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!

Luxurious, private island with a full staff, six beaches, and every activity you could ask for. Calivigny Island - Just South of Woburn Bay, Greneda

Grenada

Beachfront | Pool | AC

from $120000/Nt
25 25
Details
This large villa complex combines three villas into one estate and is the ultimate location for a group. The Pearls of Long Bay Estate consist of Pearl East, Pearls West and Lidia House

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $21000/Nt
23 23
Details
Private island resort with rustic, eco-friendly design and every activity under the sun. Thatch Caye photo

Belize

Near Beach

from $9785/Nt
15 15
Details
Totally secluded private island with luxurious amenities and a full staff. 6, 7, 8, 9, 10, 11, 12, 13 & 14 BR rates available. Over Yonder Cay is a spectacular exclusive private island south of Nassau in the Bahamas

Exuma and Cays, Bahamas

Beachfront | Pool | AC

from $46000/Nt
15 12
Details
Luxurious private estate with resort amenities, professional service, and 10 huge Master Suites. 10 BR rate available.
Has specials. Ani Villa Estate in The Dominican Republic has an amazing infinity edge pool with Caribbean views

Cabrera, Dominican Republic

Pool

from $9120/Nt
14 14
Details
Two luxurious Grace Bay villas in one easy rental. Beachfront views from Sentosa Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $22000/Nt
14 14
Details
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 photo

Terres Basses (French side), St. Martin

Pool

from $1358/Nt
14 14+
Details
A quietly luxurious, All-Inclusive Hideaway 8 BR rate available. Three Bees at Harbour Island photo

Harbour Island, Bahamas

Beachfront | Pool | AC

from $24286/Nt
13 13
Details
Arrecife 23/24/25 Estate at Punta Cana Resort photo

Punta Cana, Dominican Republic

Pool

from $4390/Nt
13 13+
Details
This totally private island will make you feel like royalty. Has specials. Necker Island, BVI 2018 Helicopter view

Necker Island, BVI, British Virgin Islands

Beachfront | Pool | AC

from $62500/Nt
12 11
Details
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 photo

Musha Cay, Bahamas

Beachfront | Pool | AC

from $39000/Nt
12 13+
Details
Six acre estate with beachfront access to coral reefs, on-site sports courts, and two freshwater pools. 5, 6, 7, 8, 9, 10 & 11 BR rates available. Lounge by the pool at Golden Clouds

Ocho Rios, Jamaica

Pool

from $1343/Nt
12 12
Details
Platinum Coast villa with 11 bedrooms, a spacious layout, and sunset views. Has specials. Sanzaru photo

Barbados

Pool

from $11000/Nt
11 11
Details
This private, beachfront villa has a full staff and five-star amenities for everyone in your party. 9 BR rate available.
Has specials. The beautiful Cerulean Villa on Barnes Bay in Anguilla

Anguilla

Beachfront | Pool | AC

from $14286/Nt
11 9+
Details
Spoil yourself with luxury amenities, beach access, and gorgeous views inside and out at this private island villa estate. Has specials. Private luxury at The Sanctuary at Parrot Cay

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $36000/Nt
11 11
Details
Gorgeous villa estate offers the ultimate in luxury with a private beach, gorgeous views, and resort amenities. Has specials. The Residence at COMO Parrot Cay photo

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $21500/Nt
11 11+
Details
Enjoy relaxing by the pool and spectacular views of the Sir Francis Drake Channel beyond

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from Call for rates
10 9
Details
Sophisticated, three-story home perfect for family vacation or getaway with friends. 5 BR rate available. The Beach House at Calivigny Island

Grenada

Beachfront | Pool | AC

from $40000/Nt
10 10
Details
A beautiful stretch of sandy beach along the front of Casa de Campo #131

Casa de Campo, Dominican Republic

Beachfront | Pool | AC

from $11200/Nt
10 10
Details
Luxurious, expansive mansion in a tropical oasis. The amazing infinity edge pool at Casa de Camp #3607 overlooks the Chavon River and the ocean beyond

Casa de Campo, Dominican Republic

Pool

from $6500/Nt
10 10+
Details
A fully equipped gym, a staff of 12, and a theater that seats 20 sets this island estate apart from the usual vacation villa Has specials. Cove Spring photo

Barbados

Beachfront | Pool | AC

from $15000/Nt
10 10+
Details
A horseback ride on a semi-private beach is just one of the suprises at this 10 acre, nine cottage oasis in Jamaica Lazy Heart Villa photo

Cabrera, Dominican Republic

Near Beach | Pool

from $1500/Nt
10 9
Details
High-end, modern elegance with two pools, two beaches, and two and a half acres. Le Bleu Villa its on 2.5 acres of beachfront in Little Harbor

Anguilla

Beachfront | Pool | AC

from $8600/Nt
10 10
Details
An impressive pool and terrace winds throughout this luxury villa. 5, 6 & 9 BR rates available.
Has specials. Aerial View of Silent Waters

Montego Bay, Jamaica

Pool

from $2320/Nt
10 6
Details
Self-contained hideaway (with its own theater) is a little chunk of paradise to make for the perfect holiday 7 & 8 BR rates available.
Has specials. Crystal Springs is a beautiful Estate located right on the beach

Barbados

Beachfront | Pool | AC

from $7245/Nt
10 11
Details
Huge luxury estate features two separate villas, a full staff, and incredible ocean views. Has specials. Ani Estate Anguilla - North and South

Anguilla

Pool

from $8600/Nt
10 10
Details
Large beachfront estate with two pools that's ideal for family and friends alike. 5, 6, 7, 8 & 9 BR rates available. Casa Sunshine photo

Guana Bay (Dutch Side), St. Martin

Beachfront | Pool | AC

from $1214/Nt
10 10
Details
The ultimate in luxury, this 10-bedroom estate sits on the best part of Grace Bay beach. 5, 6 & 8 BR rates available. The Hawksbill Villa Estate

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $6800/Nt
10 10
Details
One of the largest villas at Tryall Club, with a basketball court, game room, and playground. 9 BR rate available. Create Abundance photo

Montego Bay, Jamaica

Pool

from $3391/Nt
10 9
Details
Elegant, open-air villa with two guest houses and tons of gardens. 5 BR rate available.
Has specials. Las Brisas villa

Punta Cana, Dominican Republic

Pool

from $8040/Nt
9 9
Details
Pool area for Arrecife Villas

Punta Cana, Dominican Republic

Pool

from $2790/Nt
9 9
Details
Fully staffed, avant-garde villa with open-concept design and complimentary access to Eden Roc Beach. 5, 6, 7 & 8 BR rates available.
Has specials. Yarari Royale is a beautiful home located in Cap Cana

Cap Cana, Dominican Republic

Pool

from $2430/Nt
9 9+
Details
Chic and modern home with nine suites and tons of outdoor space. 5 BR rate available. The Overhang House at Calivigny Island

Grenada

Beachfront | Pool | AC

from $35000/Nt
9 9
Details
Glamorous, spacious villa with ultra luxurious amenities and a full staff. La Dolce Vita photo

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $16000/Nt
9 9
Details
Fully-equipped villa with easy beach access and great amenities. 1, 2, 3, 4, 5, 6, 7 & 8 BR rates available. One Perfect Day Villa is located on the Peterborg Peninsula overlooking Magens Bay

St. Thomas, USVI

Near Beach | Pool

from $5500/Nt
9 9+
Details
Grace Bay beachfront villa equipped with Apple TVs, a Jeep Wrangler, a gym, and open design. Has specials. Bella Vita is a contemporary villa located on the shores of Grace Bay

Providenciales, Turks and Caicos

Beachfront | Pool | AC

from $6250/Nt
9 7+
Details
Luxurious, bright pink villa on a pink sand beach. La Palmeraie is located on Harbour Island in the Bahamas

Harbour Island, Bahamas

Beachfront | Pool | AC

from $6380/Nt
9 8
Details
Classic beachfront estate with a full staff, luxury amenities, and a guest cottage. 6 BR rate available. Sand Dollar Estate photo

St. Thomas, USVI

Beachfront | Pool | AC

from $2536/Nt
9 9+
Details
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.
Has specials. La Bella Casa photo

Terres Basses (French side), St. Martin

Pool

from $1071/Nt
9 9
Details
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. 5, 6, 7 & 8 BR rates available. Capri Villa photo

Cap Estate, St. Lucia

Near Beach | Pool

from $850/Nt
9 9+
Details
An opulent, gated estate with everything a large group could need, including a sport court and massive pool. 6 BR rate available. Luxurious private swimming pool at Casa Varnishkes

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $2464/Nt
9 9+
Details
You'll love A La Mer's enormous pool and deck, when you're not snorkeling at Great Cruz Bay 8 BR rate available. A La Mer sits on St. John\'s coastline near Grat Cruz Bay

Great Cruz Bay, St. John

Near Beach | Pool

from $5280/Nt
9 9+
Details
Resort style luxury at Hanover Grange

Montego Bay, Jamaica

Pool

from $3052/Nt
9 9
Details
Spacious home away from home on Long Bay Beach. Santosha Villa photo

Anguilla

Beachfront | Pool | AC

from $7000/Nt
9 9
Details
Luxury oceanfront property with seven bedrooms, water-sports equipment, and access to Seven Mile Beach. Has specials. Coconut Walk Villa at twilight

Grand Cayman, Cayman

Beachfront | Pool | AC

from $5000/Nt
8 6+
Details
6 BR rate available. The luxurious patio and and infinity edge pool at Casa de Campo #3613

Casa de Campo, Dominican Republic

Pool

from $3500/Nt
8 8
Details
A resort style poo area at this villa in Casa de Campo

Casa de Campo, Dominican Republic

Pool

from $2900/Nt
8 8+
Details
6 BR rate available. Casa de Campo #3022 photo

Casa de Campo, Dominican Republic

Pool

from $2000/Nt
8 8
Details
Private beach access, full equipment, and beautiful living spaces set this villa apart. 4, 5, 6 & 7 BR rates available. The pool is nestled in a tropical landscape at Enea villa

Lorient, St. Barts

Near Beach | Pool

from $2857/Nt
8 9+
Details
Casa de Campo #602 photo

Casa de Campo, Dominican Republic

Pool

from $3500/Nt
8 8
Details
Ideal location for a large group vacation with a gorgeous ocean backdrop. A aerial view of Conch and Milestone Villas

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $5730/Nt
8 8
Details
This Punta Cana Resort villa makes relaxation and entertainment a cinch. La Serena Villa features a private dock that brings you to a beautiful private sandy beach

Punta Cana, Dominican Republic

Beachfront | Pool | AC

from $3950/Nt
8 6+
Details
Luxurious private villa with resort amenities, professional service, and a personal sandy beach area. 5 BR rate available.
Has specials. The swimming pool at the Larimar Villa overlooks the Caribbean

Cabrera, Dominican Republic

Pool

from $4720/Nt
8 8
Details
Secluded villa has 6 bedrooms and access to Sandy Lane Beach, along with a large pool and staff. 2 & 6 BR rates available.
Has specials. Bluff House and Cottage are located very near by Sandy Lane Bay

Barbados

Beachfront | Pool | AC

from $500/Nt
8 8
Details
Villa Castellamonte del Mare: Tuscan living on the northern coast of the Dominican Republic. Villa Castellamonte del Mare photo

