Caribbean Villa Rentals


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Vista Caribe

United States Virgin Islands, St. John

from $857 /night
up to 8 guests

Vista Caribe

4 bedroom 4.5 bath USVI villa in St. John

One sunset seen from the sweeping decks of 'Vista Caribe' and you’ll be head-over-heels.

Vista Del Mar

Vista del Mar at the Tryall Club

Jamaica, Montego Bay

from $1357 /night
up to 8 guests

Vista del Mar at the Tryall Club

4 bedroom 4 bath Jamaica villa in Montego Bay

One of the most enviable locations at Tryall atop Barnes Hill, Vista Del Mar is a Jamaican Classic offering charm and spectacular views.

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Vista Villa

Anguilla, Blowing Point

from $675 /night
up to 8 guests

Vista Villa

4 bedroom 4 bath Anguilla villa in Blowing Point

Vista is an idyllic, luxury four-bedroom contemporary villa superbly located on the water-front and offering magnificent views of neighboring St. Martin in the distance and the crystal azure water.

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Waters Edge Ridge Villa

British Virgin Islands, Virgin Gorda

from $3950 /night
up to 8 guests

Waters Edge Ridge Villa

4 bedroom 4 bath BVI villa in Virgin Gorda

Perched high on the north side of the community, Waters Edge Villa enjoys waves of luxury and expansive views of the Atlantic Ocean, Anegada, Oil Nut Bay and the Oil Nut Bay Resort Community.

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Westhaven

Barbados, Gibbes Beach

from $2100 /night
up to 8 guests

Westhaven

4 bedroom 4.5 bath Barbados villa in Gibbes Beach

Westhaven is a two-story, luxurious, beachfront villa located on the world renowned Gibbs Beach; a white, sandy beach lapped by the calmer blue Caribbean warm waters on the West Coast of Barbados.

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Whispering Palms at Jumby Bay

Antigua, Jumby Bay Island

from $8100 /night
up to 8 guests

Whispering Palms at Jumby Bay

4 bedroom 4.5 bath Antigua villa in Jumby Bay Island

Spacious, comfortable and beautifully furnished, Whispering Palms offers a welcoming blend of Caribbean luxury and charm.

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Whitegates

Barbados, St. James

from $1500 /night
up to 8 guests

Whitegates

4 bedroom 4.5 bath Barbados villa in St. James

Whitegates is a beautiful four-bedroom beachfront home, situated on a cliff-side with magnificent sea views.

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Wild Cane Ridge No. 5 - Gully’s Edge at Royal Westmoreland

Barbados, Alleynes Bay

from $2500 /night
up to 8 guests

Wild Cane Ridge No. 5 - Gully’s Edge at Royal Westmoreland

4 bedroom 4.5 bath Barbados villa in Alleynes Bay

Offering a tranquil retreat for those in search of a memorable holiday, Gully’s Edge is a luxurious Four-Bedroom Villa overlooking the 17th green of the Royal Wesmoreland Golf Course.

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Windjammer Landing - Hilltop Villas

St. Lucia, Labrelotte Bay

from $1076 /night
up to 8 guests

Windjammer Landing - Hilltop Villas

4 bedroom 4 bath St. Lucia villa in Labrelotte Bay

Tucked away on a lush hillside along the cobalt Caribbean Sea, Windjammer Landing Villa Beach Resort is unlike any destination you’ve witnessed.

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Windjammer Landing - The Manor Collection

St. Lucia, Labrelotte Bay

from $1911 /night
up to 12 guests

Windjammer Landing - The Manor Collection

4 bedroom 4 bath St. Lucia villa in Labrelotte Bay

Tucked away on a lush hillside along the cobalt Caribbean Sea, Windjammer Landing Villa Beach Resort is unlike any destination you’ve witnessed.

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Windsong

Jamaica, Montego Bay

from $714 /night
up to 8 guests

Windsong

4 bedroom 4 bath Jamaica villa in Montego Bay

Windsong is an exquisite and very private home just minutes from Round Hill. Designed by noted architect Kasimir Coribut, the site benefits from spectacular views day and night and the most favorable tradewinds. The east view captures the sunrise and Montego Bay ... the west view is an equally lovely vista of Round Hill, the sea and the sunset.

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Windsong - Oceanfront Penthouse Suites

Turks & Caicos, Providenciales

from $2021 /night
up to 10 guests

Windsong - Oceanfront Penthouse Suites

4 bedroom 3 bath Turks & Caicos villa in Providenciales

With a coveted setting on the pristine white sands of Grace Bay Beach, Windsong Resort is the only four-star resort on Providenciales located directly on a snorkeling reef, which lies just 20 yards offshore.

