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Jamaica Vacation Rentals
Hibiscus
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 1 2 2 $2,500 InquireInquire
Hibiscus Jamaica Vacation Rental

This beautiful split level one bedroom condominium, gives guests the pleasures of the tropics while maintaining the warmth of home

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One Love
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 1 2 2 $2,500 InquireInquire
One Love Jamaica Vacation Rental

One Love is a one bedroom condominium perfectly with views of the Tryall Golf Course and the Caribbean Sea

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Mahogany Mews
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 1 2 2 $2,500 InquireInquire
Mahogany Mews Jamaica Vacation Rental

Close to the hub of the Tryall Club, Mahogany Mews is an elegant one-bedroom condominium that is perfectly suited to couples.

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Stella Marina
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 1 2 2 $2,500 InquireInquire
Stella Marina Jamaica Vacation Rental

Stella Marina is a one-bedroom condominium with views of the golf course and sea. From the crest of the hill, at the heart of the Tryall property

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Eagle’s Nest
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 1 2 2 $2,680 InquireInquire
Eagle’s Nest Jamaica Vacation Rental

With over 2000 square feet of living space, Eagle’s Nest is the largest of Tryall’s one bedroom condominium suites and offers airy accommodations with fascinating views from its elevated promontory

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Cottonwood Cottage
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Bluefields Bay 2 2 4 $610 InquireInquire
Cottonwood Cottage Jamaica Vacation Rental

Our most nature-integrated villa, this home has two bedroom suites on four beachfront acres purchased from the Jamaican government. Dense tropical foliage has been fully-preserved, so guests enjoy full sun and also shaded seating under “tree umbrellas” on the lovely white sand Bluefields Beach

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Milestone Cottage
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Bluefields Bay 2 2 4 $585 InquireInquire
Milestone Cottage Jamaica Vacation Rental

Milestone Cottage has always been the honeymoon favorite, although also popular for small families with its two bedrooms. Built many years earlier, it was purchased in 1986 and extensively remodeled and personalized. This is when its luxurious cliffside plunge pool with underwater seats was added—the perfect place for soaking up sun

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Serenity
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 3 3 6 $4,775 InquireInquire
Serenity Jamaica Vacation Rental

High on the hillside of Copperwood Ridge and almost hidden amongst its exceptionally pretty gardens and surrounded by an aura of blissful calm is a uniquely special house called Serenity

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Linger Longer
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Hanover 3 3 6 $858 InquireInquire
Linger Longer Jamaica Vacation Rental

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. This utterly delightful home stands amidst very pretty gardens and commands a clear unobstructed view of the sea and golf course

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Eureka
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 3 3 6 $5,500 InquireInquire
Eureka Jamaica Vacation Rental

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. This utterly delightful home stands amidst very pretty gardens and commands a clear unobstructed view of the sea and golf course

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Reveille by the Sea
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 3 3 6 $5,500 InquireInquire
Reveille by the Sea Jamaica Vacation Rental

This updated three bedroom property, is an elegant, family- friendly villa that sits right on the water’s edge, with a unique private pool deck overlooking the water and beautiful views of Montego Bay in the distance

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Providence House
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Bluefields Bay 3 3.5 6 $235 InquireInquire
Providence House Jamaica Vacation Rental

Providence House was completed in 2008, and is located on the former landing site of the area’s deep-sea night fishermen. It is rumored that in 1793, Captain William Bligh (of Mutiny on the Bounty fame) arrived to this spot from Tahiti aboard the HMS Providence, bringing with him the prized cash crop breadfruit that has since become a popular local food and a valuable export

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The Hermitage
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Bluefields Bay 4 3.5 9 $1,100 InquireInquire
The Hermitage Jamaica Vacation Rental

Architect-designed and lauded as a prized jewel of our luxury Caribbean resorts, this distinctive home was completed in 1991. In building The Hermitage, major emphasis was put on using local workers and Jamaican materials (stone, marble, mahogany, cedar) to reproduce features of authentic and traditional Jamaican homes

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Cielo
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 4 4 8 $6,050 InquireInquire
Cielo at Tryall, Vacation Rental

From its high perch atop Barnes Hill, this luxury villa commands a truly breathtaking view over emerald lawns, an infinity pool and the broad expanse of Tryall Club’s legendary golf course. To complete this magical picture are infinite views of the turquoise Caribbean Sea.

