Caribbean Villa Rentals


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Chase the Sun

United States Virgin Islands, St. John

from $771 /night
up to 8 guests

Chase the Sun

4 bedroom 4.5 bath USVI villa in St. John

Chase the Sun is an incredibly private, luxury four bedroom villa located in the gated community of Virgin Grande Estates.

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Cherry Red at Royal Westmoreland

Barbados, Alleynes Bay

from $450 /night
up to 8 guests

Cherry Red at Royal Westmoreland

4 bedroom 3 bath Barbados villa in Alleynes Bay

Cherry Red at 20 Sugar Cane Ridge is a well-appointed, modern Caribbean villa, nestled in the exclusive Royal Westmoreland Golf Resort in Barbados.

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Claro de Luna at Casa de Campo

Dominican Republic, la Romana

from $1599 /night
up to 8 guests

Claro de Luna at Casa de Campo

4 bedroom 4 bath Dominican Republic villa in la Romana

Claro de Luna is a beautiful two-story villa that enhances the beauty of the Caribbean, with inviting spaces that will delight guests and occupants alike.

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Coconut Grove 1 “Spinalonga” at Royal Westmoreland

Barbados, Alleynes Bay

from $1045 /night
up to 8 guests

Coconut Grove 1 “Spinalonga” at Royal Westmoreland

4 bedroom 4.5 bath Barbados villa in Alleynes Bay

Located within the renowned Royal Westmoreland Golf Resort, Coconut Grove 1 is a spacious four-bedroom, four-and-a-half-bathroom residence ideally located within close proximity to the resort amenities.

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Coconut Grove 8 at Royal Westmoreland

Barbados, Alleynes Bay

from $1045 /night
up to 8 guests

Coconut Grove 8 at Royal Westmoreland

4 bedroom 4 bath Barbados villa in Alleynes Bay

Quietly nestled within the desirable Coconut Grove avenue of the renown Royal Westmoreland Golf Resort, Coconut Grove 8 is a spacious four-bedroom, four-and-a-half-bathroom property, ideal for those in pursuit of a tropical retreat.

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Coralina at Casa de Campo

Dominican Republic, la Romana

from $2099 /night
up to 8 guests

Coralina at Casa de Campo

4 bedroom 4 bath Dominican Republic villa in la Romana

A welcoming brick-paved driveway bordered by tropical flowers leads guests to the entrance of this one-story villa.

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Crystal Sunrise

Anguilla, Sandy Hill

from $1107 /night
up to 10 guests

Crystal Sunrise

4 bedroom 4 bath Anguilla villa in Sandy Hill

Crystal Sunrise has gorgeous views of St. Maarten and is a short walk to Sandy Hill Bay beach.

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Dreamin Blue

St. Martin, St. Martin (French)

from $1014 /night
up to 8 guests

Dreamin Blue

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

Villa Dreamin Blue, the most beautiful view of Saint Martin, which offers you a breathtaking panoramic view of the Caribbean Sea, sunrise and sunset.

EauSea

United States Virgin Islands, St. John

from $1111 /night
up to 8 guests

EauSea

4 bedroom 5.5 bath USVI villa in St. John

Fanned out atop a hillside overlooking Great Cruz Bay on St. John's south shore, EauSea boasts a wonderfully spacious floorplan and several downright glorious areas to entertain.

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Eight Rivers at Prospect Estate

Jamaica, Ocho Rios

from $1200 /night
up to 8 guests

Eight Rivers at Prospect Estate

4 bedroom 4.5 bath Jamaica villa in Ocho Rios

Set within one and a half acres of tropical gardens, populated by mature indigenous trees, plants and flowers, the Eight Rivers villa has a magnificent swimming pool and sun terrace overlooking a gazebo and the sea beyond.

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Equinox

St. Lucia, Gros Islet

from $700 /night
up to 8 guests

Equinox

4 bedroom 4 bath St. Lucia villa in Gros Islet

Equinox is situated at the prime location of Sea Breeze Hills in Cap Estate and enjoys uninterrupted views out to sea.