Cabrera, Dominican Republic

Near Beach | Pool

from $2000/Nt
8 9+
Details
Large beachfront home can accommodate up to 16 and has a child-friendly gated pool. 5 BR rate available.
Has specials. View of the villa and private pool

Barbados

Near Beach | Pool

from $625/Nt
8 6
Details
Stunning 7-bedroom vacation villa has all the privacy you want, plus an on-site staff and access to Sandy Lane Hotel facilities. 4 & 6 BR rates available.
Has specials. Enjoy lounging by the pool at Elsewhere Villa

Barbados

Pool

from $1300/Nt
8 8+
Details
Beach access with lovely sunset views over the harbor and full air-conditioning. 3, 4, 5, 6 & 7 BR rates available. Fabrizia Villa offers a great pool nestled on the hillside over Gustavia Harbor

Gustavia, St. Barts

Near Beach | Pool

from $2571/Nt
8 9
Details
Beachfront architectural masterpiece with butler, sports courts, and full entertainment system. African Sapphire Villa is just one of the -jewels- of the Villas at Altamer

Anguilla

Beachfront | Pool | AC

from Call for rates
8 9
Details
Over 20,000 square feet of enjoyment space. 2, 3, 4, 5, 6 & 7 BR rates available. Ultimacy Villa is located in Rose Hill in Island Harbor

Anguilla

Pool

from $1000/Nt
8 9+
Details
Elegant luxury combines with intense privacy at Casa Kimball Casa Kimball photo

Cabrera, Dominican Republic

Near Beach | Pool

from $3000/Nt
8 8
Details
Privacy and luxury for large groups on a two acre, beachfront tropical haven. Sunrise Villa photo

Cabrera, Dominican Republic

Beachfront | Pool | AC

from $2000/Nt
8 8
Details
Huge luxury villa in prestigious Royal Westmoreland features 8 bedrooms, ocean views, and lots of extras 4, 5 & 6 BR rates available.
Has specials. Grand views of the pool and the ocean beyond from the balcony at Plantation House

Barbados

Pool

from $1515/Nt
8 8
Details
Sprawling estate with a panoramic view that's perfect for weddings, corporate retreats, and more. 1 & 5 BR rates available. The pool and ocean views from Eco Serendib!

Rendezvous Bay, St. John

Pool

from $2200/Nt
8 8+
Details
Ultra modern and fully staffed villa with regal amenities. The Beach House features an amazing pool and outdoor area

Anguilla

Beachfront | Pool | AC

from $10714/Nt
8 9+
Details
Enjoy amazing sunsets on the balcony at Sugar Hill

Montego Bay, Jamaica

Pool

from $2857/Nt
8 8
Details
This luxurious beachfront villa has an impressive outdoor area and the ocean in its backyard. Sentosa is located along a beautiful stretch of Grace Bay Beach

Providenciales, Turks and Caicos

Beachfront | Pool | AC

from $15000/Nt
8 8
Details
5 BR rate available. Tropical Dream Villa photo

Cap Cana, Dominican Republic

Pool

from $2640/Nt
8 8
Details
The perfect villa for a family vacation, with a multi-level terrace, huge rooms, and eight bedrooms spread out over two floors. Has specials. Fischer\'s Reef Villa is located right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1950/Nt
8 8+
Details
Tropically high-tech, this 8-bedroom villa offers guests a multilevel pool, waterfall, golf simulator, tennis/basketball court, and signing privileges at nearby resorts. 5 BR rate available.
Has specials. Nevaeh is located on a beautiful stretch of Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $5980/Nt
8 7
Details
Darsena 20 Villa photo

Casa de Campo, Dominican Republic

Pool

from $2540/Nt
8 10
Details
Ultimate modern luxury set on Long Bay Beach, with a full staff and five star amenities. 5, 6 & 7 BR rates available. Aerial view of Pearl East

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $5500/Nt
8 8+
Details
Large and spacious villa with modern design that's right on Long Bay Beach. 5, 6 & 7 BR rates available. Exterior Pearl West

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $5500/Nt
8 8+
Details
Enjoy a mini golf-course and five separate units at this oceanfront beauty. 3, 4 & 5 BR rates available. Lounge on a balcony patio over looking the ocean from Anguillitta Villa

Anguilla

Near Beach | Pool

from $1150/Nt
7 6+
Details
Large, modern and completely luxurious, this impressive estate is the ultimate beachfront hideaway. Has specials. Beautiful stretch of Long Bay Beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $7250/Nt
7 6+
Details
This villa was made for family vacations, with four levels and ample lounging space. 6 BR rate available. Our Cayman Cottage sits along a beautiful stretch of beach on the north side of Grand Cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1200/Nt
7 6+
Details
Varadero photo

Cap Cana, Dominican Republic

Beachfront | Pool | AC

from $5070/Nt
7 7+
Details
Open, chic beachfront villa with a family-friendly design. Has specials. Evolution Vill offers it all - right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2138/Nt
7 7+
Details
This villa was designed to maximize privacy and relaxation, with three levels of suites and a separate apartment. Has specials. Tatenda Villa is a beautiful beach front home just along South Sound

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2070/Nt
7 7
Details
Beautiful, well-designed villa with amazing outdoor space. Has specials. The pool and beautiful beach at Kaia Kamina

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2857/Nt
7 7+
Details
Two cozy villas lie on this private island off the coast of Harbour Island. Middle Cay is a perfectly located private island just off the coast of Harbor Island in the Bahamas

Harbour Island, Bahamas

Pool

from $2571/Nt
7 6+
Details
Family-friendly resort villa with two family suites and a guest house. Arrecife 59 has beautiful Lake and Golf Course Views

Punta Cana, Dominican Republic

Pool

from $2290/Nt
7 7
Details
Beachfront villa great for families and groups, with entertainment for kids and adults alike. Coral Reef Villa is situated directly on Seven Mile Beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2860/Nt
7 7+
Details
Warm, open interiors and stunning views combine in this oceanfront villa. 3, 4 & 5 BR rates available.
Has specials. Paradise Villa photo

Anguilla

Pool

from $1200/Nt
7 5+
Details
Moroccan-inspired beachfront villa with a guest house, private pool, and access to Sapodilla Bay. 6 BR rate available. La Koubba Villa beachfront Property

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1786/Nt
7 7+
Details
Big groups will love this waterfront villa. 5 BR rate available. Private pool deck at Vieux Caribe Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1210/Nt
7 7+
Details
This gorgeous Lorient Beach estate has lots of dining and activity options for the active vacationer 4, 5 & 6 BR rates available. Relax by the pool and enjoy island luxury at La Plage Villa

Lorient, St. Barts

Beachfront | Pool | AC

from $4571/Nt
7 7
Details
This attractive getaway is perfect for couples or families who want privacy and tranquility. 1, 2, 3, 4, 5 & 6 BR rates available. Monte Bay Villa sits atop a hillside just above Monte Bay

Klein Bay, St. John

Near Beach | Pool

from $726/Nt
7 6+
Details
Sitting poolside takes on a whole new meaning at Sandyline Villa-the ultimate vacation getaway! 3, 4 & 5 BR rates available.
Has specials. Resort like pool at Sandyline Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

from $4215/Nt
7 7
Details
Six bedroom oceanfront property with a protective coral reef 6 BR rate available.
Has specials. Twin Palms Villa - the namesake beautiful palm trees

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1500/Nt
7 4
Details
18-guest villa with oceanfront privacy, 75-foot pool, and space for everyone. 5 & 6 BR rates available.
Has specials. Aerial view of Villa Mora

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1600/Nt
7 7+
Details
Oceanfront villa with private beach access, total seclusion, and unique architecture. Has specials. Spectacular views, infinity edge pool and oceanfront lounging await at Cayman Castle

Grand Cayman, Cayman

Near Beach | Pool

from $1750/Nt
7 6+
Details
Breathtaking ocean view from the pool, with private secluded beach just steps away 5 & 6 BR rates available.
Has specials. The beautiful Crystal Blue Villa is perched on a cliffside just off Queens Highway

Grand Cayman, Cayman

Pool

from $950/Nt
7 6+
Details
Enjoy simple luxury in this seven-bedroom beachfront home on Long Bay. 4 BR rate available. The entertainment patio and pool area at Conched Out Villa

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1271/Nt
7 7
Details
Oceanfront villa right on Seven Mile Beach, with accommodations for 17 guests. Seascape Villa

Grand Cayman, Cayman

Beachfront | AC

from $2700/Nt
7 5
Details
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 3, 4, 5 & 6 BR rates available.
Has specials. Private resort style pool and outdoor entertainment area at Jamoon

Barbados

Pool

from $1200/Nt
7 6+
Details
This secluded, luxury beach house boasts fantastic amenities on over four tropical acres. Turtle Tail Estate is located on the southern tip of Turtle Tail

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $10000/Nt
7 6+
Details
A luxuriously modern 5-bedroom beachfront villa. Mandalay Villa photo

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from Call for rates
7 7+
Details
Villa Corales 28 is a beautiful oceanfront villa in Punta Cana

Punta Cana, Dominican Republic

Near Beach | Pool

from $5000/Nt
7 7+
Details
Seven bedroom home set on three levels with unparalleled views. 4, 5 & 6 BR rates available. Lital Villa photo

Anse des Cayes, St. Barts

from $2714/Nt
7 7
Details
Large luxurious pool at Fratelli Cresta

St. Thomas, USVI

Pool

from $1185/Nt
7 7+
Details
Luxury blends with nature at this villa with Piton views. 4, 5 & 6 BR rates available. Cosmos photo

Soufriere, St. Lucia

Pool

from $850/Nt
7 7
Details
Pool

Punta Cana, Dominican Republic

Pool

from $2000/Nt
7 6+
Details
Ocean and pool view from back patio

Montego Bay, Jamaica

Pool

from $3143/Nt
7 7
Details
Family friendly, two-story villa just a short walk from Port St. Charles. Has specials. Plenty of comfortable seating under the covered patio at Elysium Villa

Barbados

Near Beach | Pool

from $2200/Nt
6 6+
Details
Secluded, multileveled home with tons of space and stunning views. 1, 3, 4 & 5 BR rates available. Endless views of the Caribbean from the Point at Maria Bluff

Great Cruz Bay, St. John

Pool

from $729/Nt
6 5+
Details
Casa de Campo #2305 photo

Casa de Campo, Dominican Republic

Pool

from $3500/Nt
6 6
Details
The ideal beachfront villa for large groups, with a Beach House and Cottage. The beachside pool at Grace Too - main beach house

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2564/Nt
6 5+
Details
Beautiful outdoor living space with long pool and a minibar in every room. Il Farro has amazing views of the Caribbean from the pool area

Anse des Cayes, St. Barts

Pool

from $5000/Nt
6 6
Details
Waterfront villa with close-up ocean view perfect for large groups. 3, 4 & 5 BR rates available. Loungers by the beachfront pool at Aqua Villa

Grand Cul de Sac, St. Barts

Beachfront | Pool | AC

from $4571/Nt
6 6
Details
Family-sized villa right on the beach, with a lengthy pool. 3, 4 & 5 BR rates available. The beachfront lap pool at Bleu Villa

