Caribbean Villa Rentals


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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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Amandara

St. Martin, St. Martin (French)

from $2357 /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.

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Aquaria at Casa de Campo

Dominican Republic, la Romana

from $2399 /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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Estrella at Casa de Campo

Dominican Republic, la Romana

from $2399 /night
up to 10 guests

Estrella at Casa de Campo

5 bedroom 5.5 bath Dominican Republic villa in la Romana

This gracious one-story home is full of architectural details and modern interiors.

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Lienzo at Casa de Campo

Dominican Republic, la Romana

from $2399 /night
up to 15 guests

Lienzo at Casa de Campo

5 bedroom 5 bath Dominican Republic villa in la Romana

Contemporary chic defines this wonderful one-story villa featuring sleek furnishings, natural materials, and soothing colors.

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Marmol at Casa de Campo

Dominican Republic, la Romana

from $2399 /night
up to 10 guests

Marmol at Casa de Campo

5 bedroom 5 bath Dominican Republic villa in la Romana

Majestic palms and fragrant blooms welcome you to this peaceful one-story villa.

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Toscano at Casa de Campo

Dominican Republic, la Romana

from $2399 /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.

Marfil at Casa de Campo

Dominican Republic, la Romana

from $2399 /night
up to 10 guests

Marfil at Casa de Campo

5 bedroom 5 bath Dominican Republic villa in la Romana

This beautiful villa is the perfect place to get away and relax, with a large swimming pool and a heated jacuzzi.

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The Regent Grand - Two Bedroom Oceanfront

Turks & Caicos, Providenciales

from $2400 /night
up to 4 guests

The Regent Grand - Two Bedroom Oceanfront

2 bedroom 2 bath Turks & Caicos villa in Providenciales

The Art of Exclusivity ~ Located on a pristine 300-foot stretch of powder white sand on world-famous Grace Bay Beach, the new Regent Grand is the exclusive destination that offers unparalleled indulgence and is re-writing the rules on island luxury.

Landmark House and Cottage

Barbados, St. James

from $2420 /night
up to 12 guests

Landmark House and Cottage

6 bedroom 7 bath Barbados villa in St. James

Landmark House is one of only three villas situated directly on the exclusive Sandy Lane Beach, the premier location along Barbados’ platinum coast. Set within a tropical garden, it is a most striking property.

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2B at Peter Bay

United States Virgin Islands, St. John

from $2430 /night
up to 8 guests

2B at Peter Bay

4 bedroom 4.5 bath USVI villa in St. John

Besides the amazing 2B Peter Bay Beach Villa being just steps above a sandy clear water North Shore beach within the stunning Virgin Islands National Park, this home boasts 4 master bedroom suites, a pool and a hot tub built and designed at the highest quality letting in the big multi blue views that could rival any global destination.

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Flower Hill

Jamaica, Montego Bay

from $2450 /night
up to 12 guests

Flower Hill

6 bedroom 12 bath Jamaica villa in Montego Bay

Flower Hill is one of the most luxurious villas in Montego Bay's, Spring Farm neighborhood. This Premier 19,000-sq-ft villa sits on 4 beautifully landscaped acres overlooking the Half Moon Beach Resort and Golf Club.

Smugglers Cove The Penthouse

Barbados, St. James

from $2450 /night
up to 8 guests

Smugglers Cove The Penthouse

4 bedroom 5 bath Barbados villa in St. James

Experience the ultimate luxury at Smugglers Cove Penthouse - an exclusive beachfront haven on Barbados' iconic West Coast.

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Villa Amana at Tryall

Jamaica, Montego Bay

from $2464 /night
up to 20 guests

Villa Amana at Tryall

10 bedroom 13 bath Jamaica villa in Montego Bay

With an ocean panorama that is nothing short of awe-inspiring, this grand ten-bedroom villa is the largest at Tryall. With large airy rooms exuding sophisticated style, a terrific infinity pool, a cascading garden waterfall, a children’s playground and the choice of outdoor or indoor air-conditioned living make this a one-of-a-kind villa

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Cocomaya

Barbados, St. James

from $2500 /night
up to 10 guests

Cocomaya

5 bedroom 5.5 bath Barbados villa in St. James

Experience the epitome of luxury at Cocomaya, nestled within the prestigious Apes Hill Club in Barbados.

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Eco Serendib - Presidential Suite

United States Virgin Islands, St. John

from $2500 /night
up to 2 guests

Eco Serendib - Presidential Suite

1 bedroom 1 bath USVI villa in St. John

Luxurious private spa retreat & organic garden-to-plate adventures. Indulge & experience luxury reserved for the privileged few.

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Azure Wish Villa

British Virgin Islands, Virgin Gorda

from $2500 /night
up to 8 guests

Azure Wish Villa

4 bedroom 3.5 bath BVI villa in Virgin Gorda

A short drive from Spanish Town along the stunning Nail Bay road takes visitors to the beautiful and exclusive villas of the Nail Bay Resort.