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Estate Rose

United States Virgin Islands, St. John

from $1071 /night
up to 8 guests

Estate Rose

4 bedroom 5.5 bath USVI villa in St. John

Estate Rose is a four+ bedroom luxury villa located on 1.1 acres spanning a ridge top between Great Cruz Bay and Chocolate Hole.

Etoile de Mer

Turks & Caicos, Providenciales

from $943 /night
up to 8 guests

Etoile de Mer

4 bedroom 4 bath Turks & Caicos villa in Providenciales

Etoile de Mer is surrounded by palm trees on an acre of land on Sunset Bay one of the islands prettiest beaches and known for its privacy.

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Etoile de Mer

St. Martin, Sint Maarten

from $895 /night
up to 8 guests

Etoile de Mer

4 bedroom 5 bath St. Martin villa in Sint Maarten

Etoile de Mer is located on the edge of the Caribbean Sea in a residence known a Shore Pointe.

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Eureka at Tryall Club

Jamaica, Montego Bay

from $1171 /night
up to 8 guests

Eureka at Tryall Club

4 bedroom 4 bath Jamaica villa in Montego Bay

This very special villa not only offers sweeping sea views but enjoys a very private location surrounded by a garden full of meticulously cared-for specimen flowers. Beloved by many guests and with a high repeat factor the elegant interiors are a testament to Jamaican master craftsmanship.

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Farniente

St. Martin, Sint Maarten

from $786 /night
up to 8 guests

Farniente

4 bedroom 4 bath St. Martin villa in Sint Maarten

Villa Farniente on St. Martin is a gorgeous and exceptionally popular villa located at the beautiful Shore Pointe on the exclusive, scenic Cupecoy Beach.

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Frangipani at Prospect Estate

Jamaica, Ocho Rios

from $1100 /night
up to 8 guests

Frangipani at Prospect Estate

4 bedroom 4.5 bath Jamaica villa in Ocho Rios

Frangipani takes its’ name from the tropical Frangipani tree which produces fragrant white, pink or yellow flowers. Several of these trees surround the house.

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Frangipani

Anguilla, Meads Bay

from $4100 /night
up to 8 guests

Frangipani

4 bedroom 4.5 bath Anguilla villa in Meads Bay

A part of the boutique Frangipani Beach Resort — Travel and Leisure’s 2018 #1 ranked resort in the Caribbean and #3 in the world — this Anguillan beauty combines the private villa lifestyle with the bespoke amenities of a world class resort.

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Great Turtle

United States Virgin Islands, St. John

from $681 /night
up to 8 guests

Great Turtle

4 bedroom 4.5 bath USVI villa in St. John

Notched into a beautifully-landscaped hillside, Great Turtle Villa, a four-bedroom villa commands sweeping views of Coral Bay, the Caribbean Sea and the emerald green hills of Bordeaux Mountain.

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Hacienda 82

Dominican Republic, Punta Cana

from $1080 /night
up to 10 guests

Hacienda 82

4 bedroom 4.5 bath Dominican Republic villa in Punta Cana

This amazing and mesmerizing villa presents you with one of a kind vacation experience!

Hacienda A18 - Tranquila

Dominican Republic, Punta Cana

from $1000 /night
up to 10 guests

Hacienda A18 - Tranquila

4 bedroom 4.5 bath Dominican Republic villa in Punta Cana

Indulge yourself and all your family and friends in some quality time and relaxed days in one the most secluded neighborhoods in Punta Cana.

Hacienda

St. Martin, St. Martin (French)

from $636 /night
up to 8 guests

Hacienda

4 bedroom 3 bath St. Martin villa in St. Martin (French)

This elegant Spanish-Caribbean style villa is designed to capture the views and maximize outdoor living.

Hakuna Matata

United States Virgin Islands, St. John

from $1286 /night
up to 8 guests

Hakuna Matata

4 bedroom 5.5 bath USVI villa in St. John

Worthy of the most stylish home design magazines, 'Hakuna Matata' is the epitome of high-end island living.

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Happy Bay Villa

St. Martin, St. Martin (French)

from $770 /night
up to 8 guests

Happy Bay Villa

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

Near the Caribbean's gourmet paradise - Grand Case - sits the exclusive, very private enclave of Mont Choisy, home to the stylish Happy Bay Villa.

