Caribbean Family Villas

Caribbean Family Villas

The Caribbean is a great destination choice for families or multiple families traveling together. With a private kitchen and enough space for everyone, a Caribbean villa rental can be the most economical accommodation choice. Whether you are seeking a beachfront villa, a private island or a hillside villa with an amazing view, our favorite family villas section provides some of the best villas in the Caribbean for your family vacation.

Luxurious, private island with a full staff, six beaches, and every activity you could ask for. 20 BR rate available. Calivigny Island - Just South of Woburn Bay, Greneda

Grenada

Beachfront | Pool | AC

from $132000/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
This totally private island will make you feel like royalty. 15 BR rate available.
Has specials. Necker Island, BVI 2018 Aerial view

Necker Island, BVI, British Virgin Islands

Beachfront | Pool | AC

from $77500/Nt
17 11
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 $49000/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. The stunning infinity pool at Mes Amis Villa overlooks the beauty of Baie Rouge

Terres Basses (French side), St. Martin

Pool

from $1357/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 Call for rates
13 13
Details
Three luxurious villas make up this super-sized estate. Arrecife 23/24/25 Estate at Punta Cana Resort photo

Punta Cana, Dominican Republic

Pool

from $4390/Nt
13 13+
Details
Six acre estate with beachfront access to coral reefs, on-site sports courts, and two freshwater pools. 7, 8, 9, 10 & 11 BR rates available.
Has specials. Lounge by the pool at Golden Clouds

Ocho Rios, Jamaica

Pool

from $1571/Nt
12 12
Details
Expansive oceanfront villa with three pools and eleven bedrooms. Punta Aguila 11 is located in Casa de Campo right on the ocean

Casa de Campo, Dominican Republic

Pool

from $3750/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. The beautiful Cerulean Villa on Barnes Bay in Anguilla

Anguilla

Beachfront | Pool | AC

from $14286/Nt
11 9+
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
2, 3, 4, 5, 6, 7 & 8 BR rates available. 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 $6000/Nt
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 $57200/Nt
10 10
Details
Luxurious, expansive mansion in a tropical oasis. The amazing infinity edge pool at Vista Chavon 7 overlooks the Chavon River and the ocean beyond

Casa de Campo, Dominican Republic

Pool

from $6500/Nt
10 10+
Details
Park yourself right on the beach in Jamaica's 10 bedroom jewel, Flor de Cabrera Villa Has specials. The luxurious resort like pool is just steps away from the ocean at Flor de Cabrera

Cabrera, Dominican Republic

Beachfront | Pool | AC

from $2900/Nt
10 9+
Details
High-end, modern elegance with two pools, two beaches, and two and a half acres. Has specials. 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. Aerial View of Silent Waters

Montego Bay, Jamaica

Pool

from $2482/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. Crystal Springs is a beautiful Estate located right on the beach

Barbados

Beachfront | Pool | AC

from $7245/Nt
10 11
Details
Super spacious luxury villa with next-level outdoor amenities. 5, 6, 7 & 8 BR rates available. Haystack Villa is located in the prestigious Tryall Club

Montego Bay, Jamaica

Pool

from $2000/Nt
10 10
Details
Huge luxury estate features two separate villas, a full staff, and incredible ocean views. 8 BR rate available.
Has specials. Ani Estate Anguilla - North and South

Anguilla

Pool

from $7500/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 $7100/Nt
10 10
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. Yarari Royale is a beautiful home located in Cap Cana

Cap Cana, Dominican Republic

Pool

from $2430/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
Grace Bay beachfront villa equipped with Apple TVs, a Jeep Wrangler, a gym, and open design. 7 BR rate available. Bella Vita is a contemporary villa located on the shores of Grace Bay

Providenciales, Turks and Caicos

Beachfront | Pool | AC

from $5800/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
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 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
Ultra private, beachfront estate! Has specials. Santosh a is located along a beautiful stretch of Long Bay Beach

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 $4000/Nt
8 6+
Details
6 BR rate available. The luxurious patio and and infinity edge pool at Vista Chavon 13

Casa de Campo, Dominican Republic

Pool

from $3500/Nt
8 8
Details
6 BR rate available. Las Palmas 22 is located in Casa de Campo and has a great pool

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
Cacique 2 is located in Casa De Campo with ocean views just over the golf course

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 Sunsara 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
Great service at the Sheriva Boutique Villa Hotel will put you in a Caribbean state of mind. 4, 5, 6 & 7 BR rates available.
Has specials. Harmony Villa is located above Cove Pond in the Sheriva Complex

Anguilla

Near Beach | Pool

from $3000/Nt
8 8+
Details
This secluded villa has access to Sandy Lane Beach, a large pool, and a staff. 2 & 6 BR rates available. Bluff House and Cottage are located very near by Sandy Lane Bay

Barbados

Beachfront | Pool | AC

from $500/Nt
8 8
Details
Stunning oceanfront estate offers the most in luxury and privacy, as well as a full staff to accommodate every need. 6 & 7 BR rates available.
Has specials. Mango Bay\'s patio sits right on the beach

Barbados

Beachfront | Pool | AC

from $4950/Nt
8 7+
Details
This massive beachfront villa sits on a hill overlooking Shoal Bay. 2, 4, 6 & 7 BR rates available. Beach Court Villa is settled at the western end of Shoal Bay Beach

Anguilla

Beachfront | Pool | AC

from $1100/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
Deluxe villa with a secluded beach on one side and restaurants and activities on the other. 4 & 7 BR rates available. Kaiku Villa beach front

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1660/Nt
8 6+
Details
Large oceanfront villa is Ideal for families with children and within walking distance of Shell Beach 2, 3, 4, 5 & 6 BR rates available. The enticing lap pool at La Pointe will provide just the right escape for your holiday

Gustavia, St. Barts

Near Beach | Pool

from $857/Nt
8 9
Details
Beachfront architectural masterpiece with butler, sports courts, and full entertainment system. Has specials. 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 $3250/Nt
8 8
Details
Exciting extras like a private cabana and a Mastercraft make this converted sugar mill a real treasure for discerning guests 4 & 6 BR rates available. There is a beautiful ridge side pool at Mullins Mill

Barbados

Pool

from $1825/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 $1600/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. 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.
Has specials. 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. Has specials. 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
Live like kings and queens for the duration of your vacation at Tryall Club's Round House Villa Roundhouse Villa has beautiful outdoor spaces

Montego Bay, Jamaica

Pool

from $2143/Nt
8 7
Details
Family vacation villa with a guest cottage, beach access, and huge outdoor area. 5, 6 & 7 BR rates available. Prudence Villa photo

Barbados

Near Beach | Pool

from $1435/Nt
8 6
Details
Tropical Dream Villa photo

Cap Cana, Dominican Republic

Pool

from $4060/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. 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 luxury villa offers a multilevel pool, 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 $6800/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
Fully equipped villa within a few miles of Royal Westmoreland Golf Course, Holetown, and Speightstown. 6 BR rate available. Stunning views from the infinity edged swimming pool

Barbados

Pool

from $1750/Nt
8 8+
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
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
Two-story beachfront resort villa with a guest cottage and water sports. 6 BR rate available.
Has specials. A boardwalk to the beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $2940/Nt
7 6+
Details
Family-friendly resort villa with two family suites and a guest house. 5 & 6 BR rates available. Villa Londali is located in the Punta Cana Resort and has amazing lake and golf course views

Punta Cana, Dominican Republic

Pool

from $1650/Nt
7 7
Details
Wedding-friendly resort villa with a swim-up bar and a bunk room. Casa de Suenos is located within the gated Los Suenos Resort community

Costa Rica

Pool

from $1800/Nt
7 7
Details
A three-leveled pool, three hot tubs, and the ocean are all in the backyard at this five-star villa. Blue Oasis Villa is located in a secluded area of Cap Cana

Punta Cana, Dominican Republic

Beachfront | Pool | AC

from $6940/Nt
7 7+
Details
Bring your laptop if you must; Sea Star has a wireless connection that will allow you to hop online from any place on the property 5 & 6 BR rates available. Sea Star Villa is located on Cabrita Point

St. Thomas, USVI

Beachfront | Pool | AC

from $1399/Nt
7 5+
Details
This family-friendly villa has connecting bedrooms, kids' amenities, and a convenient location. 1, 2, 3, 4, 5 & 6 BR rates available. Great Expectations overlooks Hart Bay and Chocolate Hole

Hart Bay, St. John

Near Beach | Pool

from $700/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
The private tennis court is just the beginning of this stunning estate perched right above the beach. 3, 4, 5 & 6 BR rates available. Zenaida Beach & Tennis Estate is located just above Sandy Hill Beach

Anguilla

Beachfront | Pool | AC

from $950/Nt
7 7
Details
Warm, open interiors and stunning views combine in this oceanfront villa. 3, 4 & 5 BR rates available. Paradise Villa is located near Blowing Point

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 sits on the white sands of Sapodilla Bay

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 $1225/Nt
7 7+
Details
Take full advantage of the large pool overlooking the blue ocean waters at the beautiful Alizee Villa. 3, 4, 5 & 6 BR rates available.
Has specials. Alizee Villa photo

Guana Bay (Dutch Side), St. Martin

Near Beach | Pool

from $930/Nt
7 7
Details
St. Lucia's Tamarind Villa is made for guests who don't want to wait until the kids leave the nest to start seeing the world 3 & 4 BR rates available.
Has specials. Tamarind Villa photo

Cap Estate, St. Lucia

Pool

from $575/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
Sitting poolside takes on a whole new meaning at Sandyline Villa-the ultimate vacation getaway! 3, 4 & 5 BR rates available. Resort like pool at Sandyline Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

from $4214/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 BR rate 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. Spectacular views, infinity edge pool and oceanfront lounging await at Cayman Castle

Grand Cayman, Cayman

Near Beach | Pool

from $1275/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. The entertainment patio and pool area at Conched Out Villa

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1557/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. 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
1.25 acres of pure Antiguan beachfront bliss and panoramic views to die for. 1, 2, 3, 4, 5 & 6 BR rates available.
Has specials. Palm Point Villa is located right on Jolly Harbour

Jolly Harbour, Antigua

Beachfront | Pool | AC

from $1800/Nt
7 7+
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
Family-friendly villa with a semi-private beach nearby. 6 BR rate available. On the Rocks has a beautiful pool and tropical surroundings

Grand Cayman, Cayman

Near Beach | Pool

from $935/Nt
7 4
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
Luxury blends with nature at this villa with Piton views. 4, 5 & 6 BR rates available. Cosmos photo

Soufriere, St. Lucia

Pool

from $950/Nt
7 7
Details
Ocean and pool view from back patio

Montego Bay, Jamaica

Pool

from $3143/Nt
7 7
Details
Spacious outdoor living and dining areas with a great view. 4 & 5 BR rates available. Joy photo

Joy

Marigot, St. Barts

Pool

from $4857/Nt
6 6
Details
Punta Minitas is located on the peninsula just south of Minitas Beach

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 $2821/Nt
6 5+
Details
Five-star, modern villa with all the amenities you need for a luxury vacation. Has specials. Wake Up Villa is located on the beautiful Flamands Beach

Flamands, St. Barts

Beachfront | Pool | AC

from $12143/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
Tuscan-style villa in a gated community a short walk from the beach. Casa Barana has amazing views of the Caribbean

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $1350/Nt
6 5+
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. 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
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
Stunning, all-inclusive 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 $2857/Nt
6 6
Details
Big family-style villa with modern decor and five-star amenities. 4 BR rate available. Big Chill Villa has a canal front pool with great areas to relax and entertain

Leeward, Turks and Caicos

Pool

from $1200/Nt
6 6+
Details
A two-story beachfront villa fit for a king or queen. Seaclusion is located just steps away from an amazing white sand beach

Barbados

Beachfront | Pool | AC

from $6500/Nt
6 5
Details
Waterfront villa with a game room, guest house, and outdoor space. Salacia Villa in Grace Bay offers amazing amenities

Grace Bay, Turks and Caicos

Near Beach | Pool

from $6000/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 $1430/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
Five-star amenities and arrangements for any group of travelers. 4 & 5 BR rates available.
Has specials. The elegant Shore Club Villas feature private swimming pools

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $6000/Nt
6 8
Details
Old World charm and modern appliances outfit this canalfront home. Emerald Villa is located on the Leeward Canal