Sandy Bottom

Sandy Bottom

Turks & Caicos, Providenciales

from $2500 /night
up to 8 guests

Sandy Bottom

4 bedroom 4 bath Turks & Caicos villa in Providenciales

Welcome to this cool, new, modern and contemporary property that sits on the South shores of Providenciales overlooking the turquoise Caicos Banks.

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Villa Amalia

St. Martin, Guana Bay

from $2500 /night
up to 12 guests

Villa Amalia

6 bedroom 6 bath St. Martin villa in Guana Bay

Villa Amalia in St Maarten is a stunning 6-bedroom oceanfront luxury property.

Kasa del Mar at Harbour Village

Bonaire, Kralendijk

from $2529 /night
up to 9 guests

Kasa del Mar at Harbour Village

5 bedroom 4 bath Bonaire villa in Kralendijk

Offering all of the comforts of home, together with unlimited access to the services and facilities of Harbour Village Beach Club, Kasa del Mar is the perfect fit for couples and families.

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Celestial Villa at Tryall

Jamaica, Montego Bay

from $2550 /night
up to 10 guests

Celestial Villa 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; Celestial Villa is one of the finest private homes in Jamaica where meticulous attention to detail and designers flourish resulting in the epitome of sophisticated living without compromise.

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Phoenix on the Beach at the Tryall Club

Jamaica, Montego Bay

from $2571 /night
up to 14 guests

Phoenix on the Beach at the Tryall Club

7 bedroom 8 bath Jamaica villa in Montego Bay

Phoenix sits on a spectacular seascape on Jamaica's lush North Coast at the luxurious Tryall Club 12 miles west of Montego Bay. The beach club, pro shop, first tee and driving range are within walking distance of the Phoenix front door. Nine laykold tennis courts are just a golf cart ride up the hill.

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Lindon at Fowl Cay

Bahamas, Exuma Cays

from $2587 /night
up to 2 guests

Lindon at Fowl Cay

1 bedroom 1 bath Bahamas villa in Exuma Cays

Make memories that will last a lifetime at Lindon - your own idyllic hideaway on breathtaking Fowl Cay.

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Mes Amis

St. Martin, St. Martin (French)

from $2600 /night
up to 28 guests

Mes Amis

13 bedroom 14.5 bath St. Martin villa in St. Martin (French)

Villa Mes Amis in St Martin unique 13 bedroom property, unbelievable sunset and ocean views.

Villa Paradise

Anguilla, Blowing Point

from $2600 /night
up to 14 guests

Villa Paradise

7 bedroom 6 bath Anguilla villa in Blowing Point

Villa Paradise is an exquisite 7-bedroom, 7,000-square-foot, gated vacation estate surrounded by 3.5 acres of magnificently landscaped gardens overlooking the sea.

Trinity

Trinity at Tryall

Jamaica, Montego Bay

from $2643 /night
up to 10 guests

Trinity at Tryall

5 bedroom 5 bath Jamaica villa in Montego Bay

Trinity is a recently renovated luxury villa that boasts breathtaking views, features two expansive swimming pools, offers opulent furnishings and accessories, incorporates a Sonos music system throughout, and is staffed by a team of professionally trained individuals dedicated to ensuring your vacation is unforgettable.

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Cayuco 9

Dominican Republic, Cap Cana

from $2650 /night
up to 16 guests

Cayuco 9

6 bedroom 7.5 bath Dominican Republic villa in Cap Cana

Paradise enclave with huge outdoor living and hot tub.

Villa Londali - Arrecife 59

Dominican Republic, Punta Cana

from $2650 /night
up to 16 guests

Villa Londali - Arrecife 59

7 bedroom 7.5 bath Dominican Republic villa in Punta Cana

Astonishing brand new seven bedroom villa with golf and lake views.

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Beach House

Turks & Caicos, Providenciales

from $2650 /night
up to 12 guests

Beach House

4 bedroom 6 bath Turks & Caicos villa in Providenciales

A stunning luxury beachfront retreat, the Beach House is a newly renovated 4-bedroom property which sits directly on one of Providenciales most beautiful beaches, Taylor Bay Beach.

Chez Moi - Arrecife SB6

Dominican Republic, Punta Cana

from $2650 /night
up to 14 guests

Chez Moi - Arrecife SB6

7 bedroom 7.5 bath Dominican Republic villa in Punta Cana

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

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Mare Blu

United States Virgin Islands, St. John

from $2653 /night
up to 12 guests

Mare Blu

6 bedroom 8 bath USVI villa in St. John

'Mare Blu' is a fabulous, six-bedroom villa on St. John's exclusive Rendezvous Bay. This exceptional villa overlooks the beautiful south shore and is just minutes from Cruz Bay and the National Park beaches.