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Casuarina
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 4 4 8 $6,050 InquireInquire
Casuarina at Tryall, Vacation Rental

This lovely Jamaican villa is situated in the famous Tryall Club estate. Nestled among some of the finest homes found in Jamaica. Casuarina has been newly refurbished and this 4 bedroom villa is a new addition to Jamaican Treasures Villa collection. All guests at Casuarina have a complimentary membership to the Tryall facilities. The beach is only a 2 minute golf ride away.

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Tradewinds
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 4 4 8 4,950 InquireInquire
Tradewinds Tryall Jamaica, Vacation Rental

Tradewinds is a beautiful villa with an absolute waterfront location, within the famous Tryall Club resort. This cosy home sits on two acres and is only a few minutes’ walk from Tryall’s famous beach club, pro shop, driving range and first fairway. You may use the villas own private golf carts to roam around the 2200 acre resort.

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Ma' Moura
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 4 4 8 4,950 InquireInquire
Ma’Moura Villa Tryall Club, Montego Bay Jamaica Rentals

Ma' Moura is a wonderful villa which is open and spacious with a sparkling circular swimming pool as the focal point for entertaining and relaxing. This villa is of an octagonal design takes full advantage of the view on all sides. The views of the golf greens are superb from this villa with a rolling manicured lawn leading down to the 14th green as your back yard.

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Calypso
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 4 4 8 4,950 InquireInquire
Calypso Tryall Jamaica, Holiday Rentals & Homes

Calypso is such a charming and tranquil home. It is set on four acres within the famous Tryall Resort and has beautiful gardens and orchards. From the pool area, there is a wonderful view of the golf course, the Caribbean Sea and beyond. These gardens are well manicured with beautiful local trees such as the mango, Poinciana trees, colourful bougainvillea, hibiscus and beautiful lavender orchid tree.

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Blue Bird Villa
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 4 4 8 4,950 InquireInquire
Blue Bird at Tryall Club, Jamaica Villa

Bluebird is a four-bedroom villa overlooking a magnificent tropical garden and the glittering panorama of the Caribbean Sea. A spacious, living room lifts your spirit with soft furnishings in up-tempo hues of blue and yellow accented with crisp white.

 

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Mullion Cove
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Bluefields Bay 5 4 12 $940 InquireInquire
Mullion Cove Jamaica Vacation Rental

Mullion Cove set the tone and is the original prototype for the Bluefields Bay villas helping them become one of the top luxury resorts in the caribbean. The oldest of the collection, its history was easy to adapt for truly special holiday experiences.

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Sundance
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 5 5 12 $10,909 InquireInquire
Sundance Tryall Club, Jamaica Vacation Rental

Sundance was built in 2006 and occupies a sprawling site on Mahogany Drive with magnificent views across sweeping lawns to the sea in the distance. In 2014, the villa was refurbished to an exacting standard by the new owner resulting in a level of comfort and luxury associated with a Four Seasons hotel

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Sea Salt Villa
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 5 5 10 12,000 InquireInquire
Sea Salt Tryall Jamiaca, Resort Letting, Vacation Villa

A brand new addition to the exclusive Tryall Club, Sea Salt is one of the most welcoming private homes that grace the northern coast of this Caribbean paradise. Inside, you'll find classic Jamaican architecture and 7,700 sq. ft. of living, dining and entertaining space. Outside, you're surrounded by 5.4 private acres, meticulously landscaped with native trees and indigenous plants.

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Point of View
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 5 5 10 12,000 InquireInquire
Point of View Tryall Club, Jamaica Rentals

Point of View is a truly spectacular deluxe villa perched on the top of Barnes Hill and located within the famous Tryall estate. This villa boasts breathtaking views of the Caribbean Sea from every point. The wonderful spacious veranda is a lovely focus point for relaxing, entertaining and casual dining.

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Villa Overlook
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 5 5 10 15,000 InquireInquire
Villa Overlook Tryall Club, Holiday Rental, Jamaica Montego Bay

Overlook is one of Tryall's newest additions to their collection of luxury villas in Montego Bay.  With spectacular views of the Caribbean Sea and Tryall's famous golf course, Overlook villa lives up to its name with memorizing views. There are 5 wonderful bedrooms all with air conditioning for comfort.