Leeward, Turks and Caicos

Pool

from $1275/Nt
6 5+
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
Full-service beachfront resort villa perfect for families seeking peace and beauty. Has specials. Beach Enclave Beach Front Villa Plus 1 Bedroom Cottage at Long Bay photo

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $2880/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 $2296/Nt
6 3
Details
Has specials. Kempa Kai Villa is just steps away from Starfish Point

Grand Cayman, Cayman

Beachfront | AC

from $3069/Nt
6 7
Details
Beachfront villa in the Tango Mar Resort with wildlife and activities at your fingertips. 2 BR rate available.
Has specials. The Beach at Tango Mar and Casa Oceano

Costa Rica

Beachfront | Pool | AC

from $1600/Nt
6 4
Details
Two-story villa with a game room, pool, and six suites. Casa Patron Villa is located just above Colina

Costa Rica

Pool

from $1400/Nt
6 5+
Details
Multiple couples and families can enjoy paradise at this gated community villa. The Harmon Estate Villa is located in the Eco Golf Community

Costa Rica

Pool

from $1500/Nt
6 6
Details
All-white decor and marbled accents make this six-bedroom waterfront villa a great choice for couples. Has specials. White Coral Villa is located right on the Leeward Canal

Leeward, Turks and Caicos

Pool

from $1700/Nt
6 6
Details
Unique property with Old World architecture and New World amenities, from a boat dock to a media room. Azzurra Castle sits on the southwest shore of Greneda\'s L\'Anse aux Epines

Grenada

Pool

from $1500/Nt
6 6+
Details
An ideal getaway for couples traveling together. 3, 4 & 5 BR rates available. Summer Heights is located on a hillside above Nanny Cay

Tortola, BVI, British Virgin Islands

Pool

from $550/Nt
6 5+
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
Tropical gardens and al fresco showers enhance the natural luxury of this beachfront beauty. 2, 4 & 5 BR rates available. From the balcony at Caribbean Wind Villa you have beautiful views of the pool and the ocean

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

from $929/Nt
6 6
Details
Choose between two beaches and a large private pool for your stay in paradise, or, have them all. 4 & 5 BR rates available. La Salamandre has a stunning pool with ocean views

Terres Basses (French side), St. Martin

Near Beach | Pool

from $1414/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.
Has specials. Encore Villa photo

Terres Basses (French side), St. Martin

Pool

from $979/Nt
6 6
Details
Luxury abounds at this sprawling, private retreat on the island of Providenciales. Lounge on the deck and enjoy endless Caribbean views from Bajacu Villa

Turtle Tail, Turks and Caicos

Pool

from $6000/Nt
6 7+
Details
Beachfront villa with private pool that our readers rave about 4 BR rate available. Enjoy endless views of the ocean from Calypso Blue Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $825/Nt
6 4
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
Just a couple of minutes walk down a quiet lane takes you to the best part of Grace Bay Beach. 4 & 5 BR rates available. The pool and palapa at Pelican Vista Villa

Grace Bay, Turks and Caicos

Near Beach | Pool

from $1485/Nt
6 5
Details
Two-building home near St. Lucia's Petit Piton, rainforest, botanical gardens, and dive sites. 2 & 4 BR rates available.
Has specials. Colibri Cottage sits on a hill above Soufriere Bay

Soufriere, St. Lucia

Near Beach | Pool

from $415/Nt
6 6
Details
A glamorous Antebellum villa nestled in Sandy Lane's tropical foliage. 4 BR rate available. Luxurious pool and backyard at Moon Dance Villa

Barbados

Pool

from $1300/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
Secluded cove beach villa on Anguilla's famous south shore. 3, 4 & 5 BR rates available. Triton Villa is located on LockRum Bay

Anguilla

Near Beach | Pool

from $1980/Nt
6 6+
Details
Families or active couples will find every need met at Mare Blu Villa on Rendezvous Bay 3, 4 & 5 BR rates available. Mare Blu Villa photo

Rendezvous Bay, St. John

Pool

from $1571/Nt
6 8
Details
Bright, modern and private villa situated on Providenciales' coveted Long Bay Beach. 3 & 5 BR rates available.
Has specials. Long Bay Beach House Villa is located directly on the beach with amazing Caribbean views

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1200/Nt
6 6+
Details
Gorgeous Dunes Villa on 2.5 acres accommodates four couples and offers use of three vehicles Amazing pool at Dunes Villa

Saline, St. Barts

Near Beach | Pool

from $7143/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. From Nelson Gay House the view of the ocean within its tropical garden for privacy

Barbados

Beachfront | Pool | AC

from $2000/Nt
6 6+
Details
Spacious villa with fully equipped exercise gym, close to Lorient Beach. 3, 4 & 5 BR rates available. Cumulus Villa photo

Lorient, St. Barts

Near Beach | Pool

from $1707/Nt
6 6
Details
Anticipation Villa on Montego Bay: views of the Caribbean Sea and the Tryall Golf Course will vy for your attention Anticipation Villa at Tryall Club photo

Montego Bay, Jamaica

Pool

from $2241/Nt
6 6
Details
Your group will love the views - and - the attention to the details The Luxurious pool and back yard area at Rose Cottage

Montego Bay, Jamaica

Pool

from $2338/Nt
6 7
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. 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. 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
Costa Norte Villa: Bring your big family to this hilltop spot (or bring your friends and leave the kids with Grandma) 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
Elegance is just an adjective until you stay at Paradiso Villa 3, 4 & 5 BR rates available. Amazing views of the harbor from Paradiso Villa

Oyster Pond (Dutch side), St. Martin

Pool

from $929/Nt
6 6+
Details
Amazing outdoor space with a dining area by the pool, a full service staff, and access to Sandy Lane beach. 3 & 4 BR rates available. Twilight on the patio at Sandalwood Cottage

Barbados

Near Beach | Pool

from $925/Nt
6 7
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
Large and grand luxury villa on the western end of Grace Bay. 3 & 4 BR rates available. Tamarind Villa with Grace Bay in the background

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1350/Nt
6 6+
Details
Great family house on a less developed part of Grace Bay. Serenity House Villa is located directly on Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1857/Nt
6 6+
Details
Great location and excellent water views makes Monkey's Run the best choice for your large group in Barbados 5 BR rate available. Monkey\'s Run has a great pool and outdoor space

Barbados

Pool

from $1800/Nt
6 5+
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
Luxury accommodations and a magnificent outdoor area make this large, ocean-facing property perfect for big families or groups 1, 2, 3, 4 & 5 BR rates available. Le Manoir de Lurin Villa photo

Lurin, St. Barts

Pool

from $2143/Nt
6 7
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
Spectacular views and great access to all of the sights await at Dawn Beach Villa 2, 3, 4 & 5 BR rates available. Beautiful views of the Caribbean form the pool at Dawn Beach Villa

Dawn Beach (Dutch side), St. Martin

Near Beach

from $372/Nt
6 6
Details
Modern decor and spacious amenities combine for a roomy vacation. Poolside view of Amberley House

Barbados

Near Beach | Pool

from $1400/Nt
6 5
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
Let everyone enjoy an oceanfront experience at this bright and cheery villa. 4 & 5 BR rates available.
Has specials. Coconut Beach villa is right on the Beach near Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $675/Nt
6 4
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. 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
Expansive, spacious villa with ocean views and several common areas. 2, 3, 4 & 5 BR rates available. You\'ll find contemporary class at Colibri Villa.

Anguilla

Pool

from $945/Nt
6 6
Details
Sprawling six-bedroom home with an infinity pool and wide open spaces. 2 & 4 BR rates available. Comfort and style greet guests of Villa Atlantis.

Cap Estate, St. Lucia

Pool

from $800/Nt
6 5+
Details
Luxurious and spacious villa on the Royal Westmoreland Golf Course with an impressive game room and full staff. 4 & 5 BR rates available. Beautiful pool and outdoor area at Westerings

Barbados

Pool

from $1800/Nt
6 6
Details
Tons of room, seating, entertainment, and nothing can beat this hilltop scenery! 1, 2, 3, 4 & 5 BR rates available. Clairmont Overlook photo

St. Croix, USVI

Pool

from $629/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 $1736/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. 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
Villa Oceania has a beautiful pool and shaded back patio

Cap Cana, Dominican Republic

Pool

from $4070/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. Amarone Villa is a luxurious home on the South Coast

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1550/Nt
6 7
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
Modern luxury with expansive views overlooking Chalk Sound from every room. Alta Bella Villa sits on a inlet just on chalk Sound

Chalk Sound, Turks and Caicos

Near Beach | Pool

from $1138/Nt
6 6
Details
Spectacular beachfront private island estate offers Balinese luxury. 3 BR rate available.
Has specials. A private cabana sits beachfront at Love Pumpkin

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $11000/Nt
5 5
Details
Ultra private, ultra modern villa with extensive outdoor amenities. 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
Three villas in one complex at this spacious hillside property. Bougainvillea photo

Cruz Bay, St. John

Pool

from $1093/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
Beach lovers and adventurers will love this villa's private beach access and nearness to Kaibo Yacht Club and Rum Point Club. Crystal Waters Villa sits beach front near the popular Water Cay and Kaibo Yacht Club

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1135/Nt
5 4
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 $1081/Nt
5 5+
Details
Magens Hideaway photo

St. Thomas, USVI

Pool

from $1125/Nt
5 4+
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 $1725/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
Chic interiors, a screened porch, and spacious bedrooms make this beachfront home feel like paradise. Has specials. White Cottage is a great beachfront villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1030/Nt
5 3
Details
Gated two-story estate with three levels of outdoor space and chic amenities. Great Bluff Estates sits along the beautiful northern coast of Grand cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1250/Nt
5 7
Details
Beachfront, bohemian villa with a spacious design and top technology. Has specials. Nirvana photo

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1778/Nt
5 4
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 $1250/Nt
5 6+
Details
Private and convenient Grace Bay villa with a children's room and four master suites. Second Chances Villa has plenty of outdoor space for relaxing and entertaining

Leeward, Turks and Caicos

Pool

from $2450/Nt
5 6
Details
Chic, well-decorated villa with a wraparound deck. 2, 3 & 4 BR rates available. The private pool at Dragonkey Villa

St. Thomas, USVI

Pool

from $699/Nt
5 3+
Details
Full-service, luxury villa with beach views and spacious design. Enjoy amazing sunsets at Casa de la Playa Villa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $3286/Nt
5 5
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
Beachfront Sapodilla Bay villa with a guest cottage. Mirabelle sits on a beautiful stretch of Sapodilla Bay Beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1429/Nt
5 5+
Details
Chic and luxurious five-bedroom rental on Paynes Bay. 4 BR rate available. The St. James has a lovely lap pool overlooking the beach

Barbados

Beachfront | Pool | AC

from $1650/Nt
5 5
Details
Well-decorated villa with ocean views and snorkeling access. Three Dolphins sits in a beautiful location with great ocean views

Anguilla

Beachfront | Pool | AC

from $1850/Nt
5 4+
Details
Two stories of sleeping quarters and a guest cottage lends plenty of room to relax. 2 & 4 BR rates available. Water\'s Edge Villa is located on Blowing Point

Anguilla

Near Beach | Pool

from $600/Nt
5 5
Details
Luxurious, fully staffed villa perfect for families of any age. Windfall Villa\'s open-air pool with retractable canopy

Barbados

Pool

from $1650/Nt
5 6
Details
Relaxing, but fun-filled villa for a family with teenagers or older kids. Casa Oasis Villa is located above Los Sueños popular Eco Golf Course

Costa Rica

Pool

from $1500/Nt
5 5
Details
Elegant, comfortable villa with two stories and a family-friendly design. Casa Puestra del Sol Villa is located the neighborhood of Vista Tres Bahias in Los Suenos

Costa Rica

Pool

from $1500/Nt
5 5
Details
Couple-friendly villa with rustic chic design in a gated resort community. Casa Pacifica is located in the hills of the Los Suenos Resort

Costa Rica

Pool

from $1400/Nt
5 5
Details
An expansive sun-drenched deck and beautifully decorated interiors guarantee luxury. 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
The perfect large event villa with two separate cottages and lots of outdoor entertaining space. 4 BR rate available. Luxury resort style pool area at The Carib House

Antigua

Near Beach | Pool

from $1160/Nt
5 4
Details
A separate guest cottage makes this location ideal for several travelers who want to dwell independently. Luxurious resort style pool in a lush tropical setting at Sol y Sombra

