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Jamaica Villas

1-2 Bedroom Villas (9)
3 Bedroom Villas (19)
4 Bedroom Villas (46)
 5 Bedroom Villas (14)
6+ Bedroom Villas (28)



Bienvenue - 2 BR
Bienvenue, gracious and elegant with sweeping panoramas of the sparkling Caribbean, is situated on two private acres of verdant landscaping. more

Bienvenue
Bienvenue, gracious and elegant with sweeping panoramas of the sparkling Caribbean, is situated on two private acres of verdant landscaping. more

1-2 Bedroom Villas


Bienvenue - 2 BR
Bienvenue, gracious and elegant with sweeping panoramas of the sparkling Caribbean, is situated on two private acres of verdant landscaping. more

Cottonwood Annex
Set on a hillside, amid lush tropical gardens overlooking the beautifully manicured Half Moon golf course and the Caribbean Sea is this romantic two bedroom cottage.The grand villa experience offered in a more intimate size. more

Count's Cottage - Tryall
The ideal honeymoon hideaway! This spacious villa is built around the swimming pool with vine covered verandah. more

Little Palm - Tryall (Count's Cottage)
The ideal honeymoon hideaway! This spacious villa is built around the swimming pool with vine covered verandah. more

Little Palm - Tryall (Formerly "Count's Cottage")
The ideal honeymoon hideaway! This spacious villa is built around the swimming pool with vine covered verandah. more

Little Palm - Tryall (Formerly "Count's Cottage)
The ideal honeymoon hideaway! This spacious villa is built around the swimming pool with vine covered verandah. more

Reveille - Tryall
With a view of the Tryall private beach cove and ocean, Reveille is a cozy seaside cottage.The sliding glass doors of the living room open to the terrace and pool deck beyond. more

Rum Punch
Rum Punch", an adorable architectural gem of a cottage with two bedrooms (1 large King, 2 Full beds), pool, living room, outdoor covered verandah and dining area, bar and small kitchen.Outdoor seating near the green & white "fern garden". more

Rum Punch - Tryall
Rum Punch", an adorable architectural gem of a cottage with two bedrooms (1 large King, 2 Full beds), pool, living room, outdoor covered verandah and dining area, bar and small kitchen.Outdoor seating near the green & white "fern garden". more

3 Bedroom Villas


Ackee 8 - Tryall
Near the tennis courts and named after Jamaica's national fruit, Ackee 8 is every bit as charming as its name.All three bedrooms have twin beds with private shower/bath combination. more

Calabash - Tryall
Located on Country Club Drive, the road that hugs Tryall’s ocean frontage, Calabash has an ideal position just feet from the softly lapping Caribbean. more

Eureka-Tryall
Commanding spectacular views of the blue Caribbean waters, rolling hills and Tryall's world-renowned Tryall golf course, Eureka is a very special retreat. more

No Problem - Tryall
Commanding an excellent view of the golf course and the Caribbean Sea, No Problem is a villa built in true Jamaican style. more

Pinnacle - Tryall
A dramatic feature of Pinnacle's circular living room is its Jamaican parquet floor, which leads onto the covered dining verandah with fountain that feeds the swimming pool. more

Seagrape - Tryall
The brick courtyard and fountain of Seagrape opens onto the living room and beyond to the lawn fronting the sea.To the right of the living room, across the lawn can be found the swimming pool overlooking the Caribbean. more

Serenity - Tryall
Special features of Serenity include its two living rooms: the more formal upstairs and the downstairs boasting a hand painted mural by a renowned local artist. more

Skylark
Our luxurious, fully staffed, three bedroom private villa, with pool, can be your vacation home for less than the cost of a luxury hotel room. more

Soon Cum - Tryall
This charming villa overlooks the golf course and the Caribbean Sea from every room.The Jamaican style open living room and wide verandah flow onto the pool deck, to lush gardens and expansive views. more

Sunset - Tryall
Situated on the Caribbean with its own private beach, Sunset presents breathtaking vistas of the ocean and Montego Bay.In less than two minutes you can walk to the golf practice range, putting green, and first tee. more

Wagwater
Overlooking the sea and forming part of historic Prospect Estate, Wagwater was completely renovated in 1989 and now offers three air conditioned bedrooms, each with its own bathroom. more

Bumper's Nest
With its cheerful pastel decor and quaint art work Bumper's Nest is indicative of the old world charm of Jamaica. more

