Caribbean Villa Rentals


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Moon Reach

Barbados, St. James

from $3200 /night
up to 10 guests

Moon Reach

5 bedroom 5 bath Barbados villa in St. James

Seldom can a more idyllic setting be found for a beach vacation. Serene yet spectacular this five-bedroom villa shines in a breathtaking setting on the West Coast of Barbados.

Moonshadow

Turks & Caicos, Providenciales

from $1500 /night
up to 10 guests

Moonshadow

5 bedroom 4 bath Turks & Caicos villa in Providenciales

Like Your Own Private Island.

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Nirvana

Barbados, St. James

from $3100 /night
up to 10 guests

Nirvana

5 bedroom 5 bath Barbados villa in St. James

This dazzling super luxury beachfront villa offers the same high quality contemporary interiors as Mirador but includes a fifth bedroom.

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Ocassa

Anguilla, Sandy Ground

from $845 /night
up to 10 guests

Ocassa

5 bedroom 4 bath Anguilla villa in Sandy Ground

This captivating villa has breathtaking views, a distinctive design, and is perfectly positioned to face beautiful sunsets.

Outriggerhouse

Outrigger Villa

United States Virgin Islands, St. Thomas

from $1119 /night
up to 10 guests

Outrigger Villa

5 bedroom 5.5 bath USVI villa in St. Thomas

Located on a ridge 300 ft. above town Outrigger Villa affords views of the mesmerizing Charlotte Amalie harbor with cruise ships on the Caribbean Sea, yachts, marine ports, downtown and the neighboring Water & Hassel islands' vistas.

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Overlook at Tryall

Jamaica, Montego Bay

from $1679 /night
up to 10 guests

Overlook at Tryall

5 bedroom 5 bath Jamaica villa in Montego Bay

Built on one of the prime sites at Tryall and conveniently located in easy walking distance of the Great House, gym and tennis courts, with total privacy and magnificent landscaping.

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Pavilion

Jamaica, Montego Bay

from $1286 /night
up to 10 guests

Pavilion

5 bedroom 6 bath Jamaica villa in Montego Bay

Pavilion is an exquisite villa privately located at the end of a cul-de-sac with magnificent views of the Caribbean Sea to the north and a tranquil 10-mile view of the mountains to the south. It is spacious, quiet, peaceful and beautiful.

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Penthouse at the Somerset

Turks & Caicos, Providenciales

rates on request
up to 12 guests

Penthouse at the Somerset

5 bedroom 5 bath Turks & Caicos villa in Providenciales

The Somerset on Grace Bay is peaceful luxury hideaway, amid the sprawling Turks and Caicos resorts, where you can enjoy the greatest gift of all — treasured time together.

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Petite Plage 4

St. Martin, Grand Case

from $3840 /night
up to 10 guests

Petite Plage 4

5 bedroom 5 bath St. Martin villa in Grand Case

Villa Petite Plage 4 is an exquisite and luxurious retreat situated on the picturesque shores of Petite Plage in Grand Case, St. Martin.

Pineapple House

Pineapple House at Tryall

Jamaica, Montego Bay

from $2857 /night
up to 10 guests

Pineapple House at Tryall

5 bedroom 5.5 bath Jamaica villa in Montego Bay

Pineapple House is a spacious villa located on Copper Ridge with a magnificent 180 degree view of the Caribbean Sea located on Jamaica’s exclusive North Shore

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Point of View at the Tryall Club

Jamaica, Montego Bay

from $2877 /night
up to 10 guests

Point of View at the Tryall Club

5 bedroom 5 bath Jamaica villa in Montego Bay

Located on the highest point at the renowned Tryall Club, Point of View sits on one of the most spectacular sites in the Caribbean … indeed, in the world. From its unique vantage point, a sweeping panorama stretches down the mountain and across the 18-hole championship golf course to the deep blue Caribbean and distant horizon. Breathtaking at every turn.

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Quinntessential at Tryall

Jamaica, Montego Bay

from $2429 /night
up to 10 guests

Quinntessential at Tryall

5 bedroom 5 bath Jamaica villa in Montego Bay

Offering what is undoubtedly the most magnificent ocean view in Tryall from a commanding position atop Garden Hill; Quinntessential is one of the finest private homes in Jamaica where meticulous attention to detail and designers flourish result in the epitome of sophisticated living without compromise.