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Wymara Resort - Acua Villa

Turks & Caicos, Providenciales

from $5250 /night
up to 9 guests

Wymara Resort - Acua Villa

4 bedroom 4.5 bath Turks & Caicos villa in Providenciales

Whether planning an intimate escape with friends or a family getaway, Wymara’s four-bedroom villas are ideal for those looking for luxurious seclusion, while enjoying the abundance of amenities Wymara Resort has to offer.

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5 Bedroom Artist Villa at Amanyara

Turks & Caicos, Providenciales

rates on request
up to 12 guests

5 Bedroom Artist Villa at Amanyara

5 bedroom 5 bath Turks & Caicos villa in Providenciales

A nature lover's paradise, Amanyara sits on a promontory on the western shore of Providenciales.

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Adagio

British Virgin Islands, Virgin Gorda

from $740 /night
up to 10 guests

Adagio

5 bedroom 6 bath BVI villa in Virgin Gorda

Paradise awaits in this vacation rental in Virgin Gorda.

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Alinna Villa

Turks & Caicos, Providenciales

from $2151 /night
up to 10 guests

Alinna Villa

5 bedroom 6.5 bath Turks & Caicos villa in Providenciales

Villa Alinna is located in the area of Chalk Sound and is a gorgeous five-bedroom, full suite villa with breathtaking views of Chalk Sound National Park.

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Alizee

Turks & Caicos, Providenciales

from $6429 /night
up to 10 guests

Alizee

5 bedroom 5 bath Turks & Caicos villa in Providenciales

Immerse yourself in private paradise at Alizee Villa, a 5-bedroom, 5-bathroom luxury vacation villa on 1.9 acres in beautiful Chalk Sound, Providenciales.

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Allamanda

Jamaica, Montego Bay

from $1357 /night
up to 10 guests

Allamanda

5 bedroom 4 bath Jamaica villa in Montego Bay

ALLAMANDA is a brilliant contemporary private villa with large heated pool, an excellent staff including top-rated chef and nearby membership at Round Hill.

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Amandara

St. Martin, St. Martin (French)

from $2786 /night
up to 10 guests

Amandara

5 bedroom 6 bath St. Martin villa in St. Martin (French)

Set above the gorgeous Baie Rouge Beach along Marigot Bay, Villa Amandara is a brand-new property in the Terres Basses area of St. Martin.

Anguilla Villa

Amarilla

Anguilla, Island Harbor

from $1800 /night
up to 10 guests

Amarilla

5 bedroom 6.5 bath Anguilla villa in Island Harbor

Set on a magnificent stretch of dramatic coastline with sweeping views of the Caribbean, 5-bedroom Villa Amarilla is the epitome of a perfect luxury island retreat.

Amethyst

St. Martin, Terres Basses

from $1000 /night
up to 10 guests

Amethyst

5 bedroom 5 bath St. Martin villa in Terres Basses

From its privileged cliffside position overlooking the Pointe du Bluff in Terres Basses, on French St. Martin’s northern coastline, Villa Amethyst is nestled between the Baie aux Cayes and the spectacular natural rock archway known as the “Trou de David''.

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Aquamare

British Virgin Islands, Virgin Gorda

from $34000 /night
up to 12 guests

Aquamare

5 bedroom 5 bath BVI villa in Virgin Gorda

Welcome to an unparalleled luxury villa experience in the Caribbean.

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Aquaria at Casa de Campo

Dominican Republic, la Romana

from $2249 /night
up to 10 guests

Aquaria at Casa de Campo

5 bedroom 5.5 bath Dominican Republic villa in la Romana

Full of luxurious amenities like marble floors, dramatic art, and fashionable interiors, no detail has been spared in this one-story villa.

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Arc En Ciel

St. Lucia, Soufriere

from $2550 /night
up to 10 guests

Arc En Ciel

5 bedroom 5.5 bath St. Lucia villa in Soufriere

'Arc En Ciel' is a wonderful property, spectacularly situated on Beau Estate, between the World Heritage site of the Pitons. The property is situated above the Caribbean Sea and is a short distance from Jalousie Beach and hotel. The nearest town is Soufriere, which is a sleepy fishing village.

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Arrecife 25

Dominican Republic, Punta Cana

from $2080 /night
up to 12 guests

Arrecife 25

5 bedroom 5.5 bath Dominican Republic villa in Punta Cana

This tropical Villa presents you with one of a kind accommodation experience!

Ashiana Villa

St. Lucia, Marigot Bay

from $750 /night
up to 11 guests

Ashiana Villa

5 bedroom 4.5 bath St. Lucia villa in Marigot Bay

Villa Ashiana is a spacious 5-bedroom 4.5 bath villa in Marigot Bay with gorgeous panoramic views, excellent for families, groups or entertaining.