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Bougainvillea
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 5 5 10 $10,910 InquireInquire
 Bougainvillea Villa Tryall Club, Montego Bay Jamaica, Resorts Montego Bay

Bougainvillea House is one of Tryall’s newest villas which is quickly apparent in the unsurpassed luxury it provides. Designed by one of Jamaica’s best known architects, it is built in classic Caribbean Georgian style but discreetly includes every 21st century luxury. It covers more than 8,000 square feet and sits in a panoramic location with 180 degree sea views.

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Villa Rococo
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 5 5 10-14 5,000 InquireInquire
Jamaica Vacation Villa Roco, Montego Bay

Villa Roco captures the allures of Western Jamaica sharing an ideal spanning of hundreds of acres of lush forestation and swirling vista valley. Perched atop the spectacular content Estate in the heart of paradise this exquisite home rises to complement the splendid landscape and embraces mountainous backdrop, and partial ocean and city view. This remarkable estate home was built to fulfill your every expectation.

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Infinity Villa
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 5 5 10 12,000 InquireInquire
Infinity Villa Jamaica Tryall Resort, Tryall Infinity Villa Rental, Accommodations Tryall Resort

Among the newest Premier villas 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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Elysian Plain
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 5 5 10 7,700 InquireInquire
Elysian Plain Tryall Club, Jamaica Tryall Golf Club, Vacations Rentals Caribbean

Elysian Plain is a waterfront villa which has a wonderful majestic, tall palm tree which guards the entrance of this villa. The unique feature of this villa is its location which sits literally at the edge of the clear, blue Caribbean Sea. The views from here are spectacular. "Elysian Plain" is aptly named after the resting place of the Greek Gods.

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Pineapple House
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 5 5 10 $13,637 InquireInquire
Pineapple House Tryall Club, Jamaica Tryall Golf Club, Vacations Rentals Caribbean

Luxury living is all about the details and Pineapple House does just this and more. Distinctive in its architecture, Pineapple House’s extensive fret-work and ‘Oliver Messel’ design is defined by its Messel-green shutters, coral stone exterior, authentic Saltillo tile and rustic elegance

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Mahogany Hill
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 5 5 10 $12,300 InquireInquire
Mahogany Hill Tryall Club, Jamaica Tryall Golf Club, Vacations Rentals Caribbean

Mahogany Hill sits amidst a very private 4 acre forest garden on the crest of Mahogany Drive. It commands superb views of the Tryall fairways, countryside and Caribbean Sea. The architecture of Mahogany Hill is influenced by the Caribbean, Asian and colonial Spain. It is built on three levels and exudes a Zen-like aura of calm

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Someday Soon
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 5 5 10 $16,370 InquireInquire
Someday Soon Tryall Club, Jamaica Tryall Golf Club, Vacations Rentals Caribbean

This outstanding villa features Jamaican influenced architecture and furnishings with a wonderful collection of original paintings by well-known Jamaican artists such as Errol Allen, Messam, and Jeffrey Samuels. Hand-knotted Persian rugs and Jamaican grass rugs add a flourish to the floors

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Trinity Villa
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Montego Bay 5 7 10 $2,071 InquireInquire
Trinity Villa Tryall Golf Resort Jamaica

Trinity's exquisitely appointed great room opens out to the top patio area where the lap pool is located. There is a formal dining room for elegant candlelit dinners, complete with a beautiful custom made table. For more casual dining options, Trinity has a terrace dining table, as well as a covered gazebo that over looks the dramatic waterfalls.

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Villa Stella
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Montego Bay 6 6 12 Inquire Inquire Inquire
Villa Stella  Tryall Golf Resort Jamaica

Villa Stella offers views of the Caribbean Sea and the Tryall Club estate from its two levels of spacious terraces. Villa Stella is situated on the brow of Copperwood Ridge. It is an easy walk to Tryall’s world class tennis courts, its gym, spa and other amenities, and a 3-minute ride by the villa’s complimentary golf cart to the hampionship Tryall Golf course and private beach.

