Jamaica Villa Rentals
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.
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.
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.
2 bedroom 2 bath Jamaica villa in Montego Bay
Tryall's only two bedroom estate villa, Little Palm lives large nestled on a 3 acre property, on the 17th hole and a short walk or quick golf car ride to the beach.
4 bedroom 4 bath Jamaica villa in Montego Bay
Little Hill was built in 1959 by an architect Robert Hartley. It was the first villa to be built at The Tryall Club in the Classic West Indies style around a circular 30 foot diameter swimming pool with extensive covered terraces throughout.
3 bedroom 4 bath Jamaica villa in Discovery Bay
This 3-bedroom casual cottage shares a delightful waterfront site with its neighboring Villa, on the clear waters of Discovery Bay. Linga-Awile sits on a lovely, long, large lawn. Beyond the lawn and swimming pool is its sugary white sand beach with two thatched roof umbrellas for shade.
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.
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
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.
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.
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 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 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 8 bath Jamaica villa in Montego Bay
Hummingbird House is one of the finest properties within the Tryall Club!
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.
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.
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 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.
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.
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.
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.
2 bedroom 2 bath Jamaica villa in Ocho Rios
Each of GoldenEye's stand-alone villas is its own private world, set in a verdant garden of native greenery and sitting directly on the beach or lagoon.
6 bedroom 7 bath Jamaica villa in Ocho Rios
17th Century fortress restored as a remarkable private home on a perfect private Caribbean beach.
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.
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.
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 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.
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.
5 bedroom 5.5 bath Jamaica villa in Montego Bay
Everything Nice is a lovely waterfront property on Emerald Quay sitting on the edge of the Bogue Lagoon. Nestled in between the Breathless & Secrets Hotels & within walking distance of the Montego Bay Yacht Club.
4 bedroom 4 bath Jamaica villa in Montego Bay
This very special villa not only offers sweeping sea views but enjoys a very private location surrounded by a garden full of meticulously cared-for specimen flowers. Beloved by many guests and with a high repeat factor the elegant interiors are a testament to Jamaican master craftsmanship.
1 bedroom 1 bath Jamaica villa in Montego Bay
A beautifully presented one-bedroom villa with outstanding ocean views looking east towards Montego Bay.
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.
5 bedroom 5 bath Jamaica villa in Montego Bay
This spacious five bedroom villa has a magical location and sits literally at the edge of the clear blue Caribbean Sea, with panoramic views stretching from east to west.
4 bedroom 4.5 bath Jamaica villa in Ocho Rios
Set within one and a half acres of tropical gardens, populated by mature indigenous trees, plants and flowers, the Eight Rivers villa has a magnificent swimming pool and sun terrace overlooking a gazebo and the sea beyond.
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.
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.
7 bedroom 8 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 The Coach House villa & The Great House villa can be rented together to offer 14 bedrooms, accommodating 28 guests.
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.
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!
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.
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 Course nearby.
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.
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.
9 bedroom 9.5 bath Jamaica villa in Ocho Rios
This stunning 6-bedroom villa & 3-bedroom Sea Biscuit cottage 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 & cottage is through the private compound of Hermosa Cove Boutique Resort.
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.
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.
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.
2 bedroom 3 bath Jamaica villa in Montego Bay
Bee Happy, This beautifully renovated 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!
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.
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.
Find Jamaica Villas
Villa Destinations
- Caribbean
- All Caribbean Villas
- Anguilla
- All Anguilla Villas
- Altamer
- Barnes Bay
- Black Garden Bay
- Blowing Point
- Cove Bay
- Crocus Bay
- Dropsey Bay
- Forest Bay
- Island Harbor
- Limestone Bay
- Little Bay
- Little Harbor
- Long Bay Village
- Long Pond
- Meads Bay
- Pelican Bay
- Rendezvous Bay Beach
- Sandy Ground
- Sandy Hill
- Shoal Bay
- Shoal Bay East
- Shoal Bay West
- West End
- Antigua
- Aruba
- Bahamas
- Barbados
- All Barbados Villas
- Alleynes Bay
- Bridgetown
- Christ Church
- Church Point
- Derricks
- Dover Beach
- Fitts Village
- Gibbes Beach
- Gibbs Bay
- Holetown
- Mullins Bay
- Mullins Beach
- Oistins
- Paynes Bay
- Porters
- Reed’s Bay
- Royal Westmoreland
- Saint Andrew
- Saint James
- Saint Peter
- Sandy Lane
- Speightstown
- St. James
- St. Lucy
- St. Peter
- The Garden
- Bonaire
- British Virgin Islands
- Dominica
- Dominican Republic
- Grand Cayman
- Grenada
- Grenadines
- Jamaica
- Nevis
- St. Barthélemy
- St. Kitts
- St. Lucia
- St. Martin
- Turks & Caicos
- US Virgin Islands
- Central America
- Europe
- Mexico
- United States
- More Destinations
- Villa Rental Info