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Avanti

St. Martin, St. Martin (French)

from $2000 /night
up to 10 guests

Avanti

5 bedroom 5.5 bath St. Martin villa in St. Martin (French)

A superbly appointed five-bedroom residence in Terres Basses, Avanti welcomes you from its impressive gated entrance along a palm-lined driveway to the main entrance doors fronted by stone fountains.

Bajan Heights at Royal Westmoreland

Barbados, St. James

from $1250 /night
up to 10 guests

Bajan Heights at Royal Westmoreland

5 bedroom 5 bath Barbados villa in St. James

This gorgeous executive five bedroom villa sits atop the ridge overlooking the shimmering West Coast of Barbados and is a blend of modern finishes and classic chic island style.

Bali Hai

Bali Hai at the Tryall Club

Jamaica, Montego Bay

from $1786 /night
up to 10 guests

Bali Hai at the Tryall Club

5 bedroom 6 bath Jamaica villa in Montego Bay

On seven acres overlooking the Tryall golf course and the Caribbean Sea, Bali Hai is among the most beautiful and spacious private homes at the Tryall Club. The unique architecture has situated all bedrooms for maximum privacy.

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Baltazar

St. Martin, St. Martin (French)

from $786 /night
up to 10 guests

Baltazar

5 bedroom 5.5 bath St. Martin villa in St. Martin (French)

Located on St. Martin’s northern coastline and overlooking the scenic island of Pinel, Villa Baltazar offers five bedrooms, a private pool and an unobstructed view over the water of the sheltered bay of Cul de Sac.

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Beach Enclave Grace Bay - 5 Bedroom Ocean View Villa

Turks & Caicos, Providenciales

from $5200 /night
up to 10 guests

Beach Enclave Grace Bay - 5 Bedroom Ocean View Villa

5 bedroom 5.5 bath Turks & Caicos villa in Providenciales

The prestigious collection of villas and beach houses is ideal for families, multi-generational vacations, romantic getaways, small corporate retreats, and intimate weddings. With a modern design, dedicated staff, and thoughtfully considered amenities, each stay is an entirely bespoke experience. Personalized experiences and impeccable service define Beach Enclave, and it all begins well in advance of your arrival. Thoughtfully designed by our island experts, our services and amenities ensure a blissful, worry-free stay — so that you can slip seamlessly into the rhythm of the Turks and Caicos Islands from the moment you arrive on Providenciales.

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Beach Enclave Long Bay Beach - 5 Bedroom Beachfront Villa

Turks & Caicos, Providenciales

from $5300 /night
up to 10 guests

Beach Enclave Long Bay Beach - 5 Bedroom Beachfront Villa

5 bedroom 5 bath Turks & Caicos villa in Providenciales

The prestigious collection of villas and beach houses is ideal for families, multi-generational vacations, romantic getaways, small corporate retreats, and intimate weddings. With a modern design, dedicated staff, and thoughtfully considered amenities, each stay is an entirely bespoke experience. Personalized experiences and impeccable service define Beach Enclave, and it all begins well in advance of your arrival. Thoughtfully designed by our island experts, our services and amenities ensure a blissful, worry-free stay — so that you can slip seamlessly into the rhythm of the Turks and Caicos Islands from the moment you arrive on Providenciales.

Villa Paprika

Beach Villa Paprika

Turks & Caicos, Providenciales

from $2686 /night
up to 12 guests

Beach Villa Paprika

5 bedroom 5.5 bath Turks & Caicos villa in Providenciales

Rejuvenate in Caribbean classical grandeur at an elegant three-story beachfront estate on Grace Bay Beach. Grace Bay is voted “World’s Top Beach” year after year.

Beachcomber

British Virgin Islands, Virgin Gorda

from $1457 /night
up to 10 guests

Beachcomber

5 bedroom 5.5 bath BVI villa in Virgin Gorda

Mahoe Beach's white sand and azure waters are just steps from this lovely, very deluxe, five-bedroom home.

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Beachert at Jumby Bay

Antigua, Jumby Bay Island

from $13000 /night
up to 10 guests

Beachert at Jumby Bay

5 bedroom 5.5 bath Antigua villa in Jumby Bay Island

Occupying an unrivaled beachfront position, Beachert provides truly dramatic views of Davis Bay and the Caribbean Sea looking across to the hills of mainland Antigua.

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Beaches Edge

Anguilla, Blowing Point

from $1500 /night
up to 10 guests

Beaches Edge

5 bedroom 5 bath Anguilla villa in Blowing Point

Welcome to Beaches Edge Rental Villa on Anguilla.