Hemingway House

Barbados, Gibbes Beach

from $2150 /night
up to 8 guests

Hemingway House

4 bedroom 4.5 bath Barbados villa in Gibbes Beach

Top architect Larry Warren's latest plantation style designed Hemingway House is tucked away between the serenity of Gibbes Beach and the highly popular Mullins Beach.

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High Spirits at Royal Westmoreland

Barbados, Alleynes Bay

from $1050 /night
up to 8 guests

High Spirits at Royal Westmoreland

4 bedroom 4.5 bath Barbados villa in Alleynes Bay

This impressive four-bedroom villa is strategically positioned on a ridge, commanding breathtaking views across the immaculately-groomed golf course, a Robert Trent Jones Jr. design, to the alluring turquoise waters of the West Coast shoreline.

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Illusion at Sugar Hill

Barbados, Holetown

from $2250 /night
up to 10 guests

Illusion at Sugar Hill

4 bedroom 4.5 bath Barbados villa in Holetown

'Illusion' is a custom-built, private villa nestled in the gated resort community of the very popular Sugar Hill Resort.

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Island Rider

United States Virgin Islands, St. John

from $1171 /night
up to 8 guests

Island Rider

4 bedroom 6 bath USVI villa in St. John

Located in the exclusive enclave of Point Rendezvous on the south shore of St. John, Island Rider is a fully renovated villa that sits upon the open breezy hillside above Klein Bay with sprawling verandas that overlook the gentle curves of Rendezvous Bay and Ditliff Point.

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Jessamine

Barbados, Gibbes Beach

from $540 /night
up to 8 guests

Jessamine

4 bedroom 4 bath Barbados villa in Gibbes Beach

Situated on the West Coast of Barbados, Jessamine is set amidst lush tropical gardens approximately a 5-minute walk from the magnificent beach at Gibbs Bay, St. Peter.

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Klairan

Barbados, Holetown

from $1950 /night
up to 8 guests

Klairan

4 bedroom 4.5 bath Barbados villa in Holetown

Set in over an acre of tropical gardens in the heart of the exclusive Sandy Lane Estate, 'Klairan' offers luxury island living.

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La Bella Vita

United States Virgin Islands, St. John

from $857 /night
up to 8 guests

La Bella Vita

4 bedroom 4.5 bath USVI villa in St. John

With full air-conditioning, four luxurious master suites, a poolside bar, outdoor grilling station, and gourmet kitchen designed by a professional chef, the beauty of La Bella Vita is in the details.

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La Mirage

Barbados, St. James

from $1950 /night
up to 8 guests

La Mirage

4 bedroom 4 bath Barbados villa in St. James

La Mirage is a luxury beachfront penthouse holiday apartment on the West Coast of Barbados.

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La Pinta

St. Martin, St. Martin (French)

from $770 /night
up to 8 guests

La Pinta

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

Down the long driveway lined with coral stone walls and flamboyant, you arrive in the courtyard of this elegant Creole style villa.

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Le Rocher

St. Martin, St. Martin (French)

from $1000 /night
up to 8 guests

Le Rocher

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

A four-bedroom jewel that sits in the hills of the Terres Basses.

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L’Ecume Des Jours

St. Martin, St. Martin (French)

from $1000 /night
up to 8 guests

L’Ecume Des Jours

4 bedroom 4 bath St. Martin villa in St. Martin (French)

Villa L'Ecume des Jours in St Martin gorgeous beach front villa on Plum bay.

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Little Hill at Tryall

Jamaica, Montego Bay

from $2286 /night
up to 8 guests

Little Hill at Tryall

4 bedroom 4 bath Jamaica villa in Montego Bay

Little Hill was built in 1959 by an architect Robert Hartley. It was the first villa to be built at The Tryall Club in the Classic West Indies style around a circular 30 foot diameter swimming pool with extensive covered terraces throughout.

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Los Pinos at Casa de Campo

Dominican Republic, la Romana

from $2099 /night
up to 8 guests

Los Pinos at Casa de Campo

4 bedroom 4 bath Dominican Republic villa in la Romana

With living areas on the main floor and bedrooms upstairs, this two-story villa is the perfect set-up for sharing good times together while still enjoying individual privacy.