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from $2075/Nt
5 5+
Details
This ideal family getaway is close to beaches and tennis courts 1, 2, 3 & 4 BR rates available.
Has specials. Lounge by the pool on the deck at Crystal Seaview and enjoy the views of Chocolate Hole

Chocolate Hole, St. John

Pool

from $571/Nt
5 4+
Details
This villa has five spacious suites with sea view terraces. Has specials. 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. Has specials. Lounge in luxury at Sand Villa on Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $3100/Nt
5 4+
Details
Native stone and breathtaking views make Blue Serenity Villa an ideal spot for relaxation 3 & 4 BR rates available. Blue Serenity is located on Nazereth Bay

St. Thomas, USVI

Near Beach | Pool

from $1395/Nt
5 5
Details
Elegance at Dene Court at Sandy Lane with a prviate beach cabana 3 & 4 BR rates available. Luxurious pool at Dene Court is

Barbados

Pool

from $800/Nt
5 5+
Details
This Maria Bluff villa enjoys 360-degree sunrise and sunset views. A aerial view of the beautiful Villa Kismet property

Chocolate Hole, St. John

Pool

from $2000/Nt
5 6+
Details
These two villas offer privacy, flexibility, and access to Meads Bay Beach. Beach Palm

Anguilla

Near Beach | Pool

from $1050/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 $1143/Nt
5 5
Details
Guests can expect stunning sunset views and a full staff at this oceanfront villa. Melissa Villa photo

Barbados

Near Beach | Pool

from $1095/Nt
5 5
Details
Delightful architecture in an airy villa on the secret south side of Barbados. Luxurious water front pool at Ocean Mist

Barbados

Near Beach | Pool

from $985/Nt
5 2+
Details
A castle filled with gorgeous finishes and modern technology. Carlota Villa photo

Peter Bay, St. John

Pool

from $2230/Nt
5 6+
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
Enjoy views, comfort, and ample entertainment at La Grande Vigie's five-bedroom villa Has specials. La Grande Vigie

Oyster Pond (Dutch side), St. Martin

Pool

from $495/Nt
5 5+
Details
Couples will love this expansive, well-organized villa with gorgeous ocean views. 3 & 4 BR rates available. Tesori Villa has a beautiful pool and entertainment balcony

Rendezvous Bay, St. John

Pool

from $786/Nt
5 5+
Details
Balinese elegance gives this villa a peaceful ambiance ideal for self-reflection and relaxation. 4 BR rate available. Java Bay is located in Calijanda in Westmoreland and is less than two miles from the beach

Barbados

Pool

from $1265/Nt
5 5
Details
The quintessential villa for the active, sports-loving family, the 5 bedroom Decaj Villa is full of wonderful suprises 2, 3 & 4 BR rates available.
Has specials. Decaj Villa photo

Cap Estate, St. Lucia

Pool

from $395/Nt
5 4+
Details
The stunning views reflect off the infinity edge pool at this Asian-Indonesian villa. 4 BR rate available. Golden Pavilion photo

Tortola, BVI, British Virgin Islands

Pool

from $1714/Nt
5 5+
Details
With four twin suites that can convert into kings, this home is perfect for guests of any age. 4 BR rate available. Casuarina Villa has a pool right on the golf course

Barbados

Pool

from $1350/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
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. Has specials. 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
A beautiful home with gorgeous furnishings, ideally suited to a large family. 1, 2, 3 & 4 BR rates available. Solitude House photo

St. Croix, USVI

Near Beach | Pool

from $429/Nt
5 4+
Details
Ultra-modern upscale Anguilla villa with glass walls that face the sea. Champagne Shores villa sits on a secluded beach near Pelican Bay

Anguilla

Near Beach | Pool

from $1700/Nt
5 5+
Details
Designed with island fun in mind, Cinnamon Ridge Villa has 'family vacation' written all over it 1, 2, 3 & 4 BR rates available. Cinnamon Ridge Villa photo

Catherineberg, St. John

Pool

from $593/Nt
5 5
Details
Kalorama villa has a unique Great Room, but with views like these, you're likely to spend most of your time on the spacious deck. 1, 2, 3 & 4 BR rates available. From the upper deck looking down on the pool area at Kalorama Villa

Virgin Grand Estates, St. John

Pool

from $860/Nt
5 4+
Details
Striking four-story villa beachfront villa with ocean views and a private tennis court. Has specials. 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
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
Bali Dreams Villa offers 7200 feet of beauty on Orchid Bay Bali Dreams Villa photo

Cabrera, Dominican Republic

Near Beach | Pool

from $1200/Nt
5 6
Details
Light and airy, and with a delightful name, Monkey Puzzle will bring charm to days spent within prestigious Westmoreland. St. James 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 $1000/Nt
5 5
Details
Chic, plantation-style estate with full staff. 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 1 BR rate available. Villa Arrecife 25 at Tortuga Bay photo

Punta Cana, Dominican Republic

Pool

from $1720/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
Superb luxury villa with a private beachfront location and tons of indoor/outdoor living space. 1, 2, 3 & 4 BR rates available. Arushi Villa is located on the western end of Rendezvous Bay

Anguilla

Beachfront | Pool | AC

from $2800/Nt
5 5+
Details
This warm villa sits near the French/Dutch border and offers the best of both worlds. 4 BR rate available.
Has specials. Stone House Villa photo

Oyster Pond (Dutch side), St. Martin

Near Beach | Pool

from $543/Nt
5 4+
Details
The self-contained, detached guest house offers a wonderful private getaway for newlyweds or couples wanting to spend some time on their own. Has specials. Lush tropical greenery surrounds Sade Villa

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from Call for rates
5 5
Details
Spacious and comfortable 5-bedroom villa has a great location, endless views, and everything your large group needs for a relaxing vacation 3 & 4 BR rates available. Esprit de la Mer Villa photo

Terres Basses (French side), St. Martin

Near Beach | Pool

from $800/Nt
5 5+
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
Affordable Shoal Bay villa with a large pool, open design, and a location five minutes from the beach. 2 & 4 BR rates available. Tamarind Villa photo

Anguilla

Pool

from $500/Nt
5 5
Details
Huge beachfront villa with housekeeping, five bedrooms, and 18 acres of land. The pool area at Amazing Grace Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4950/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
Exclusive private island rental! Peaceful with some of the most amazing views of the Caribbean Sea! Royal Belize Private Island

Belize

Beachfront | AC

from $6200/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 $2557/Nt
5 4
Details
Exclusive beachfront villa boasts amazing views, sumptuous accommodations, and every luxury you'll want Luxurious pool just steps away from the beach at The Dream Villa

Barbados

Beachfront | Pool | AC

from $4000/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
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.
Has specials. Aja Villa photo

Tortola, BVI, British Virgin Islands

Near Beach

from $800/Nt
5 5
Details
Experience a snorkeling fantasy when you book Coral Kai Villa 4 BR rate available.
Has specials. Aerial view of Coral Kai Villa on Rum Point Grand Cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $950/Nt
5 5
Details
Huge outdoor space with a wet bar and pool, just minutes from the beach. 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
Luxury vacationing, Jamaican style There are fabulous ocean views from the porch at Overlook Villa

Montego Bay, Jamaica

Pool

from Call for rates
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
Private beachfront villa great for families, with scuba diving at the Cayman Wall. 4 BR rate available.
Has specials. Literally steps to the beach at Cayman Sands Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $750/Nt
5 5
Details
Large 5 bedroom home offering private white sand beach and turquoise waters right at your door step 4 BR rate available. The pool at Kai Conut is just steps away from the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $750/Nt
5 3
Details
Beachfront island home with plenty of room for family getaways 4 BR rate available. 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. 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. 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. Blue Palm Villa is surrounded by lush tropical greenery

Terres Basses (French side), St. Martin

Near Beach | Pool

from $786/Nt
5 6+
Details
This elevated two-story villa has five Master Suites, ocean views in every room, and direct access to beautiful Long Bay beach. Amazing beachfront infinity edged pool on Long Bay Beach at Villa Isla

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1643/Nt
5 5+
Details
Exquisite luxury estate with saltwater swimming pool and massive wraparound porch. Pure luxury and elegance are found at High Cane Villa

Barbados

Near Beach | Pool

from $2750/Nt
5 6+
Details
Beachfront home with white sands and turquoise waters ready to greet you each morning! Lounge by the beachside pool at Island View Beach House

Jolly Harbour, Antigua

Beachfront | Pool | AC

from $1429/Nt
5 4
Details
Ocean front villa ideal for families with young children Sunset at the Tryall Club has a beautiful beachfront pool and hot tub

Montego Bay, Jamaica

Beachfront | Pool | AC

from $1949/Nt
5 5
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 $786/Nt
5 5+
Details
An elegant Queens Fort haven, with a pool, gazebo, outdoor shower, and just a couple of minutes from the shoreline 3 BR rate available. The pool at Queens fort 10 is surrounded by beautiful tropical landscaping

Barbados

Near Beach | Pool

from $1140/Nt
5 5+
Details
Luxurious ocean view villa where you will see every hue of the blue sky and ocean. 2, 3 & 4 BR rates available. Relax by the pool and enjoy the ocean view at Sky Blue

Dawn Beach (Dutch side), St. Martin

Near Beach | Pool

from $608/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
Beachfront, five bedroom property with luxe design, a grand piano, and spacious design. 3 & 4 BR rates available. View from Old Trees#6 Firefly

Barbados

Beachfront | Pool | AC

from $1500/Nt
5 5+
Details
Nearly beachfront villa with books, TV, and a gourmet kitchen. 2 BR rate available. Aerial view of Galley Bay Heights Villa #104 and the beautiful beachfront

Galley Bay, Antigua

Near Beach | Pool

from $1150/Nt
5 4
Details
Mahogany Hill is for travelers in want of high-class resort accommodations, top-of-the-line luxury and privacy, and plenty of activities to do Lush tropical landscaping and private pool at Mahogany Villa

Montego Bay, Jamaica

Pool

from $1624/Nt
5 5
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
A beautiful 5-bedroom home over Brewers Bay with extreme comfort and easy ocean access Outer Banks photo

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from Call for rates
5 4+
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. Ocean Kai sits directly on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1100/Nt
5 5
Details
Plenty of room for either large groups as well as private intimate nooks. 3 & 4 BR rates available. Vista Villa photo

Almond Grove Estate, St. Martin

Pool

from $457/Nt
5 6
Details
Relaxing modern villa on Long Bay Beach with fantastic outdoor space and a unique master suite. Lounge chairs facing the ocean to soak up the Caribbean sun

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1557/Nt
5 5+
Details
Fully air-conditioned villa with tons of outdoor activities and a beach in the backyard. 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
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. Windemere 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
A Long Bay stay with direct beach access and an unbeatable view of the south shore waters. 3 BR rate available. Aerial Views of Sandy Beaches

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1114/Nt
5 5
Details
Relaxing, chic villa secluded on the Peterborg Peninsula. 3 & 4 BR rates available. Back of villa over looking Magen\'s Bay Beach

St. Thomas, USVI

Pool

from $899/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
Amaryllis is a five bedroom, tri-level waterfront beauty with boat dock. 2 & 3 BR rates available. Amaryllis photo

Simpson Bay (Dutch side), St. Martin

Pool

from $643/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
Bright, spacious and modern, the setting of this house is perfect for those that like to hang by the pool and relax. Perfect patio to enjoy waterfront views at Sunset Close Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1143/Nt
4 4
Details
A chic, beachfront villa with resort amenities. Located on a stretch of white sand beach Frangipani Villa enjoys all of the resort amenities

Anguilla

Beachfront | Pool | AC

from $3500/Nt
4 4+
Details
Two-story beachfront villa just steps away from snorkeling and sea life. Amazing ocean views

Barbados

Beachfront | Pool | AC

from $950/Nt
4 4+
Details
Villa B53 at Tortuga Bay

Punta Cana, Dominican Republic

Pool

from $720/Nt
4 4+
Details
Luxury villa with spacious rooms and a circular layout wrapped around a cobalt tiled pool. Casuarina photo

Montego Bay, Jamaica

Pool

from $1299/Nt
4 4
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
Family-friendly villa with water activities and childcare at Punta Cana Resort. Starfish photo

Punta Cana, Dominican Republic

Pool

from $1080/Nt
4 4+
Details
Chic and modern villa with the perfect design for a family or two. 3 BR rate available. SAX Villa photo

