 5 BR rates available Belair Great House, Barbados villa

Belair Great House

Barbados

Near Beach | Pool

From
$625/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
Stunning 7-bedroom vacation villa has all the privacy you want, plus an on-site staff and access to Sandy Lane Hotel facilities. Offers Specials. 4 & 6 BR rates available Elsewhere Villa, Barbados villa

Elsewhere Villa

Barbados

Pool

From
$1,300/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
Beachfront architectural masterpiece with butler! 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
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
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
This Rendezvous Beach villa is meant for groups like destination wedding parties or large family reunions, providing state-of-the-art everything and a full staff 5 BR rates available Caribera Villa, Anguilla villa

Caribera Villa

Anguilla

Near Beach

From
$2,660/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, an undiscovered gem on Providenciales. 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, this luxury 8 bedroom sits 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. 5 BR rates available Coconut Walk, Cayman villa

Coconut Walk

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$3,600/Nt
Serenity At Lancaster Ridge, Barbados villa
From
$6,000/Nt
Anguillitta Villa, Anguilla villa

Anguillitta Villa

Anguilla

Pool

From
$2,340/Nt
Large, modern and completely luxurious, the ultimate beachfront hideaway. Triton Villa, Turks and Caicos villa

Triton Villa

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$5,200/Nt
Deluxe villa great for families and groups! Offers Specials. Coral Reef Villa, Cayman villa

Coral Reef Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$2,600/Nt
Near two popular beaches, Amancaya Villa is also near restaurants and groceries for ideal access during your St. Barts stay 2, 3, 4 & 5 BR rates available Amancaya Villa, St. Barts villa

Amancaya Villa

Anse des Cayes, St. Barts

Pool

From
$2,714/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
Palmera Villa in the prominent Thompson Cove area: Sprawling Luxury on the North Shore. 6 BR rates available Palmera Villa, Turks and Caicos villa

Palmera Villa

Providenciales, Turks and Caicos

Near Beach | Pool

From
$1,243/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
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
Monte Bay Villa: an attractive getaway with a master suite that will make you want to spend your entire vacation in bed 1, 2, 3 & 5 BR rates available Monte Bay Villa, St. John villa

Monte Bay Villa

Klein Bay, St. John

Near Beach | Pool

From
$660/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
Offers Specials. 3, 4, 5 & 6 BR rates available Caye Blanche, St. Martin villa

Caye Blanche

Anse Marcel (French side), St. Martin

Pool

From
$714/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
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
$150/Nt
Golf lovers' paradise, refreshing seven-bedroom property on golf course with sea views Offers Specials. 5 BR rates available Casablanca Villa, Barbados villa

Casablanca Villa

Barbados

Near Beach | Pool

From
$2,500/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. 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
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
Offers Specials. 5 BR rates available Deja View, St. John villa

Deja View

Gift Hill, St. John

From
$1,507/Nt
Turtle Tail Estate: a secluded, high-end Provo beach house that boasts fantastic amenities on over 4 tropical acres . Turtle Tail Estate, Turks and Caicos villa

Turtle Tail Estate

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$9,000/Nt
Luxury on Long Bay Beach! 4 BR rates available Santosha Villa, Anguilla villa

Santosha Villa

Anguilla

Beachfront | Pool | AC

From
$8,857/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
3, 4, 5 & 6 BR rates available Lital Villa, St. Barts villa

Lital Villa

Anse des Cayes, St. Barts

From
$2,286/Nt
Turtle Crossing, Antigua villa

Turtle Crossing

Jumby Bay Resort, Antigua

Pool

From
$12,550/Nt
Fratelli Cresta, St. Thomas, USVI villa

Fratelli Cresta

St. Thomas, USVI

Pool

From
$1,342/Nt
Tortuga Bay C-19, Dominican Republic villa

Tortuga Bay C-19

Punta Cana, Dominican Republic

Pool

From
$2,000/Nt
Hummingbird House, Jamaica villa

Hummingbird House

Montego Bay, Jamaica

Pool

From
$3,143/Nt
Ultimate modern luxury and completely private. Tip of the Tail, Turks and Caicos villa

Tip of the Tail

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$6,000/Nt
Cherub House, Barbados villa

Cherub House

Barbados

Pool

From
$2,250/Nt
Elysium, Barbados villa

Elysium

Barbados

Near Beach | Pool

From
$2,200/Nt
1, 3 & 4 BR rates available The Point at Maria Bluff, St. John villa

The Point at Maria Bluff

Great Cruz Bay, St. John

Pool

From
$729/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
Grace Too Estate, Turks and Caicos villa

Grace Too Estate

Providenciales, Turks and Caicos

Beachfront | Pool | AC

From
$2,564/Nt
Il Farro, St. Barts villa

Il Farro

Anse des Cayes, St. Barts

Pool

From
$9,286/Nt
3, 4 & 5 BR rates available Aqua Villa, St. Barts villa

Aqua Villa

Grand Cul de Sac, St. Barts

Beachfront | Pool | AC

From
$4,571/Nt
3, 4 & 5 BR rates available Bleu Villa, St. Barts villa

Bleu Villa

Grand Cul de Sac, St. Barts

Beachfront | Pool | AC

From
$4,571/Nt
With 21,000 square feet at your disposal, you'll feel like you're at a resort but with all the comforts of home 1, 2, 3, 4 & 5 BR rates available Mystique Villa, Anguilla villa

Mystique Villa

Anguilla

Near Beach | Pool

From
$995/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