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Bumper's Nest Villa
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 6 6 12 $13,636 InquireInquire
Golf Holiday Villa Jamaica

Bumper's Nest encapsulates all that is synonymous with elegant Caribbean living with its lavish master cottage, handsome interiors and stunning views. From a three acre garden, at the peak of Mahogany Hill, Bumper's Nest takes full advantage of views of the Caribbean Sea

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Sea Grapes
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Discovery Bay 6 6 12 $785 InquireInquire
Trinity Villa Tryall Golf Resort Jamaica

Harmony lives here…the house keeps you in touch with the surrounding elements in such subtle ways that you wonder why you feel so good . A spacious verandah waits to accommodate your drifting moods and a large green cushion of a lawn extends down to your own private beach cove. Here, you can decide whether to launch off in to the crystal blue seas using the kayaks perched by your side, or just melt gently into the warm Caribbean sea

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San Michele
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Bluefields Bay 6 6 13 $1,220 InquireInquire
San Michele Jamaica Vacation Rental

This authentic home sits on the Caribbean with wraparound natural vistas of mountains and sea. Most distinctive, San Michele has a private island reached by footbridge where you can spend countless hours truly “on” the sea. After days of water sports, excursions, relaxation, and delicious repasts to your specifications, fall asleep to sea sounds from an authentic Jamaican four-poster canopy bed.

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Villa Viviana at Tryall
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Tryall Club 6 6 12 15,000 InquireInquire
Villa Viviana at Tryall Club, Jamaica Vacation Rental

On 6 beautifully landscaped acres, Villa Viviana sits in a serene and enchanting location at the world-famous Tryall Club. This beautiful villa offers the finest balance of sophisticated luxury and private comfort: elegant and cozy, majestic and inviting.

 

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Jubilation
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Tryall Club 6 6 12 $16,000 InquireInquire
Villa Viviana at Tryall Club, Jamaica Vacation Rental

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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Hammerstein Highland House
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 6 6 12 $6,500 InquireInquire
Hammerstein Highland House, Jamaica Vacation Rental, Accommodation Montego Bay

Rising from the hills, the seven rooftops of the Luxurious Highland Estate cover over 7,000 square feet. With six bedroom suites, the estate can accommodate up to 12 guests for overnight stays and larger parties for special events. Neighboring villas are available for additional overnight guests.

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Anticipation
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 6 6 12 10,000 InquireInquire
Anticipation Tryall Villa, Wedding Venue Jamaica, Luxury Wedding Caribbean

Newly reconstructed villa combines Caribbean architecture with European style décor privately nestled at the top of the hill on Copper Ridge. Arguably, one of the best positioned locations at the Tryall Club, which boasts an uninterrupted 180 degree panoramic view of the Caribbean Ocean. The infinity pool allows one of the best viewing locations.

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Keela Wee Villa
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Discovery Bay 6 6 12 12,000 InquireInquire
Keela Wee Vacation Rental, Jamaica Luxury Beachfront Vacation Home, Vacation Home Discovery Bay

Imagine your own private luxury beach resort. There is no better "getaway from it all"! Luxury Villa Jamaica is a magnificent two story, six bedroom, six bathroom villa situated on its own private white sand beach and swimming cove in Discovery Bay - one of the most lovely, tranquil beach resort areas of Jamaica.

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Following Seas
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Montego Bay 6 6 12 $2,857 InquireInquire
Following Seas Villa Tryall Golf Club Jamaica

Following Seas is a one-of-a-kind vacation hideaway offering the ultimate in luxury, comfort and breathtaking décor. Following Seas' casual elegance seamlessly balances original artwork with classic Jamaican architecture

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Karma Bay
Location Beds Baths Sleeps Weekly Low Nightly High Nightly Peak
Hanover 6 6 12 $13,640 InquireInquire
Karma Bay Villa Tryall Golf Club Jamaica

For a taste of paradise where the waves lap the shore and the trade winds caress the palm trees, Karma Bay has all the attributes that make for an unforgettable experience

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Wheel House
Location Beds Baths Sleeps Weekly Low Nightly High Nightly Peak
Hanover 6 6 12 $7,300 InquireInquire
Wheel House Villa Tryall Golf Club Jamaica

Wheel House combinines all the attributes of Caribbean living with privacy and seclusion. The open floor plan and indoor garden embraces the mountain breezes whilst celebrating fabulous ocean views.

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Windward
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 6 6.5 12 $11,365 InquireInquire
Windward

Windward is aptly named for the continuous cross current of trade winds that traverse the property. This graceful 6 bedroom home has the most spectacular 180 degree views from every room and from both levels

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Makana
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Discovery Bay 6 6.5 12 $14,500 InquireInquire
Makana

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. The architecture is superb.

