Caribbean Villa Rentals


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Wag Water at Prospect Estate

Jamaica, Ocho Rios

from $700 /night
up to 6 guests

Wag Water at Prospect Estate

3 bedroom 3 bath Jamaica villa in Ocho Rios

Wag Water is a charming cottage with a water front location, named after the river which meanders through the local parish of St Mary.

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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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West Bay Club - Ocean Front Luxury One Bedroom Suite

Turks & Caicos, Providenciales

rates on request
up to 3 guests

West Bay Club - Ocean Front Luxury One Bedroom Suite

1 bedroom 1 bath Turks & Caicos villa in Providenciales

Ocean Front Luxury 1 Bedroom Suites offer breathtaking ocean front view.

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West Bay Club - Ocean Front Luxury Two Bedroom Suite

Turks & Caicos, Providenciales

rates on request
up to 5 guests

West Bay Club - Ocean Front Luxury Two Bedroom Suite

2 bedroom 2 bath Turks & Caicos villa in Providenciales

The ultimate option for small families, the Ocean Front Luxury 2 Bedroom Suite offers more than 2,250 square feet of living space.

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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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Wheel House at Tryall

Jamaica, Montego Bay

from $1357 /night
up to 12 guests

Wheel House at Tryall

6 bedroom 6 bath Jamaica villa in Montego Bay

Welcome to the Wheel House Villa!

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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 $2000 /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.

Windsong

Windsong - Lanai Bungalow Suites

Turks & Caicos, Providenciales

from $745 /night
up to 6 guests

Windsong - Lanai Bungalow Suites

2 bedroom 2 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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Windsong - Bungalow Suites

Turks & Caicos, Providenciales

from $548 /night
up to 8 guests

Windsong - Bungalow Suites

3 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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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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Windsong - Oceanfront Suites

Turks & Caicos, Providenciales

from $798 /night
up to 4 guests

Windsong - Oceanfront Suites

2 bedroom 2 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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Windsong - Resort Suites

Turks & Caicos, Providenciales

from $548 /night
up to 3 guests

Windsong - Resort Suites

1 bedroom 1 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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Windward

Barbados, St. James

from $3000 /night
up to 10 guests

Windward

5 bedroom 5.5 bath Barbados villa in St. James

Windward is a luxurious two-story villa on Cooper Hill within Sandy Lane Estate in Barbados featuring a swimming pool, 5 bedrooms suites, and 5.5 bathrooms.

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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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Wymara Resort - Cinco Villa

Turks & Caicos, Providenciales

from $6250 /night
up to 11 guests

Wymara Resort - Cinco Villa

5 bedroom 4.5 bath Turks & Caicos villa in Providenciales

With five gorgeously-appointed bedrooms, our peaceful and secluded Five Bedroom Cinco Villa has ample space for you and your loved ones and on-demand access to every amenity Wymara Resort has to offer.

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Wymara Resort - Oceanfront Penthouse Suite

Turks & Caicos, Providenciales

from $5195 /night
up to 6 guests

Wymara Resort - Oceanfront Penthouse Suite

3 bedroom 3.5 bath Turks & Caicos villa in Providenciales

Our Oceanfront Penthouse Suite measures over 3,700 square feet and boasts one of the most impressive and unforgettable views on Providenciales.

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Wymara Resort - One Bedroom Oceanfront Suite

Turks & Caicos, Providenciales

from $1655 /night
up to 2 guests

Wymara Resort - One Bedroom Oceanfront Suite

1 bedroom 1 bath Turks & Caicos villa in Providenciales

Apartment convenience meets island living in our One Bedroom Oceanfront Suite.

New One Bedroom Suite Full View

Wymara Resort - Three Bedroom Oceanfront Suite

Turks & Caicos, Providenciales

from $6659 /night
up to 6 guests

Wymara Resort - Three Bedroom Oceanfront Suite

3 bedroom 3 bath Turks & Caicos villa in Providenciales

Overflowing with understated extravagance, our Three Bedroom Oceanfront Suite offers some of the most stunning views in Turks + Caicos as well as an amount of room normally reserved for private homes.

New One Bedroom Suite Full View

Wymara Resort - Two Bedroom Oceanfront Suite

Turks & Caicos, Providenciales

from $4995 /night
up to 4 guests

Wymara Resort - Two Bedroom Oceanfront Suite

2 bedroom 2 bath Turks & Caicos villa in Providenciales

Space, style and sophistication become synonymous in this Two Bedroom Suite.

Yarari Royale

Dominican Republic, Punta Cana

from $3420 /night
up to 20 guests

Yarari Royale

9 bedroom 9.5 bath Dominican Republic villa in Punta Cana

Discover a new concept of luxury vacation, where good taste, relaxation, fitness, modernism, and minimalism are blended in such a way you will have a unique experience at the new Yarari Royale.