Bumper's Nest - Tryall
With its cheerful pastel decor and quaint art work Bumper's Nest is indicative of the old world charm of Jamaica. more

Eureka - Tryall
Commanding spectacular views of the blue Caribbean waters, rolling hills and Tryall's world-renowned Tryall golf course, Eureka is a very special retreat. more

Heron Cove
Heron Cove, completely renovated in 2003, is dramatically situated on 2 acres on a point overlooking the sea, offering perfect sunset viewing.All rooms have water views. more

Heron Cove - Tryall
Heron Cove, completely renovated in 2003, is dramatically situated on 2 acres on a point overlooking the sea, offering perfect sunset viewing.All rooms have water views. more

Island House - Tryall
The delightfully refurbished Island House has a panoramic view of Tryall’s championship golf course and the Caribbean Sea from every room. more

Linger Longer - Tryall
Unique in that its entrance is an enclosed courtyard with a swimming pool, Linger Longer is situated directly overseeing the 13th hole of the golf course and the ocean beyond. more

Vista Del Mar - Tryall
An alley of palms leads up to Vista Del Mar, at the top of Tryall.Aptly named, this magnificent villa commands a breathtaking view over the rolling greens of the property’s famous golf course and glittering Caribbean Sea. more

4 Bedroom Villas


Bienvenue
Bienvenue, gracious and elegant with sweeping panoramas of the sparkling Caribbean, is situated on two private acres of verdant landscaping. more

Bluebird - Tryall
Opening off the large colorful living room are the separate dining room, master bedroom with king bed, and the second and third bedrooms with twin beds.All bedrooms have en suite private bathrooms. more

Calypso - Tryall
Quietly situated overlooking the sixteenth green and the ocean beyond, Calypso radiates a charm all of its own. more

Cielo - Tryall
From its high perch atop Barnes Hill, this recently remodeled, luxurious villa commands a truly breathtaking view over first a sloping lawn, an "infinity" pool, then the broad expanse of Tryall's lush, green golf course. more

Clive House - Tryall
Built in the true Jamaican Great House style, Clive House is a beautiful combination of cut stone walls and cedar floors.Situated adjacent to the front entrance by the expansive pool terrace is a charming mini-lounge. more

Eight Rivers
Surrounded by one and a half acres of tropical land, overlooking the crystal clear waters of the Caribbean Sea, is the newly built, ultra-luxurious Eight Rivers villa.This 5000 sq. more

Eve Song
This beautifully appointed villa offers magnificent views of the golf course and ocean.Eve Song, with its elegant furnishings, parquet wood floors and large French doors, conveys a feeling of old world charm. more

Fairwinds - Tryall
From the fountain and rockery at the base of the twin entrance stairway, every corner you turn in Fairwinds holds something new. more

Fern Hill - Tryall
Comfortable yet sophisticated, Fern Hill boasts not only a covered verandah running the full length of the house, but two master bedrooms with king beds.One of the master suites is located in a separate gazebo across the pool. more

Frankfort
Frankfort is possibly the most desirable property in Jamaica.The secluded white sand beach is an attraction that has been enjoyed by some of the greatest luminaries of the 20th century including: Sir Winston Churchill, Dr. more

Great House
Prospect Great House is possibly the best preserved of all the Jamaican Great Houses that are still kept as residences.This 18th century house has hosted some of the greatest luminaries of the 20th century including: Sir Winston Churchill, Dr. more

Hart House - Tryall
Perched regally atop a mountain, this secluded four bedroom villa offers a breathtaking view of ocean, mountain, and valley.Verandahs adjoining each room allow for quiet contemplation or romantic island dining. more

Ladywood House
Ladywood House accommodates up to eight people in 4 air conditioned bedrooms.There is a family room, living room, dining room and kitchen providing ample living space. more

Ma'Moura - Tryall
This villa is a wonderful example of circular and octagonal design taking full advantage of the view on all sides.Just inside the entrance, the red brickwork around the circular pool in the center of the villa leads to the four bedrooms and living room. more

Mahogany View
Situated above the famous Robert Trent Jones designed Half Moon Golf Course, this four bedroom, four bath, ocean view villa is truly deluxe. more

Merryland - Tryall
One of the finest villas at Tryall, Merryland has all the inviting atmosphere of an elegant private island home and all the amenities necessary to ensure a successful Caribbean vacation. more

