The Caribbean, your way

ISLAND
ESCAPES

Beautiful villas, unforgettable settings and the freedom to create your own Caribbean escape.

Your Caribbean, Your Way

Island Escapes

Discover a collection of beautiful Caribbean villas made for effortless island living. From relaxed beachfront stays to private retreats tucked into some of the region’s most desirable communities, each escape offers its own way to experience the Caribbean.

Whether you’re planning a family holiday, a romantic getaway or simply looking for somewhere to slow down and reconnect, our Island Escapes offer the space, privacy and comfort to settle in and experience the Caribbean at your own pace.

18 Available

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From
$1,075.00/night

Windward - 5BR Ocean Front Villa

This luxurious villa is designed to offer the ultimate blend of elegance and tranquillity, making it your perfect escape. Magnificent main house with four opulent bedrooms, each featuring a king-sized bed and a lavish en-suite bath. Additionally,...

10 5 6

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From
$185.00/night

Blue Ocean -A Sky Harbour Oceanfront Twin Suite

Welcome to Sky Harbour Suites, a brand-new luxury retreat in the heart of Montego Bay, conveniently located right above Harbour City Mall. This comfortable suite features a plush King bed, making it a perfect choice for couples or solo travellers,...

2 1 1

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From
$239.00/night

Syd’s Too - Modern Oceanfront Loft w/ Kitchenette

Inside, you’ll find a cozy setup with a king floor sofa bed and full bathroom on the main level, while the upstairs loft offers a queen bed and a half bathroom. A private balcony opens up to stunning ocean views—the perfect spot for sunrise coffee or...

4 Studio 1

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From
$195.00/night

Horizon-Sky Harbour Oceanview Superior King Suite

Welcome to Sky Harbour Suites, a brand-new luxury retreat in the heart of Montego Bay, conveniently located right above Harbour City Mall. This comfortable suite features a plush King bed, making it a perfect choice for couples or solo travellers,...

2 1 1

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From
$185.00/night

Surfs Up - A Sky Harbour Oceanfront King Suite

Welcome to Sky Harbour Suites, a brand-new luxury retreat in the heart of Montego Bay, conveniently located right above Harbour City Mall. This comfortable suite features a plush King bed, making it a perfect choice for couples or solo travellers,...

2 1 1

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From
$185.00/night

The Tides - A Sky Harbour Oceanfront King Suite

Welcome to Sky Harbour Suites, a brand-new luxury retreat in the heart of Montego Bay, conveniently located right above Harbour City Mall. This comfortable suite features a plush King bed, making it a perfect choice for couples or solo travellers,...

2 1 1

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From
$345.00/night

Adrift- 3BR Cozy Cottage in Gated Estate w/ Staff

Welcome to your Tropical Paradise! We've crafted our villa to be your "home away from home," where every detail is designed to make you feel cozy and cared for. Before you arrive, we'll reach out to learn about your preferences, from food to trans...

6 3 2

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From
$190.00/night

The Syd - Oceanfront King Suite w/ Kitchenette

Step inside to a cozy king bedroom with an ensuite bath and shower. The private balcony opens to sweeping ocean views—perfect for savoring your morning coffee or unwinding with sunset cocktails. Your stay includes housekeeping service and a dedica...

2 Studio 1

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From
$185.00/night

The Bloom - A Sky Harbour Oceanfront King Suite

Welcome to Sky Harbour Suites, a brand-new luxury retreat in the heart of Montego Bay, conveniently located right above Harbour City Mall. This comfortable suite features a plush King bed, making it a perfect choice for couples or solo travellers,...

2 1 1

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From
$608.00/night

The Happy Place- 4BR Beachfront w/ Eternity Pool

A lovely villa retreat located in the picturesque Estate of Silvers Sands, Jamaica. This stunning property offers an exceptional blend of comfort, style, and relaxation, making it the perfect destination for those seeking a tranquil escape. At th...

8 4 5

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From
$195.00/night

The Twilight - A Sky Harbour Superior King Suite

Welcome to Sky Harbour Suites, a brand-new luxury retreat in the heart of Montego Bay, conveniently located right above Harbour City Mall. This comfortable suite features a plush King bed, making it a perfect choice for couples or solo travellers,...