Saint Jean, St. Barts

Near Beach

from $3571/Nt
4 4
Details
Spanish style villa with lush gardens and proximity to Sandy Lane Beach and Holetown. Casa Bella photo

Barbados

Near Beach | Pool

from $500/Nt
4 3
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
Chic, modern villa with an ideal location near all of Grace Bay's amenities. Has specials. Aerial view of the Turquoise Villa property

Grace Bay, Turks and Caicos

Near Beach | Pool

from $1300/Nt
4 4
Details
Vibrant three-level villa just off Taylor Bay beach. Etoile De Mer pool with furnished gazebo

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $714/Nt
4 4
Details
Beachfront villa for any group of travelers, with peaceful privacy and an unfussy design. Jolly Harbour#oo8 has a beautiful location right on the beach

Jolly Harbour, Antigua

Beachfront | Pool | AC

from $1200/Nt
4 4
Details
Relaxing, tropical family vacation villa with convenient location and modern design. Calmaro Villa has a beautiful pool and entertainment patio

Barbados

Beachfront | Pool | AC

from $1800/Nt
4 4+
Details
This villa's gorgeous exterior was made for entertaining. Punta Aguila 46 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
Modern, private beachfront villa with a stylish rooftop deck. An aerial view of Olympus Villa and the beautiful beachfront

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1500/Nt
4 4+
Details
Rum Point villa with two decks and a cozy interior. An aerial view of Hilltime Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $750/Nt
4 4
Details
Luxurious indoor-outdoor living in a lush garden setting. Limones is located near Minitas Beach and has a great pool

Casa de Campo, Dominican Republic

Near Beach | Pool

from $1220/Nt
4 4+
Details
Three pools, the ocean, and the beach will keep guests entertained. Has specials. The Estate pools

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4800/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
Four equal king suites, two Jacuzzis, and resort amenities perfect for a couples' getaway. The Estate swimming pool

Grace Bay, Turks and Caicos

Beachfront | AC

from $8600/Nt
4 4
Details
Sleek, open-concept villa with modern architecture and Grace Bay access. Villa Islander is located just off the famous Grace Bay Beach

Grace Bay, Turks and Caicos

Near Beach | Pool

from $1880/Nt
4 4
Details
Elegant and chic Long Bay resort villa with an open floor plan. Has specials. Beach Enclave Beach Front Villas on Long Bay

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $2640/Nt
4 4+
Details
Chic, modern four-bedroom villa with beach access and a private chef. Imagine photo

Barbados

Beachfront | Pool | AC

from $850/Nt
4 4+
Details
Beachfront villa with a large terrace and lush gardens for privacy. Mirador is located in Fitts Village - right on the beach

Barbados

Beachfront | Pool | AC

from $1500/Nt
4 4+
Details
Four king suites and a multi-leveled lounging area outside. 1, 2 & 3 BR rates available.
Has specials. EauSea photo

Great Cruz Bay, St. John

Pool

from $857/Nt
4 4
Details
Sunny beachfront villa with an open design and cozy suites. Sand Castle Villa is located directly on Lorient Bay Beach

Lorient, St. Barts

Beachfront | AC

from $1429/Nt
4 3
Details
Chic golf course villa with simply modern design. Spero Villa sits directly on Puna Cana\'s beautiful Hacienda Golf Course

Punta Cana, Dominican Republic

Pool

from $1000/Nt
4 4
Details
Chalk Sound villa with four family-friendly suites. Has specials. Alainn Villa is located right on the water on Chalk Sound

Chalk Sound, Turks and Caicos

Pool

from $1214/Nt
4 3
Details
A guest cottage and an elegant main house make this four-bedroom the perfect retreat. La Perla Villa is located in Altamira, just above the Marina in Los Suenos

Costa Rica

Pool

from $1800/Nt
4 4
Details
Four bedrooms well-designed for a multi-generational family vacation. Casa Campana is located in the Los Suenos Resort

Costa Rica

Pool

from $1100/Nt
4 4
Details
Open-concept villa with expansive common areas and easy access to Orient Bay. 2 & 3 BR rates available. Albacore Villa is located on the heights of Orient Bay

Orient Bay (French side), St. Martin

Pool

from $643/Nt
4 4
Details
Four king suites, two verandas, and spacious common areas make this villa luxurious. Coco de Mer sits on top of the Sandy Lane Estate

Barbados

Pool

from $3900/Nt
4 4+
Details
Child-friendly beachfront villa with 10,000 sq. feet of Tuscan architecture. 3 BR rate available.
Has specials. Pool with view of ocean

Anguilla

Beachfront | Pool | AC

from $1600/Nt
4 4+
Details
A children's suite connected to the master bedroom combines with direct beach access for the ideal family vacation rental. Five Turtles Villa is just steps away from Taylor Bay Beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1214/Nt
4 3+
Details
A scenic, spacious luxury villa for families with children or couples traveling together. 2 & 3 BR rates available. Pallina Villa photo

St. Thomas, USVI

Pool

from $715/Nt
4 3+
Details
Hakuna Matata Villa: Bring the whole family to this first rate, gated estate! 2 BR rate available.
Has specials. The ocean and pool views from Hakuna Matata villa!

Catherineberg, St. John

Pool

from $893/Nt
4 5+
Details
A four-bedroom estate situated right on the beach that is family friendly with lots of extras. 2 BR rate available. The amazing pool at Villa on the Beach!

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from $886/Nt
4 5
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
Private Barbados beachfront home is contemporary and stylish with lots of space for guests Thespina Villa

Barbados

Beachfront | AC

from $850/Nt
4 4
Details
Stay close to the action within minutes of shopping, tennis courts, water sports, beaches, and several gourmet restaurants. 2 & 3 BR rates available. Euphoria Villa looks out over Leverick Bay

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

from $471/Nt
4 3
Details
Stunning beachfront villa on Long Bay Beach has incredible views and plenty of space inside and out 2 & 3 BR rates available. Beautiful beachfront pool at Blue Beach Villa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $929/Nt
4 4
Details
Anse Chastanet Beach is minutes away from the spacious Tamarind House Villa 2 BR rate available. Uninterrupted views of the Pitons

Soufriere, St. Lucia

Pool

from $640/Nt
4 4
Details
A deluxe villa on Gibbs Beach, this brand new property has thought of everything for your Caribbean adventure 3 BR rate available. Tropical surroundings greet you at the pool at Bonavista Villa

Barbados

Beachfront | Pool | AC

from $1280/Nt
4 4+
Details
A deluxe accommodation with entertainment for all ages. 3 BR rate available. The stunning Evergreen property, in the prestigious Sandy Lane neighborhood, from an aerial view

Barbados

Pool

from $1100/Nt
4 5
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 $786/Nt
4 4
Details
Families with children will find Oceane in Terres Basses to be the ideal locale. 2 & 3 BR rates available. Oceane is located in Terres Basses with great views over Plum Bay

Terres Basses (French side), St. Martin

Near Beach | Pool

from $586/Nt
4 4+
Details
A charming couples' retreat on Sapodilla Bay. Valentina Villa has a beautiful pool and patio

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1500/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
Enjoy easy access to beaches and St. John's national park from this two-story beauty. 1, 2 & 3 BR rates available.
Has specials. La Virage is located near the Battery Gut area and has amazing Caribbean views

Rendezvous Bay, St. John

Pool

from $414/Nt
4 4
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
Ideal location near the beach and outdoor activities, with an open design. 1, 2 & 3 BR rates available. Casa del Sol is located close to Orient Beach

Orient Bay (French side), St. Martin

Near Beach | Pool

from $500/Nt
4 4
Details
Bright, spacious decor, an expansive lawn with tons of lounging space, and direct beach access. Take a dip in the pool at High Trees Villa

Barbados

Beachfront | Pool | AC

from $920/Nt
4 4
Details
Located high above Petit Anse, this new villa is great for families with older children 2 BR rate available. Ushuaia Villa has great views over Flammands

Flamands, St. Barts

Near Beach | Pool

from $936/Nt
4 4
Details
Very private, waterfront vacation home with a huge infinity pool and beach access. Lounge by the infinity edge pool with amazing Caribbean views at Alandra

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1129/Nt
4 4+
Details
Spacious and tasteful St. John villa is perfect for vacationing couples looking to entertain and unwind 2 & 3 BR rates available. Relax and enjoy the amazing view poolside from Abrigado Villa

Virgin Grand Estates, St. John

Pool

from $643/Nt
4 4+
Details
Great service, 20-second walk to an Anguilla beach and a fitness room for the exercise enthusiast. The beautiful pool and Caribbean views from Alegria Villa

Anguilla

Near Beach | Pool

from $1462/Nt
4 4
Details
Perfect for a family vacation or getaway with friends with incredible views and gorgeous design. 2 & 3 BR rates available. Lounge poolside and enjoy amazing ocean views from Claridge Villa

Anse des Cayes, St. Barts

Beachfront | Pool | AC

from $1429/Nt
4 4
Details
Expect stunning sunset views at this Virgin Grand Estates villa. 1, 2 & 3 BR rates available.
Has specials. Vista Caribe Villa photo

Virgin Grand Estates, St. John

Pool

from $643/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
Luxurious beachfront villa with a fantastic outdoor space and ideal location near Turtle Cove. 3 BR rate available. Dawn Beach Villa has a beautiful pool and a hot tub

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1214/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
Just a short walk from Grand Cul de Sac, Summer Breeze Villa has all the amenities you want 2 & 3 BR rates available. The infinity edge pool and patio deck overlook Grand-cul-de-sac

Grand Cul de Sac, St. Barts

Near Beach | Pool

from $986/Nt
4 4
Details
Beachfront villa with kayaks, an entertainment system, and everything you need to relax. Picturesque beach front Villa - Five Little Cays

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $1071/Nt
4 4
Details
Relaxed oceanfront vacation oasis on the south shore that's completely private yet close to everything. Breezy Villa sits directly on the ocean

Long Bay, Turks and Caicos

Pool

from $929/Nt
4 4
Details
Escape stress and relax at this waterfront Chalk Sound villa. 2 & 3 BR rates available. Bright Idea has great views of Chalk Sound

Chalk Sound, Turks and Caicos

Near Beach | Pool

from $800/Nt
4 4+
Details
Beyond Fabulous Kitchen, amazing villa just minutes to the renowned Shoal Bay. Sandcastle Pointe Villa is located on the waterfront on Shoal Bay

Anguilla

Pool

from $1000/Nt
4 4
Details
Open-air villa in Pointe Milou features modern style and amazing views of the sunset 1 & 3 BR rates available. Bali Villa has uninterrupted view of Lorient and the sunset past St. Jean Bay

Pointe Milou, St. Barts

Pool

from $786/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. Great Escape Villa is very close to the beautiful beach

Grand Cayman, Cayman

Near Beach | Pool

from $750/Nt
4 3
Details
Lime Hill Villa: Priceless views and amazing service will make Antigua your favorite place to vacation Lime Hill Villa photo

English Harbour, Antigua

Near Beach | Pool

from $875/Nt
4 4
Details
Everything within walking distance from stunning Mango Villa in Orient Bay 2 & 3 BR rates available. Pool deck at Mango Villa

Orient Bay (French side), St. Martin

Near Beach | Pool

from $643/Nt
4 4
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. Lounge by the ocean front pool at La Percha

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1500/Nt
4 4+
Details
Rapture Villa is 5000 sq. feet of Caribbean style with modern comforts 1, 2 & 3 BR rates available. Rapture Villa photo

Virgin Grand Estates, St. John

Pool

from $749/Nt
4 4
Details
Jolly Harbor's most comfortable locale with lots of island activities to choose from. The vibrant colors at Turtle Villa provide for a fun atmosphere right on the beach

Jolly Harbour, Antigua

Beachfront | Pool | AC

from $1843/Nt
4 4+
Details
Light and airy tropical beach house right on Grace Bay Beach. 2 BR rate available. Reef Beach House is located near Smith Reef along Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $750/Nt
4 3
Details
Every bedroom leads to the deck and pool at this chic villa. 2 & 3 BR rates available. Seabird Villa has beautiful sunset views

Anguilla

Near Beach | Pool

from $650/Nt
4 4+
Details
Blue Point Villa has delightful views, open-air living, and a beachfront location. A private beachside pool offers relaxation at Blue Point Villa

Barbados

Beachfront | Pool | AC

from $1800/Nt
4 4+
Details
Regal, colonial home steps from serene Reeds Bay. Caprice Villa sits in it\'s stately location on the Gold Coast Beachfront

