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.
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.
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.
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.
7 bedroom 8 bath Jamaica villa in Montego Bay
Hummingbird House is one of the finest properties within the Tryall Club!
7 bedroom 7.5 bath Jamaica villa in Discovery Bay
Happy Hour Villa is the newest villa on the beautiful Discovery Bay shore. The modern design & architecture of this 13,000 sq ft villa is complemented with luxurious and beautiful finishes. Happy Hour villa is a resort in itself, a calm sandy beach front, tennis/pickle court, gym, spa, sauna, games room, media room, infinity pool, Baja ledge/kiddies pool, hot tub, indoor/outdoor living & so much more.
10 bedroom 10 bath Jamaica villa in Montego Bay
Villa Indigo at HALF MOON is one of the undisputed finest private homes in this collection.
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.
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.
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
One of the most glamorous villas in Jamaica, Endless Summer is a turreted mansion with breathtaking views of the Caribbean Sea.
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 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.
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.
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.
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.
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 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.
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.
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.
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.
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.
8 bedroom 8.5 bath Jamaica villa in Ocho Rios
MALATAI has just undergone a Fabulous renovation, with 8 newly renovated bedrooms and bathrooms, a beachfront, and a top-rated chef, directly on the translucent waters of Mammee Bay, near Ocho Rios. While privately located, Malatai is only minutes from Dolphin Cove, famous Dunn‘s River Falls, and lively Ocho Rios with its wide selection of duty-free shopping, excursions, and music.
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..
4 bedroom 6 bath Jamaica villa in Montego Bay
Aqua Bay is an amazing seafront property and is one of the premier villas at The Tryall Club.
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.
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.
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.
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.
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.
5 bedroom 6 bath Jamaica villa in Montego Bay
Classic Jamaican architecture meets lovely spacious accommodation! Set on five acres of gently sloping land with a sea view and is surrounded by manicured lawns.
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 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 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.
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!
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 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 7 bath Jamaica villa in Ocho Rios
17th Century fortress restored as a remarkable private home on a perfect private Caribbean beach.
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.
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.
4 bedroom 4 bath Jamaica villa in Ocho Rios
The morning sun has turned the sea and the dew on the palm trees to silver. The non-stop trade winds waft through the rooms of the villa and the aroma of fresh-baked bread works its way from the kitchen to my bedroom window.
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.
3 bedroom 2.5 bath Jamaica villa in Montego Bay
This lovely villa and grounds sit on a hilltop overlooking Montego Bay and beyond. Perfectly situated only 20 minutes from the airport and 15 minutes from the Tryall Club. Blue Heaven also comes with a complimentary driver on 7-night reservations.
4 bedroom 4 bath Jamaica villa in Treasure Beach
Out of the Blue is an oxymoron: a contemporary home in Old Jamaica. And what a home it is! The villa sits on the longest uninterrupted expanse of sea view at beach level of any other beach property in this group.
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.
4 bedroom 4.5 bath Jamaica villa in Ocho Rios
Frangipani takes its’ name from the tropical Frangipani tree which produces fragrant white, pink or yellow flowers. Several of these trees surround the house.
2 bedroom 2 bath Jamaica villa in Montego Bay
With over 2,500 square feet of living space, Moments is a two-bedroom villa suite that offers spectacular views and a spacious patio.
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.
4 bedroom 4 bath Jamaica villa in Ocho Rios
Somewhere Villa is a lovely traditional style villa with an open, airy and spacious sitting room which opens on to a covered verandah, allowing for inside/outside living.
3 bedroom 3 bath Jamaica villa in Ocho Rios
Wag Water is a charming cottage with a water front location, named after the river which meanders through the local parish of St Mary.
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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