Jamaica Villa Rentals


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Rio Chico on the Beach

Ocho Rios Villa

from $8753 /night
up to 24 guests

Rio Chico on the Beach

12 bedroom 12 bath Jamaica villa in Ocho Rios

Magnificent 14-acre oceanfront estate. Here is the rich character of The Riviera married to the superb service of Colonial Jamaica ... on a magnificent seascape just west of Ocho Rios on Jamaica's renowned north coast. Rio Chico's guest list includes diplomats, industrialists and celebrities from around the world.

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Haystack at the Tryall Club

Montego Bay Villa

from $2286 /night
up to 20 guests

Haystack at the Tryall Club

10 bedroom 10 bath Jamaica villa in Montego Bay

Its remarkable architecture defines spacious bedroom suites, a long furnished verandah, a striking inside dining room and large family play room ~ all enhanced by overviews of the long private pool and acres of landscaped lawns and breathtaking views of the deep blue Caribbean Sea.

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Villa Amana at Tryall

Montego Bay Villa

from $3391 /night
up to 20 guests

Villa Amana at Tryall

10 bedroom 13 bath Jamaica villa in Montego Bay

Occupying a commanding elevated location, Villa Amana offers magnificent ocean views and a backdrop of deeply forested hills.

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Buttonwood Reef

Ocho Rios Villa

from $2450 /night
up to 18 guests

Buttonwood Reef

9 bedroom 9.5 bath Jamaica villa in Ocho Rios

This brand new 6 bedroom villa & 3 bedroom Sea Biscuit cottage was completed in March 2020. Its location is stunning, right on the water’s edge, overlooking the crystal clear blue waters that Ocho Rios is well-known for. Entry to the villa is through the private compound of Hermosa Cove Boutique Resort.

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Fortlands Point on the Beach

Discovery Bay Villa

from $2000 /night
up to 18 guests

Fortlands Point on the Beach

9 bedroom 9 bath Jamaica villa in Discovery Bay

On a stunning promontory, once the site of an old stone fort, sits a remarkable home named Fortlands Point. From its breathtaking location on the tip of the peninsula, the commanding view encompasses the turquoise water of Discovery Bay on one side and the deep blue Caribbean Sea on the other.

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Hanover Grange at Tryall

Montego Bay Villa

from $3052 /night
up to 18 guests

Hanover Grange at Tryall

9 bedroom 9.5 bath Jamaica villa in Montego Bay

Hanover Grange is a showcase of the very best of modern Jamaica.

Sundown on the Beach

Discovery Bay Villa

from $2109 /night
up to 18 guests

Sundown on the Beach

9 bedroom 10 bath Jamaica villa in Discovery Bay

Sundown is an exquisite staffed home on a private white sand beach next to the turquoise waters of Discovery Bay.

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Greatview

Montego Bay Villa

from $1629 /night
up to 14 guests

Greatview

8 bedroom 8 bath Jamaica villa in Montego Bay

Greatview is one of the most glamorous private homes overlooking the Half Moon golf course and vast ocean vista. Three world-class golf courses (Cinnamon Hill, Half Moon and White Witch) are within a five-minute drive. The view is breathtaking ~ the deep blue sea to the north and magnificent mountains to the south.

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Malatai on the Beach

Ocho Rios Villa

from $2571 /night
up to 16 guests

Malatai on the Beach

8 bedroom 8.5 bath Jamaica villa in Ocho Rios

MALATAI has just undergone a Fabulous renovation, with 8 newly renovated bedrooms and bathrooms, beach front and a top-rated chef, directly on the translucent waters of Mammee Bay, near to Ocho Rios. While privately located, Malatai is only minutes from Dolphin Cove, famous Dunn‘s River Falls and lively Ocho Rios with its wide selection of duty-free shopping, excursions and music.

Promiseas

Ocho Rios Villa

from $3000 /night
up to 16 guests

Promiseas

8 bedroom 8 bath Jamaica villa in Ocho Rios

Promiseas Villas are located on a fabulous private sandy cove which are newly completed and exceptional in every way imaginable.

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Silent Waters

Montego Bay Villa

from $2482 /night
up to 20 guests

Silent Waters

8 bedroom 6 bath Jamaica villa in Montego Bay

Silent Waters is one of the most glamorous private homes in the Caribbean. It is distinguished by world-class architecture and design, breathtaking location, and exquisite accommodations and service.