Reefside

Reefside Villa

United States Virgin Islands, St. John

from $1000 /night
up to 10 guests

Reefside Villa

5 bedroom 5.5 bath USVI villa in St. John

Set on a private sand beach in Chocolate Hole on St. John's south shore, Reefside Villa boasts a wonderfully spacious floor plan and a downright glorious pool area.

Rhapsody

United States Virgin Islands, St. John

from $1190 /night
up to 10 guests

Rhapsody

5 bedroom 5.5 bath USVI villa in St. John

Villa Rhapsody St. John is a beautiful and very special 5 -bedroom luxury vacation villa located on the western shores of St. John, U.S. Virgin Islands.

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Saint Peter’s Bay

Barbados, Speightstown

from $2149 /night
up to 10 guests

Saint Peter’s Bay

5 bedroom 6 bath Barbados villa in Speightstown

With its beautiful beaches, welcoming culture and rich history, this area of the island retains an untarnished, genuine charm.

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Sand Castle

British Virgin Islands, Virgin Gorda

from $1553 /night
up to 10 guests

Sand Castle

5 bedroom 5.5 bath BVI villa in Virgin Gorda

Welcome to Sandcastle, your luxury five bedroom villa on the beach with private pool, tennis, and spectacular beach sunsets.

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Sand Villa

Anguilla, Long Bay Village

from $4700 /night
up to 12 guests

Sand Villa

5 bedroom 4.5 bath Anguilla villa in Long Bay Village

Named after the sugar sand of Long Bay Beach, Sand Villa sits on the west side of the property close to the beach featuring the gentle sound of the waves and private stairs.

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Sandcastle Villa

Anguilla, Limestone Bay

from $3700 /night
up to 10 guests

Sandcastle Villa

5 bedroom 5 bath Anguilla villa in Limestone Bay

A secluded beachside Tuscan inspired 10,000 sq. ft. 5 bedroom villa on the North Shore of Anguilla with magnificent views of the ever changing shades of blue of the Atlantic Ocean.

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Saramanda

Barbados, St. James

from $2200 /night
up to 10 guests

Saramanda

5 bedroom 5.5 bath Barbados villa in St. James

Saramanda is a luxurious and spacious five-bedroom villa with a large swimming pool located in the heart of the prestigious Sandy Lane Estate in St. James on the West Coast of Barbados.

Saving Grace

Turks & Caicos, Providenciales

from $3600 /night
up to 8 guests

Saving Grace

5 bedroom 3.5 bath Turks & Caicos villa in Providenciales

Located in a residential area on Grace Bay Beach, Saving Grace Villa Providenciales is a 4,000+ square foot, two-story, L-shaped Colonial style villa nestled discreetly into a sunset-facing cove on this world-famous beach.

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Scotch on the Rocks

Jamaica, Ocho Rios

from $1380 /night
up to 10 guests

Scotch on the Rocks

5 bedroom 5 bath Jamaica villa in Ocho Rios

SCOTCH ON THE ROCKS is a charming turquoise villa overlooking the Caribbean Sea.

Sea Forever

United States Virgin Islands, St. John

from $1587 /night
up to 10 guests

Sea Forever

5 bedroom 5.5 bath USVI villa in St. John

This villa’s name has layers of meaning – not only can you can see forever from its vantage point above St. John’s southwestern shore, but you could also, happily, spend forever gazing at that incomparable panorama.

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Seacliff

Turks & Caicos, Providenciales

from $1575 /night
up to 10 guests

Seacliff

5 bedroom 5.5 bath Turks & Caicos villa in Providenciales

Set high atop the cliff in scenic Chalk Sound, Villa Seacliff is a striking luxury villa with incredible 180-degree oceanfront panoramas.

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Seacove

United States Virgin Islands, St. John

from $2451 /night
up to 10 guests

Seacove

5 bedroom 5.5 bath USVI villa in St. John

Overlooking sublime views of Peter Bay and beyond, Seacove is one of the most beautifully-detailed homes we offer, set within lush landscaping replete with bananas, lime, papayas, citrus, coconut palms, and a soothing garden waterfall.