Grand Cul de Sac, St. Barts

Beachfront | Pool | AC

from $4571/Nt
6 6
Details
Experience the ease of a stress-free vacation at Punta Cana Resort, where childcare, on-site activities, and white sand beach alleviate every burden. Yellow Bear Villa - Very large pool and outdoor areas

Punta Cana, Dominican Republic

Pool

from $1750/Nt
6 6+
Details
Waterfront property on Leeward Canal, with easy access to several beaches, restaurants, and activities. 4 BR rate available. Acajou Villa has a magical backyard

Leeward, Turks and Caicos

Near Beach | Pool

from $990/Nt
6 5+
Details
Large beachfront villa with wraparound ocean views and lots of room for decompressing! Expansive living area has endless views of the ocean

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2929/Nt
6 7
Details
Rustic accents balance elegant design and luxurious amenities at this Punta Cana villa. Has specials. Villa Corales 114 has a decadent lawn and pool area

Punta Cana, Dominican Republic

Near Beach | Pool

from $1800/Nt
6 6+
Details
Family-style villa with Italian inspiration and convenient location near town. 5 BR rate available. Al fresco dining for eight

English Harbour, Antigua

Pool

from $850/Nt
6 6
Details
Three intimate villas perfect for a family vacation or romantic getaway. The beach front at the Beach Bungalows on Calivigny Island

Grenada

Beachfront | AC

from $27000/Nt
6 6
Details
Six-bedroom villa floor-to-ceiling windows and beach access. 3, 4 & 5 BR rates available. The Estate at Daniel Bay #024, is situated in Willoughby Bay

English Harbour, Antigua

Beachfront | Pool | AC

from $1161/Nt
6 6
Details
Fully-equipped large group villa with several family-friendly suites and lots of outdoor space. Has specials. Beachfront pool at Oceanus Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2138/Nt
6 7+
Details
Combine two properties into one for access to six bedrooms, three pools, two kitchens, and tons of space. Stunning beach and ocean views from Crescent Beach Villa

Bequia, St. Vincent & Grenadines

Pool

from $786/Nt
6 6
Details
Modern Saint Jean villa with the island's largest pool and panoramic views. NEO Villa has amazing views of the ocean below

Saint Jean, St. Barts

Pool

from $10000/Nt
6 6
Details
Stunning property dripping with luxury. 4 BR rate available.
Has specials. Enjoy amazing sunsets from the beach at the Amber Villa

Cabrera, Dominican Republic

Pool

from $4000/Nt
6 6
Details
Multileveled terrace with stunning ocean views and a wheelchair accessible main pavilion. 2 & 4 BR rates available. Villa Blackstone is nestled in the hillside above Marigot Bay

Marigot, St. Barts

Pool

from $2286/Nt
6 6
Details
Pelican Beach villa with a staff, tons of beach toys, and six bedroom retreats. Viatu is just a very short distance to Grace Bay Beach

Leeward, Turks and Caicos

Near Beach | Pool

from $1700/Nt
6 6+
Details
Family-friendly resort villa with a gym, six bedrooms, and perfectly manicured grounds. Las Colinas 17 is located directly on the golf course in Casa de Campo

Casa de Campo, Dominican Republic

Pool

from $1750/Nt
6 6+
Details
Family-friendly villa with expansive exterior and bedrooms conveniently close together. Mandala Villa is located right on the La Cana Golf Course

Punta Cana, Dominican Republic

Pool

from $1750/Nt
6 6+
Details
Relaxing, elegant villa in a quiet location in Anse des Cayes. 4 BR rate available. Villa Les Lataniers sits at the very end of Anse des Cayes

Anse des Cayes, St. Barts

Pool

from $2857/Nt
6 6
Details
A beautiful infinity pool and impressive home theater offer the best of both worlds in this modern Caribbean getaway. 3, 4 & 5 BR rates available. Covered outdoor seating area

Corossol, St. Barts

Pool

from $3571/Nt
6 6
Details
Family-friendly, three-story home near Harbour Island's pink sand beaches. The beautiful beach is just a short walk away from Sapodilla House at Valentines Resort

Harbour Island, Bahamas

from $2000/Nt
6 3
Details
This 21,000 square feet villa has all the comforts of home and the luxury of a resort. 3, 4 & 5 BR rates available. This is one of three pools a Mystique Villa

Anguilla

Near Beach | Pool

from $2800/Nt
6 8+
Details
Quiet location that's still close to activities and restaurants. 2, 3 & 4 BR rates available. Loblolly Villa photo

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

from $486/Nt
6 6
Details
Wonderful architectural design suited for anyone with an artist's tastes, this property dates back to 1791 3, 4 & 5 BR rates available. Enjoy relaxing poolside at Estate Belvedere

St. Croix, USVI

Pool

from $860/Nt
6 6+
Details
Encore Villa will have you wanting to visit over and over, and over, again. 4 & 5 BR rates available. Encore Villa photo

Terres Basses (French side), St. Martin

Pool

from $979/Nt
6 6
Details
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 is perched just above Great Cruz Bay

Great Cruz Bay, St. John

Pool

from $1429/Nt
6 6+
Details
Near two popular beaches, Amancaya Villa is also near restaurants and groceries for ideal access during your St. Barts stay 1, 2, 3, 4 & 5 BR rates available. Amancaya Villa photo

Anse des Cayes, St. Barts

Pool

from $2429/Nt
6 6
Details
Two-building home near St. Lucia's Petit Piton, rainforest, botanical gardens, and dive sites. 2, 3 & 4 BR rates available.
Has specials. View from pool

Soufriere, St. Lucia

Near Beach | Pool

from $415/Nt
6 6
Details
6 bedrooms, a mansion on a hilltop with commanding views and easy access to Terres Basses beaches Luxurious pool with plenty of space to lounge in the sun at Always villa

Terres Basses (French side), St. Martin

Pool

from $1714/Nt
6 6
Details
Large groups or families will enjoy all that Maison de Reve has to offer, including the amazing Baie Rouge Beach just minutes away. 4 & 5 BR rates available. Maison de Reve is located on a hillside in the Terres Basses area

Terres Basses (French side), St. Martin

Near Beach | Pool

from $857/Nt
6 6+
Details
Stay right on Grace Bay Beach on two private, tropical acres that feel like a small resort. 5 BR rate available. Turtle Breeze is a beachfront getaway like no other on Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1971/Nt
6 6
Details
Bright, modern and private villa situated on Providenciales' coveted Long Bay Beach. 3 & 5 BR rates available.
Has specials. Aerial views from the ocean

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1500/Nt
6 6+
Details
Little Whale Cay offers three secluded villas for maximum privacy and pleasure, accommodating up to 12 persons. 3 BR rate available. Little Whale Cay private island retreat in the Berry Islands

Berry Islands, Bahamas

Pool

from $14760/Nt
6 6
Details
Vintage charm, private cottages and a great beachfront location. 4 & 5 BR rates available.
Has specials. From Nelson Gay House the view of the ocean within its tropical garden for privacy

Barbados

Beachfront | Pool | AC

from $1870/Nt
6 6+
Details
Privacy within a gated community are yours at this 6-bedroom property that features a main house and guest house overlooking the sea. 4 BR rate available.
Has specials. Go Easy Vill at Sugar hills offers a beautiful pool area

Barbados

from $1580/Nt
6 6+
Details
This sleek, modern, private property is just above Little Bay on Anguilla. Has specials. Ani Villa South in Anguilla is an excellent destination in the Caribbean

Anguilla

Pool

from $6400/Nt
6 6
Details
Sprawling 6-bedroom villa is situated among tropical gardens and comes with a huge private pool. Has specials. Vistamar features a poolside gazebo and an ample sundeck

Barbados

Pool

from $1800/Nt
6 5
Details
Huge 6-bedroom villa on the beach has tons of amenities, including a full staff and the use of Jamaica's famed Tryall Club Lounge just steps away from the ocean - by the pool at Karma Bay Villa

Montego Bay, Jamaica

Pool

from $2143/Nt
6 6+
Details
All modern amenities and entertainment options, Les Trois Jours Villa is great for groups who want to enjoy life together. 5 BR rate available. Les Trois Jours photo

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $1929/Nt
6 6+
Details
Costa Norte Villa: Bring your big family to this hilltop spot (or bring your friends and leave the kids with Grandma) Has specials. Costa Norte Villa photo

Cabrera, Dominican Republic

Pool

from $800/Nt
6 6+
Details
Experience sunrises and sunsets from Panache Villa in St. John's exclusive Estate Rendezvous 3 & 5 BR rates available.
Has specials. Panache Villa has amazing views over Rendezvous Bay

Rendezvous Bay, St. John

Pool

from $857/Nt
6 6
Details
A rainbow of offerings with 5 bedrooms and private beach access on St. Barthelemy. 3 BR rate available. Silver Rainbow Villa looks out into Petit Cul De Sac

Petit Cul de Sac, St. Barts

Near Beach | Pool

from $6143/Nt
6 6
Details
From beaches to sports, Casa del Mar Villa within exclusive Domaine du Levant has something for everyone Tropical ambiance surrounds Casa del Mar Villa

Petit Cul de Sac, St. Barts

Near Beach | Pool

from $6429/Nt
6 6+
Details
Gorgeous six-bedroom villa offers spacious accommodations, unbelievable views, and privacy for a dream vacation 4 & 5 BR rates available. Bon Temps Villa photo

Pointe Milou, St. Barts

Pool

from $3143/Nt
6 6
Details
This contemporary villa has panoramic ocean views, 2 pools, and tons of space with its 6 bedrooms 4 & 5 BR rates available. The large pool at Roxanne villa overlooks the Caribbean

Gustavia, St. Barts

Pool

from $4286/Nt
6 6
Details
Huge 6-bedroom oceanfront villa has access to a private beach, comes with a full staff, and has tons of extras Annabella Villa Estate located at the Tryall Club

Montego Bay, Jamaica

Pool

from $1714/Nt
6 6
Details
Spectacular 6-bedroom villa with resort amenities, privacy, views, and plenty of activities Following Seas Villa at Tryall Club photo

Montego Bay, Jamaica

Pool

from $2273/Nt
6 6
Details
Windward Villa offers fun, sun, and relaxation in a spacious and stunning Jamaican villa Windward Villa at Tryall Club photo

Montego Bay, Jamaica

Near Beach | Pool

from $1624/Nt
6 6
Details
Eclectic estate on the southern shore with its own private beach and bay. The Mani property is one largest high-end destinations in the Turks and Caicos

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $6000/Nt
6 6+
Details
Family-friendly villa with a bunk room, huge Great Room, outdoor amenities, and an ideal location in Rum Point. Has specials. The perfect image for Sun Salutations Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2498/Nt
6 5+
Details
Six-bedroom seaside villa with private courtyard and large entertainment area 5 BR rate available.
Has specials. Moon Kai has a beachfront pool where you can lounge in the Caribbean sun

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2225/Nt
6 6
Details
Grand and spacious ocean front property with some of the best snorkeling on the island 4 & 5 BR rates available.
Has specials. Far Tortuga Villa is on the north side of Grand Cayman, on the way to Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $750/Nt
6 5+
Details
Tropical villa for multiple families to share. 2 & 4 BR rates available. Aerial view of Villa Susanna