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Sugar Hill at the Tryall Club

Montego Bay Villa

from $1633 /night
up to 16 guests

Sugar Hill at the Tryall Club

8 bedroom 8 bath Jamaica villa in Montego Bay

Sugar Hill is a luxurious eight-bedroom villa perched atop a lush three-acre property with breathtaking views over the Tryall Club to the Caribbean Sea and horizon. This glamorous home is ideal for golf and tennis buffs, couples, large groups and families. Children welcome!

A Summer Place

A Summer Place on the Beach

Discovery Bay Villa

from $1571 /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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Amanoka on the Beach

Discovery Bay Villa

from $2286 /night
up to 14 guests

Amanoka on the Beach

7 bedroom 8 bath Jamaica villa in Discovery Bay

Located on beautiful Discovery Bay, Amanoka is one of the most stunning villas in this collection. From the spacious verandah and pool, a barefoot stroll leads down a soft lawn to the 70’ white sand beach, clear turquoise water and waterfront gazebo with suspended canvas swings.

Bambu

Montego Bay Villa

from $1179 /night
up to 14 guests

Bambu

7 bedroom 7 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 six-bedroom private villa distinguished by its classic architecture and appreciated by discerning vacationers.

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Canoe Cove on the Beach

Ocho Rios Villa

from $2814 /night
up to 14 guests

Canoe Cove on the Beach

7 bedroom 8 bath Jamaica villa in Ocho Rios

In the 1950’s, Kingston attorney Clinton Hart happened onto this remarkable 3-acre waterfront location, bought it and built a simple beach cottage for his family. Through four generations, Canoe Cove has been a beloved family home, virtually unembellished. In 2015, Hart’s grandson replaced the worn cottage with a new sort of architecture, straightforward, uncomplicated and loaded with thoughtful comforts and essentials to redefine luxury in a beachy, barefoot lifestyle.

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Coach House at Good Hope

Montego Bay Villa

from $800 /night
up to 14 guests

Coach House at Good Hope

7 bedroom 8 bath Jamaica villa in Montego Bay

The Coach House is a fantastic gathering place for families, retreats, and friends,- with space for togetherness, space for discovering nature, space for alone time. Like travelling 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, service is relaxed and meals are served family style.

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Dragonfly at Tryall

Montego Bay Villa

from $2571 /night
up to 14 guests

Dragonfly at Tryall

7 bedroom 7 bath Jamaica villa in Montego Bay

Occupying a commanding position on Garden Hill, this sensational new villa is a dramatic new addition to the Tryall Club.

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Endless Summer

Montego Bay Villa

from $1214 /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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Fairway Manor

Montego Bay Villa

from $1770 /night
up to 16 guests

Fairway Manor

7 bedroom 9 bath Jamaica villa in Montego Bay

Stunning for its massive renovation and outstanding new features. 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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Hummingbird House at the Tryall Club

Montego Bay Villa

from $2571 /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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Makana on the Beach

Discovery Bay Villa

from $2214 /night
up to 14 guests

Makana on the Beach

7 bedroom 7 bath Jamaica villa in Discovery Bay

Makana is one of the most glamorous private villas on the precious strip of land that borders Discovery Bay. The site itself is remarkable: a spacious villa with private tennis court and swimming pool on a sugary white sand beach bordering translucent swimming and kayaking water.

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Phoenix on the Beach at the Tryall Club

Montego Bay Villa

from $2338 /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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Round House at the Tryall Club

Montego Bay Villa

from $1339 /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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Sundance at Tryall

Montego Bay Villa

from $3143 /night
up to 14 guests

Sundance at Tryall

7 bedroom 7 bath Jamaica villa in Montego Bay

Sundance is located on Mahogany Drive with magnificent views across vast sweeping lawns to the sea in the distance.

Tranquility

Tranquillity on the Beach

Montego Bay Villa

from $1214 /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.

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Whispering Waters on the Beach

Discovery Bay Villa

from $2214 /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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Zion Hill at Tryall

Montego Bay Villa

from $2571 /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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Ambiance Sea Salt at the Tryall Club

Montego Bay Villa

from $1559 /night
up to 12 guests

Ambiance Sea Salt at the Tryall Club

6 bedroom 6 bath Jamaica villa in Montego Bay

Ambiance Sea Salt is one of the most stylish villas in this collection. Exquisite classic Jamaican architecture defines 7,700 square feet of living, dining, entertaining and relaxation spaces. Exteriors are lushly landscaped with native trees and a host of flowering plants.

