Jamaica Villa Rentals

Jamaica is a Caribbean destination that is a must-visit at least once in your lifetime. This island paradise can be found in the western Caribbean. It has an enchanting vibe filled with carnival, reggae music, art, and culture. Beach lovers will thrill in the awe-inspiring beaches. Some are uniquely set between mountains or within lush gardens. For a change of pace, take a day trip to the Blue Mountains, a hiker’s paradise. Jamaica is an excellent destination for luxury villa holidays. Our villas are unique. They offer an interesting blend of the local vibe combined with world-class amenities.


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Etoile at the Tryall Club

Montego Bay Villa

from $357 /night
up to 2 guests

Etoile at the Tryall Club

1 bedroom 1 bath Jamaica villa in Montego Bay

A beautifully presented one-bedroom villa with outstanding ocean views looking east towards Montego Bay.

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Mirador at the Tryall Club ~ A Great House Villa Suite

Montego Bay Villa

from $357 /night
up to 4 guests

Mirador at the Tryall Club ~ A Great House Villa Suite

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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Stella Marina at Tryall

Montego Bay Villa

from $357 /night
up to 2 guests

Stella Marina at Tryall

1 bedroom 2 bath Jamaica villa in Montego Bay

Stella Marina is a very smart and well-presented one-bedroom villa with stunning ocean and golf course views.

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Bee Happy at the Tryall Club ~ A Two-Bedroom Great House Villa

Montego Bay Villa

from $571 /night
up to 4 guests

Bee Happy at the Tryall Club ~ A Two-Bedroom Great House Villa

2 bedroom 3 bath Jamaica villa in Montego Bay

Bee Happy, newly renovated and newly named! The home owners have done a masterful job. This 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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GoldenEye Beach and Lagoon Villas

Ocho Rios Villa

from $1365 /night
up to 4 guests

GoldenEye Beach and Lagoon Villas

2 bedroom 2 bath Jamaica villa in Ocho Rios

Each of GoldenEye's stand-alone villas is its own private world, set in a verdant garden of native greenery and sitting directly on the beach or lagoon.

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Poinciana at Tryall Club

Montego Bay Villa

from $520 /night
up to 4 guests

Poinciana at Tryall Club

2 bedroom 2 bath Jamaica villa in Montego Bay

Poinciana is an exquisite 2-bedroom Great House Villa with a private plunge pool on a quiet corner of its spacious terrace and with far-reaching views of the Tryall golf course and Caribbean Sea.

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Blue Heaven

Montego Bay Villa

from $643 /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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Jus Paradise at Rose Hall

Montego Bay Villa

from $743 /night
up to 6 guests

Jus Paradise at Rose Hall

3 bedroom 6 bath Jamaica villa in Montego Bay

JUS' PARADISE is an charming private villa located in a gated residential area of upscale homes in the lush hills of Rose Hall. This well-located home sits between two renowned golf courses: the challenging White Witch and championship Cinnamon Hill course. Five minutes west is the famous Half Moon course.

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Linga-Awile Cottage on the Beach

Discovery Bay Villa

from $471 /night
up to 8 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 sister property, Coral Cove 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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Naseberry at Idle Awhile

Negril Villa

from $1050 /night
up to 6 guests

Naseberry at Idle Awhile

3 bedroom 3.5 bath Jamaica villa in Negril

Naseberry Villa is part of the Idle Awhile group of villas. Located on a private 300-foot stretch of shimmering white sand on Negril’s world-famous Seven Mile Beach, Idle Awhile’s Villas are a small collection of exquisitely appointed, fully staffed villas ranging in size from one to five bedrooms. Surrounded by fragrant tropical gardens and affording breathtaking views of the ocean, each villa sits just steps from the beach, beckoning guests to curl up in a hammock, sunbathe, snorkel or sail in the Caribbean’s warm turquoise waters.