Marigot Bay, St. Lucia

Near Beach | Pool

from $1700/Nt
6 7
Details
Relax like royalty with stunning views and regal architecture. 2 & 4 BR rates available. Villa Hall photo

Cap Estate, St. Lucia

Near Beach | Pool

from $1000/Nt
6 6+
Details
With a media room that doubles as a children's suite, this villa is perfect for multi-family vacations. 5 BR rate available. Deja View photo

Gift Hill, St. John

from $1507/Nt
6 6+
Details
This villa's full staff and beach access eliminates any potential stressors for your Caribbean vacation. 4 BR rate available.
Has specials. Kishti Villa East on Meads Bay offers relaxing outdoor spaces

Anguilla

Beachfront | Pool | AC

from $4200/Nt
6 6+
Details
Modern beachside villa with sound system, expansive outdoor space, and a gourmet kitchen. C\'est La Vie Villa photo

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $4714/Nt
6 6
Details
Witenblauw Estate has every creature comfort, three pools, and beach access. Witenblauw Estate Villa photo

Pelican Key (Dutch side), St. Martin

Beachfront | Pool | AC

from $2071/Nt
6 6+
Details
A private Grand Cayman estate with tranquil design and a Master Suite that feels like a spa. Has specials. Tranquility Cove Villa has a luxurious infinity edge pool

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2070/Nt
6 6+
Details
Cascade Villa provides guests with the utmost in privacy, ocean views, and jaw-dropping pool design. 4 BR rate available. Sunset over the Caribbean - from Cascade Villa

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $1571/Nt
6 6+
Details
Four-level villa with expansive patio. 3, 4 & 5 BR rates available. Coco Rock Villa photo

Petit Cul de Sac, St. Barts

Pool

from $1714/Nt
6 6
Details
Fully air-conditioned villa right on the water, with kayaks and bicycles to take to Rum Point Beach. 4 BR rate available.
Has specials. An aerial view of Hidden Cove Villa - it is located just adjacent to the Bio-luminescent Bay

Grand Cayman, Cayman

Near Beach | Pool

from $700/Nt
6 5
Details
Las Hamacas Villa photo

Cap Cana, Dominican Republic

Beachfront | AC

from $5870/Nt
6 6
Details
Relaxation by the amazing pool at Villa Sirena

Punta Cana, Dominican Republic

Near Beach | Pool

from $2670/Nt
6 6
Details
Two story, beachfront villa with spacious rooms and a large balcony. 4 & 5 BR rates available.
Has specials. Amarone Villa is a luxurious home on the South Coast

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1550/Nt
6 7
Details
Arrecife 55 photo

Punta Cana, Dominican Republic

Pool

from $2290/Nt
6 6
Details
Cayuco 9 Villa photo

Cap Cana, Dominican Republic

Pool

from $1600/Nt
6 6
Details
Has specials. Tortuga Bay C-17 photo

Punta Cana, Dominican Republic

Near Beach | Pool

from $2000/Nt
6 6+
Details
2 & 4 BR rates available. Trou Rolland Villa photo

Marigot Bay, St. Lucia

Near Beach | Pool

from $492/Nt
6 6+
Details
South Sound Beach villa with five star amenities and no shortage of entertainment. Has specials. Point of View Villa is located on a picturesque Caribbean beachfront

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2857/Nt
6 6+
Details
Eye-catching six bedroom villa with outdoor retreat and private tennis court. 4 & 5 BR rates available. Pool / Beach View

Lurin, St. Barts

Pool

from $4286/Nt
6 6
Details
Spectacular beachfront private island estate offers Balinese luxury. 2 & 3 BR rates available.
Has specials. A private cabana sits beachfront at Love Pumpkin

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $8000/Nt
5 5
Details
Cliffside villa with ocean access and a guest cottage. 2, 3 & 4 BR rates available.
Has specials. The infinity edge pool at Sea\'s Edge has amazing views of the ocean

Rendezvous Bay, St. John

Pool

from $929/Nt
5 5+
Details
Ultra private, ultra modern villa with extensive outdoor amenities. Has specials. Tip of the Tail Villa sits on the peninsula for which it is named

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $3800/Nt
5 6
Details
Lounge by the pool in the Jamaican sun at Retreat villa

Montego Bay, Jamaica

Near Beach | Pool

from $714/Nt
5 5
Details
Privacy and luxury within a secluded beach hideaway. 3 & 4 BR rates available.
Has specials. The pool and view of the ocean from Beach Enclave Ocean View Villas

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $2000/Nt
5 5
Details
Enjoy total tranquility in a main house and guest cottage set amongst the lush hillside. 2, 3 & 4 BR rates available. Darcini Villa is located in Fish Bay with a south facing view of rolling hills

Fish Bay, St. John

Pool

from $514/Nt
5 5+
Details
Three beaches on a private Preserve surrounded by the lush jungle. Langarra Estate photo

St. Thomas, USVI

Pool

from $1071/Nt
5 5+
Details
Magens Hideaway photo

St. Thomas, USVI

Pool

from $979/Nt
5 4+
Details
Exquisite villa with breathtaking outdoor spaces. 3 BR rate available.
Has specials. High Breeze photo

Barbados

Pool

from $1175/Nt
5 5+
Details
Luxury waterfront home located on the edge of paradise. Hesperides House has amazing uninterrupted ocean views

Taylor Bay/Sapodilla Bay, Turks and Caicos

Pool

from $1643/Nt
5 5
Details
Private boat dock, beach, and panoramic ocean views at this fully air-conditioned villa. The Beach House photo

St. Thomas, USVI

Beachfront | AC

from $1300/Nt
5 4+
Details
Elegant, refined villa with beachfront access, luxurious amenities, and an open layout. The luxury pool at Coral Pavilion Villa sits just a few yard from the beautiful Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4950/Nt
5 5
Details
Gated two-story estate with three levels of outdoor space and chic amenities. Has specials. Great Bluff Estates sits along the beautiful northern coast of Grand cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1425/Nt
5 7
Details
Well-equipped villa with a game room, kids room, pool deck, and ocean access. Alinna sits just along Chalk Sound with beautiful water views

Chalk Sound, Turks and Caicos

Pool

from $1200/Nt
5 6+
Details
Two stories of chic bedrooms, sunny terraces, and elegant lounging space. 3 & 4 BR rates available. La Case Créole is located on a hilltop above St. Jean Bay

Saint Jean, St. Barts

Pool

from $1929/Nt
5 5
Details
Large Del Mar Villa is only minutes from Anse Marcel Beach 3 & 4 BR rates available. A large patio area by the pool at Del Mar Villa

Anse Marcel (French side), St. Martin

Pool

from $500/Nt
5 5
Details
Panoramic ocean views and an abundance of outdoor amenities makes this villa perfect for a large group. 1, 2, 3 & 4 BR rates available. Le Chant de la Mer Villa is located on a hillside on Point Milou

Pointe Milou, St. Barts

Pool

from $2143/Nt
5 6
Details
Casa Bougainvillea is as fresh and lively as its name implies, surrounded by exotic tropical gardens 2, 3 & 4 BR rates available. Casa Bougainvillea Villa has a beautiful private pool

St. Thomas, USVI

Beachfront | Pool | AC

from $853/Nt
5 4
Details
Entertaining is a joy at Silk Cotton Villa onSt. Thomas with ample space for lively group conversation 2, 3 & 4 BR rates available. Silk Cotton Villa photo

St. Thomas, USVI

Pool

from $600/Nt
5 5
Details
Set on the cliffs of Falaise des Oiseaus is La Dacha, a gorgeous five-bedroom villa will be the star of your Caribbean holiday. Pool area with spectacular ocean views

Terres Basses (French side), St. Martin

Near Beach | Pool

from $2429/Nt
5 5+
Details
The perfect large event villa with two separate cottages and lots of outdoor entertaining space. 4 BR rate available.
Has specials. Luxury resort style pool area at The Carib House

Antigua

Near Beach | Pool

from $1160/Nt
5 4
Details
Adagio Villa is an excellent choice for families or couples traveling together who also want privacy. Handicap accessible. 1, 2, 3 & 4 BR rates available. Adagio Villa photo

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

from $500/Nt
5 5+
Details
This boutique resort offers guests an amazing staff, large gathering spaces, and two private acres. Baraka Point photo

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from Call for rates
5 5+
Details
Convenient to golf, tennis, and sandy beaches, La Provencale Villa can accommodate up to five couples 3 & 4 BR rates available. La Provencale Villa photo

Terres Basses (French side), St. Martin

Pool

from $714/Nt
5 5
Details
Enjoy sunset views over the ocean from Mer Soleil, a charming villa set on the hillside 3 & 4 BR rates available. Mer Soleil Villa photo

Terres Basses (French side), St. Martin

Pool

from $743/Nt
5 5
Details
This villa has five spacious suites with sea view terraces. Sea Villa is situated facing the beach with amazing unobscured ocean views

Anguilla

Beachfront | Pool | AC

from $3300/Nt
5 5+
Details
Enjoy easy beach access and spacious bedrooms. Lounge in luxury at Sand Villa on Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $3100/Nt
5 4+
Details
Giselle Villa has all the right equipment for a working vacation, but it won't feel like work with those views surrounding you. 3 & 4 BR rates available.
Has specials. Beautiful views pool side at Giselle Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

from $821/Nt
5 5
Details
This Maria Bluff villa enjoys 360-degree sunrise and sunset views. 3 BR rate available. A aerial view of the beautiful Villa Kismet property

Chocolate Hole, St. John

Pool

from $2450/Nt
5 6+
Details
5 bedroom secluded villa with pool, hot tub and room to breathe 4 BR rate available.
Has specials. Ecstasea has a beautiful pool and patio area with the ocean in the background

Grand Cayman, Cayman

Beachfront | Pool | AC

from $850/Nt
5 5
Details
With sweeping views, and tastefl appointments, Panaromic View Villa is ideal for large gatherings and hosting parties 2, 3 & 4 BR rates available. Pool side luxury with truly Panoramic views

Lurin, St. Barts

Pool

from $2486/Nt
5 5
Details
Set up high for fantastic pool views and a beachfront location on Taylor Bay. 4 BR rate available. Alizee Villa is located just a short distance away from Taylor Bay Beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1000/Nt
5 5
Details
Beautifully and thoughtfully designed for year-round solitude and relaxation. 3 & 4 BR rates available. Beautiful Anguillan sunset from the back porch at Amarilla

Anguilla

Near Beach | Pool

from $2100/Nt
5 5+
Details
Located very near the water, enjoy five bedrooms with all the perks at Rhapsody St. John Villa. 2, 3 & 4 BR rates available.
Has specials. Rhapsody sits atop a hillside on Contant Point

Great Cruz Bay, St. John

Pool

from $929/Nt
5 5+
Details
Spacious, with an amphitheater and built-in seating; the expansive Coco de Mer is great for a wedding 2, 3 & 4 BR rates available. Coco de Mer at Peter Bay photo

Peter Bay, St. John

Near Beach | Pool

from $1400/Nt
5 6+
Details
Private and spacious beachfront villa with a media room, gym, and extensive outdoor space. 2, 3 & 4 BR rates available. Beautiful infinity edge pool over looking Petit cul de sac