Phoenix - Tryall
The Phoenix is situated on beautifully landscaped grounds above the Caribbean Sea.Ideal for entertaining in style, this dramatic seaside villa has a large covered terrace, as well as an open circular pool deck. more

Point Of View - Tryall
Step through a private entrance into a world all your own, where inside you will be greeted by a breathtaking view of the Caribbean Sea from every point in this gracious villa. more

Randolins - Tryall
Randolins Villa is a charming five bedroom beach cottage set on two acres of waterfront between the 17th tees and the sea. more

Reef House - Tryall
Through the entrance gazebo and across the bridge over the lily pond is the picturesque living room of Reef House.The air conditioned dining room opens off one side. more

Retreat - Tryall
Retreat is a gracious sanctuary in a breathtaking setting with views of the sea and the 18th fairway and within easy walking distance to the beach.Just a few yards from Tryall's private beach cove, Retreat is a "hacienda style" villa. more

Riverlot Gardens - Tryall
Riverlot Gardens is a luxurious four-bedroom villa situated amidst lush tropical foliage.Gently sloping, redbrick steps leads lead both to the main house and the guest cottage. more

Roaring Pavilion
Roaring Pavilion Villa and Spa is located on a beachfront estate where the Roaring River meets the Caribbean Sea in St.Ann’s Bay, Jamaica, just a few minutes outside of Ocho Rios. more

Seafore - Tryall
The octagonal swimming pool and deck has a clear view of the sixteenth hole and fairway.Manicured grounds are adorned by graceful palm, lime, mango and poinciana trees and brilliant hibiscus and bougainvillea. more

Seaspray - Tryall
At Seaspray, the shady entrance courtyard leads to the large living room with covered dining terrace that opens to the pool deck.The octagonal swimming pool and deck offer beautiful views. more

Solitude - Tryall
Solitude boasts two master bedrooms (queen size beds), one of which is located in a separate, private cottage.The three bedrooms in the main house are reached by corridors that open to the sea breezes. more

Somewhere
Somewhere villa is nestled in Prospect Estate's lush tropical garden atop a bank overlooking the crystal clear waters of the Caribbean sea. more

Stella - Tryall
This stunning villa, just recently completely renovated, offers breathtaking views of the Caribbean sea and the Tryall grounds. more

Sunrise - Tryall
Right at the water’s edge, Sunrise looks out over a private beach and the clear-blue shallows of the Caribbean Sea to a snorkeling reef and the indigo waters beyond.Just across the lane are the emerald-green fairways of Tryall’s famous golf course. more

Tradewinds - Tryall
Tradewinds sits right on the shore of the Caribbean.As soon as you walk through the front door, you get your first view of the sea, and almost every room in the villa takes full advantage of its magnificent coastal view. more

Tranquility - Tryall
Down the entrance staircase, the large living room of Tranquility, complete with stone fountain, opens to the terrace that juts into the swimming pool. more

Yellowbird - Tryall
This beautifully appointed villa, completed in 1991, offers spectacular views of both the golf course and ocean.Modern furnishings, tile floors, dark wood trims and shutters, give the feeling of old world charm and casual elegance. more

Blue Bird - Tryall
Opening off the large colorful living room are the separate dining room, master bedroom with king bed, and the second and third bedrooms with twin beds.All bedrooms have en suite private bathrooms. more

Cooyah
This captivating villa is situated on lush landscaping right on the golf course at hole 13 and overlooks the Caribbean Sea.Four uniquely-designed bedrooms (all with air-conditioning) open up to the natural beauty of Jamaica. more

Cooyah - Tryall
Coo Yah is a four-bedroom villa located on lush landscaping overlooking the verdant golf course and hypnotic Caribbean Sea.Tastefully decorated in a tropical theme, the living room balances the rhythm of tranquil days and lively evenings. more

Destiny Villa
Owner’s Suite # complimentary Internet access # DSS (Digital Satellite System) television in all bedrooms # 12-speaker sound system with CD player # full staff: butler, chef, chambermaids, laundress, gardeners, night watchman # multi-layer cushione more

Eve Song - Tryall
This beautifully appointed villa offers magnificent views of the golf course and ocean.Eve Song, with its elegant furnishings, parquet wood floors and large French doors, conveys a feeling of old world charm. more

Folly - Tryall
Just past the garden courtyard and indoor/outdoor dining area, there is a large living room, open on four sides.Sunlit gardens, with a Moorish fountain, line the covered paths to three of the bedrooms, each with an ocean view. more