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No Problem at Tryall

Montego Bay Villa

from $786 /night
up to 6 guests

No Problem at Tryall

3 bedroom 3 bath Jamaica villa in Montego Bay

Commanding excellent views of the Caribbean Sea and Tryall Club’s golf course, No Problem is a cozy two-story villa.

Serenity Pool And House

Serenity at Tryall

Montego Bay Villa

from $571 /night
up to 6 guests

Serenity at Tryall

3 bedroom 4 bath Jamaica villa in Montego Bay

The three-bedroom villa Serenity sits high on Copperwood Ridge, surrounded with landscaped gardens, bright with tropical flowers.

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Wag Water at Prospect Estate

Ocho Rios Villa

from $500 /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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Almond at Idle Awhile

Negril Villa

from $1260 /night
up to 8 guests

Almond at Idle Awhile

4 bedroom 4 bath Jamaica villa in Negril

Almond Villa is part of the Idle Awhile group of villas. Located on a private 300-foot stretch of shimmering white sand on Negril’s world-famous Seven Mile Beach, Idle Awhile’s Villas are a small collection of exquisitely appointed, fully staffed villas ranging in size from one to five bedrooms. Surrounded by fragrant tropical gardens and affording breathtaking views of the ocean, each villa sits just steps from the beach, beckoning guests to curl up in a hammock, sunbathe, snorkel or sail in the Caribbean’s warm turquoise waters.

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Almond Hill

Montego Bay Villa

from $863 /night
up to 8 guests

Almond Hill

4 bedroom 4 bath Jamaica villa in Montego Bay

Almond Hill was designed by Prince Kasimir Korybut in 1993. It was brilliantly renovated, creating a contemporary beautifully decorated home with french doors opening from all of the bedrooms to the garden and new bathrooms. Almond Hill is a lovely private home located on a former 500-acre coconut plantation just 22 minutes west of Montego Bay and a two-minute drive from posh Round Hill where guests enjoy complimentary resort membership.

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Aqua Bay at the Tryall Club

Montego Bay Villa

from $2571 /night
up to 10 guests

Aqua Bay at the Tryall Club

4 bedroom 6 bath Jamaica villa in Montego Bay

Aqua Bay was completely renovated & refurbished in 2017 (formerly Calabash Villa). This amazing sea front property is one of the newest premier villas at The Tryall Club.

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Avalon at Tryall

Montego Bay Villa

from $786 /night
up to 8 guests

Avalon at Tryall

4 bedroom 4 bath Jamaica villa in Montego Bay

Avalon is a beautiful home nestled at the end of a lane overlooking both the valley to the east and the ocean to the north. Two cottages, each with two bedrooms sit in a lush garden filled with fruit trees and flowering shrubs. Soft comfortable colors and wooden floors flow through this home. All rooms open to the ocean view

Calypso Shores

Montego Bay Villa

from $850 /night
up to 8 guests

Calypso Shores

4 bedroom 4 bath Jamaica villa in Montego Bay

Calypso Shores is located in a lovely California-style residential neighborhood named Lagoons. Its prize location is a waterfront acre on a calm lagoon. Lovers of water sports will revel in this location.

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Caribbean Jewel

Montego Bay Villa

from $714 /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 & White Witch Golf Courses nearby.

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Casuarina at Tryall

Montego Bay Villa

from $1299 /night
up to 8 guests

Casuarina at Tryall

4 bedroom 4 bath Jamaica villa in Montego Bay

Casuarina is a remarkably welcoming four-bedroom villa which offers the most magical views of the Caribbean Sea from its prestigious vantage point on Barnes Hill.

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Eight Rivers at Prospect Estate

Ocho Rios Villa

from $857 /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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Eureka at Tryall Club

Montego Bay Villa

from $1000 /night
up to 6 guests

Eureka at Tryall Club

4 bedroom Jamaica villa in Montego Bay

Eureka is the closest anyone is ever likely to get to stay in a Jamaican Great House that is furnished of the period and opportunities such as this do not come along very often.