Petit Cul de Sac, St. Barts

Beachfront | Pool | AC

from $2429/Nt
5 5+
Details
Relax in this villa's infinity pool, beach cabana and hammock and enjoy the close proximity to George Town Has specials. Lounge poolside on the beach at Pease Bay House

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1950/Nt
5 6
Details
Beachfront luxury villa with a home theater, entertainment room, and impressive Great Room. The luxurious pool at Blue Diamond Villa

Anguilla

Beachfront | Pool | AC

from Call for rates
5 7
Details
Great economical villa high up in Cap Estate. The best feature of this property are the fantastic ocean views. 2, 3 & 4 BR rates available. Amazing views of the ocean from the pool and patio at Bliss Villa

Cap Estate, St. Lucia

Near Beach | Pool

from $300/Nt
5 5
Details
The Beach House is an adventure destination perfect for the outdoor person in tune with nature Lounge and enjoy views of the Caribbean from the deck at The Beach House

St. Thomas, USVI

Beachfront | AC

from $650/Nt
5 3+
Details
Unparalleled luxury and access to the only golf course on Anguilla. Sky Villa is the most private of the Long Bay Villas located just off the beach

Anguilla

Near Beach | Pool

from $2900/Nt
5 4+
Details
Great for a small wedding or honeymoon, this hidden hillside villa has thought of everything 2, 3 & 4 BR rates available. Lounge poolside at Mystic villa and enjoy views of famous St. Jean Bay

Saint Jean, St. Barts

Pool

from $2136/Nt
5 5+
Details
Ultra-modern upscale Anguilla villa with glass walls that face the sea. Has specials. Champagne Shores villa sits on a secluded beach near Pelican Bay

Anguilla

Near Beach | Pool

from $1700/Nt
5 5+
Details
Striking four-story villa beachfront villa with ocean views and a private tennis court. Antilles Pearl Villa is located on Shoal Bay Beach at the Altamer Villas

Anguilla

Beachfront | Pool | AC

from $3214/Nt
5 6
Details
Gorgeous aerial views of the Caribbean, private chef, all-inclusive St. Bernard\'s Hill House photo

Tortola, BVI, British Virgin Islands

from $3643/Nt
5 6+
Details
Beachfront at Klein Bay! 1, 2, 3 & 4 BR rates available. Serenata de la Playa has a beautiful pool

Klein Bay, St. John

Beachfront | Pool | AC

from $565/Nt
5 5+
Details
Cliff-side and family friendly, Fushi Villa can accommodate a large family or group with 5 bedrooms. 3 & 4 BR rates available. The pool meets the ocean at Fushi Villa

Grenada

Pool

from $700/Nt
5 5
Details
Light and airy, and with a delightful name, Monkey Puzzle will bring charm to days spent within prestigious Westmoreland. St. James Has specials. Monkey Puzzle photo

Barbados

Pool

from $2000/Nt
5 5+
Details
Great for groups or large families who want large bedrooms and expansive living spaces. 2 & 4 BR rates available. Bellevue Villa photo

Marigot, St. Barts

Pool

from $857/Nt
5 5
Details
Chic, plantation-style estate with full staff. Has specials. Coral House sits on a beautiful stretch of the world famous Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4310/Nt
5 5+
Details
Resort fun with easy beach access and ocean views Villa Arrecife 25 at Tortuga Bay photo

Punta Cana, Dominican Republic

Pool

from $1720/Nt
5 5
Details
The view is unmatched anywhere in Tryall Club! No Le Hace is a beautiful villa over looking the ocean from the Tryall club

Montego Bay, Jamaica

Pool

from $1429/Nt
5 5
Details
Opulent villa with a full staff and luxurious decor. Infinity Villa at Tryall Club photo

Montego Bay, Jamaica

Pool

from $2091/Nt
5 5+
Details
An air-conditioned mini-gym and a shady area to enjoy an afternoon massage await at Palm Beach Villa. 4 BR rate available. The pool at Palm Beach is just steps away from the beach

Lorient, St. Barts

Near Beach

from $3571/Nt
5 5
Details
Huge two-level villa near Flamands Beach with gorgeous island views and tons of amenities. 3 & 4 BR rates available. Eternity villa is tucked into at tropical hillside above Flamands

Flamands, St. Barts

Pool

from $2143/Nt
5 5
Details
Ample relaxing space on two outdoor terraces with hammocks, seating, al fresco dining, and wading pool. 1, 2, 3 & 4 BR rates available. Tucked away on a hillside Sky Villa has a private pool that provides some amazing views

Petite Saline, St. Barts

Pool

from $971/Nt
5 6+
Details
Francis Bay Estate Villa: Caribbean ambiance abounds both indoors and out 3 BR rate available.
Has specials. Francis Bay Estate Villa is surrounded by lush tropical greenery

North Shore, St. John

Near Beach | Pool

from $957/Nt
5 5+
Details
The self-contained, detached guest house offers a wonderful private getaway for newlyweds or couples wanting to spend some time on their own. Lush tropical greenery surrounds Sade Villa

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from Call for rates
5 5
Details
Located in Peter Bay, this five-star villa has an entire floor dedicated to entertainment. 3 BR rate available. Welcome to Delfina Villa

Peter Bay, St. John

Near Beach | Pool

from $1686/Nt
5 6+
Details
Beachfront decks combine with easy access to Smiths Reef for island elegance. Villa Paprika is located on Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1400/Nt
5 5+
Details
Classically Caribbean villa with an impressive pool and gorgeous mountain views. 3 BR rate available. Arc En Ciel Villa photo

Soufriere, St. Lucia

Near Beach | Pool

from $1900/Nt
5 5
Details
This villa has an upstairs pool and deck space, giving amazing views down the beach. Turtle Beach Villa has amazing views of Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1114/Nt
5 5
Details
A collection of bungalows and two pools offer privacy and relaxation. 1 & 3 BR rates available. Shaded patio area looks over the Caribbean

Deve, St. Barts

Pool

from $1643/Nt
5 5
Details
Huge beachfront villa with housekeeping, five bedrooms, and 18 acres of land. Has specials. The pool area at Amazing Grace Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4950/Nt
5 5+
Details
Five-bedroom villa with a private dock, a pool, and easy access to island attractions. Has specials. Aerial view of Calypso and Sapodilla Bay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1500/Nt
5 5
Details
Super modern, upscale villa with glass walls and a spacious design. Lounge by the pool and enjoy amazing ocean views at Beaches Edge East Villa

Anguilla

Near Beach | Pool

from $1400/Nt
5 5+
Details
One-of-a-kind modern villa takes luxury to a new level and boasts incredible views of the Caribbean Sea 3 BR rate available. Stunning infinity edge pool

Pointe Milou, St. Barts

Pool

from $4800/Nt
5 6
Details
Gorgeous beachfront property boasts incredible views, tons of space, and easy walking access to island attractions. Beautiful Casa Grande Villa on Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2357/Nt
5 4
Details
Get the best of both worlds with this fully air-conditioned villa, private and scenic but minutes from shopping and beaches. 1, 2, 3 & 4 BR rates available. Beautiful ocean views from the pool at OM villa

Mont Jean, St. Barts

Pool

from $1571/Nt
5 5
Details
Exclusive beachfront villa boasts amazing views, sumptuous accommodations, and every luxury you'll want Has specials. Luxurious pool just steps away from the beach at The Dream Villa

Barbados

Beachfront | Pool | AC

from $4000/Nt
5 5
Details
Luxurious, extremely modern villa with stunning sunset views, privacy, and lots of space. 3 BR rate available. Kishti Villa on Blackgarden is situated to enjoy amazing ocean views

Anguilla

Near Beach | Pool

from $2500/Nt
5 5+
Details
This stunning 5-bedroom villa has a great location near Cruz Bay and North Shore beaches! Has specials. Casa Coram Deo photo

Great Cruz Bay, St. John

Beachfront | Pool | AC

from $1629/Nt
5 5+
Details
Stunning views you won't find just anywhere make this 3-bedroom contemporary villa the perfect escape for couples and friends 3 & 4 BR rates available. Acqua Villa - Amazing views of the lagoon from the pool

Terres Basses (French side), St. Martin

Pool

from $714/Nt
5 5+
Details
Bright and beautiful gated property with modern amenities, full air-conditioning, and snorkeling nearby. 2 BR rate available. Castaway Villa is the perfect place to relax - endless Caribbean views

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $1000/Nt
5 5
Details
Privacy, luxury, and simplicity with a view await at beautiful Villa Aja 2, 3 & 4 BR rates available. Aja Villa photo

Tortola, BVI, British Virgin Islands

Near Beach

from $885/Nt
5 5
Details
Huge outdoor space with a wet bar and pool, just minutes from the beach. Has specials. Tradewinds Villa is located in the Sandy Lane neighborhood

Barbados

Pool

from $2500/Nt
5 5
Details
Lovely hillside villa with pool, a full staff, and Tryall Club amenities View of Caribbean

Montego Bay, Jamaica

Pool

from $1429/Nt
5 5
Details
Palatial, secluded oceanfront mansion near great snorkeling. 2, 3 & 4 BR rates available. Miramar Villa has amazing ocean views

St. Croix, USVI

Near Beach | Pool

from $1680/Nt
5 5+
Details
Five identical bedrooms with a gorgeous outdoor area. Pool at La Petite Sereine overlooking the ocean

Pointe Milou, St. Barts

Pool

from $7143/Nt
5 6
Details
Beachfront island home with plenty of room for family getaways 4 BR rate available.
Has specials. The pool and this cabana are located right on the beach at Reef Romance Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $950/Nt
5 5
Details
Modern and luxurious five bedroom home on Barbados’ West coast 4 BR rate available.
Has specials. Still Fathoms is a super stylish villa just steps away from the beach

Barbados

Beachfront | Pool | AC

from $1770/Nt
5 5+
Details
A regal two-story Sandy Lane villa with a full staff and beach access. Has specials. Windward Villa in Sandy Lane offers luxurious amenities

Barbados

Pool

from $2800/Nt
5 5
Details
Located steps from the beautiful beach of Plum Bay, Blue Palm is a modern haven of luxury. 3 & 4 BR rates available.
Has specials. Blue Palm Villa is surrounded by lush tropical greenery

Terres Basses (French side), St. Martin

Near Beach | Pool

from $1000/Nt
5 6+
Details
Four-level, comfortable villa near the beach. 1, 2, 3 & 4 BR rates available.
Has specials. Views into Chocolate Hole Bay from Reefside Villa

Chocolate Hole, St. John

Near Beach | Pool

from $857/Nt
5 5+
Details
Inviting resort villa with five master suites and full service. 1, 2, 3 & 4 BR rates available. CeBleu Villas are located on the northern end of crocus Bay

Anguilla

Near Beach | Pool

from $795/Nt
5 6
Details
The Sanskrit word for “Paradise” is Nandana, and this villa fits the name perfectly through its outstanding accommodations, amenities, and unbeatable location. 3 BR rate available. Nandana Villa in the Bahamas