Barbados

Beachfront | Pool | AC

from $1800/Nt
4 4+
Details
Great for large families or four couples who want privacy and plenty of space. 2 & 3 BR rates available. Amarillo Villa is located in True Blue Grenada

Grenada

Pool

from $390/Nt
4 4
Details
Quiet, family-friendly villa near Gibbs Bay. 3 BR rate available. Set amid lush tropical greenery Jessamine offers a beautiful private pool

Barbados

Near Beach | Pool

from $475/Nt
4 4
Details
Beachfront villa has stunning sea views and tons of space for you and your loved ones. Hemingway House is tucked in a cove between Gibbs Beach and Mullins Beach

Barbados

Beachfront | Pool | AC

from $2150/Nt
4 4+
Details
Aptly named, this villa is across the way from Holders Hill and is a little bit of island paradise Amazing pool - with the ocean in the backdrop at Shangri La Villa

Barbados

Pool

from $935/Nt
4 3+
Details
Looking for an amazing villa with a gourmet kitchen on St. Jean? Phebus Villa has you covered Phebus Villa photo

Saint Jean, St. Barts

Near Beach

from $1143/Nt
4 4
Details
Absolutely gorgeous water view villa in Terres Basses is contemporary, stylish, and serene. 2 & 3 BR rates available.
Has specials. La Hacienda Villa photo

Terres Basses (French side), St. Martin

Pool

from $636/Nt
4 3
Details
Architecturally beautiful with artistic comfort, Carlisle House is a great option for families who enjoy a wide range of cultural exchanges. 1, 2 & 3 BR rates available. Carlisle House photo

St. Croix, USVI

Pool

from $414/Nt
4 4+
Details
Gorgeous four-bedroom villa with views, a pool, and comfortable accommodations for a dream vacation. Sea Breeze Villa has a beautiful private pool

Providenciales, Turks and Caicos

Near Beach | Pool

from $1095/Nt
4 4
Details
Great for kids, with access to several beaches on St. John's north shore. Has specials. Villa Lantano is located in the Peter Bay Estates

Peter Bay, St. John

Pool

from $1571/Nt
4 4+
Details
Water, water everywhere around this four-bedroom villa: one reader even called it heaven on earth. 2 & 3 BR rates available.
Has specials. Exterior view of the villa and pool.

Catherineberg, St. John

Pool

from $771/Nt
4 5
Details
Tropical luxury on Sandy Hill Beach. 1, 2 & 3 BR rates available. The beautiful Bird of Paradise Villa

Anguilla

Near Beach | Pool

from $1850/Nt
4 4+
Details
Seclusion and sun await just off Friar's Bay at the Happy Bay Villa 2 & 3 BR rates available. Happy Bay Villa is located on the northern coast of the island within walking distance of Friars Bay

Happy Bay (French Side), St. Martin

Near Beach | Pool

from $700/Nt
4 4+
Details
2B at Peter Bay Villa has a unique multi-tiered layout to make the most of the views 2B at peter Bay is perched on a tropical hillside above the west end of Peter Bay

North Shore, St. John

Near Beach | Pool

from $1857/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
Handicap accessible with an elevator to complement the views and other amenities Beautiful views from the balcony at Illusion Villa

Barbados

Pool

from $2400/Nt
4 4+
Details
Contemporary 4-bedroom villa on the Dutch Side has excellent water views and all the modern amenities you could ask for 2 & 3 BR rates available. Rising Star Villa photo

Tamarind Hill (Dutch Side), St. Martin

Pool

from $358/Nt
4 4
Details
This villa offers stunning views of the mountains of St. Marten and the Caribbean Sea from all angles. 3 BR rate available. Lounge by the pool at Anani and enjoy views of the Caribbean and the mountains of St. Maarten beyond

Anguilla

Beachfront | Pool | AC

from $1455/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! Enjoy amazing views of the Caribbean from the pool at Turquesa Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1250/Nt
4 4+
Details
Super private and spacious villa has great water views, easy access to the beach, and use of nearby tennis courts 2 & 3 BR rates available. OUI Villa photo

Petit Cul de Sac, St. Barts

Near Beach | Pool

from $1429/Nt
4 4
Details
Open and airy villa has a relaxing atmosphere, with views over the sea and extra touches you won't find just anywhere 2 & 3 BR rates available. Lounge pool side and enjoy views of St. Jean Bay

Saint Jean, St. Barts

Pool

from $1286/Nt
4 4
Details
Modern amenities, spacious design, and a separate bungalow make this hilltop villa the epitome of bliss. 3 BR rate available. Venusville Villa has a beautiful pool and deck for entertaining

Petite Saline, St. Barts

Pool

from $3286/Nt
4 4
Details
Gorgeous Barbados townhome is just 10 minutes from Holetown and includes lots of great resort amenities, including a restaurant and bar Your own hot tub at E 119

Barbados

Pool

from $400/Nt
4 3
Details
Gorgeous luxury villa is perched on a cliff overlooking the ocean and offers incredible panoramic views and supreme privacy 1, 2 & 3 BR rates available. An aerial view of the Cap au Vent Estate

Pointe Milou, St. Barts

Pool

from $1700/Nt
4 4
Details
Capri Manor means adding a bit of luxury to your Barbados vacation Capri Manor is located just across the street from Gibbs Beach

Barbados

Near Beach | Pool

from $550/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
Modern design and sleek finishes make this villa totally luxurious. Atelier Villa has modern architectural lines and a beautiful pool

Barbados

Near Beach | Pool

from $1500/Nt
4 3+
Details
Enjoy the Gourmet Life When You Stay At Ariana Villa 2 & 3 BR rates available.
Has specials. Ariana Villa photo

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from $550/Nt
4 3+
Details
Let Unforgettable Views Define Your Next Holiday At Ana Capri Estate 1, 2 & 3 BR rates available. Ana Capri Estate photo

Tortola, BVI, British Virgin Islands

Pool

from $572/Nt
4 4+
Details
Located in the exclusive Leeward development, only a short walk from the best part of Grace Bay Beach. 3 BR rate available. Pelican\'s Nest Villas - Cocoa is located near Grace Bay Beach

Grace Bay, Turks and Caicos

Near Beach | Pool

from $857/Nt
4 3+
Details
Good times await at Montego Bay Yellowbird Villa photo

Montego Bay, Jamaica

Pool

from $786/Nt
4 4
Details
Beachfront villa, close to water sports and local restaurants 2 BR rate available. Bora Bora Lower apartment offers a beautiful beachfront

Barbados

Beachfront | AC

from $325/Nt
4 4
Details
Perfect blend of seclusion and excitement close to Holetown 2 BR rate available. Bora Bora Upper Villa photo

Barbados

Beachfront | AC

from $310/Nt
4 4
Details
Modern, crescent-shaped villa with panoramic views from every room. Lounge in luxury, poolside at Marsh Mellow Villa

Barbados

Pool

from $965/Nt
4 4+
Details
Four bedroom home with private beach and fabulous snorkeling Has specials. View from above Castaway Villa - you can see the beach and the ocean

Grand Cayman, Cayman

from $565/Nt
4 3+
Details
Island elegance at its best with perfect beach nearby Resort style luxury awaits at Greentails Residence One Villa

Barbados

Pool

from $1000/Nt
4 4+
Details
Eco-friendly beachfront villa conveniently located near Rum Point Club. Has specials. Kai Vista photo

Grand Cayman, Cayman

Beachfront | Pool | AC

from $995/Nt
4 4
Details
Breathtaking ocean view, bar and infinity pool 1, 2 & 3 BR rates available.
Has specials. Lounge in the Caribbean sun at Sea La Vie Villa

Tamarind Hill (Dutch Side), St. Martin

Pool

from $400/Nt
4 5
Details
Tropical island elegance, Cayman style Has specials. An amazing view from the balcony at Zara Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1100/Nt
4 4+
Details
Relaxing garden mansion with beach access and four private suites. Has specials. Edge of Paradise is located on the Southern shore of Meagan\'s Bay

St. Thomas, USVI

Near Beach | Pool

from $1214/Nt
4 4+
Details
Spacious, contemporary hillside home with plunge pool. 2 & 3 BR rates available.
Has specials. Rose Dog Villa has a beautiful infinity edge pool

Vitet, St. Barts

Pool

from $1043/Nt
4 4
Details
Contemporary and alluring pool and conveniently located 2 & 3 BR rates available. Black Pearl Villa photo

Marigot, St. Barts

Pool

from $1143/Nt
4 4
Details
Lush gardens, scenic views and great snorkeling minutes away. 2 & 3 BR rates available. Amazing ocean views and out to neighboring islands - St. Barts - from Seascapes Villa

Dawn Beach (Dutch side), St. Martin

Pool

from $400/Nt
4 4
Details
Intimate hilltop villa with unobstructed Caribbean views. 2 & 3 BR rates available. Villa Aurea sits just above Lorient Beach

Lorient, St. Barts

Pool

from $1143/Nt
4 4
Details
Beachfront boutique resort with snorkeling access, elegant design, and a convenient location. Seabreeze 8 has a balcony overlooking the ocean

Grand Cayman, Cayman

Beachfront | AC

from $900/Nt
4 4+
Details
Panoramic views and a pool like no other in this Red Pond Estate villa. 2 & 3 BR rates available. Villa Rosa has amazing views out into the Caribbean and across the St. Barthelemy channel

Guana Bay (Dutch Side), St. Martin

Near Beach | Pool

from $429/Nt
4 4
Details
A private, beachfront villa that offers comfort and ease on beautiful Grace Bay. Has specials. Saving Grace Villa photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2300/Nt
4 3
Details
Palermo assures ultimate privacy with fantastic ocean views and space to relax. Palermo Villa is located directly on the ocean

Turtle Tail, Turks and Caicos

Pool

from $1000/Nt
4 4+
Details
Encompassing view of Orient Bay within 15 minutes of both the French and Dutch capitals. 2 & 3 BR rates available. Monte Verde is located in Hope Hill and has great views of Orient Bay

Orient Bay (French side), St. Martin

Pool

from $600/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 is located on the hillside above St. Jean Bay

Saint Jean, St. Barts

Pool

from $1786/Nt
4 4
Details
Large condo with luxury amenities, ideal location, and spacious rooms. 2 & 3 BR rates available.
Has specials. Aqua Vue photo

Cupecoy (Dutch side), St. Martin

Near Beach

from $336/Nt
4 4+
Details
Convenient location in the Vitet countryside perfect for children. 1, 2 & 3 BR rates available. Pastels Villa photo

Vitet, St. Barts

Pool

from $700/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 $1030/Nt
4 3
Details
Family vacation villa with snorkeling, big bedrooms, and a quiet location. 3 BR rate available. A beachfront pool awaits you at Christmas Palms Villa

Grand Cayman, Cayman

Pool

from $600/Nt
4 3+
Details
Beachfront, two story villa with central air-conditioning, an open floor plan, and walls of windows to take in the view. The beach set up in front of Tarasand Villa

Grand Cayman, Cayman

Beachfront | AC

from $995/Nt
4 3
Details
Villa Jaguey 3 photo

Punta Cana, Dominican Republic

Pool

from $1150/Nt
4 4
Details
Beachfront villa with gorgeous ocean views and kayaks to take out on the water. 3 BR rate available. Villa Caymanas has a large raised beachfront pool

Grand Cayman, Cayman

Near Beach | Pool

from $610/Nt
4 4+
Details
Four queen suites and warm interiors make this perfect for couples. 2 BR rate available. Galley Bay Heights Villa - #007 photo

Galley Bay, Antigua

Near Beach

from $1300/Nt
4 4
Details
Contemporary, California style villa with private patios, a roof top patio, and a gazebo. 2 & 3 BR rates available. Bahia Blue photo

Terres Basses (French side), St. Martin

Near Beach | Pool

from $572/Nt
4 4
Details
Beachfront villa rental with sunset views and rooftop deck. 3 BR rate available. Picture Perfect Villa has many options for a fun holiday

Grand Cayman, Cayman

Beachfront | Pool | AC

from $710/Nt
4 3+
Details
Panoramic views of Flamands Bay just a short walk away from the beach. 2 & 3 BR rates available. Estrela Villa photo

Flamands, St. Barts

Near Beach | Pool

from $571/Nt
4 4
Details
Family-friendly home on the beach with a cozy interior. Has specials. The white sandy beach in front of the villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $710/Nt
4 4
Details
A simple outdoor area and proximity to town makes this villa perfect for family and friends alike. 2 & 3 BR rates available. Pool and ocean view