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Frangipani at Prospect Estate

Ocho Rios Villa

from $786 /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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Ma Moura at the Tryall Club

Montego Bay Villa

from $1299 /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.

Noble House on the Beach

Montego Bay Villa

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.

Out of the Blue on the Beach

Treasure Beach Villa

from $750 /night
up to 8 guests

Out of the Blue on the Beach

4 bedroom 4 bath Jamaica villa in Treasure Beach

Out of the Blue is an oxymoron: a contemporary home in Old Jamaica. And what a home it is! The villa sits on the longest uninterrupted expanse of sea view at beach level of any other beach property in this group.

Reef House Pool To House Late Afternoon

Reef House at Tryall

Montego Bay Villa

from $1714 /night
up to 8 guests

Reef House at Tryall

4 bedroom Jamaica villa in Montego Bay

Reef House celebrates beach life with its casual breezy feel and beautiful setting right on the ocean front.

Sea Haven Jamaica Villas

Sea Haven on Discovery Bay

Discovery Bay Villa

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. It sits directly on the edge of beautiful Discovery Bay.

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Seaside Villa at Round Hill

Montego Bay Villa

from $3572 /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.

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Seaspray at Tryall

Montego Bay Villa

from $1286 /night
up to 8 guests

Seaspray at Tryall

4 bedroom Jamaica villa in Montego Bay

This idyllic setting sets a splendid tone for invigorating days in the sun and sea.

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Serenity on the Beach

Montego Bay Villa

from $1021 /night
up to 8 guests

Serenity on the Beach

4 bedroom 4 bath Jamaica villa in Montego Bay

SERENITY is one of the most beloved and often revisited villas on Jamaica's beautiful north coast. Its prize location is a waterfront acre 8 miles west of Montego Bay. Grounds include a shared tennis court and basketball hoop and a heated pool.

Seven Seas Jamaica Villas

Seven Seas on the Beach

Ocho Rios Villa

from $1071 /night
up to 8 guests

Seven Seas on the Beach

4 bedroom 4 bath Jamaica villa in Ocho Rios

The morning sun has turned the sea and the dew on the palm trees to silver. The non-stop trade winds waft through the rooms of the villa and the aroma of fresh-baked bread works its way from the kitchen to my bedroom window.

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Somewhere at Prospect Estate

Ocho Rios Villa

from $740 /night
up to 8 guests

Somewhere at Prospect Estate

4 bedroom 4 bath Jamaica villa in Ocho Rios

Somewhere Villa is a lovely traditional style villa with an open, airy and spacious sitting room which opens on to a covered verandah, allowing for inside/outside living.

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Spanish Cove

Runaway Bay Villa

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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Summertime at Silver Sands

Montego Bay Villa

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.

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Tradewinds at the Tryall Club

Montego Bay Villa

from $1929 /night
up to 8 guests

Tradewinds at the Tryall Club

4 bedroom 4 bath Jamaica villa in Montego Bay

Tradewinds was completely renovated and refurbished in January 2018. This amazing sea front property sits on two acres at the famous Tryall Club – directly on the Caribbean Sea. 300 feet of waterfront from the north perimeter of the property, and it is one of the newest premier villas at The Tryall Club.

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Windsong

Montego Bay Villa

from $786 /night
up to 8 guests

Windsong

4 bedroom 4 bath Jamaica villa in Montego Bay

Windsong is an exquisite and very private home just minutes from Round Hill. Designed by noted architect Kasimir Coribut, the site benefits from spectacular views day and night and the most favorable tradewinds. The east view captures the sunrise and Montego Bay ... the west view is an equally lovely vista of Round Hill, the sea and the sunset.

Yellowbird

Yellowbird at the Tryall Club

Montego Bay Villa

from $786 /night
up to 8 guests

Yellowbird at the Tryall Club

4 bedroom 4 bath Jamaica villa in Montego Bay

Yellowbird is an excellent family home on a large, lovely landscaped site overlooking the Tryall golf course and the Caribbean Sea. The tradewinds are delightful; the view is wonderful.