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Rose Cottage
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 6 7 12 $15,000 InquireInquire
Rose Cottage Tryall Club, Accommodations Tryall, Holiday Lettings Tryall

Rose Cottage sits quietly yet dramatically on a plateau affording exceptional mountain and ocean views. Designed by Nancy D. Maffasanti in the old traditional Jamaican style, the house is decorated in an elegant arrangement of themes influenced by Asia, Jamaica and Europe…it is both elegant and comfortable and meant to be enjoyed.

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Villas at Half Moon
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Montego Bay 7 - 16 $1,200 InquireInquire
Villas at Half Moon Jamaica

For years Half Moon's Royal Villas have played "home away from home" for many discerning clients. These 33-individual villas with private swimming pools, provide the ultimate Caribbean style escape. For the ultimate in luxury, we invite you to discover one of our Royal Villas

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Hummingbird House
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 7 7 14 $16,364 InquireInquire
Hummingbird House at Tryall Club, Jamaica Vacation Rental

With one of the most panoramic views in all of The Tryall Club and a meticulous attention to detail and design, guests staying at the 7-bedroom Hummingbird House are often so captivated that they book it again before completing their current vacation

 

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Seaclusion
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 7 7 14 $23,637 InquireInquire
Seaclusion at Tryall Club, Jamaica Vacation Rental

Those who have read "Rebecca" by Daphne du Maurier wistfully imagine themselves being at Manderley, running through the rooms, out of the doors, through the garden and into the sea. Seaclusion offers a twenty-first century experience of being able to do just this but in an environment that is simply inspirational in its celebration of the ocean, the sky and modern Jamaican creativity and craftsmanship

 

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Twin Palms
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 7 7 14 $24,546 InquireInquire
Twin Palms at Tryall Club, Jamaica Vacation Rental

In the eighteenth century there were 488 plantations with Great Houses in Jamaica. Twin Palms is inspired by, acknowledges and pays tribute to a handful of those that have survived. It is also a house that is testament to the creativity and craftsmanship of Jamaica

 

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Whispering Waters
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Discovery Bay 7 7 14 $14,000 InquireInquire
Whispering Waters Discovery Bay Jamaica

Perched on a gentle slope along Discovery Bay’s prestigious Fortlands Road, Whispering Waters exudes a warm tropical ambiance while offering world class amenities and impeccable service. A 9000 square foot home , dressed in a colorful exterior, offers a glimpse of the vibrant hues and charm that wait within her welcoming doors.

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Zion Hill
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 7 7 14 $12,500 InquireInquire
Zion Hill Bay Jamaica

Zion Hill boasts a three-bedroom main building, a two-bedroom guests building and an optional two-bedroom cottage, which is available to groups interested in renting seven bedrooms only.This exotic and enchanting villa is a 14.000 square-foot construction, seated on a lush six-acre Caribbean estate, 300 feet above sea level, offering a magnificent uninterrupted 180-degree view of the Caribbean Sea.

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Harmony Hill
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Hanover 7 7 14 12,500 InquireInquire
Harmony Hill Tryall Club, Montego Bay villa at Tryall Montego Bay in Jamaica, holiday rentals in

Harmony Hill Villa offers the finest in Caribbean living, combining Jamaica’s rich architectural tradition with today’s modern amenities and service.  Nestled over 350 feet above sea level on seven acres of tropical splendor, the seven bedroom villa enjoys inspirational panoramic views of the Caribbean Sea, deep valleys and golf course.

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Phoenix
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Sandy Bay 7 7 14 $10,000 InquireInquire
Phoenix at Tryall Jamaica,  Rental Caribbean, Family Friendly Jamaica Travel

Unique to Phoenix is a fabulous location on the sea affording it two private sand beaches and extensive sea-front verandas. Constructed in the traditional West Indian style, the breezes and lapping waters of the Caribbean are a constant reminder of this tropical paradise.

 

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Villa Paradiso
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Ocho Rios 8 7 16 $13,000 InquireInquire
Villa Paradiso Ocho Rios Jamaica

This luxurious fully staffed Villa is situated in Mammee Bay Estate, Ocho Rios and boasts a glistening white sand beach with 150 feet of its own beach frontage. The Villa can be rented in a five bedroom or seven bedroom configuration; which would includes the two bedroom cottage just steps away from the main house on the property. 