Grand Bahama Island, Bahamas

Pool

from $10000/Nt
5 6
Details
Lush surrounding and tropical vistas at Villa Lolita

Montego Bay, Jamaica

Pool

from $1949/Nt
5 5
Details
A luxurious five-bedroom retreat with a full staff, entertainment system, and Meads Bay location. 4 BR rate available.
Has specials. Relax in the pool and hot tub during your stay at Kishti Villa West

Anguilla

Beachfront | Pool | AC

from $4200/Nt
5 6+
Details
Entertain a large crowd flawlessly with this 5-bedroom Magens Bay villa–there is plenty of room inside and out Viento Villa photo

St. Thomas, USVI

Pool

from $1150/Nt
5 5+
Details
Enjoy the private beachfront villa experience with the comforts of a five-star resort. 4 BR rate available.
Has specials. The Residences on Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $3400/Nt
5 5+
Details
Two pools, a gym, and musician-inspired bedrooms set this villa apart from others on the island. 3 & 4 BR rates available. My Way Villa sits on a hillside looking over the Flamands Bay

Flamands, St. Barts

Pool

from $3571/Nt
5 5
Details
There is no chance of missing the elevated views of Long Bay with this villa, and the size and space make Ridgemont extra impressive 3 & 4 BR rates available. Ridgemont House photo

Tortola, BVI, British Virgin Islands

Pool

from $1000/Nt
5 6
Details
A charming, private estate on the Mont Jean hillside close to Pointe Milou. 3 & 4 BR rates available. Turtle Villa photo

Mont Jean, St. Barts

Pool

from $1071/Nt
5 5
Details
Ideal location in a luxurious, family-friendly villa. BOM Villa is located on the beach in St. Jean Bay

Saint Jean, St. Barts

Beachfront | Pool | AC

from $8764/Nt
5 5
Details
Spacious, minimalistic beachfront villa with a loft for kids and a central living area. 4 BR rate available.
Has specials. Ocean Kai sits directly on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1200/Nt
5 5
Details
Fully air-conditioned villa with tons of outdoor activities and a beach in the backyard. Has specials. Sea Grape Villa sits just on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $700/Nt
5 4
Details
Villa Corales 18 photo

Punta Cana, Dominican Republic

Beachfront | Pool | AC

from $4550/Nt
5 5+
Details
This eco-friendly villa enjoys a beachfront location and resort amenities. 3 & 4 BR rates available.
Has specials. The interior pool and dining palapa at the Dunes Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $3200/Nt
5 5+
Details
Endless ocean view with massive living spaces and three stories of luxury. 3 & 4 BR rates available. Castle Rock Villa photo

Camaruche, St. Barts

Pool

from $4000/Nt
5 5
Details
A beautifully designed villa on the canal with a gorgeous pool, private dock, and beach service on Grace Bay. Has specials. Windemer is located along the canals at the far east end of Provo

Providenciales, Turks and Caicos

Near Beach | Pool

from $1714/Nt
5 4+
Details
Swanky waterfront villa with resort-like amenities and a boat dock. The Reef Villa photo

Simpson Bay (Dutch side), St. Martin

Pool

from $1143/Nt
5 5
Details
60-foot pool and panoramic views at this 5 bedroom villa. 3 & 4 BR rates available. Ginger Villa sits in the hills above Lorient Bay

Petite Saline, St. Barts

Pool

from $2000/Nt
5 5
Details
Luxuriously modern resort villa with stunning ocean views and private beach access. 3 & 4 BR rates available.
Has specials. Beach Enclave Beachfront Villas offer amazing ocean views

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $2650/Nt
5 5
Details
Marina 2 photo

Punta Cana, Dominican Republic

Near Beach

from $3290/Nt
5 5+
Details
Glamorous, spacious villa with water access, chic decor, and stunning views. 1, 2, 3 & 4 BR rates available.
Has specials. Pool and backyard facing Great Cruz Bay at Ardisia Villa

Great Cruz Bay, St. John

Pool

from $1500/Nt
5 5+
Details
Zen decor fills this luxury retreat in St. Jean bay. 3 BR rate available. Ixfalia photo

Saint Jean, St. Barts

Pool

from $3571/Nt
4 4+
Details
Amazing sunset views and walking distance to all Gustavia has to offer. 2 & 3 BR rates available. Amazing Caribbean views from Axel Rocks Villa

Gustavia, St. Barts

Pool

from $3571/Nt
4 4
Details
Spacious, beachfront villa with a boat dock and spacious floor plans. Has specials. Right on the beach with a dock leading to a gazebo Faroway is an ideal Cayman destination

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1215/Nt
4 5
Details
Gated community villa minutes from town and St. John's beaches. 1, 2 & 3 BR rates available. Blue Papaya photo

Virgin Grand Estates, St. John

Pool

from $593/Nt
4 4
Details
Chic and modern villa with the perfect design for a family or two. 2 & 3 BR rates available. SAX Villa photo

Saint Jean, St. Barts

Near Beach

from $2000/Nt
4 4
Details
Nearly 6,000 square feet of luxury, with up close and personal ocean views. Has specials. The four bedroom Beachfront Villas at Sailrock Resort

South Caicos, Turks and Caicos

Beachfront | Pool | AC

from $3850/Nt
4 4
Details
Hillside villa with handicap access, an ideal location, and an open floor plan. 3 BR rate available. Alpaka Villa has beautiful views from its hillside location over Flamands Beach

Flamands, St. Barts

Pool

from $1143/Nt
4 4
Details
This villa's gorgeous exterior was made for entertaining. Casa de Campo #146 sits on the 13th hole of the -Teeth of the Dog- Golf Course

Casa de Campo, Dominican Republic

Pool

from $1500/Nt
4 4+
Details
Super private beachfront villa with water sports, a home theater, and ocean views. Has specials. Stepping Stone Villa is located along a beautiful beach at the East End of Grand Cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1778/Nt
4 4+
Details
Luxurious resort property with full service and amenities. Has specials. Grace Bay Club Resort pool

Grace Bay, Turks and Caicos

Beachfront | AC

from $5330/Nt
4 4
Details
Two levels of eclectic interiors with gorgeous ocean views. 1, 2 & 3 BR rates available. Limin\' da Coconut sits directly on the ocean in Little Harbor

Anguilla

Near Beach | Pool

from $1000/Nt
4 4
Details
If you love St. Jean Beach, the views from Nomade Villa in Lurin are a feast for the eyes 2 & 3 BR rates available. Nomade Villa photo

Lurin, St. Barts

Pool

from $1429/Nt
4 4
Details
Pallina Villa is a marvelous location for families with small children or for couples traveling together. 2 & 3 BR rates available. Pallina Villa photo

St. Thomas, USVI

Pool

from $715/Nt
4 3+
Details
This villa sits right on Mahoe Beach's white sands, perfect for beach lovers. 2 BR rate available. Wonderful beach just steps away from the pool at Beach Dreams Villa

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from $886/Nt
4 4+
Details
Immaculate, contemporary house with ocean views from every room. 3 BR rate available.
Has specials. Endless ocean views from the pool deck at Turquoze Villa

Orient Bay (French side), St. Martin

Pool

from $693/Nt
4 4+
Details
Bright and modern villa with amazing ocean views everywhere you look. 3 BR rate available. Ocean Palms sits along the coast of Turtle Tail

Turtle Tail, Turks and Caicos

Pool

from $786/Nt
4 4
Details
Ideal for families with older children who want to spread their wings in their own apartment. 2 & 3 BR rates available. Bellamare Villa photo

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

from $543/Nt
4 8+
Details
Entertain on the expansive deck, or pick a nook for reading as Clair de Lune offers spaces for family bliss or sweet serenity 2 & 3 BR rates available. Lounge in Caribbean beauty by the pool at Clair de Lune Villa

Terres Basses (French side), St. Martin

Pool

from $700/Nt
4 4+
Details
Location, location, location! Pool deck is St. John is perfect for groups with diverse tastes. 1, 2 & 3 BR rates available.
Has specials. Altagracia Villa photo

Great Cruz Bay, St. John

Pool

from $571/Nt
4 4
Details
Secluded villa on Simpson Bay comes with tons of amenities and is very close to beaches, shops, restaurants, and more. 3 BR rate available.
Has specials. Mirabelle Villa photo

Terres Basses (French side), St. Martin

Near Beach | Pool

from $857/Nt
4 4
Details
The sleek and modern Milonga Villa overlooks the extraordinary Marigot and Grand Cul de Sac Bay 2 & 3 BR rates available. Milonga Villa photo

Marigot, St. Barts

Pool

from $971/Nt
4 4
Details
The pool is a focal point of this island stunner-large enough for laps but tranquil and relaxing enough to enjoy the entire day there. 2 & 3 BR rates available. La Pergola photo

Terres Basses (French side), St. Martin

Pool

from $600/Nt
4 4+
Details
A little slice of heaven on St. Barth, within walking distance of St. Jean beach, shopping, and dining. 2 & 3 BR rates available. Kir Royal Villa has a great pool

Saint Jean, St. Barts

Near Beach | Pool

from $700/Nt
4 4
Details
Comfortable Living Just Above the Water's Edge of St. Jean Bay 2 & 3 BR rates available. Sous La Falaise photo

Saint Jean, St. Barts

Near Beach | Pool

from $1143/Nt
4 4
Details
Located in Vitet, Kermao Villa is a four-bedroom house located on a tropical hillside 1, 2 & 3 BR rates available. Kermao Villa photo

Vitet, St. Barts

Pool

from $535/Nt
4 4
Details
Spacious and secluded waterfront villa where you can access Chocolate Hole for a swim 2 BR rate available.
Has specials. Beach Garden has a great outdoor pool area

Chocolate Hole, St. John

Near Beach | Pool

from $971/Nt
4 4
Details
Large villa on Klein Bay in St. John is great for family vacations with access to a lovely semi-private beach 1, 2 & 3 BR rates available.
Has specials. Ami La Vita Villa has amazing views of the Caribbean

Klein Bay, St. John

Near Beach | Pool

from $571/Nt
4 3+
Details
Ocean Villa offers incredible views in every direction and is very kid-friendly. View to the ocean and pool from the 4 bedroom ocean villa!

Northeast Coast, Puerto Rico

Beachfront | AC

from $536/Nt
4 3+
Details
Tuscan/Mediterranean style in a Caribbean location -- looking down over Chocolate Hole 1, 2 & 3 BR rates available.
Has specials. Lounge on the deck poolside and enjoy views of the Caribbean

Chocolate Hole, St. John

Pool

from $386/Nt
4 5
Details
Natural stone landscaping and a man-made waterfall set this villa apart. 2 & 3 BR rates available.
Has specials. On the Rocks Villa is nestled along the hillside providing amazing views

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

from $1071/Nt
4 4
Details
Four-bedroom sanctuary near St. Jean Beach with gorgeous gazebo and infinity edge pool 2 & 3 BR rates available. The infinity pool blends into the views of St. Jean Bay

Saint Jean, St. Barts

Near Beach | Pool

from $1329/Nt
4 4
Details
Serene setting and lots of natural beauty greet you at Peace & Plenty Villa. 2 & 3 BR rates available. Peace & Plenty Villa photo

Catherineberg, St. John

Pool

from $750/Nt
4 4+
Details
The airy Chateau La Tete Rouge Villa makes indoor and outdoor living almost indistinguishablr 1, 2 & 3 BR rates available.
Has specials. Chateau La Tete Rouge Villa photo

Rendezvous Bay, St. John

Pool

from $571/Nt
4 3+
Details
Open-concept luxury villa, close to several beaches and Gustavia harbor 2 & 3 BR rates available. Stunning view of St. Jean Bay from the pool at Pasha villa!

