Montego Bay Villa Rentals

Jamaica


Villaa 2

Etoile at the Tryall Club

Montego Bay, Jamaica

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, Jamaica

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, Jamaica

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, Jamaica

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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Poinciana at Tryall Club

Montego Bay, Jamaica

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, Jamaica

from $643 /night
up to 6 guests

Blue Heaven

3 bedroom 2.5 bath Jamaica villa in Montego Bay

The grounds are adorned by elegant palm trees, bougainvillea, hibiscus, ginger lilies, frangipani, bamboo, ferns, lavender and periwinkle. Velvety soft zoysia grass invites barefoot walks around the lawn.

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Jus Paradise at Rose Hall

Montego Bay, Jamaica

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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No Problem at Tryall

Montego Bay, Jamaica

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, Jamaica

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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Almond Hill

Montego Bay, Jamaica

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, Jamaica

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, Jamaica

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, Jamaica

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, Jamaica

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, Jamaica

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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Eureka at Tryall Club

Montego Bay, Jamaica

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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Ma Moura at the Tryall Club

Montego Bay, Jamaica

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, Jamaica

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.

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Reef House at Tryall

Montego Bay, Jamaica

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.

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Seaside Cottage at Round Hill

Montego Bay, Jamaica

from $3572 /night
up to 8 guests

Seaside Cottage 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, Jamaica

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, Jamaica

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.

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Summertime at Silver Sands

Montego Bay, Jamaica

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, Jamaica

from $1570 /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, Jamaica

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.

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Yellowbird at the Tryall Club

Montego Bay, Jamaica

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, Jamaica

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, Jamaica

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.

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Bougainvillea at the Tryall Club

Montego Bay, Jamaica

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, Jamaica

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, Jamaica

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, Jamaica

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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Elysian Plain at Tryall

Montego Bay, Jamaica

from $1100 /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, Jamaica

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, Jamaica

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, Jamaica

from $2091 /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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Kenyan Sunset Golf Villa in Rose Hall

Montego Bay, Jamaica

from $1014 /night
up to 14 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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Overlook at Tryall

Montego Bay, Jamaica

from $1559 /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.

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Pavilion

Montego Bay, Jamaica

from $1200 /night
up to 14 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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Point of View at the Tryall Club

Montego Bay, Jamaica

from $2572 /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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Quinntessential at Tryall

Montego Bay, Jamaica

from $2143 /night
up to 10 guests

Quinntessential 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.

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Sunset on the Beach at the Tryall Club

Montego Bay, Jamaica

from $1929 /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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Tek Time Golf Villa on Cinnamon Hill

Montego Bay, Jamaica

from $1641 /night
up to 12 guests

Tek Time Golf Villa on Cinnamon Hill

5 bedroom 6 bath Jamaica villa in Montego Bay

TEK TIME is Jamaican patois for advice that almost all of us need: TAKE TIME to slow down and take in all that’s good and beautiful around us. Living in a glamorous villa with a staff of six who pamper their guests without ever intruding makes it easy to heed that advice.

Villa Christina

Montego Bay, Jamaica

from $2071 /night
up to 10 guests

Villa Christina

5 bedroom 6.5 bath Jamaica villa in Montego Bay

Set on the historic Rose Hall Estate, Villa Christina welcomes couples, families, and friends to Caribbean luxury in a remarkable 10,000 sq. ft. well-appointed Tuscan style villa located in the Greens at Rose Hall - a private gated-community on the Cinnamon Hill Golf Course.

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Villa Rosa

Montego Bay, Jamaica

from $1557 /night
up to 11 guests

Villa Rosa

5 bedroom 6 bath Jamaica villa in Montego Bay

Villa Rosa is our newest villa in Montego Bay's Spring Farm neighborhood. It is a stunning, modern villa, brilliantly designed for an extraordinary indoor-outdoor lifestyle with a full complement of impressive luxuries for the upscale traveler.

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Ambiance Sea Salt at the Tryall Club

Montego Bay, Jamaica

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, Jamaica

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, Jamaica

from $1624 /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, Jamaica

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, Jamaica

from $1857 /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.

Jubilation at Tryall

Montego Bay, Jamaica

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, Jamaica

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.

Nutmeg

Montego Bay, Jamaica

from $1150 /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, Jamaica

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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Villa Stella at Tryall Club

Montego Bay, Jamaica

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, Jamaica

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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Windward at the Tryall Club

Montego Bay, Jamaica

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!

Bambu

Montego Bay, Jamaica

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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Coach House at Good Hope

Montego Bay, Jamaica

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, Jamaica

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, Jamaica

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, Jamaica

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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Harmony Hill at Tryall

Montego Bay, Jamaica

from $2700 /night
up to 14 guests

Harmony Hill at Tryall

7 bedroom 7.5 bath Jamaica villa in Montego Bay

Harmony Hill is a private oasis offering the finest in Caribbean living, combining Jamaica’s rich architectural tradition with today’s modern amenities and service.

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Hummingbird House at the Tryall Club

Montego Bay, Jamaica

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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Longview Villa on Round Hill

Montego Bay, Jamaica

from $2357 /night
up to 14 guests

Longview Villa on Round Hill

7 bedroom 7 bath Jamaica villa in Montego Bay

If you, family or friends are looking for a certain kind of hideout in a tropical seclusion with timeless elegance and understated luxury, Longview Villa on Round Hill is a pretty favorable address.

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Pharos Summertime

Montego Bay, Jamaica

from $714 /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, glimmering with reflections of cruise ships and the romantic night lights of Montego Bay nine miles away.

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Phoenix on the Beach at the Tryall Club

Montego Bay, Jamaica

from $2357 /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, Jamaica

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, Jamaica

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.

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Tranquillity on the Beach

Montego Bay, Jamaica

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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Zion Hill at Tryall

Montego Bay, Jamaica

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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Greatview

Montego Bay, Jamaica

from $1629 /night
up to 16 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.

Janus On Round Hill Jamaica Villas

Janus on Round Hill

Montego Bay, Jamaica

from $2357 /night
up to 16 guests

Janus on Round Hill

8 bedroom 8 bath Jamaica villa in Montego Bay

Located at the highest point on one of the largest individual tracts of land on Round Hill, Janus is one of the most stylish additions to this collection. A stunning four-bedroom villa, Janus was designed to be extraordinarily comfortable and chic.

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Silent Waters

Montego Bay, Jamaica

from $2482 /night
up to 24 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, Jamaica

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!

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Hanover Grange at Tryall

Montego Bay, Jamaica

from $1714 /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.

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Haystack at the Tryall Club

Montego Bay, Jamaica

from $2857 /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, Jamaica

from $2012 /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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