Yellow Bear

Dominican Republic, Punta Cana

from $1860 /night
up to 14 guests

Yellow Bear

6 bedroom 6.5 bath Dominican Republic villa in Punta Cana

After a long working year, we all yearn for a well deserved vacation in a relaxed paradise far away from the honking cars, skyscrapers, and big cities.

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Zenaida Estate

Anguilla, Sandy Hill

from $1100 /night
up to 14 guests

Zenaida Estate

7 bedroom 7.5 bath Anguilla villa in Sandy Hill

Zenaida Beach and Tennis Estate is nestled on three acres of lush tropical gardens with majestic, sweeping views of the Caribbean Sea and the mountains of St. Martin and St. Barts beyond.

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Zion Hill at Tryall

Jamaica, Montego Bay

from $2751 /night
up to 14 guests

Zion Hill at Tryall

7 bedroom 7 bath Jamaica villa in Montego Bay

From its splendid location 300 ft above sea level, this luxurious five bedroom villa offers bewitching, unobstructed views of the ocean, its own private spa and Turkish bath and a cinema.

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Bee Happy at the Tryall Club

Jamaica, Montego Bay

from $711 /night
up to 4 guests

Bee Happy at the Tryall Club

2 bedroom 3 bath Jamaica villa in Montego Bay

Bee Happy, This beautifully renovated staffed two-bedroom villa at the legendary Tryall Great House is sumptuous. The villa is distinguished by beautiful Jamaican crafted artisan work, including dramatic new ceilings in the entrance and living areas, bespoke furnishings and artwork, breathtaking views of sea, sky, and mountain from its comfy furnished veranda and spacious interiors, top that with a private plunge pool and you may never need to leave!

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Mirador at the Tryall Club

Jamaica, Montego Bay

from $482 /night
up to 2 guests

Mirador at the Tryall Club

1 bedroom 2 bath Jamaica villa in Montego Bay

Mirador is a stylish one-bedroom apartment at the posh Tryall Club. Its prize location provides both proximity to the elegant Tryall Club Great House and a breathtaking view over the deep blue Caribbean Sea and the manicured championship golf course.

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Blue Heaven

Jamaica, Montego Bay

from $714 /night
up to 6 guests

Blue Heaven

3 bedroom 2.5 bath Jamaica villa in Montego Bay

This lovely villa and grounds sit on a hilltop overlooking Montego Bay and beyond. Perfectly situated only 20 minutes from the airport and 15 minutes from the Tryall Club. Blue Heaven also comes with a complimentary driver on 7-night reservations.

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Coach House at Good Hope

Jamaica, Montego Bay

from $1125 /night
up to 14 guests

Coach House at Good Hope

7 bedroom 8 bath Jamaica villa in Montego Bay

The Coach House at Good Hope is a fantastic informal gathering place for families, retreats, and friends - with space for togetherness, space for discovering nature, and space for alone time. Like traveling through a time warp, to visit Jamaica's countryside is to experience another Jamaica of 30 years ago. The pace is slow, the lifestyle uncomplicated, the people are kind and calm, the service is relaxed and meals are served family style. For larger groups The Coach House villa & The Great House villa can be rented together to offer 14 bedrooms, accommodating 28 guests.

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Sandcastle Beach House

Anguilla, Limestone Bay

from $2300 /night
up to 8 guests

Sandcastle Beach House

4 bedroom 4.5 bath Anguilla villa in Limestone Bay

Welcome to Anguilla’s newest rental property, Sandcastle Beach House! We offer a one of a kind experience for couples, families, or private events.

Silver Sands

Silver Sands

Turks & Caicos, Thompson Cove

from $5800 /night
up to 16 guests

Silver Sands

8 bedroom 7.5 bath Turks & Caicos villa in Thompson Cove

This spectacular, spacious 8 bedroom family home has been extended and renovated with love, a European design flare and imagination.

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Spanish Cove

Jamaica, Runaway Bay

from $957 /night
up to 8 guests

Spanish Cove

4 bedroom 4 bath Jamaica villa in Runaway Bay

Located on Runaway Bay, Spanish Cove is perched on a beautiful sandy beach nearby the heart of town. Runaway Bay is known for beautiful beaches, coral reefs, excellent scuba diving as well as the well-known Green Grotto Caves. It is also conveniently located and within easy reach of Ocho Rios for restaurants, excursions, and shopping.

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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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Linga-Awile Cottage on the Beach

Jamaica, Discovery Bay

from $519 /night
up to 6 guests

Linga-Awile Cottage on the Beach

3 bedroom 4 bath Jamaica villa in Discovery Bay

This 3-bedroom casual cottage shares a delightful waterfront site with its neighboring Villa, on the clear waters of Discovery Bay. Linga-Awile sits on a lovely, long, large lawn. Beyond the lawn and swimming pool is its sugary white sand beach with two thatched roof umbrellas for shade.

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Sea Haven on Discovery Bay

Jamaica, Discovery Bay

from $500 /night
up to 8 guests

Sea Haven on Discovery Bay

4 bedroom 4 bath Jamaica villa in Discovery Bay

Located on a private waterfront acre, Sea Haven is a traditional West Indian cottage dressed in charming periwinkle blue and sitting directly on the edge of beautiful Discovery Bay.