2 1 1

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From
$190.00/night

Dorey - Oceanfront Double Suite w/ Kitchenette

Welcome to Tropical Treasure at the West! Set along Negril’s famous cliffs, our cozy villa is the perfect place to relax and soak in Jamaica’s beauty. Start your mornings with a cup of coffee on the porch as the sun rises over the ocean, and wind do...

4 Studio 1

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From
$195.00/night

Blue Heron- A Sky Harbour Superior Oceanfront Twin Suite

Welcome to Sky Harbour Suites, a brand-new luxury retreat in the heart of Montego Bay, conveniently located right above Harbour City Mall. This comfortable suite features a plush King bed, making it a perfect choice for couples or solo travellers,...

2 1 1

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From
$185.00/night

Boardwalks - A Sky Harbour Oceanfront Twin Suite

Welcome to Sky Harbour Suites, a brand-new luxury retreat in the heart of Montego Bay, conveniently located right above Harbour City Mall. This comfortable suite features a plush King bed, making it a perfect choice for couples or solo travellers,...

2 1 1

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From
$122.00/night

Aurelia-1BR Beachfront at Paradasiac Beach Club

Tucked into a peaceful coastal setting at the Paradisiac Beach Club, this calm retreat offers a thoughtfully designed one-bedroom suite with a cozy queen-size bed and air conditioning—perfect for restful nights after sun-filled days. Step onto you...

2 1 1

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From
$195.00/night

The Dawn- A Sky Harbour Oceanfront Superior King Suite

Welcome to Sky Harbour Suites, a brand-new luxury retreat in the heart of Montego Bay, conveniently located right above Harbour City Mall. This comfortable suite features a plush King bed, making it a perfect choice for couples or solo travellers,...

2 1 1

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From
$185.00/night

Blue Fins - A Sky Harbour Oceanfront Twin Suite

Welcome to Sky Harbour Suites, a brand-new luxury retreat in the heart of Montego Bay, conveniently located right above Harbour City Mall. This comfortable suite features a plush King bed, making it a perfect choice for couples or solo travellers,...

2 1 1

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From
$2,462.00/night

Santosha - 10BR Beach Front Luxury Villa

Imagine yourself surrounded by stunning oceanfront property, with your own private white-sand beach and secluded swimming cove. This undiscovered paradise is where Jamaica's true charm comes to life, away from the crowds. Immerse yourself in the pris...

20 10 11

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Featured Island Escapes

A closer look at where you could stay.

01 02 03 04 / 04

01 Island Escape

Modern Beachfront Living

Tideline

Platinum Coast · Barbados

A contemporary four-bedroom escape set directly on the shoreline, created for effortless indoor-outdoor living and unhurried days beside the Caribbean Sea.

8 Guests 4 Bedrooms 4 Bathrooms

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02 Island Escape

Sea-View Hillside Retreat

Hummingbird Villa

Westmoreland Hills · St. James · Barbados

An elegant three-bedroom sea-view retreat with airy open-plan living, a covered terrace and a private plunge pool within the prestigious Westmoreland Hills community.

6 Guests 3 Bedrooms 2 Bathrooms

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Westmoreland Hills 35 overlooking the Caribbean Sea

03 Island Escape

Elevated Caribbean Views

Westmoreland Hills 35

Westmoreland Hills · St. James · Barbados

A striking four-bedroom villa overlooking the Caribbean Sea, with an infinity pool, generous indoor-outdoor living and flexible two-, three- or four-bedroom stays.

8 Guests 4 Bedrooms 4 Bathrooms

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04 Island Escape

Golf Estate Escape

Royal Villa 8

Royal Westmoreland · Barbados

A relaxed three-bedroom hideaway within one of Barbados’ most recognised resort communities, pairing villa privacy with easy access to the island’s west coast.

6 Guests 3 Bedrooms 3 Bathrooms

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Tideline Beachfront

Hummingbird Villa Westmoreland Hills

Westmoreland Hills 35 Sea View

Royal Villa 8 Royal Westmoreland

100%

Fewer rooms. Still entirely yours.

Travelling with a smaller group? Selected villas are available in flexible bedroom configurations, while the entire villa, pool, gardens and shared spaces remain exclusively yours. Explore the available options and varying bedroom rates.

View Flexible Villa Options