Lurin, St. Barts

Pool

from $1271/Nt
4 4
Details
Chalk Sound villa rental with a boat dock, game room, and private pool. Breezy Palms villa looks direct out into Chalk Sound

Chalk Sound, Turks and Caicos

Pool

from $571/Nt
4 3+
Details
A private four-bedroom villa, Great Turtle Villa offers great views at an affordable rate! 2 & 3 BR rates available. Pool views of the ocean and island at Great Turtle villa

Coral Bay, St. John

Pool

from $430/Nt
4 4+
Details
Four-bedroom resort villa right on Grace Bay beach. Has specials. The West Bay Club by night

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2020/Nt
4 4
Details
Located on one of the most beautiful beaches of the island. 2 & 3 BR rates available. Angelique Villa photo

Saint Jean, St. Barts

Pool

from $1429/Nt
4 4
Details
Kayaks, hammocks, screened porches, and a boat dock makes this fully air-conditioned villa perfect for sun-lovers. 3 BR rate available.
Has specials. Great Escape Villa is very close to the beautiful beach

Grand Cayman, Cayman

Near Beach | Pool

from $750/Nt
4 3
Details
Located between Lorient and Marigot, Captain Cook villa has easy access to many island amenities 1, 2 & 3 BR rates available. A private pool and hot tub area the perfect place to vacation at Captain Cook Villa

Pointe Milou, St. Barts

Pool

from $714/Nt
4 4
Details
Belle Bague Villa is great for couples wanting to entertain in the trendy area of Colombier 2 & 3 BR rates available. Belle Bague Villa photo

Colombier, St. Barts

Pool

from $1714/Nt
4 6
Details
A huge pool deck and several gazebos provides the ultimate relaxation with a view. 2 & 3 BR rates available.
Has specials. Ambiance is located in the heart of Terres Basses with access to beautiful beaches nearby

Terres Basses (French side), St. Martin

Pool

from $857/Nt
4 4+
Details
Set between Taylor Bay and Sapodilla Bay, this house has a modern vibe and amazing ocean views. Has specials. Lounge by the ocean front pool at La Percha

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1350/Nt
4 4+
Details
Secluded villa is on the sunset side of Point Milou will make your St. Barts visit unforgettable. 2 & 3 BR rates available. Domingue Villa has amazing ocean views

Pointe Milou, St. Barts

Pool

from $1329/Nt
4 4
Details
Great for large families with kid friendly beach within walking distance 1, 2 & 3 BR rates available. Villa Amarillo photo

Grenada

Near Beach | Pool

from $400/Nt
4 4
Details
Art lovers take note: Sunspot villa offers modern architecture while maintaining island charm 2 & 3 BR rates available. Sunspot Villa photo

Peter Bay, St. John

Near Beach | Pool

from $1453/Nt
4 4+
Details
Gorgeous 4 bedroom villa in Vitet Close to Everything You Need 2 & 3 BR rates available. Pool and deck

Vitet, St. Barts

from $786/Nt
4 4
Details
This ultra modern villa has a private concierge and take your breath away sunsets. Has specials. Ani Villa North is a beautiful location for a Caribbean getaway

Anguilla

Pool

from $5100/Nt
4 4+
Details
Four couples can enjoy great views and shopping opportunities from this ocean view villa. 1, 2 & 3 BR rates available.
Has specials. Impressive views of the Caribbean from the pool and deck area at Island Rider Villa

Rendezvous Bay, St. John

Pool

from $886/Nt
4 4+
Details
Breathtaking ocean views engulf this ultra-chic, spacious villa. 2 & 3 BR rates available.
Has specials. Terrasse de Mer Villa sits above Baie Rouge providing stunning scenery

Terres Basses (French side), St. Martin

Pool

from $814/Nt
4 4
Details
Close to the beach and restaurants, Vigie overlooks sparkling Saint Jean Bay and has tons of amenities 2 & 3 BR rates available. A view of St. Jean Bay - from the pool at Vigie Villa

Saint Jean, St. Barts

Pool

from $1000/Nt
4 4
Details
Mango Bay Villa at Catherineburg offers exceptional views of St. John's north shore 2 & 3 BR rates available.
Has specials. Views of the Caribbean from the pool and deck at Mango Bay Villa

Catherineberg, St. John

Pool

from $714/Nt
4 4+
Details
Great Cruz Bay's La Bella Vita Villa: Perfect for counting islands (we count fourteen on a clear day) or counting stars at night 1, 2 & 3 BR rates available.
Has specials. Pool at La Bella Vita

Virgin Grand Estates, St. John

Pool

from $643/Nt
4 4+
Details
This Grace Bay beauty has modern luxury, a fantastic pool bar, and an upstairs dining room. Beautiful resort-like pool and landscaping at Avalon Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1857/Nt
4 4
Details
Seclusion and sun await just off Friar's Bay at the Happy Bay Villa 2 & 3 BR rates available.
Has specials. Happy Bay Villa photo

Happy Bay (French Side), St. Martin

Near Beach | Pool

from $700/Nt
4 4+
Details
A formal, modern villa located in the privacy of Estate Shoys with all the amenities a gated community offers Mango Hill is located on the eastern end of St. Croix

St. Croix, USVI

Pool

from $843/Nt
4 4+
Details
Great for a family with older children or a group, Angelina Villa is conveniently located close to Shell Beach with views over Gustavia harbor 1 & 3 BR rates available. Angelina villa has great views of the harbor

Gustavia, St. Barts

Near Beach | Pool

from $1357/Nt
4 4
Details
Panoramic views are something to write home about! 2 & 3 BR rates available. From the pool deck at Globe Trotter Villa you will enjoy beautiful views of the Caribbean

Lurin, St. Barts

Pool

from $1414/Nt
4 4
Details
Classically comfortable island home with endless views of Sapodilla Bay! Has specials. Enjoy amazing views of the Caribbean from the pool at Turquesa Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1350/Nt
4 4+
Details
Beautiful Greco-Roman style villa is very private with a rooftop terrace and great views 2 & 3 BR rates available. Amazing infinity edge pool at Agora Villa

Terres Basses (French side), St. Martin

Pool

from $843/Nt
4 4+
Details
Enjoy contemporary luxury, great ocean views, and a refreshing pool with this spacious four-bedroom villa 1 & 3 BR rates available. Casa Tigre Villa has beautiful Caribbean views

Vitet, St. Barts

from $1714/Nt
4 4
Details
Set above a private beach, this villa is tucked away yet close to everything. Amazing Caribbean views at Roi Soleil

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $1564/Nt
4 4
Details
Expansive space and great ocean views spell simple relaxation at Anna Villa Good News photo

Petit Cul de Sac, St. Barts

Pool

from $4143/Nt
4 4
Details
Grab your camera for a trip to Villa Jasmine and a hilltop view you won't forget 1, 2 & 3 BR rates available. Luxurious tiled pool and sun deck at Jasmine Villa

Gouverneur, St. Barts

Pool

from $2000/Nt
4 5+
Details
Peaceful tranquility combines with beachfront luxury at this Leeward villa. Beachfront Villa Aquazure has amazing beachfront views

Leeward, Turks and Caicos

Beachfront | Pool | AC

from $1271/Nt
4 4
Details
Enjoy the Gourmet Life When You Stay At Ariana Villa 2 & 3 BR rates available. Ariana Villa photo

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from $550/Nt
4 3+
Details
Architecturally striking villa with unique design and proximity to St Jean Bay. 2 & 3 BR rates available. Enjoy your private pool perched hillside in St. Jean with views of St. Jean Bay

Saint Jean, St. Barts

Pool

from $2286/Nt
4 4
Details
This private resort offers full service and off the grid luxury. Amanyara Beach Villa photo

Providenciales, Turks and Caicos

Beachfront | Pool | AC

from Call for rates
4 4
Details
Amanyara Resort satisfies every want and need, surrounded by an unbelievable setting. Amanyara Oceanfront Villa photo

Providenciales, Turks and Caicos

Pool

from Call for rates
4 4
Details
Observe the majesty of the sun setting over the ocean right from your balcony lounge chair. 1 & 3 BR rates available. Sunset Beach House is tucked away in the rather remote in Black Garden Bay area

Anguilla

Near Beach | Pool

from $700/Nt
4 4
Details
Versatile villa with cozy interiors and great views. 1, 2 & 3 BR rates available. View from pool (no longer a hot tub)

Klein Bay, St. John

from $564/Nt
4 4
Details
Contemporary villa with stunning sunsets and views. 2 BR rate available. What Else Villa photo

Pointe Milou, St. Barts

Pool

from $1171/Nt
4 4
Details
Abundance of space and light in this multi-building villa on St Jean. 2 & 3 BR rates available. W View Villa photo

Saint Jean, St. Barts

Pool

from $1786/Nt
4 4
Details
Family-friendly villa with a bunk room for kids, a kayak, and a great location between Rum Point and Seven Mile Beach. 3 BR rate available. An aerial view of Present Moment Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $650/Nt
4 4
Details
Beachfront villa with its own strip of sand, an oceanfront pool, and lots of windows. Has specials. An aerial view of in Harmony Villa located directly on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $850/Nt
4 4
Details
Oceanfront villa near snorkeling reefs, Seven Mile Beach, and marine life. Has specials. Deck and patio area

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1215/Nt
4 3
Details
Madras Villa is an wonderful retreat for couples, with 4 king bedrooms and spacious terrace. 2 & 3 BR rates available.
Has specials. Madras Villa photo

Terres Basses (French side), St. Martin

Near Beach | Pool

from $500/Nt
4 4+
Details
Three bungalows make up this villa, which is within walking distance of the beach. 2 & 3 BR rates available. Xanadu Villa photo

Saint Jean, St. Barts

Near Beach

from $1357/Nt
4 4
Details
Spacious, chic villa with beautiful suites and easy access to activities. Pool

Punta Cana, Dominican Republic

Near Beach | Pool

from $1290/Nt
4 4
Details
Chic villa with panoramic, tropical views. 1, 2 & 3 BR rates available.
Has specials. View of Coral Bay from the villa pool area

Coral Bay, St. John

Pool

from $714/Nt
4 4
Details
Villa Arrecife 24 at Tortuga Bay photo

Punta Cana, Dominican Republic

Pool

from $1080/Nt
4 4
Details
Warm, family-sized villa a short walk from Sandy Hill Bay. 1 & 2 BR rates available. Villa Kai photo

Anguilla

Pool

from $500/Nt
3 3
Details
Private villa within a resort neighborhood with a private beach and walking distance to yacht clubs. Has specials. The private pool at Kai Zen is tucked away to the side of the villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $750/Nt
3 3+
Details
Sunny villa with lush vegetation and floor to ceiling windows in luxurious COMO Parrot Cay resort. Has specials. Point House at COMO Parrot Cay photo