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Belle Etoile

St. Martin, St. Martin (French)

from $2714 /night
up to 10 guests

Belle Etoile

5 bedroom 5.5 bath St. Martin villa in St. Martin (French)

Belle Etoile in St. Martin is a stunning estate villa with a French Caribbean style.

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Belle Fontaine

St. Martin, St. Martin (French)

from $990 /night
up to 10 guests

Belle Fontaine

5 bedroom 5 bath St. Martin villa in St. Martin (French)

Villa Belle Fontaine in St Martin an elegant French Provence property that meets Creole style

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Benjoli Breeze at Royal Westmoreland

Barbados, Alleynes Bay

from $2035 /night
up to 10 guests

Benjoli Breeze at Royal Westmoreland

5 bedroom 6 bath Barbados villa in Alleynes Bay

The grand, colonial-style entrance opens to a grand lobby area, which includes a powder room/bathroom and an office that can be converted to a bedroom.

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Bohemia Sandy Lane

Barbados, Sandy Lane

from $3500 /night
up to 10 guests

Bohemia Sandy Lane

5 bedroom 5 bath Barbados villa in Sandy Lane

Bohemia Sandy Lane is a spectacular ridge-front luxury holiday home in Barbados with breathtaking sea views.

Bougainvillea

Bougainvillea at the Tryall Club

Jamaica, Montego Bay

from $1767 /night
up to 10 guests

Bougainvillea at the Tryall Club

5 bedroom 6 bath Jamaica villa in Montego Bay

Bougainvillea is one of the most stylish homes in this collection. Brilliant architecture and design have resulted in a luxurious state-of-the-art vacation home that is elegant but not daunting.

Calliaqua

Calliaqua at Sugar Hill

Barbados, Holetown

from $1150 /night
up to 10 guests

Calliaqua at Sugar Hill

5 bedroom 5 bath Barbados villa in Holetown

Embark on an unforgettable journey. Step through the doors of 'Calliaqua' and experience the intrigue, adventure and romance of this beautiful five-bedroom villa.

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Calypso

Turks & Caicos, Providenciales

from $1750 /night
up to 10 guests

Calypso

5 bedroom 5 bath Turks & Caicos villa in Providenciales

Escape to your own bit of paradise – Villa Calypso. With its five air-conditioned bedrooms and bathrooms, Villa Calypso is the definition of luxury.

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Carlota

United States Virgin Islands, St. John

from $4575 /night
up to 10 guests

Carlota

5 bedroom 6.5 bath USVI villa in St. John

Perched 500 feet on a hillside in the gated enclave of Upper Peter bay is an elegant, five-bedroom sanctuary in a mesmerizing setting.

Casa Cervo

St. Martin, St. Martin (French)

from $1714 /night
up to 10 guests

Casa Cervo

5 bedroom 4.5 bath St. Martin villa in St. Martin (French)

Set in a tropical courtyard with circular drive, the grand raised entrance begins the crescendo for the view.

Casa de la Playa

St. Martin, Terres Basses

from $3171 /night
up to 10 guests

Casa de la Playa

5 bedroom 5 bath St. Martin villa in Terres Basses

Villa Casa de la Playa, in Saint Martin, incredible luxurious property on the beach of Baie Longue.

Casuarina

Barbados, Holetown

from $1350 /night
up to 10 guests

Casuarina

5 bedroom 5.5 bath Barbados villa in Holetown

Commanding views of the verdant fairway and the Caribbean Sea beyond, is Casuarina House on the West Coast.

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C’est La Vie

St. Lucia, Bois D'Orange

from $950 /night
up to 12 guests

C’est La Vie

5 bedroom 5.5 bath St. Lucia villa in Bois D’Orange

Situated on the northernmost peninsula of St. Lucia and entirely surrounded by lush tropical foliage, C’est la Vie Villa offers total tranquility and relaxation to its guests.

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Champagne Shores

Anguilla, Blowing Point

from $1775 /night
up to 10 guests

Champagne Shores

5 bedroom 5.5 bath Anguilla villa in Blowing Point

Champagne Shores Villa is a private luxury villa with light-filled indoor/outdoor living and fresh modern interiors that showcase the resplendent natural views of the Caribbean and St. Martin.

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Cielo at the Tryall Club

Jamaica, Montego Bay

from $1786 /night
up to 10 guests

Cielo at the Tryall Club

5 bedroom 6 bath Jamaica villa in Montego Bay

Cielo means "sky" and "heaven" and the name tells a lot about living in this wonderful villa on a hill. Add the all-day panorama of blue Caribbean Sea at every glance and "heaven" gets even better!

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