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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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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Linga-Awile Cottage on the Beach

Discovery Bay Villa

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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Mirador at the Tryall Club

Montego Bay Villa

from $571 /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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Etoile at the Tryall Club

Montego Bay Villa

from $571 /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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Moments at the Tryall Club

Montego Bay Villa

from $621 /night
up to 4 guests

Moments at the Tryall Club

2 bedroom 2 bath Jamaica villa in Montego Bay

With over 2,500 square feet of living space, Moments is a two-bedroom villa suite that offers spectacular views and a spacious patio.

Sea Haven Sea

Sea Haven on Discovery Bay

Discovery Bay Villa

from $643 /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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Wag Water at Prospect Estate

Ocho Rios Villa

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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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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Poinciana at Tryall Club

Montego Bay Villa

from $743 /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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Little Palm at Tryall

Montego Bay Villa

from $751 /night
up to 4 guests

Little Palm at Tryall

2 bedroom 2 bath Jamaica villa in Montego Bay

Tryall's only two bedroom estate villa, Little Palm lives large nestled on a 3 acre property, on the 17th hole and a short walk or quick golf car ride to the beach.

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Bee Happy at the Tryall Club

Montego Bay Villa

from $760 /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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Cliffside Cottage

Montego Bay Villa

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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Windsong

Montego Bay Villa

from $794 /night
up to 8 guests

Windsong

4 bedroom 4 bath Jamaica villa in Montego Bay

Windsong is an exquisite and very private home. 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 towards Negril, the sea, and the sunset.

Balcony View

Out of the Blue on the Beach

Treasure Beach Villa

from $835 /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.

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Blue Heaven

Montego Bay Villa

from $857 /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

Montego Bay Villa

from $900 /night
up to 14 guests

Coach House at Good Hope

7 bedroom 7.5 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 there are 2 extra bedrooms, just 50 paces away that may be available for an occupancy of 18 pax.

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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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No Problem at Tryall

Montego Bay Villa

from $994 /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.

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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 architecture meets lovely spacious accommodation! Set on five acres of gently sloping land with a sea view and is surrounded by manicured lawns.

Sea Grapes on the Beach

Discovery Bay Villa

from $1000 /night
up to 12 guests

Sea Grapes on the Beach

6 bedroom 6 bath Jamaica villa in Discovery Bay

On its own sugary white sand beach lapped by the clear turquoise waters of Discovery Bay sits the charming home Sea Grapes. The translucent azure waters here are excellent for swimming and kayaking. Surrounding the swimming pool is a spacious grassy lawn, wonderful for children and games.

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Pharos Summertime

Montego Bay Villa

from $1000 /night
up to 14 guests

Pharos Summertime

7 bedroom 6 bath Jamaica villa in Montego Bay

6,000-square-foot private villa on 5 acres with magnificent views of the Caribbean Sea. After sunset, the view transforms from brilliant blue water to the mesmerizing beauty of the sea at night.

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Kenyan Sunset Golf Villa in Rose Hall

Montego Bay Villa

from $1014 /night
up to 10 guests

Kenyan Sunset Golf Villa in Rose Hall

5 bedroom 7 bath Jamaica villa in Montego Bay

In the Rose Hall residential expanse of fine homes, Kenyan Sunset Golf Villa is designed for families and golfers.

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Caribbean Jewel

Montego Bay Villa

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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Noble House on the Beach

Montego Bay Villa

from $1050 /night
up to 10 guests

Noble House on the Beach

5 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.

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Serenity on the Beach

Montego Bay Villa

from $1093 /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.

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Almond Hill

Montego Bay Villa

from $1150 /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 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 five-minute drive from Round Hill where guests enjoy complimentary resort membership.

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Eight Rivers at Prospect Estate

Ocho Rios Villa

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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Somewhere at Prospect Estate

Ocho Rios Villa

from $1200 /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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Skyline at Tryall

Montego Bay Villa

from $1214 /night
up to 2 guests

Skyline 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.

Seven Seas

Seven Seas on the Beach

Ocho Rios Villa

from $1243 /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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Eureka at Tryall Club

Montego Bay Villa

from $1265 /night
up to 8 guests

Eureka at Tryall Club

4 bedroom 4 bath Jamaica villa in Montego Bay

This very special villa not only offers sweeping sea views but enjoys a very private location surrounded by a garden full of meticulously cared-for specimen flowers. Beloved by many guests and with a high repeat factor the elegant interiors are a testament to Jamaican master craftsmanship.