Pointe Milou, St. Barts

Pool

from $1000/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
Family-friendly villa with open design, gorgeous views, and three king suites. Overview of villa and ocean

St. Thomas, USVI

Pool

from $595/Nt
4 3+
Details
Beachfront villa with large rooms and easy snorkeling access. Gypsy Villa has a beautiful beach front private pool

Grand Cayman, Cayman

Beachfront | Pool | AC

from $850/Nt
4 4
Details
Relaxing villa with creamy neutral decor and an ideal location on Chalk Sound. A private water front pool with beautiful views await you at Villa Capri

Chalk Sound, Turks and Caicos

Pool

from $1400/Nt
4 4+
Details
Two-story villa with large bedrooms and luxury finishes. 2 & 3 BR rates available. Latitude Adjustment photo

St. Thomas, USVI

Pool

from $699/Nt
4 3+
Details
Villa Arrecife 24 at Tortuga Bay photo

Punta Cana, Dominican Republic

Pool

from $1080/Nt
4 4
Details
Resort condo with a huge terrace, Jacuzzi tub, and unobstructed ocean view. Sandy Lane Beach just steps outside of Smugglers Cove

Barbados

Beachfront | AC

from $1400/Nt
4 4+
Details
Oceanfront property with beach access and panoramic views. Stunning infinity edge pool

Long Bay, Antigua

Pool

from $1718/Nt
4 4+
Details
This penthouse villa has completely amazing views: miles of sand and blue sea. Has specials. Penthouse at The Venetian photo

Grace Bay, Turks and Caicos

Beachfront | AC

from $1425/Nt
3 3
Details
Warm, family-sized villa a short walk from Sandy Hill Bay. 1 & 2 BR rates available. Villa Kai is located on Sandy Hill Bay

Anguilla

Pool

from $500/Nt
3 3
Details
Modern yet warm with a barefoot attitude and great sunsets. 2 BR rate available. Sasha photo

Corossol, St. Barts

Pool

from $1357/Nt
3 3
Details
Minimalist three bedroom overlooking Lorient Bay. 1 & 2 BR rates available. Bikini Villa photo

Lorient, St. Barts

Near Beach | Pool

from $457/Nt
3 3
Details
Minimalist, convenient villa located in the heart of St. Jean. 2 BR rate available.
Has specials. Alaia photo

Saint Jean, St. Barts

Near Beach | Pool

from $864/Nt
3 3
Details
Open-air villa within steps of Long Bay Beach and minutes from the island's best spots. 2 BR rate available. The White Villas are located very close to the beautiful Long Bay Beach

Long Bay, Turks and Caicos

Near Beach | Pool

from $486/Nt
3 4
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 $3395/Nt
3 3
Details
Canal-front villa with kayaks, paddle boards, and a short drive to everything. Cassis is located along the canal and has a beautiful pool and backyard area

Leeward, Turks and Caicos

Pool

from $700/Nt
3 3
Details
Waterfront villa on Marigot Bay with private beach access and three upper level bedrooms. Javacanou villa overlooks the beautiful protected waters of Marigot Bay

Deve, St. Barts

Near Beach | Pool

from $2143/Nt
3 3
Details
Extremely private, oceanfront villa with access to the island's best shallow snorkeling site. Has specials. The private pool at Babylon Reef has a man made -beach- surrounding it

Grand Cayman, Cayman

Beachfront | Pool | AC

from $550/Nt
3 2+
Details
Two-story villa with ocean and hillside views, just minutes from Flamands Beach. 2 BR rate available. Villa Ipanema on Flamands has a great pool

Flamands, St. Barts

Near Beach | Pool

from $621/Nt
3 3
Details
A chic and spacious villa right on the Royal Westmoreland golf course. Sienna Villa

Barbados

Pool

from $1000/Nt
3 3
Details
Al fresco dining and chic furniture set this beachfront property apart. Paynes Bay Beach is just below the balcony at Smugglers Cove #4

Barbados

Beachfront | AC

from $995/Nt
3 3
Details
Fully air-conditioned, peaceful villa with sunset views and lush gardens. 1 BR rate available. Crescent Beach Villa is located above Crescent Beach and has amazing ocean views

Bequia, St. Vincent & Grenadines

Pool

from $321/Nt
3 3
Details
Family vacation villa in a well-equipped resort community. Has specials. There is an amazing beach cove at Casa Luan Villas

Grand Cayman, Cayman

Beachfront | AC

from $1030/Nt
3 4
Details
Grace Bay villa with simple luxury and modern decor. Turnstone is located just a few minutes away from Grace Bay Beach

Leeward, Turks and Caicos

Near Beach | Pool

from $1050/Nt
3 3
Details
Well-equipped Grace Bay villa with tons of beach amenities. Edge of Paradise is located just a few minutes from Grace Bay Beach

Leeward, Turks and Caicos

Near Beach | Pool

from $1050/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
Beachfront villa with sleek, white interiors and access to Turtle Cove Marina. Aerial view of the Sandpebble property

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $786/Nt
3 3+
Details
Every amenity under the sun, including a private boat. Ocean Eleven is located in the marina at Cap Cana

Cap Cana, Dominican Republic

Pool

from $2490/Nt
3 3+
Details
Family-friendly beachfront home with amenities for guests of all ages. Has specials. Conch Pointe Villa is located on the beach just minutes from Seven Mile Beach Corridor

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1030/Nt
3 3
Details
Smith's Reef villa surrounded by private gardens. Tradewinds Villa is located near Grace Bay Beach

Providenciales, Turks and Caicos

Near Beach | Pool

from $457/Nt
3 3
Details
Beachfront three-story home with huge outdoor space. Seashells Villa is set on a beautiful stretch of beach

Barbados

Beachfront | Pool | AC

from $495/Nt
3 3+
Details
Luxury beachfront villa with endless amenities and event-friendly design. The Sandcastle Beach House is located on a beautiful beach in Limestone Bay

Anguilla

Beachfront | AC

from $1250/Nt
3 3+
Details
Chic minimalism combines with Orient Bay views for an idealistic getaway. 1 & 2 BR rates available. Discovery Villa\'s infinity edge pool

Orient Bay (French side), St. Martin

Pool

from $500/Nt
3 3
Details
Dramatic sunset views and a great family house. Osprey is located on the ocean side of Chalk Sound

Taylor Bay/Sapodilla Bay, Turks and Caicos

Pool

from $1100/Nt
3 3
Details
Close to town but still private, with great ocean views. 1 & 2 BR rates available.
Has specials. Arcadia Villa has great views overlooking Oyster Bay

Oyster Pond (Dutch side), St. Martin

Pool

from $286/Nt
3 3
Details
Charming private villa enjoys an excellent location on the beach and is close to the popular Royal Westmoreland and Sandy Lane Hotels. Hibiscus has a private plunge pool as well as access to the Merlin Bay common pool

Barbados

Beachfront | Pool | AC

from $450/Nt
3 3
Details
Newly refurbished Hummingbird Villa has spacious open floor plans and the feel of a treehouse 1 BR rate available. Hummingbird Villa photo

Cap Estate, St. Lucia

Pool

from $250/Nt
3 3
Details
Saline Reef: Two pools and a waterfall will tempt you to stay home and skip all of the nearby activities 2 BR rate available. Saline Reef has a beautiful pool and patio

Cap Estate, St. Lucia

Near Beach | Pool

from $580/Nt
3 3
Details
The drinks never stop flowing at this stunning, modern home with breathtaking ocean views. 1 & 2 BR rates available. Lounge poolside with amazing views of the ocean

Anguilla

Near Beach | Pool

from $990/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
One acre of thick, leafy gardens surrounds this cozy, sunlit home. Pool and house at Anchorage Villa

Barbados

Pool

from $700/Nt
3 3
Details
Walk to famous St. Jean beach, nearby restaurants and shops! 1 & 2 BR rates available. Maison Villa photo

Saint Jean, St. Barts

Near Beach | Pool

from $707/Nt
3 3
Details
Canefield House is a distinctive island estate with 10 acres of tropical plants and trees to color your stay-a photographer's dream. 1 & 2 BR rates available. Canefield House photo

Tortola, BVI, British Virgin Islands

Pool

from $541/Nt
3 3+
Details
Open and airy villa in Vitet with stunning water views and extreme privacy. 2 BR rate available. Abby Villa photo

Vitet, St. Barts

Pool

from $857/Nt
3 3
Details
Luxury resort villa that puts a private beach, spa, and water sports at your disposal. Has specials. Spectacular beachfront pool at Dhyani House

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $6000/Nt
3 3
Details
Gorgeous three-bedroom villa offers outstanding views, exceptional service, and privacy in COMO Parrot Cay private island resort. Has specials. The pool at Rocky Point villa!

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC

from $6000/Nt
3 3
Details
Angelina Villa offers great value in a modern villa overlooking Oyster Pond Marina from its hillside perch. 1 & 2 BR rates available. Fabulous views of the Caribbean from the pool at Angelina Villa

Oyster Pond (Dutch side), St. Martin

Pool

from $271/Nt
3 2+
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
Well-designed for two or three couples who want a convenient, quiet location. 2 BR rate available. Sweet Return Villa is located near the golf course and Rendezvous Bay

Anguilla

Pool

from $500/Nt
3 3
Details
A Refreshing Getaway: One Place, Reverie Villa 2 BR rate available. Reverie Villa sits directly on St. Jean Beach

Saint Jean, St. Barts

Beachfront | AC

from $1000/Nt
3 3
Details
This reasonably priced, 3,000 sq. ft. villa is only a few minutes' walk from Grace Bay Beach. Pelican\'s Nest Villas - Cinnamon is located near Grace Bay Beach

Grace Bay, Turks and Caicos

Near Beach | Pool

from $857/Nt
3 3+
Details
Furnished in Contemporary Italian Style, Sandy Cove 201 is comfort and luxury combined Sandy Cove Resort

Barbados

Beachfront | Pool | AC

from $750/Nt
3 3+
Details
This contemporary villa in Colombier has excellent sea views and an open floor plan. 2 BR rate available. Casawapa Villa sits on the Colombier hillside

Colombier, St. Barts

Pool

from $757/Nt
3 3
Details
St. Barth's romantic Dasha Villa is quickly building a following of ardent admirers 1 & 2 BR rates available. Dasha Villa photo

Lurin, St. Barts

Pool

from $943/Nt
3 3
Details
Escape to Lorient Beach and enjoy local attractions while making this gorgeous villa your base camp. 1 & 2 BR rates available. Tropical retreat at Escape Villa

Lorient, St. Barts

Near Beach | Pool

from $416/Nt
3 2
Details
Mahogany Villa is close to Flamands Beach and many water sport activities 1 & 2 BR rates available. Lounge by the pool with great ocean views at Mahogany Villa

Flamands, St. Barts

Near Beach | Pool

from $400/Nt
3 2
Details
Victoria Villa is minutes from the ferry terminal, so you can expand your vacation exploration with a day trip to St. Bart's. 2 BR rate available.
Has specials. Victoria Villa photo

Oyster Pond (Dutch side), St. Martin

Pool

from $295/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 $643/Nt
3 3
Details
Just one minute from Plum Bay Beach, Monchal Villa comes with tons of room and a private pool/jacuzzi. 1 & 2 BR rates available. Monchal Villa photo

Terres Basses (French side), St. Martin

Near Beach | Pool

from $279/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 $6490/Nt
3 3
Details
This condo offers everything you would expect from the Ritz Carlton-luxury, privacy, and more amenities than you can count The Ritz Carlton Club Condo photo

St. Thomas, USVI

Beachfront | AC

from $915/Nt
3 3+
Details
A modern apartment ideal for 2 couples, sitting at the heart of Paynes Bay 2 BR rate available. Paynes Bay Beach just a short walk from Coral Cove

Barbados

Beachfront | AC

from $495/Nt
3 3
Details
Open and inviting 3-bedroom villa is just steps from Gibbs Beach perfect for those wanting to lounge in the sand all day. Harmony House is just steps away from Gibbes Beach

Barbados

Beachfront | Pool | AC

from $850/Nt
3 3+
Details
Perfect for family beach getaways right on Grace Bay. Fantastic snorkeling right off the beach. 2 BR rate available. Ocean kayaks - Ask for availability