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Sugar Hill Villa
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 8 8 16 $20,000 InquireInquire
Sugar Hill at Tryall Jamaica, Child Friendly Home Rental Caribbean, Family Friendly Jamaica Travel

Sugar Hill is a stunning 8- bedroom, luxury island home privately perched atop a lush 3-acre property overlooking the glittering Caribbean Sea and the historic Tryall Club estate

 

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Round House Villa
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 8 8 16 $15,000 InquireInquire
Round House Villa Tryall Resort Jamaica

Located on a brow of Copperwood Ridge, Round House is an easy walk to Tryall’s world class tennis courts, its gym, spa and other amenities, and a 3-minute ride by the villa’s complimentary golf cart to the championship Tryall Golf course and private beach.

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Haystack Villa
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 8 8 16 $18,182 InquireInquire
Haystack Villa Tryall Jamaica, Jamaica Tryall Villas, Resorts Montego Bay Jamaica

Haystack is found on Ocean View Drive and is set in rolling lawns with views of the ocean and landscapes of Tryall. Configured on three levels, Haystack features architecture with Colonial influences and interiors that are open and airy. Classic black and white marble tiles set the stage for a grand welcome into an elegant gallery and arcade

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Hanover Grange
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Montego Bay 9 9 18 $ 2,150 Inquire Inquire
Silent Waters Villa, Montego Bay Jamaica

Hanover Grange is one of the latest additions to the Tryall family of Estate Villas. The homeowner is Jamaican-Born Theresa Roberts who has lived for many years in the United Kingdom but now divides her time between Knightsbridge in central London and Hanover Grange.

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Golden Clouds Estate
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Ocho Rios 9 9 20 $12,500 InquireInquire
Golden Clouds Estate Ocho Rios, Jamaica Luxury Rental

Golden Clouds Estate is a luxurious 9-suite estate situated in a park-like 6-acre setting. It is a spectacular oceanfront villa located on Jamaica's fabled North Coast in the picturesque village of Oracabessa, short drive to Ocho Rios.

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L’Dor V’Dor
Location Beds Baths Sleeps Nightly Low Nightly High Nightly Peak
Montego Bay 9 13 20 $ 3,785 InquireInquire
Silent Waters Villa, Montego Bay Jamaica

Tucked away on a hill overlooking the majestic Tryall Club and providing 360 degree panoramic views of Montego Bay and Hanover, L’Dor V’Dor is a haven waiting to be discovered. The largest villa on the property; it has great flexibility to meet the needs of the most discriminating adult or large families with children.

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Silent Waters
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Montego Bay 10 6 20 14,500 InquireInquire
Silent Waters Villa, Montego Bay Jamaica

Silent Waters Villa Rental is a superb location for a family reunion, corporate retreat, destination wedding (seating 54 guests) or just a small group of friends seeking a most unusual holiday experience. Nestled in the hills of Jamaica, overlooking pristine forests and the spectacular turquoise waters of Montego Bay sits a truly remarkable private Jamaica resort property .... an enchanting heaven.

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About Jamaica & Villa Rentals

Jamaica boasts some of the best beaches and friendly residents that you will ever find.  Not only is Jamaica considered a treat to visit but affordability is also a great part of why Jamaica stays on the map for vacations.  Most people love the idea of traveling to the Caribbean and finding that right mix of sun and fun, so why not make it a Jamaica Holiday this year.


When you visit Jamaica, the best places are Kingston for those who want to go back in time and see the way Jamaica started out, Montego Bay for it’s nightlife and culture and amazing strips, Negril for its family friendly atmosphere, beaches, and lovely skyline, Ocho Rios for the waterfalls which people love to see, Port Antonio which draws the rich and famous to its magical coasts, and the South Coast for the  local hotspots and great sunsets.


Some of the beaches include, Seven Mile Beach, Doctors Cave in Montego Bay, Aquasol, James Bond in Ocho Rios, Duns River Falls, Treasure Beach on the South Coast, Frenchman’s Cove in Port Antonio, and the Blue Lagoon.


No matter when you travel remember the climate changes in late May and we hit Rainy Season.  So, traveling between November and early May are great choices.  You can find some great deals during the summertime however, so check back often.  Those traveling internationally, we highly recommend you take out Traveler’s Insurance, as these are by owner vacation rentals.


Jamaica offers holiday homes from beachfront to Oceanside, these homes are great for families traveling together and wanting to explore somewhere different, there are great resorts and homes throughout Jamaica.

 

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