Great House - Tryall
Prospect Great House is possibly the best preserved of all the Jamaican Great Houses that are still kept as residences.This 18th century house has hosted some of the greatest luminaries of the 20th century including: Sir Winston Churchill, Dr. more

Karma Bay - Tryall
Solitude boasts two master bedrooms (queen size beds), one of which is located in a separate, private cottage.The three bedrooms in the main house are reached by corridors that open to the sea breezes. more

Ladywood Main House
Ladywood House accommodates up to eight people in 4 air conditioned bedrooms.There is a family room, living room, dining room and kitchen providing ample living space. more

No Le Hace
Breathtaking views from No Le Hace will be etched forever in your mind.This four bedroom villa provides almost every amenity for comfort and relaxation. more

No Le Hace - Tryall
Breathtaking views from No Le Hace will be etched forever in your mind.This four bedroom villa provides almost every amenity for comfort and relaxation. more

Pineapple House - Tryall
Down the entrance staircase, the large living room of Pineapple House, complete with stone fountain, opens to the terrace that juts into the swimming pool. more

Sea Island
Caribbean Sea # dramatically renovated in 2005 # 4 air-conditioned bedrooms, each with new en-suite bathroom # two outdoor showers # staff of 7: cook, butler, chambermaids, laundress, gardeners # 20' x 40' pool # tennis court # satellit more

Yellow Bird - Tryall
This beautifully appointed villa, completed in 1991, offers spectacular views of both the golf course and ocean.Modern furnishings, tile floors, dark wood trims and shutters, give the feeling of old world charm and casual elegance. more

5 Bedroom Villas


Cottonwood
Set on a hillside, amid lush tropical gardens overlooking the beautifully manicured Half Moon golf course and the Caribbean Sea is the five bedroom Cottonwood Villa.Completed in 1987, Cottonwood is both spacious and very comfortable. more

Elysian Plain - Tryall
Aptly named (the “Elysian Plain” was the resting place of the Greek Gods), the villa sits literally at the edge of the clear, blue Caribbean Sea. more

Heron Cove and Rum Punch - Tryall
Heron Cove is dramatically situated on a point overlooking the sea offering perfect sunset viewing.All rooms have water views. more

Mahogany Hill - Tryall
This charming villa is one of the few that not only overlooks the golf course and Caribbean Sea but across to Montego Bay.Mahogany Hill is situated atop a hill facing the sea and affords spectacular views. more

Windrush - Tryall
This entirely renovated luxury villa is beautifully situated on five acres of lush gardens.Commanding a panoramic view of the Tryall Great House, tennis courts, golf course and ocean, Windrush is unique in design. more

Xanadu - Tryall
Located at the peak of Barnes Hill, the view from Xanadu is truly breathtaking - rolling green fairways and the blue Caribbean waters. more

Greatview
You’ll see at once how Greatview got its name.An easy 10-minute drive from Montego Bay’s international airport, step into its peaceful and secluded gardens, then take in a spectacular view of the ocean and mountains beyond. more

Heron Cove & Rum Punch - Tryall
Heron Cove is dramatically situated on a point overlooking the sea offering perfect sunset viewing.All rooms have water views. more

Little Hill - Tryall
A professional staff of ten serves your every whim at Little Hill, where a circular swimming patio serves as a delightful focal point. more

Sea Grapes
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. more

Sea Grapes - 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. more

Sugar Bay
On its own sugary white sand beach lapped by the turquoise waters of Discovery Bay sits the exquisite home Sugar Bay. more

Sundance Villa
Sundance is a stunning 5 bedroom, traditional Palladian style villa completed in 2006, extending to 6,000 square feet and occupying a quiet 2 acre site with views of the Caribbean. more

Tradewinds
Tradewinds is a newly constructed 5 bedroom home located in the heart of the exclusive Sandy Lane Estate. more

6+ Bedroom Villas


Following Seas - Tryall
A "one of a kind design" villa, Following Seas' colorful decor accentuates its unusual layout.The four bedrooms in the main house and two in the separate cottage, are fully air-conditioned with full bathrooms and cable television. more

Frangipani
Frangipani is situated high above L'Ansecoy Bay on the north end of the island.Designed by the renowned architect Paolo Piva in 1992, Frangipani offers unrivaled luxury with unparalleled views. more