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $729/Nt
3 3
Details
This beachfront, amenity-packed home is the quintessential family vacation villa. An aerial view of Conch Beach Villa and the surrounding property

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $850/Nt
3 3
Details
Island Time is the best time to be on, or to stay at, for a relaxing and unhurried tropical vacation 2 BR rate available. On Island Time photo

Oyster Pond (Dutch side), St. Martin

Pool

from $379/Nt
3 3+
Details
Step right off the terrace and onto Mullins Beach, or take advantage of nearby golf and tennis. Aquamarine is just steps away from Mullins Beach

Barbados

Beachfront | AC

from $380/Nt
3 2
Details
Townhouse living right on the edge of the Caribbean Sea is about as good as it gets Fathom\'s End - Mahogany Bay photo

Barbados

Beachfront | AC

from $555/Nt
3 3+
Details
This dreamy villa can accommodate up to 10 people and it is wheelchair accessible. 2 BR rate available. Blue Lagoon Villa photo

Virgin Gorda, BVI, British Virgin Islands

Near Beach | Pool

from $557/Nt
3 3
Details
Funny name, you say? Don't worry. After one night here, Bambooshay will become your new favorite word. 1 & 2 BR rates available. Relax and enjoy yourself while in the pool or hang\'n in the hammock at Bambooshay

St. Croix, USVI

Pool

from $343/Nt
3 3+
Details
Named for an English Lord and Lady, Brimstage Estate is on par with its royal background. 1 & 2 BR rates available. Brimstage Estate photo

St. Croix, USVI

Pool

from $286/Nt
3 2+
Details
Ideal for three couples or a family, overlooks Marigot Bay. 1 & 2 BR rates available. Bel\'Ombre photo

Marigot, St. Barts

Pool

from $643/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. Sol e Luna is located in the desirable Terres Basses

Terres Basses (French side), St. Martin

Pool

from $521/Nt
3 3
Details
Escapade Villa offers easy access to activities at Marigot Bay 1 & 2 BR rates available. Views of Marigot Bay from the pool and the large deck at Escapade Villa

Marigot, St. Barts

Near Beach | Pool

from $500/Nt
3 3
Details
Secluded and laid-back retreat in West End Village. 2 BR rate available. Panarea is located in Anguilla\'s West End, just minutes away from the island\'s most beautiful beache

Anguilla

Near Beach | Pool

from $640/Nt
3 3
Details
Seclusion without sacrifice at Villa Rivendell, Flamands? 1 & 2 BR rates available. Amazing view of Flamands Bay from the infinity edge pool

Flamands, St. Barts

Pool

from $714/Nt
3 3
Details
Small, quiet, luxurious resort with ocean views from every room and five-star amenities. 1 & 2 BR rates available.
Has specials. Tuscany photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $775/Nt
3 3
Details
Fountains and lush gardens invite guests to relax and rest at this luxuriously spacious villa. 1 & 2 BR rates available. Villa Gardenia is surrounded by beautiful tropical foliage

St. Thomas, USVI

Pool

from $499/Nt
3 3+
Details
Great 3-bedroom villa on Flamands Beach in St. Barts boasts stunning views and a convenient location 2 BR rate available. Private waterfront pool at Ecoute les Vagues

Flamands, St. Barts

Beachfront | Pool | AC

from $600/Nt
3 2
Details
Well-equipped villa located in Rodney Bay that's close to everything. 1 & 2 BR rates available.
Has specials. The Harbor Townhouses

Rodney Bay, St. Lucia

Near Beach

from $275/Nt
3 3+
Details
Excellent location overlooking St. Jean Bay, Lataniers Villa on St. Barts is cute, comfortable, and affordable 1 & 2 BR rates available. Beautiful views from Lataniers Villa

Saint Jean, St. Barts

Pool

from $514/Nt
3 2
Details
Fabulous three-bedroom hillside villa with ocean views and a pool. 2 BR rate available.
Has specials. Roc Flamands 11 is located just above Flamand Beach

Flamands, St. Barts

Near Beach

from $564/Nt
3 2
Details
Quiet and private villa with beautiful local beaches nearby. 1 & 2 BR rates available. Perched on the hillside of Colombier - Hurakan provides beautiful views of Gustavia Harbour

Colombier, St. Barts

from $469/Nt
3 3
Details
Each villa has a balcony overlooking Grace Bay at this luxury resort complex. 1 & 2 BR rates available.
Has specials. The Venetian photo

Grace Bay, Turks and Caicos

Beachfront | AC

from $875/Nt
3 3+
Details
Spacious 3-bedroom villa sits right on the beach and is close to lots of island amenities, but is still very private Latitude Villa photo

Barbados

Beachfront | Pool | AC

from $1100/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 $886/Nt
3 3
Details
Contemporary villa enjoys a quiet, hillside location and great island views 1 & 2 BR rates available. Anakao Villa photo

Saint Jean, St. Barts

Pool

from $557/Nt
3 2
Details
Stunning sunset and ocean views with a location just minutes from the beach and town. 2 BR rate available. Coco Villa sits above Lorient Bay Beach looking toward St. Jean

Lorient, St. Barts

Pool

from $1143/Nt
3 3
Details
Spacious 3-bedroom colonial style villa features a private pool, landscaped courtyard, and easy access to the beach 2 BR rate available.
Has specials. The private pool at Les Zephyrs offers your own tropical getaway

Terres Basses (French side), St. Martin

Pool

from $414/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
For luxurious views, accommodations, and privacy, this beachfront three-bedroom villa is a dream come true (literally!) 1 & 2 BR rates available.
Has specials. A Dream Come True Villa has amazing ocean views and a fun pool area

Devers Bay, St. John

Beachfront | AC

from $400/Nt
3 3+
Details
Three-bedroom Cap Estate villa with a stunning interior, tropical views, and amenities. 1 & 2 BR rates available.
Has specials. Kessi Villa photo

Cap Estate, St. Lucia

Pool

from $430/Nt
3 3
Details
Gorgeous three-bedroom villa boasts privacy, exceptional views, and simple luxury 1 & 2 BR rates available. Cheyenne Villa photo

Vitet, St. Barts

Pool

from $471/Nt
3 3
Details
3-bedroom contemporary villa has it all, including panoramic ocean views that will take your breath away Lounge chairs on the deck over looking the Caribbean

Pointe Milou, St. Barts

from $2000/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
Stunning contemporary villa offers extreme privacy and lots of space, and you will love the incredible sunset views over the ocean 2 BR rate available. Ti Moun Villa sits just above Gustavia Harbor

Lurin, St. Barts

from $1271/Nt
3 3
Details
Luxury penthouse located on Paynes Bay with staff to meet every need Coral Cove complex

Barbados

Beachfront | AC

from $850/Nt
3 3
Details
Stunning ocean views, beach access, and tons of amenities await you at this comfortable 3-bedroom condo. The pool and view of the ocean from Sapphire Beach

Barbados

Beachfront | AC

from $440/Nt
3 3
Details
Resort living right on the beach! 3-bedroom apartment looks out to the ocean and is conveniently located near St. Lawrence Gap 2 BR rate available. Sapphire Beach #205 photo

Barbados

Beachfront | AC

from $335/Nt
3 3
Details
Spend your next holiday with a bird's eye view of the Carribean from the hill at Summerwinds Villa 2 BR rate available. Summerwinds Villa photo

Oyster Pond (Dutch side), St. Martin

Pool

from $500/Nt
3 3+
Details
Acamar Villa offers gorgeous ocean views with unique, modern living spaces 1 & 2 BR rates available.
Has specials. Enjoy endless ocean views from the patio and pol at Acamar Villa

Toiny, St. Barts

Pool

from $1500/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
A great location, daily housekeeping, and cozy interiors await at this fully screened villa. 1 & 2 BR rates available. Soleil Villa is located in a great area near Meads Bay

Anguilla

Near Beach | Pool

from $400/Nt
3 2+
Details
Enjoy a stunning view of Dover Beach while basking in the luxury of Barbados Sapphire Beach #213 photo

Barbados

Beachfront | Pool | AC

from $440/Nt
3 3
Details
Rethink your priorities with the Dover Beach breeze rushing over you at this Sapphire Beach rental The Sapphire Beach community

Barbados

Beachfront | Pool | AC

from $440/Nt
3 3
Details
Simplicity is at your fingertips when you reserve space at Palisades in Barbados Amazing Caribbean beach in Barbados - Palasides 6A

Barbados

Near Beach | Pool

from $290/Nt
3 3+
Details
Contemporary villa with infinity pool and breathtaking ocean views 1 & 2 BR rates available. Amazing views from the deck at Upside Villa

Pointe Milou, St. Barts

from $557/Nt
3 3
Details
Explore Your Wild Side When You Reserve La Roche Dans L'Eau Villa 1 & 2 BR rates available. A beautiful beach entry pool at La Roche dans l’Eau

Grand Fond, St. Barts

Pool

from $557/Nt
3 3
Details
Private hillside villa with secluded beach and panoramic ocean views 1 & 2 BR rates available.
Has specials. Infinity edge pool with amazing views of Trunk Bay Beach at Soleil villa

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from $560/Nt
3 2
Details
Private terrace, garden dining, and more are waiting at DAN Villa. Amazing ocean views from the pool deck at DAN Villa

Colombier, St. Barts

Pool

from $643/Nt
3 3
Details
Seclusion and convenience to nearby Gustavia and Shell Beach, plus much more at Suite Harbour Villa 1 & 2 BR rates available. Suite Harbour Apartment is located in in the center of the action at Gustavia Harbor

Gustavia, St. Barts

Near Beach

from $571/Nt
3 2
Details
Serene, private Caribbean vacation retreat in the gated community of Villas on the Green Fairwind Villa is located very near to the St. Lucia golf club

Cap Estate, St. Lucia

Near Beach | Pool

from $250/Nt
3 3
Details
Beachfront, steps from Payne’s Bay, St. James, Coral Cove #8 is a stylish apartment with terrific views The balcony at Coral Cove # 8 has a hot tub!

Barbados

Beachfront | AC

from $550/Nt
3 3
Details
Sprawling hillside home with two pools and walking distance to the beach. 2 BR rate available. Lagon Vert Villa photo

Petit Cul de Sac, St. Barts

Near Beach | Pool

from $814/Nt
3 3
Details
Perfect location to enjoy it all, or just relax in your own penthouse 2 BR rate available. Syriana Villa photo

Cupecoy (Dutch side), St. Martin

Near Beach | Pool

from $430/Nt
3 3
Details
Penthouse with private roof deck, near Plaza of Porto Cupecoy for restaurants and entertainment 2 BR rate available. Corfu Villa photo

Cupecoy (Dutch side), St. Martin

Near Beach | Pool

from $429/Nt
3 3
Details
Resort pool, ocean front property and boardwalk nearby Palm Beach Complex in Barbados

Barbados

Beachfront | Pool | AC

from $475/Nt
3 3
Details
Fully staffed and located within Jamaica’s exclusive and premier Tryall Club Luxurious pool area at Linger Longer Villa

Montego Bay, Jamaica

Pool

from $650/Nt
3 3
Details
Private, Greek-inspired community with Cupecoy Beach just a stones' throw away. 1 & 2 BR rates available. Luna Villa is located in the Shore Point complex near La Semanna

Cupecoy (Dutch side), St. Martin

Near Beach | Pool

from $464/Nt
3 4+
Details
Enjoy a beachfront view from your porch while relaxing in your Jacuzzi Sit on the patio at Coral Cove 12 and enjoy beautiful views of the Caribbean

Barbados

Beachfront | AC

from $550/Nt
3 3+
Details
Located directly on Paynes Beach, with an open-concept floor plan and sleek, modern design. Coral Cove #5 - Shutters photo

Barbados

Beachfront | AC

from $550/Nt
3 3
Details
Stunning ocean view from private terrace, and walking distance to fun Coral Cove 6 - The Ivy has great views from the patio - Plus a hot tub

Barbados

Beachfront | AC

from $550/Nt
3 3+
Details
Spacious three bedroom with ocean view and fabulous property amenities 1 & 2 BR rates available. The Schooner Bay complex pool

Barbados

Beachfront | AC

from $480/Nt
3 3
Details
Posh beach front property with heated infinity pool Portico 1 has a beautiful ocean view terrace

Barbados

Near Beach | Pool

from $1100/Nt
3 3
Details
Hillside home with stunning ocean views, a plunge pool, and a gym. 2 BR rate available.
Has specials. Topaze Villa is located on a hillside above Orient Bay