Seaduced at Royal Westmoreland

Barbados, St. James

from $1850 /night
up to 10 guests

Seaduced at Royal Westmoreland

5 bedroom 5 bath Barbados villa in St. James

Seaduced is one of the few contemporary architect designed holiday villas available for rent in Royal Westmoreland, home to one of the finest golf courses in the Caribbean.

Seagrace Villa

Turks & Caicos, Providenciales

from $1500 /night
up to 10 guests

Seagrace Villa

5 bedroom 4 bath Turks & Caicos villa in Providenciales

Seagrace Villa is nestled on the canal in the gated community of Leeward, just moments away from Salt Bar and Grill.

Seascape

Turks & Caicos, Providenciales

from $4320 /night
up to 10 guests

Seascape

5 bedroom 5.5 bath Turks & Caicos villa in Providenciales

Located on the tranquil shores of Grace Bay, Seascape epitomizes luxury island lifestyles.

Serena

St. Martin, St. Martin (French)

from $1643 /night
up to 10 guests

Serena

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

This elegant, beachfront, villa is truly exceptional.

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Seventh Heaven at Royal Westmoreland

Barbados, Alleynes Bay

from $1210 /night
up to 10 guests

Seventh Heaven at Royal Westmoreland

5 bedroom 5.5 bath Barbados villa in Alleynes Bay

"Seventh Heaven" is a spacious and luxurious, non-smoking, five-bedroom villa situated within the Royal Westmoreland Golf Resort.

Sirena Blue

Dominican Republic, Punta Cana

from $6430 /night
up to 14 guests

Sirena Blue

5 bedroom 5 bath Dominican Republic villa in Punta Cana

The villa of a globetrotter!

Sky Blue

St. Martin, Sint Maarten

from $608 /night
up to 11 guests

Sky Blue

5 bedroom 5.5 bath St. Martin villa in Sint Maarten

Sky Blue is a luxurious, five-bedroom, ocean-view villa where you will see all the hues of the blue sky and ocean, located in the exclusive gated community of Dawn Beach Estates on St. Maarten.

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Sky Villa

Anguilla, Long Bay Village

from $4500 /night
up to 10 guests

Sky Villa

5 bedroom 4 bath Anguilla villa in Long Bay Village

Inspired by cloudless skies, Sky Villa offers an elevated slice of island life.

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St. Bernard’s Hill House

British Virgin Islands, Tortola

from $3973 /night
up to 10 guests

St. Bernard’s Hill House

5 bedroom 6.5 bath BVI villa in Tortola

Surrounded within a lush oasis of royal palms, this private 8-acre hilltop estate provides an amazing 300-degree bird's-eye view of the Virgins and miles and miles of azure sea and sky to the distant horizon.

Starfish

Dominican Republic, Punta Cana

from $1250 /night
up to 12 guests

Starfish

5 bedroom 5.5 bath Dominican Republic villa in Punta Cana

Indulge yourself by staying at one of the most modern, yet comfortable golfview villas in one of the most lauded resorts in the whole Caribbean - Punta Cana Resort.

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Still Fathoms

Barbados, St. James

from $1685 /night
up to 10 guests

Still Fathoms

5 bedroom 5.5 bath Barbados villa in St. James

Still Fathoms is a modern and stylish villa located directly on the ocean at Reed's Bay on the West Coast of Barbados.

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Sugar Bay on the Beach

Jamaica, Discovery Bay

from $1964 /night
up to 10 guests

Sugar Bay on the Beach

5 bedroom 5.5 bath Jamaica villa in Discovery Bay

On its own sugary white sand beach lapped by the turquoise waters of Discovery Bay sits the exquisite home Sugar Bay. Interiors have just been refreshed throughout and are distinguished by elegant custom-designed furniture, gleaming breadnut floors, and fascinating objets d`art from around the world. There has also been an addition of a brand new air conditioned Gym!

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Sundog

Turks & Caicos, Providenciales

from $4480 /night
up to 10 guests

Sundog

5 bedroom 5.5 bath Turks & Caicos villa in Providenciales

Striking a balance between environmental responsibility and contemporary design, the freestanding private beachfront villa Sundog has set a new standard of excellence for luxury villa homes on the Turks & Caicos Islands from its location on Smith’s Reef, approximately a 9-minute drive from the resort.

