Jamaica Villa Rentals
Jamaica is a Caribbean destination that is a must-visit at least once in your lifetime. This island paradise can be found in the western Caribbean. It has an enchanting vibe filled with carnival, reggae music, art, and culture. Beach lovers will thrill in the awe-inspiring beaches. Some are uniquely set between mountains or within lush gardens. For a change of pace, take a day trip to the Blue Mountains, a hiker’s paradise. Jamaica is an excellent destination for luxury villa holidays. Our villas are unique. They offer an interesting blend of the local vibe combined with world-class amenities.
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.
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.
10 bedroom 13 bath Jamaica villa in Montego Bay
With an ocean panorama that is nothing short of awe-inspiring, this grand ten-bedroom villa is the largest at Tryall. With large airy rooms exuding sophisticated style, a terrific infinity pool, a cascading garden waterfall, a children’s playground and the choice of outdoor or indoor air-conditioned living make this a one-of-a-kind villa
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.
9 bedroom 9.5 bath Jamaica villa in Montego Bay
Hanover Grange has become one of the highest profile, privately owned villas in the Caribbean, welcoming a succession of international celebrities, politicians and business leaders as guests.
8 bedroom 8.5 bath Jamaica villa in Ocho Rios
MALATAI is a fabulous contemporary home with modern updated bedrooms and noteworthy bathrooms nestled on a wide beachfront on the beautiful Old Fort Bay Beach. 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.
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.
8 bedroom 6 bath Jamaica villa in Montego Bay
Set atop one of the highest mountaintops overlooking Montego Bay and the Caribbean Sea, Silent Waters Villa offers a secluded retreat just 4.6 miles west of Montego Bay. This breathtaking 16.5-acre estate combines world-class architecture and design with unparalleled luxury, making it an ideal destination for family gatherings, weddings, retreats, and milestone celebrations.
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!
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.
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.
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.
7 bedroom 7.5 bath Jamaica villa in Montego Bay
The Coach House at Good Hope is a fantastic informal gathering place for families, retreats, and friends - with space for togetherness, space for discovering nature, and space for alone time. Like traveling through a time warp, to visit Jamaica's countryside is to experience another Jamaica of 30 years ago. The pace is slow, the lifestyle uncomplicated, the people are kind and calm, the service is relaxed and meals are served family style. For larger groups there are 2 extra bedrooms, just 50 paces away that may be available for an occupancy of 18 pax.
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.
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.
7 bedroom 9 bath Jamaica villa in Montego Bay
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.
7 bedroom 7.5 bath Jamaica villa in Discovery Bay
This 13,000 sq ft villa is complemented with luxurious and beautiful finishes. Happy Hour villa is a resort in itself, with a calm sandy beachfront, tennis/pickle court, gym, spa, sauna, games room, media room, infinity pool, Baja ledge/kiddies pool, hot tub, indoor/outdoor living & so much more.
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.
7 bedroom 8 bath Jamaica villa in Montego Bay
Hummingbird House is one of the finest properties within the Tryall Club!
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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 a golf course, Bumper's Nest was designed by distinguished architect Kasimir Korybut in 1995. A brilliant renovation has recreated one of the most glamorous homes at the Tryall Club. Here is an extraordinary private home with simply the best of everything.
6 bedroom 6.5 bath Jamaica villa in Ocho Rios
This stunning 6- bedroom villa is located 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.
6 bedroom 12 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.
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.
6 bedroom 7 bath Jamaica villa in Ocho Rios
17th Century fortress restored as a remarkable private home on a perfect private Caribbean beach.
6 bedroom 8 bath Jamaica villa in Montego Bay
Premier Villa on Two Acres on Tryall Club’s Chic West End! Hanover Windward sits atop of a hill with far reaching views to the Caribbean 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.
6 bedroom 8 bath Jamaica villa in Montego Bay
Hyde Park is a large and lavish home with glorious views of the lush Jamaican mountains and the deep blue Caribbean Sea. Its design is a stylish blend of Jamaican, Asian, and European elements with an emphasis on extraordinary comfort.
6 bedroom 5.5 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.
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.
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.
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..
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.
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.
6 bedroom 6 bath Jamaica villa in Discovery Bay
On its own sugary white sand beach lapped by the clear turquoise waters of Discovery Bay sits the charming home Sea Grapes. The translucent azure waters here are excellent for swimming and kayaking. Surrounding the swimming pool is a spacious grassy lawn, wonderful for children and games.
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.
6 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.
6 bedroom 6 bath Jamaica villa in Montego Bay
Welcome to the Wheel House Villa!
5 bedroom 4 bath Jamaica villa in Montego Bay
ALLAMANDA is a brilliant contemporary private villa with large heated pool, an excellent staff including top-rated chef and a nearby membership at the Tryall Club.
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.
5 bedroom 5 bath Jamaica villa in Montego Bay
Nine miles west of Montego Bay is a large private site overlooking perhaps the most glorious view of sea and sky on Jamaica’s renowned north coast. Elegantly perched on eight and a half acres atop this hill is Bambu, a grand five-bedroom private villa distinguished by its classic architecture and appreciated by discerning vacationers.
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