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Ma Moura at the Tryall Club

Jamaica, Montego Bay

from $1929 /night
up to 8 guests

Ma Moura at the Tryall Club

4 bedroom 4.5 bath Jamaica villa in Montego Bay

Built and owned by the same family for over forty years, Ma’Moura’s unique setting sits high on a hill overlooking the 17th green and the Caribbean Sea. Enjoying cool breezes and unobstructed views, this villa provides one of the most private yet outdoor experiences at Tryall.

Mandarin Oriental, Canouan - Lagoon Villas

Grenadines, Canouan Island

from $10200 /night
up to 10 guests

Mandarin Oriental, Canouan - Lagoon Villas

4 bedroom 4 bath Grenadines villa in Canouan Island

The impressive three-story, four-bedroom, colonial-style Lagoon Villas are nestled on a hillside with captivating views of Godahl Beach and the Atlantic Ocean.

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Mango Bay

United States Virgin Islands, St. John

from $929 /night
up to 8 guests

Mango Bay

4 bedroom 4.5 bath USVI villa in St. John

Mango Bay, a four-bedroom, four-and-a-half-bath villa, offers unparalleled luxury and breathtaking views in an exquisite villa set high above St. John’s glorious North Shore.

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Mango

St. Martin, St. Martin (French)

from $986 /night
up to 8 guests

Mango

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

Villa Mango is a beautiful contemporary styled, 4 bedrooms, 4 bathrooms, villa ideally located in the heart of the Orient Bay gated community.

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Mariposa

St. Martin, St. Martin (French)

from $750 /night
up to 8 guests

Mariposa

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

Villa Mariposa is an elegant Caribbean style villa with a romantic tropical atmosphere.

Martangie

Barbados, Speightstown

from $1500 /night
up to 8 guests

Martangie

4 bedroom 4.5 bath Barbados villa in Speightstown

Nestled between two of our finest beaches……

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Mirador

Barbados, St. James

from $1665 /night
up to 8 guests

Mirador

4 bedroom 4.5 bath Barbados villa in St. James

Mirador is a newly constructed, contemporary beachfront villa on the West Coast of Barbados.

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Mon Repos

British Virgin Islands, Virgin Gorda

from $627 /night
up to 8 guests

Mon Repos

4 bedroom 3 bath BVI villa in Virgin Gorda

Your Caribbean retreat awaits at this villa for rent on Mahoe Bay.

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Montastraea Estate

British Virgin Islands, Virgin Gorda

from $4150 /night
up to 8 guests

Montastraea Estate

4 bedroom 4.5 bath BVI villa in Virgin Gorda

The Montastraea Villa, named for the protected great star coral of the Caribbean Sea, 
shines bright on the north side of the community with unobstructed breathtaking views of Eustatia Sound, Necker Island and Anegada.

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Barbados, Mullins Bay

from $500 /night
up to 8 guests

Mullins View 14

4 bedroom 4 bath Barbados villa in Mullins Bay

This spacious, four-bedroom villa is impeccably furnished, has a comfortable living area and a large, covered terrace with both dining and living areas.

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New Mansion

Barbados, St. James

from $1260 /night
up to 8 guests

New Mansion

4 bedroom 4.5 bath Barbados villa in St. James

A modern coral stone villa located on the exclusive West Coast beachfront.

Noble House on the Beach

Jamaica, Montego Bay

from $1050 /night
up to 8 guests

Noble House on the Beach

4 bedroom 6 bath Jamaica villa in Montego Bay

A paradigm of elegance and style, Noble House on the Beach is an architectural gem, unique in the Caribbean.

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Oceana at Sugar Hill

Barbados, St. James

from $1000 /night
up to 8 guests

Oceana at Sugar Hill

4 bedroom 4 bath Barbados villa in St. James

Overlooking the Caribbean Sea, 'Oceana' is a magnificent, four-bedroom estate villa on the prime location of Ocean Ridge in the exclusive gated community of Sugar Hill.

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