Orient Bay (French side), St. Martin

Pool

from $630/Nt
3 3
Details
Off the beaten path, this is a true Caribbean beachside gem. 1 & 2 BR rates available. A secluded stretch of beach is located just in front of Lo D\'Amour Villa

Marigot, St. Barts

Beachfront | AC

from $457/Nt
3 3+
Details
Classically lovely garden villa just steps from the beach. The plunge pool at Jasmine Villa is a great place to unwind and take a refreshing dip

Barbados

from $400/Nt
3 3
Details
A three-bedroom villa that sits on an acre of luscious island land and boasts endless views of the Caribbean waters 2 BR rate available. Ocean Haven Villa photo

St. Thomas, USVI

Pool

from $475/Nt
3 3
Details
Perfect for 3 couples with beautiful sea views from each room. Sea Dream Villa is near Happy Bay and just a short trip to Friar\'s Bay Beach

Happy Bay (French Side), St. Martin

Pool

from $386/Nt
3 3
Details
This spacious, warm villa is close to everything Rodney Bay has to offer. 1 & 2 BR rates available.
Has specials. Amazing infinity edge pool at Villa Chloesa

Cap Estate, St. Lucia

Pool

from $225/Nt
3 3
Details
A relaxing beachfront villa on Cupecoy with a fantastic beach life and a number of activities from which to choose 2 BR rate available. Bahari Villa photo

Cupecoy (Dutch side), St. Martin

Beachfront | Pool | AC

from $715/Nt
3 3
Details
Spacious penthouse suite on Dover Beach with nautical decor and gorgeous ocean views. Sapphire Beach Complex

Barbados

Beachfront | Pool | AC

from $440/Nt
3 3
Details
An excellent 3-bedroom villa on the hill of Trunk Bay with a pool, easy access to the beach, and very little to get in the way of you and the scenery 1 & 2 BR rates available. Lune villa has amazing ocean views from the pool area

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from $475/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
Charming villa with multiple living and dining areas. 2 BR rate available. Festiva Villa photo

Pointe Milou, St. Barts

Pool

from $1286/Nt
3 3
Details
A serene, extremely private villa that provides views of the mountains, sunrise, and sunset! 1 & 2 BR rates available. Ocean Gem is located on Long Pond Bay and has great ocean views

Anguilla

Pool

from $500/Nt
3 3+
Details
This villa's two-level Great Room gives guests room to relax. 1 & 2 BR rates available.
Has specials. Sea Palms Villa photo

Great Cruz Bay, St. John

Pool

from $571/Nt
3 3+
Details
A beautiful, family-friendly villa overlooking the gorgeous and famous Shoal Bay East. 1 & 2 BR rates available. Dream Catcher Villa is located less than a mile from Shoal Bay Beach

Anguilla

Near Beach | Pool

from $625/Nt
3 3+
Details
Exquisitely posh 3 bedroom villa close to Orient Bay and Grand Case 1 BR rate available. 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
Family-friendly villa with views over wild Toiny Bay. 1 & 2 BR rates available. Enzuma Villa photo

Toiny, St. Barts

Pool

from $571/Nt
3 2+
Details
Lies in preserved section of St. Barth with watersport access and great value. 1 & 2 BR rates available. Overlooking the hills

Grand Fond, St. Barts

Pool

from $350/Nt
3 3
Details
Elegantly rustic hilltop home with a private pool. 1 & 2 BR rates available. Spectacular views from the pool and veranda at Caribbean Palm Villa

Rendezvous Bay, St. John

from $643/Nt
3 3+
Details
Sandy Lane Estate villa with beautiful decor and a spacious layout. Pool at Galena villa surrounded by lush tropical gardens

Barbados

Pool

from $650/Nt
3 3+
Details
Beautiful living spaces with ample outdoor lounging. 1 & 2 BR rates available. Villa with view of ocean

Lurin, St. Barts

Pool

from $1536/Nt
3 3
Details
Family villa in the hills looking over the forests of St. Barth. Patio deck and pool at Villa Indyana

Lurin, St. Barts

Pool

from $829/Nt
2 2+
Details
Well-appointed two bedroom villa a short walk from Meads Bay Beach. Has specials. Beachside 2 Villa at Meads Bay has direct access to Meads Bay Beach

Anguilla

Near Beach

from $750/Nt
2 2+
Details
Short walk to one of the top-rated beaches in the world. 1 BR rate available.
Has specials. Beachside Villa 3 at Meads Bay has a personal pool, and beach access

Anguilla

Near Beach | Pool

from $550/Nt
2 2+
Details
Private pool at the Palm Grove 2 Bedroom Villa

Nevis

Near Beach | Pool

from $1400/Nt
2 2
Details
South Caicos resort villa with two equal bedrooms. Has specials. Enjoy endless ocean views from the patio at Sailrock Resort Beach Fron Villa 2 bedroom

South Caicos, Turks and Caicos

Beachfront | Pool | AC

from $2345/Nt
2 2
Details
Split-level beachfront property with resort amenities. Great views of the ocean from Sapphire Beach 104

Barbados

Beachfront | AC

from $335/Nt
2 2
Details
The views are golden from this villa's heated infinity pool and tri-level deck. 1 BR rate available. Golden View Villa sits above Toiny Bay on the Vitet hillside

Vitet, St. Barts

Pool

from $1000/Nt
2 2
Details
Intimate and affordable beach house just steps from beautiful Dawn Beach 1 BR rate available.
Has specials. Beach House Younes photo

Dawn Beach (Dutch side), St. Martin

Near Beach | Pool

from $379/Nt
2 2+
Details
Two minutes to Lorient Beach, this villa has exquisite water views in a cozy, romantic setting. 1 BR rate available. Easy Villa photo

Lorient, St. Barts

Near Beach | Pool

from $421/Nt
2 2
Details
Sunrock Villa is a great place for a family with younger children. 1 BR rate available. Cocktails on the covered patio or a dip in the infinity pool are both great options at Sunrock Villa

Colombier, St. Barts

Pool

from $343/Nt
2 2
Details
With a huge private pool, tennis courts, and gym, this villa is perfect for active couples or families. 1 BR rate available.
Has specials. La Nina is located in Terres Basses overlooking the Caribbean

Terres Basses (French side), St. Martin

Pool

from $371/Nt
2 2
Details
A lovely villa within a short walk to Flamands Beach and close to Isle de France hotel 1 BR rate available.
Has specials. Beautiful views of the ocean from your own pool at Magic bird Villa

Flamands, St. Barts

Near Beach | Pool

from $857/Nt
2 2
Details
Amazing views in a picturesque and relaxed setting Glitter Bay Resort

Barbados

Beachfront | Pool | AC

from $490/Nt
2 2
Details
The privacy of a villa and convenience of a full-service concierge all under one roof on Meads Bay. Has specials. Enjoy endless Caribbean views from the Meads Bay Beachside Villa

Anguilla

Near Beach | Pool

from $750/Nt
2 2+
Details
Contemporary and modern villa with all the amenities, perfect for exploring Flamands Beach 1 BR rate available. Les Embruns Villa photo

Flamands, St. Barts

Near Beach | Pool

from $467/Nt
2 2
Details
Your very own exotic, secluded paradise with an earthy, open feel Perfect pool - Walk out the door and take a dip!!

Cap Estate, St. Lucia

Pool

from $300/Nt
2 2
Details
The Ritz Carlton Club Condo offers the best in both private and social areas for couples or small families traveling together The Ritz Carlton Club Condo photo

St. Thomas, USVI

Beachfront | AC

from $730/Nt
2 2+
Details
Luxury Resort Villa with Kids Club The Ritz Carlton Club Suite Condominium photo

St. Thomas, USVI

Beachfront | AC

from $730/Nt
2 2
Details
Comfortable, family-friendly villa right on Mullins Beach. Sunset Reach Villa photo

Barbados

Beachfront | AC

from $424/Nt
2 2
Details
The Perfect Day is what Green Flash #3 at Coral Cove offers to bring to your vacation Coral Cove

Barbados

Beachfront | AC

from $375/Nt
2 2+
Details
Villa 21 is near the beaches of Lorient and Salines; take a 4-wheel drive into this ultra-private residence 1 BR rate available. Enjoy beautiful views of Lorient Bay form 21 Villa

Petite Saline, St. Barts

Pool

from $529/Nt
2 2
Details
Spacious and stylish split-level condo with two bedrooms is right on the beach. Sapphire Beach #118 photo

Barbados

from $335/Nt
2 2
Details
This darling, tropical hideaway is 100 yards from Mead's Bay Beach. Beach Palm Villa has a great patio and pool

Anguilla

Near Beach | Pool

from $695/Nt
2 2+
Details
Stunning contemporary villa offers sun, fun, and endless views for a luxurious vacation experience Grain de Folie Villa photo

Colombier, St. Barts

Pool

from $714/Nt
2 2
Details
Newly remodeled two-bedroom apartment comes with lots of amenities and direct access to the beach and pool 1 BR rate available. Glitter Bay 103 Sea View offers great ocean views

Barbados

Beachfront | Pool | AC

from $340/Nt
2 2
Details
Newly refurbished condo on Barbados' West Coast with amazing beach, large pool, restaurant and the best kids pool on the island 1 BR rate available. Glitter Bay 113 Sea Wind 2 has a great patio

Barbados

Beachfront | AC

from $300/Nt
2 2
Details
Caneel Trailside Cottage Caneel Trailside Cottage offers great access to nature in the heart of VI National Parkin the heart of VI National Park 1 BR rate available.
Has specials. Caneel Trailside Villa is located right next to the Virgin Islands National Park

Cruz Bay, St. John

Pool

from $386/Nt
2 2
Details
A naturalistic villa on a hillside in Marigot will make your St. Barts vacation perfect 1 BR rate available. The pool is situated in a beautiful tropical setting at Kyody Villa

Marigot, St. Barts

Pool

from $371/Nt
2 2
Details
Relaxing hideaway with amenities and beaches close by Val Andre Villa is just steps away from the ocean

Saint Jean, St. Barts

Near Beach

from $920/Nt
2 2
Details
Great contemporary villa is brand new and enjoys incredible island and water views, with convenient access to Gustavia 1 BR rate available. Harry\'s Villa photo

Saline, St. Barts

Near Beach | Pool

from $571/Nt
2 2
Details
Gorgeous 2-bedroom overlooking Flamands Beach offers privacy, luxury, and a ton of fun activities nearby 1 BR rate available. Bijou Villa photo

Flamands, St. Barts

Pool

from $429/Nt
2 2
Details
A gorgeous 2-bedroom resort villa on famous Grace Bay Beach - West Bay Club has a restaurant, beach bar and staff to attend to your vacation needs. Has specials. Grace Bay Beach along the West Bay Club

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1020/Nt
2 2
Details
Airy 2-bedroom apartment, close to the beach and amenities, offers views, pool, privacy, and service 1 BR rate available. The view of the ocean from Glitter Bay 101 - Oceanside

Barbados

Beachfront | Pool | AC

from $340/Nt
2 2
Details
A Wyndham Resort stay with a beachfront location and tons of activity options! Rio Mar Beach Resort Luxury Ocean Villa photo

Northeast Coast, Puerto Rico

Beachfront | Pool | AC

from $450/Nt
2 2
Details
Escape to this Chalk Sound villa for rest and relaxation. Jayla Villa is just on Chalk Sound

Chalk Sound, Turks and Caicos

Pool

from $400/Nt
2 2
Details
Wake up to a view of the Orient Bay when you reserve L'Agua Villa 1 BR rate available.
Has specials. L\'Agua Villa photo

Oyster Pond (Dutch side), St. Martin

Pool

from $379/Nt
2 2
Details
Luxury apartment on beautiful Simpson bay 1 BR rate available. Unforgettable at Las Arenas is a ground floor unit with great views of Simpson Bay

Simpson Bay (Dutch side), St. Martin

Beachfront | AC

from $340/Nt
2 2
Details
Bright and airy villa set on a hilltop with stunning panoramic ocean views. 1 BR rate available. Oceana Villa is located on a hill above Crocus Bay

Anguilla

Near Beach | Pool

from $420/Nt
2 2
Details
Quaint Caribbean villa near Gustavia 1 BR rate available. Villa Gros Ilets photo

Lurin, St. Barts

Pool

from $506/Nt
2 2
Details