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Sunset on the Beach at the Tryall Club

Jamaica, Montego Bay

from $2357 /night
up to 10 guests

Sunset on the Beach at the Tryall Club

5 bedroom 5 bath Jamaica villa in Montego Bay

Sunset is a beautiful five-bedroom villa that sits on the edge of the Caribbean Sea with a private beach offering the perfect escape for all those who love waterside living.

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Tamar

British Virgin Islands, Virgin Gorda

from $821 /night
up to 10 guests

Tamar

5 bedroom 5.5 bath BVI villa in Virgin Gorda

Elegance and island charm greet you at this beautiful rental villa at Leverick Bay.

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The Shore Club - Five Bedroom Villa

Turks & Caicos, Providenciales

from $7450 /night
up to 12 guests

The Shore Club - Five Bedroom Villa

5 bedroom 5 bath Turks & Caicos villa in Providenciales

The ultimate in privacy, luxury and ease is now open for enjoyment with the completion of the spectacular oceanfront Villas at The Shore Club.

The Villa at The St. James

Barbados, St. James

from $325 /night
up to 10 guests

The Villa at The St. James

5 bedroom 5.5 bath Barbados villa in St. James

Situated on the ground floor of the West Coasts newest luxury development and overlooking the pristine white sands and turquoise waters of Paynes Bay, this condo is a treasure for guests looking to enjoy the ultimate vacation experience.

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Tom Tom

Barbados, Alleynes Bay

from $1800 /night
up to 10 guests

Tom Tom

5 bedroom 6 bath Barbados villa in Alleynes Bay

Tom Tom is a well-appointed, contemporary five-bedroom villa located in Westmoreland St. James, overlooking the exclusive West Coast of Barbados.

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Toscano at Casa de Campo

Dominican Republic, la Romana

from $2249 /night
up to 10 guests

Toscano at Casa de Campo

5 bedroom 5 bath Dominican Republic villa in la Romana

Nestled amongst palm trees and tropical flowers, this one-story villa has been cleverly designed to introduce elements of the beautiful outdoor surroundings into the airy interior spaces.

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Tradewinds

Barbados, Holetown

from $3000 /night
up to 10 guests

Tradewinds

5 bedroom 5.5 bath Barbados villa in Holetown

Tradewinds is a striking five-bedroom mansion within the prestigious Sandy Lane Estate.

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Truffle

St. Martin, St. Martin (French)

from $1143 /night
up to 10 guests

Truffle

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

An amazing, luxurious, and modern five-bedroom villa on St Martin.

The Dunes Featured

Turtle Inlet

Turks & Caicos, Providenciales

from $4480 /night
up to 10 guests

Turtle Inlet

5 bedroom 5.5 bath Turks & Caicos villa in Providenciales

Striking a balance between environmental responsibility and contemporary design, the beachfront residences of The Dunes have set a new standard of excellence for luxury villa homes on the Turks & Caicos Islands.

Villa Christina

Jamaica, Montego Bay

from $2071 /night
up to 10 guests

Villa Christina

5 bedroom 6.5 bath Jamaica villa in Montego Bay

Set on the historic Rose Hall Estate, Villa Christina welcomes couples, families, and friends to Caribbean luxury in a remarkable 10,000 sq. ft. well-appointed Tuscan style villa located in the Greens at Rose Hall - a private gated-community on the Cinnamon Hill Golf Course.

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Villa Portofino

Turks & Caicos, Providenciales

from $6760 /night
up to 10 guests

Villa Portofino

5 bedroom 5.5 bath Turks & Caicos villa in Providenciales

Designed by Edinburgh, Scotland-based Coast Architects.

Villa Rosa

Jamaica, Montego Bay

from $1900 /night
up to 10 guests

Villa Rosa

5 bedroom 6 bath Jamaica villa in Montego Bay

Villa Rosa is our newest villa in Montego Bay's Spring Farm neighborhood. It is a stunning, modern villa, brilliantly designed for an extraordinary indoor-outdoor lifestyle with a full complement of impressive luxuries for the upscale traveler.

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Villa Rosa

Barbados, Royal Westmoreland

from $1155 /night
up to 10 guests

Villa Rosa

5 bedroom 5 bath Barbados villa in Royal Westmoreland

Situated in an enviable position on Coronation Drive and adjacent to the Royal Westmoreland Golf Course, Villa Rosa is a stunning, well-maintained five-bedroom family villa boasting views across the fairways to the Caribbean Sea beyond.

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