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Seaside Villa at Round Hill

Jamaica, Montego Bay

from $4400 /night
up to 8 guests

Seaside Villa at Round Hill

4 bedroom 4 bath Jamaica villa in Montego Bay

Seaside was completely renovated & refurbished in 2018. This amazing sea front property is one of the newest premier villas at Round Hill.

Sentosa

Turks & Caicos, Providenciales

from $15000 /night
up to 16 guests

Sentosa

8 bedroom 8 bath Turks & Caicos villa in Providenciales

Sentosa (Peace and Tranquility) Villa is a beautiful contemporary style home on 1.5 acres of land on the number 1 rated beach in the world.

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Summertime at Silver Sands

Jamaica, Montego Bay

from $500 /night
up to 8 guests

Summertime at Silver Sands

4 bedroom 4 bath Jamaica villa in Montego Bay

Summertime at Silver Sands has a wonderful beach vibe, it benefits from cool sea breezes and is a relaxed and unfussy villa located on the renowned Silver Sands Beach Club, a collection of privately owned villas all overlooking the Caribbean sea.

Vision Beach

Turks & Caicos, Providenciales

from $8500 /night
up to 10 guests

Vision Beach

5 bedroom 7 bath Turks & Caicos villa in Providenciales

Vision Beach is a modern beach house located on the exclusive Prince of Wales Drive along a quiet stretch of Grace Bay Beach, one of the best beaches in the world.

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A Summer Place on the Beach

Jamaica, Discovery Bay

from $2100 /night
up to 14 guests

A Summer Place on the Beach

7 bedroom 9 bath Jamaica villa in Discovery Bay

Nestled on its own sandy beach by the blue waters of Discovery Bay, A Summer Place is a spacious and playful family home. The design is of typical Caribbean gingerbread style with hand-carved fretwork trimming the length of the house.

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Aqua Bay at the Tryall Club

Jamaica, Montego Bay

from $2889 /night
up to 8 guests

Aqua Bay at the Tryall Club

4 bedroom 6 bath Jamaica villa in Montego Bay

Aqua Bay is an amazing seafront property and is one of the premier villas at The Tryall Club.

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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.

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Caribbean Jewel

Jamaica, Montego Bay

from $1035 /night
up to 8 guests

Caribbean Jewel

4 bedroom 4 bath Jamaica villa in Montego Bay

Caribbean Jewel is a 5,000 square-foot Mediterranean-style villa, with a blend of modern Caribbean elegance, privately located on the exclusive gated Spring Farm Estate with spectacular sea views & Golf at Cinnamon Hill Course nearby.

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Cliffside Cottage

Jamaica, Montego Bay

from $786 /night
up to 10 guests

Cliffside Cottage

5 bedroom 5 bath Jamaica villa in Montego Bay

Dramatically perched on a lush green hillside above the sea, Cliffside Cottage commands stunning views of the deep blue Caribbean Sea by day and romantic lights that glisten across Montego Bay after sunset. Sunrise and sunset vistas from this vantage point are mesmerizing.

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Endless Summer

Jamaica, Montego Bay

from $1643 /night
up to 14 guests

Endless Summer

7 bedroom 7 bath Jamaica villa in Montego Bay

One of the most glamorous villas in Jamaica, Endless Summer is a turreted mansion with breathtaking views of the Caribbean Sea.

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Everything Nice by the Sea

Jamaica, Montego Bay

from $1850 /night
up to 10 guests

Everything Nice by the Sea

5 bedroom 5.5 bath Jamaica villa in Montego Bay

Everything Nice is a lovely waterfront property on Emerald Quay sitting on the edge of the Bogue Lagoon. Nestled in between the Breathless & Secrets Hotels & within walking distance of the Montego Bay Yacht Club.

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Fairway Manor

Jamaica, Montego Bay

from $2010 /night
up to 14 guests

Fairway Manor

7 bedroom 9 bath Jamaica villa in Montego Bay

Today’s Fairway Manor is a stylish multi-faceted 10,000-square-foot private home. Its rooms feature cool marble floors and overlook the famous Half Moon 18-hole Robert Trent Jones golf course and a dramatic panorama of the Caribbean Sea.

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Hidden Bay by the Sea

Jamaica, Runaway Bay

from $1929 /night
up to 12 guests

Hidden Bay by the Sea

6 bedroom 6 bath Jamaica villa in Runaway Bay

HIDDEN BAY by the SEA perches dramatically on a cliffside and is one of the most remarkable sites on Jamaica’s renowned North Coast.

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Hummingbird House at the Tryall Club

Jamaica, Montego Bay

from $2986 /night
up to 14 guests

Hummingbird House at the Tryall Club

7 bedroom 8 bath Jamaica villa in Montego Bay

Hummingbird House is one of the finest properties within the Tryall Club!

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