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Allamanda

Montego Bay Villa

from $1286 /night
up to 10 guests

Allamanda

5 bedroom 4 bath Jamaica villa in Montego Bay

ALLAMANDA is a brilliant contemporary private villa with large heated pool, an excellent staff including top-rated chef and nearby membership at Round Hill.

Bali Hai at the Tryall Club

Montego Bay Villa

from $1429 /night
up to 10 guests

Bali Hai at the Tryall Club

5 bedroom 6 bath Jamaica villa in Montego Bay

On seven acres overlooking the Tryall golf course and the Caribbean Sea, Bali Hai is among the most beautiful and spacious private homes at the Tryall Club. The unique architecture has situated all bedrooms for maximum privacy.

Bougainvillea

Bougainvillea at the Tryall Club

Montego Bay Villa

from $1754 /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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Cielo at the Tryall Club

Montego Bay Villa

from $1429 /night
up to 10 guests

Cielo at the Tryall Club

5 bedroom 6 bath Jamaica villa in Montego Bay

Cielo means "sky" and "heaven" and the name tells a lot about living in this wonderful villa on a hill. Add the all-day panorama of blue Caribbean Sea at every glance and "heaven" gets even better!

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Cliffside Cottage

Montego Bay Villa

from $643 /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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Coconut Cottage

Montego Bay Villa

from $1800 /night
up to 10 guests

Coconut Cottage

5 bedroom 6 bath Jamaica villa in Montego Bay

COCONUT is a very private 5-bedroom cottage nestled into an acre on a gentle hillside that was the original 500-acre plantation of Round Hill Estate. Set in a storybook wooded lot, the villa accommodates couples and families in three bedrooms in the Main House and two more bedrooms in the Cottage just a few yards away.

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Coral Cove Villa on the Beach

Discovery Bay Villa

from $707 /night
up to 10 guests

Coral Cove Villa on the Beach

5 bedroom 5 bath Jamaica villa in Discovery Bay

Located on the beach of Discovery Bay, Coral Cove Villa is a five bedroom, two story villa with a comfy put-your-feet-up signature feeling that allows an at-home, informal, relaxed lifestyle.

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Cottonwood at Idle Awhile

Negril Villa

from $1575 /night
up to 10 guests

Cottonwood at Idle Awhile

5 bedroom 5.5 bath Jamaica villa in Negril

Cottonwood Villa is part of the Idle Awhile group of villas. Located on a private 300-foot stretch of shimmering white sand on Negril’s world-famous Seven Mile Beach, Idle Awhile’s Villas are a small collection of exquisitely appointed, fully staffed villas ranging in size from one to five bedrooms. Surrounded by fragrant tropical gardens and affording breathtaking views of the ocean, each villa sits just steps from the beach, beckoning guests to curl up in a hammock, sunbathe, snorkel or sail in the Caribbean’s warm turquoise waters.

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Elysian Plain at Tryall

Montego Bay Villa

from $1286 /night
up to 10 guests

Elysian Plain at Tryall

5 bedroom 5 bath Jamaica villa in Montego Bay

Aptly named "Elysian Plain", the resting place of the Greek Gods, this spacious, 5 bedroom villa sits literally at the edge of the clear, blue Caribbean Sea.

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Everything Nice by the Sea

Montego Bay Villa

from $1750 /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 water front property on Emerald Quay. Nestled in between the Breathless & Secrets Hotels & within walking distance to the Montego Bay Yacht Club.

Great River House

Montego Bay Villa

from $1000 /night
up to 10 guests

Great River House

5 bedroom 6 bath Jamaica villa in Montego Bay

Classic Jamaican glamour meets luxurious modern conveniences! Set on five acres of gently sloping land with sea view and surrounded by manicured lawns.

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Infinity at the Tryall Club

Montego Bay Villa

from $2300 /night
up to 10 guests

Infinity at the Tryall Club

5 bedroom 6 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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