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Infinity at the Tryall Club

Jamaica, Montego Bay

from $2657 /night
up to 12 guests

Infinity at the Tryall Club

6 bedroom 5.5 bath Jamaica villa in Montego Bay

A Premier villa at the renowned Tryall Club, Infinity is a halcyon haven overlooking the Caribbean Sea. Its rooms are large and tastefully furnished -- some traditional, some eclectic -- with a designer’s eye to comfort throughout. Named for its seemingly endless private pool, Infinity is a vacationer’s paradise for golf and tennis enthusiasts, spa weeks, family reunions or merely relaxing into the good life for a week or more.

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Arc En Ciel

St. Lucia, Soufriere

from $2680 /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.

Leamington Pavilion

Barbados, Speightstown

from $2680 /night
up to 6 guests

Leamington Pavilion

3 bedroom 3.5 bath Barbados villa in Speightstown

Leamington Pavilion, an opulent beachfront villa on Barbados' platinum coast, is the perfect Caribbean holiday rental for families or groups seeking the luxury of a five-star hotel with the privacy and personalization of a luxury Barbados villa.

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Casablanca at Sandy Lane

Barbados, St. James

from $2700 /night
up to 14 guests

Casablanca at Sandy Lane

7 bedroom 7.5 bath Barbados villa in St. James

Casablanca at Sandy Lane is an elegant seven-bedroom luxury West Coast villa.

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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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Villa Indigo

Jamaica, Montego Bay

from $2750 /night
up to 10 guests

Villa Indigo

5 bedroom 5.5 bath Jamaica villa in Montego Bay

Villa Indigo at HALF MOON is one of the undisputed finest private homes in this collection.

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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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La Bella Casa

St. Martin, Terres Basses

from $2786 /night
up to 24 guests

La Bella Casa

12 bedroom 12 bath St. Martin villa in Terres Basses

La Bella Casa is a charming Caribbean estate surrounded by lush tropical gardens and sprawling green lawns.

Footprints Main Villa

Barbados, St. James

from $2800 /night
up to 10 guests

Footprints Main Villa

5 bedroom 5.5 bath Barbados villa in St. James

Step inside a modern luxury vacation rental on Barbados' best beaches.

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Seacove

United States Virgin Islands, St. John

from $2807 /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.

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Corales 114

Dominican Republic, Punta Cana

from $2830 /night
up to 14 guests

Corales 114

6 bedroom 6.5 bath Dominican Republic villa in Punta Cana

Blissful images of a well deserved vacation are usually only found on colorful postcards, but when you step for the first time through the long corridor you are automatically wrapped in a unique stylish ambiance, ready to fulfill your most lavish desires and whims to make from your stay an unforgettable experience.

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Silent Waters

Jamaica, Montego Bay

from $2853 /night
up to 16 guests

Silent Waters

8 bedroom 6 bath Jamaica villa in Montego Bay

Set atop one of the highest mountaintops overlooking Montego Bay and the Caribbean Sea, Silent Waters Villa offers a secluded retreat just 4.6 miles west of Montego Bay. This breathtaking 16.5-acre estate combines world-class architecture and design with unparalleled luxury, making it an ideal destination for family gatherings, weddings, retreats, and milestone celebrations.

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Whispering Waters on the Beach

Jamaica, Discovery Bay

from $2857 /night
up to 14 guests

Whispering Waters on the Beach

7 bedroom 7 bath Jamaica villa in Discovery Bay

Whispering Waters offers seven bedrooms and en-suite bathrooms. Overlooking one of Jamaica’s loveliest crystal clear bodies of water, Discovery Bay. On its own private coral cove, this newest property can be rented alone ~ or in combination with its neighboring sister villa – Keela Wee.

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El Grande Azure

St. Martin, St. Martin (French)

from $2857 /night
up to 12 guests

El Grande Azure

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

Villa El Grande Azure in St Martin a dive in luxury

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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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Sailrock South Caicos Resort - 2 Bedroom Beachfront Premier Villa

Turks & Caicos, South Caicos Island

from $2945 /night
up to 4 guests

Sailrock South Caicos Resort - 2 Bedroom Beachfront Premier Villa

2 bedroom 2 bath Turks & Caicos villa in South Caicos Island

Wake up to the sounds of the ocean washing ashore

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Kaia Kamina

Grand Cayman, Rum Point

from $2950 /night
up to 18 guests

Kaia Kamina

7 bedroom 9 bath Grand Cayman villa in Rum Point

Welcome to Kaia Kamina, a luxury oceanfront estate among the swaying palm trees and tropical vistas of beautiful Cayman Kai.

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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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Fischer’s Reef

Grand Cayman, Rum Point

from $2995 /night
up to 20 guests

Fischer’s Reef

8 bedroom 8.5 bath Grand Cayman villa in Rum Point

Located only one mile from the famous Rum Point Club, Fischer's Reef is a perfectly designed eight bedroom oceanfront villa ideal for large families or group getaways.

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