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $9500/Nt
3 3
Details
Totally private, beachfront villa with all the amenities of a luxury resort. Has specials. The three bedroom Beachfront Villas at Sailrock Resort

South Caicos, Turks and Caicos

Beachfront | Pool | AC

from $3375/Nt
3 3
Details
Relaxing, open-concept villa on the Columbier hillside. 2 BR rate available. D\'Zir Villa offers amazing views over Gustavia Harbor

Colombier, St. Barts

Pool

from $1714/Nt
3 3
Details
Enjoy easy access to Grace Bay and luxurious service from the resort. Has specials. The Estate at Grace Bay Club

Grace Bay, Turks and Caicos

Beachfront | AC

from $3700/Nt
3 3+
Details
Private villa located right on Baie Longue Beach is the ideal getaway on St. Martin 1 & 2 BR rates available.
Has specials. Baie Longue Beach House photo

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $771/Nt
3 3
Details
Gorgeous Dawn Beach villa has direct beach access and tons of perks 2 BR rate available.
Has specials. Bell\'mare photo

Dawn Beach (Dutch side), St. Martin

Near Beach | Pool

from $412/Nt
3 3
Details
Let reflection be your goal in the Asian-inspired surroundings of Serenity Villa 1 & 2 BR rates available. Villa Serenity has a beautiful deck and unparalleled views of Gustavia Harbour

Gustavia, St. Barts

Near Beach | Pool

from $1071/Nt
3 3
Details
Spend time with family or friends at Armor Villa overlooking Grand Cul de Sac and Pointe Milou. 1 & 2 BR rates available. Lounge poolside with the ocean just beyond at Armor Villa

Mont Jean, St. Barts

Pool

from $714/Nt
3 3+
Details
Fitness enthusiasts will enjoy Maracuja Villa and its workout gym and infinity pool 2 BR rate available. Maracuja Villa photo

Vitet, St. Barts

Pool

from $679/Nt
3 3
Details
Tropical, expansive villa with three independent bedrooms and beautiful sea views. 1 & 2 BR rates available. Perched above Klein Bay Carnival Beach House has amazing ocen views

Klein Bay, St. John

Beachfront | Pool | AC

from $405/Nt
3 3
Details
Enjoy sea views and luxurious accommodations amidst a five-star private island resort. Has specials. Private pool at Lucky House

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $6000/Nt
3 3
Details
Light and airy villa has a huge pool and tons of space for families or larger groups and is just minutes from two great beaches. 1 & 2 BR rates available.
Has specials. Lounge by the pool at La Favorita

Terres Basses (French side), St. Martin

Pool

from $614/Nt
3 3+
Details
Le Moulin's signature windmill beckons you to relax in paradise. 1 & 2 BR rates available. The landmark -Windmill- at Le Moulin Villa

Saint Jean, St. Barts

Beachfront | Pool | AC

from $1429/Nt
3 3
Details
Bright and open, La Magnolia is a splendid getaway for all types of travelers seeking peace, privacy, and relaxation. 1 & 2 BR rates available. View out to the ocean beyond at La Magnolia Villa

Terres Basses (French side), St. Martin

Pool

from $457/Nt
3 3
Details
A St. Bart's villa with stunning water and island views 1 & 2 BR rates available. Au Coeur du Rocher is a great tropical getaway

Marigot, St. Barts

Pool

from $543/Nt
3 3
Details
Great for families and children, Cactus Villa on the northwest side of St. Barts will keep you entertained 2 BR rate available. Cactus Villa has amazing views of Gustavia Harbor wether it be by day or by night

Colombier, St. Barts

Pool

from $714/Nt
3 3
Details
Warm and inviting, Ker Anna Villa has great ocean views and plenty of space for your small group. 2 BR rate available. Ker Anna Villa enjoys unique views of St. Jean Bay and across to the Gustaf III runway

Saint Jean, St. Barts

Pool

from $600/Nt
3 3
Details
Mer Soleil: A True Tropical Paradise on the Hillside of Long Bay Beach 2 BR rate available. Beautiful outdoor space at Mer Soleil

Gouverneur, St. Barts

Pool

from $1857/Nt
3 3
Details
Privacy and fantastic views, with Taylor Bay Beach just 50 paces from your front door. 1 & 2 BR rates available. Mariposa Villa is located at the very end of Sapodilla Bay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $614/Nt
3 3
Details
With a 2,500 ft. deck and 1350 sq. ft. infinity pool, you'll have all the space you need to unwind. Has specials. Island Beach Villas at COMO Parrot Cay photo

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $6000/Nt
3 3
Details
Three-bedroom beachfront villa on Turks and Caicos, with beachside luxury and relaxation. Has specials. COMO Villa at COMO Parrot Cay photo

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $4500/Nt
3 3
Details
Spacious villa with views galore and a private infinity pool 1 & 2 BR rates available. Carolina Villa photo

Coral Bay, St. John

from $514/Nt
3 3
Details
Cozy and affordable Beacon Hill villa has 3 bedrooms, great views, and easy walking access to town. 1 & 2 BR rates available. La Casita Villa photo

Beacon Hill (Dutch side), St. Martin

Near Beach | Pool

from $343/Nt
3 6
Details
Get in touch with nature by taking advantage of the outdoor shower and private, au natural swimming pool. 1 & 2 BR rates available.
Has specials. Resort style pool and surroundings at Sol e Luna Villa

Terres Basses (French side), St. Martin

Pool

from $521/Nt
3 3
Details
This brand new villa offers an inviting retreat after a long day of water sports and sightseeing. 1 & 2 BR rates available. Villa and pool view

Terres Basses (French side), St. Martin

Pool

from $557/Nt
3 3
Details
Modern villa boasts great views from the large private pool and living spaces. 2 BR rate available. Casa Azul overlooks Anse Toiny

Vitet, St. Barts

Pool

from $700/Nt
3 3
Details
Spacious 3-bedroom villa has a unique nautical ambiance and stunning ocean views 1 & 2 BR rates available. Ever Sail Villa photo

Grand Cul de Sac, St. Barts

Pool

from $643/Nt
3 3
Details
Tons of space with great island/water views, Super Sky is ideal for 3 couples 1 & 2 BR rates available. Super Sky Villa photo

Saint Jean, St. Barts

Pool

from $714/Nt
3 3
Details
Beautiful three-bedroom mutli-level villa offers incredible Lorient Bay views, a pool, and luxurious outdoor living space 1 & 2 BR rates available. LUZ Villa enjoys amazing views of Lorient Bay

Camaruche, St. Barts

Pool

from $629/Nt
3 3
Details
A great location and unbeatable views make this a perfect choice for couples, friends, and families. 1 & 2 BR rates available. Nikki Villa has great views right into St. Jean Bay

Saint Jean, St. Barts

Near Beach | Pool

from $1143/Nt
3 3
Details
Stunning beachfront resort villa has spectacular views, access to Grace Bay Beach, and includes resort amenities of the West Bay Club. Has specials. The West Bay Club from Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1680/Nt
3 3
Details
Spacious villa has incredible ocean views and tons of ambiance in its 2 levels, and tons of extras to boot 1 & 2 BR rates available. Entrance to Almost Heaven Villa

Coral Bay, St. John

Pool

from $375/Nt
3 3
Details
Paradise and contemporary amenities combine at the Just in Paradise Villa. 1 & 2 BR rates available.
Has specials. Beautiful pool and outdoor area at Just in Paradise

Terres Basses (French side), St. Martin

Pool

from $743/Nt
3 3+
Details
Acamar Villa offers gorgeous ocean views with unique, modern living spaces 2 BR rate available.
Has specials. Enjoy endless ocean views from the patio and pol at Acamar Villa

Toiny, St. Barts

Pool

from $1357/Nt
3 3
Details
Invite relaxation into your life when you stay at Les Amis du Vent Villa 1 & 2 BR rates available. Stunning outdoor areas with views to the caribbean at Les Amis Du Vent

Mont Jean, St. Barts

Pool

from $1429/Nt
3 6
Details
Relaxation awaits you at this beautiful island retreat 1 & 2 BR rates available.
Has specials. Pool surrounded by tropical foliage at Greystone Villa

Terres Basses (French side), St. Martin

Pool

from $286/Nt
3 3
Details
Spanish for “window,” Ventana Villa is the place for outstanding views from anywhere in the house! 1 & 2 BR rates available. Ventana Villa photo

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from $550/Nt
3 3
Details
Airy architecture with beautiful decor makes this hilltop villa truly beautiful. MOH Villa photo

Lurin, St. Barts

Pool

from $1286/Nt
3 3
Details
Exquisitely posh 3 bedroom villa close to Orient Bay and Grand Case 1 BR rate available.
Has specials. Emvie Villa photo

Orient Bay (French side), St. Martin

Pool

from $557/Nt
3 3
Details
Traditional Caribbean villa with full air-conditioning and a home theater. Has specials. A aerial view of Casuarina Cove shows the dock into the water

Grand Cayman, Cayman

Beachfront | AC

from $550/Nt
3 3+
Details
Personalized amenities in a clean-lined, simply luxurious retreat. Has specials. Como Parrot Cay Two Bedroom Beach Villa has a great beach front swimming pool

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $3550/Nt
2 3
Details
The Captain’s House provides peace and privacy within the villa while reveling in the beauty of Long Bay right from your balcony! 1 BR rate available. Captain\'s House villa commands a breathtaking view of the ocan

Tortola, BVI, British Virgin Islands

Pool

from $310/Nt
2 2
Details
Terrahawk: A two-bedroom hillside retreat inside VI National park that's still convenient to the beach Has specials. Views of Hawksnest Bay from the deck at Terrahawk

North Shore, St. John

Near Beach

from $400/Nt
2 2
Details
Expansive and private villa in Colombier is a remote island hideaway for adults only 1 BR rate available.
Has specials. Byzance Villa photo

Colombier, St. Barts

Pool

from $857/Nt
2 2
Details
Near Gustavia and Shell Beach, Sky Vista is an ideal accommodation for island romance A beautiful view from the pool and deck at Sky Vista Villa

Gustavia, St. Barts

Near Beach | Pool

from $857/Nt
2 2
Details
Adorable Petit Lagon is within easy walking distance of the beach and great for honeymooners 1 BR rate available. Petit Lagon photo

Petit Cul de Sac, St. Barts

Near Beach | Pool

from $571/Nt
2 2
Details
Within exclusive Estate Shoys, Royal Palms Villa is close to golf and tennis activities, as well as the beach 1 BR rate available. Royal Palms Villa photo

St. Croix, USVI

Pool

from $525/Nt
2 2+
Details
Newly refurbished two-bedroom villa in Pointe Milou is great for couples traveling together 1 BR rate available. Alizee d\'Eden Villa photo

Pointe Milou, St. Barts

Pool

from $371/Nt
2 2
Details
Great views and a bright, roomy space make Bonjour Villa a great choice in St. Bart's 1 BR rate available. Bonjour Villa photo

Saint Jean, St. Barts

Near Beach | Pool

from $410/Nt
2 2+
Details
Contemporary amenities with a breathtaking view defines Diamond Villa 1 BR rate available. Diamond Villa offers great views over Gustavia

Saint Jean, St. Barts

Pool

from $929/Nt
2 2
Details