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Tranquillity on the Beach

Montego Bay Villa

from $1321 /night
up to 14 guests

Tranquillity on the Beach

7 bedroom 6 bath Jamaica villa in Montego Bay

True to its name, Tranquillity on the Beach is a place for relaxing into the calm ambiance of an exquisite home on a beautiful beachfront site ~ while being gently pampered by a competent staff.

Nutmeg

Montego Bay Villa

from $1350 /night
up to 12 guests

Nutmeg

6 bedroom 6 bath Jamaica villa in Montego Bay

Nutmeg is a charming 6 bedroom villa in the upscale residential neighborhood of Spring Farm ~ just five minutes from three world-class golf courses, designer shops, bars, restaurants and beaches.

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Allamanda

Montego Bay Villa

from $1357 /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 a nearby membership at the Tryall Club.

Vista Del Mar

Vista del Mar at the Tryall Club

Montego Bay Villa

from $1357 /night
up to 8 guests

Vista del Mar at the Tryall Club

4 bedroom 4 bath Jamaica villa in Montego Bay

One of the most enviable locations at Tryall atop Barnes Hill, Vista Del Mar is a Jamaican Classic offering charm and spectacular views.

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Bambu

Montego Bay Villa

from $1358 /night
up to 10 guests

Bambu

5 bedroom 5 bath Jamaica villa in Montego Bay

Nine miles west of Montego Bay is a large private site overlooking perhaps the most glorious view of sea and sky on Jamaica’s renowned north coast. Elegantly perched on eight and a half acres atop this hill is Bambu, a grand five-bedroom private villa distinguished by its classic architecture and appreciated by discerning vacationers.

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Wheel House at Tryall

Montego Bay Villa

from $1466 /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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Pavilion

Montego Bay Villa

from $1479 /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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Coconut Cottage

Montego Bay Villa

from $1495 /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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Frangipani at Prospect Estate

Ocho Rios Villa

from $1500 /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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Elysian Plain at Tryall

Montego Bay Villa

from $1571 /night
up to 10 guests

Elysian Plain at Tryall

5 bedroom 5 bath Jamaica villa in Montego Bay

This spacious five bedroom villa has a magical location and sits literally at the edge of the clear blue Caribbean Sea, with panoramic views stretching from east to west.

Jubilation Pool Looking North

Jubilation at Tryall

Montego Bay Villa

from $1575 /night
up to 12 guests

Jubilation at Tryall

6 bedroom 6.5 bath Jamaica villa in Montego Bay

Jubilation Villa is the latest reason to enjoy your Jamaican vacation at The Tryall Club. This newly created tropical paradise is elegantly furnished throughout with carefully selected antique treasures, locally built mahogany four poster beds and uniquely crafted local wood carvings.

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Scotch on the Rocks

Ocho Rios Villa

from $1620 /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.

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Endless Summer

Montego Bay Villa

from $1714 /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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Round House at the Tryall Club

Montego Bay Villa

from $1718 /night
up to 14 guests

Round House at the Tryall Club

7 bedroom 10 bath Jamaica villa in Montego Bay

From the moment one approaches its colorful entrance, the eponymous architecture of Round House is intriguing. Spiral stairways and balconies connect multiple living, dining and sleeping areas in this eight-bedroom staffed villa at the Tryall Club.

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Anticipation at Tryall

Montego Bay Villa

from $1738 /night
up to 12 guests

Anticipation at Tryall

6 bedroom 6 bath Jamaica villa in Montego Bay

An absolutely gorgeous villa; modern, bright, airy and with a stunning contemporary finish that is blessed with magnificent ocean views that are hard to beat.

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Sweet Spot on the Beach

Runaway Bay Villa

from $1778 /night
up to 12 guests

Sweet Spot on the Beach

6 bedroom 6.5 bath Jamaica villa in Runaway Bay

Located on a wide sandy beach, Sweet Spot is like a pretty jewel box next to the sea. Its remarkable location is the best of all worlds ... a 6,000-square-foot private home with a huge lawn and beach.

Bali Hai

Bali Hai at the Tryall Club

Montego Bay Villa

from $1786 /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.

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Overlook at Tryall

Montego Bay Villa

from $1846 /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.

Ee Dji

Everything Nice by the Sea

Montego Bay Villa

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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