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Anticipation at Tryall

Montego Bay Villa

from $1560 /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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Bumper’s Nest at the Tryall Club

Montego Bay Villa

from $1623 /night
up to 12 guests

Bumper’s Nest at the Tryall Club

6 bedroom 6 bath Jamaica villa in Montego Bay

On three acres of land with a commanding view of the Caribbean Sea, lush green mountains and golf course, Bumper's Nest was designed by distinguished architect Kasimir Korybut in 1995. A brilliant renovation completed in 2015 has recreated one of the most glamorous homes at the Tryall Club. Here is an extraordinary private home with simply the best of everything.

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Flower Hill

Montego Bay Villa

from $2429 /night
up to 12 guests

Flower Hill

6 bedroom 14 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.

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Following Seas at the Tryall Club

Montego Bay Villa

from $2273 /night
up to 12 guests

Following Seas at the Tryall Club

6 bedroom 7 bath Jamaica villa in Montego Bay

Following Seas is a marvelous private villa with the top rating of Premier. It is tastefully renovated with thoughtful comforts, amenities and stylish bathrooms throughout.

Frankfort on the Beach

Ocho Rios Villa

from $3174 /night
up to 12 guests

Frankfort on the Beach

6 bedroom 7 bath Jamaica villa in Ocho Rios

17th Century fortress restored as a remarkable private home on a perfect private Caribbean beach.

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Hidden Bay by the Sea

Runaway Bay Villa

from $1714 /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.

Jubilation At Tryall Jamaica

Jubilation at Tryall

Montego Bay Villa

from $1429 /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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Karma Bay at the Tryall Club

Montego Bay Villa

from $1500 /night
up to 12 guests

Karma Bay at the Tryall Club

6 bedroom 6 bath Jamaica villa in Montego Bay

A sprawling double lot directly on the Caribbean Sea is among the most stunning waterfront locations in all Jamaica. This is the rarefied site of the private villa named Karma Bay.

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Keela Wee on the Beach

Discovery Bay Villa

from $1714 /night
up to 12 guests

Keela Wee on the Beach

6 bedroom 6 bath Jamaica villa in Discovery Bay

Located on a private coral cove, this pretty yellow stone villa overlooks one of Jamaica's loveliest 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 – Whispering Waters..

Nutmeg

Montego Bay Villa

from $1254 /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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Sea Glass at Tryall Club

Montego Bay Villa

from $1299 /night
up to 12 guests

Sea Glass at Tryall Club

6 bedroom 8 bath Jamaica villa in Montego Bay

Formerly named Annabella, Sea Glass sits on a remarkable six private acres on a plum site at the prestigious Tryall Club. Uniquely private, the feeling is being in a world of your own, wonderfully quiet and tranquil while just minutes away by complimentary golf cart are the amenities that have defined the Tryall Club as one of the finest private clubs in the world.

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Sweet Spot on the Beach

Runaway Bay Villa

from $1275 /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.

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Villa Stella at Tryall Club

Montego Bay Villa

from $1559 /night
up to 12 guests

Villa Stella at Tryall Club

6 bedroom 6 bath Jamaica villa in Montego Bay

Redolent of a classical Jamaican house with deep shaded verandas and tall ceilings, Villa Stella offers splendid ocean views from its elevated setting.

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Wheelhouse at Tryall

Montego Bay Villa

from $1043 /night
up to 12 guests

Wheelhouse at Tryall

6 bedroom 6 bath Jamaica villa in Montego Bay

Welcome to the Wheel House Villa!

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Windrush at the Tryall Club

Montego Bay Villa

from $1732 /night
up to 12 guests

Windrush at the Tryall Club

6 bedroom 6 bath Jamaica villa in Montego Bay

WINDRUSH overlooks the manicured Tryall Club golf course and the Caribbean Sea. Large and quite well-decorated, this fine private home is distinguished by antiques, original art and extraordinary comfort. The panoramic view of the sea is breathtaking.

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Windward at the Tryall Club

Montego Bay Villa

from $1299 /night
up to 12 guests

Windward at the Tryall Club

6 bedroom 8 bath Jamaica villa in Montego Bay

Premier Villa on Two Acres on Tryall Club’s Chic West End!

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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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