Golden Clouds
Golden Clouds Country Estate is a spectacular waterfront villa located in the picturesque banana port village of Oracabessa. more

High Hope
Enjoy in total luxury and ultimate privacy, the lifestyle of the Plantocracy in this seven bedroom, seven bathroom mansion.High Hope Estate is a 15th Century Venetian-style villa set on 40 acres of land overlooking twenty miles of Caribbean coastline. more

Ladywood
Ladywood accommodates up to twelve people with the master bedroom and two twin bedrooms on the upper floor, and another master with king bed and two twin bedrooms on the ground floor.All the bedrooms are air conditioned and all have en suite bathrooms. more

Naseberry Hill
Naseberry Hill is located in the heart of Springfarm Estate. more

Round House - Tryall
With a panoramic view of the Tryall Great House, golf course and Caribbean Sea, the large semicircular terrace at Round House is a favorite spot for relaxation. more

Summerhill Villa
After arriving at Montego Bay, you will travel through a scenic 15 minute drive that will take you past several resorts , alongside the sea, through the entrance of the world class Half Moon Golf and Country Club, winding up the hill past several beautifu more

Sweet Spot Villa
This exquisite, deluxe villa is ideally situated on Runaway Bay, beside the Breezes Golf and Tennis Resort.Its remarkable and unique location, being directly on the beach and adjacent to a championship golf course, is second to none. more

Thomas House
Spectacularly situated in a three acre Thomas Estate on Springfarm Drive, Rose Hall, you will find one of the best appointed villas in Montego Bay. more

Trident Castle
Located on a beautiful peninsula in Jamaica, Trident Castle is breathtaking.Here you will find 40,000 square feet of luxury with panoramic ocean views, helicopter pad, 30'x55' private pool, eight servants, and more. more

Wheel House - Tryall
The large living room with indoor garden has French doors that open to the pool deck with a large swimming pool and view of the golf course and ocean beyond. more

A Summer Place
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. more

Amanoka
Amanoka is one of the newest and largest villas on beautiful Discovery Bay.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. more

Coral Cove Cottages
Two casual cottages share a delightful waterfront site on the clear waters of Discovery Bay.The cottages sit on a lovely large lawn. more

Drambuie Estate
DVD, VCR's and 6 cable televisions # sound system and boom boxes with CD players # antique pool table, croquet, books, games, videos, large cassette and CD collection # computer and complimentary SKY WEB satellite Internet access # massag more

Fairway Manor
This is a villa description.Now is the time for all good men to come to the aid of their party. more

Fortlands Point
On a stunning promontory, once the site of an old stone fort, sits a remarkable new home named Fortlands Point. more

Haystack - Tryall
An exquisite, superbly welcoming villa, Haystack furnishes you with a vacation experience unmatched in elegance and serenity. more

High Hope - Tryall
Enjoy in total luxury and ultimate privacy, the lifestyle of the Plantocracy in this seven bedroom, seven bathroom mansion.High Hope Estate is a 15th Century Venetian-style villa set on 40 acres of land overlooking twenty miles of Caribbean coastline. more

Hill Top - Tryall
With panoramic views of the golf course and the ocean, Hill Top radiates the comfortable elegance of a charming Jamaican home.The large living area opens to a spacious covered dining patio overlooking the swimming pool. more

Keela Wee
Located on a private coral cove, this pretty yellow stone villa overlooks one of Jamaica's loveliest bodies of water ~ Discovery Bay. more

Ladywood Villa
Ladywood accommodates up to twelve people with the master bedroom and two twin bedrooms on the upper floor, and another master with king bed and two twin bedrooms on the ground floor.All the bedrooms are air conditioned and all have en suite bathrooms. more

Makana
Makana is one of the newest and most glamorous private villas on the precious strip of land that borders Discovery Bay. more

Mermaid's Dream Siren's Song
St.Thomas's undeveloped, pristine west end and offers stretches of sand, rock and coral shoreline just below the villa for snorkeling on live reefs and beachcombing with not another soul in sight. more

Summertime (Pharos Villa)
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. more

Sundown
Sundown is an exquisite staffed home on a private white sand beach next to the turquoise waters of Discovery Bay.Interiors are beautifully decorated in rich fabrics on dark wicker and mahogany. more

Villa Paradiso
This spectacular villa is only 10 minutes from Ocho Rios and its attractions, Dunn's River Falls and Dolphin Cove. more

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