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.
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
Almond Hill was designed by Prince Kasimir Korybut in 1993. It was brilliantly renovated, creating a contemporary beautifully decorated home with french doors opening from all of the bedrooms to the garden and bathrooms. Almond Hill is a lovely private home located on a former 500-acre coconut plantation just 22 minutes west of Montego Bay and a five-minute drive from Round Hill where guests enjoy complimentary resort membership.
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.
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!
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.
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.
4 bedroom 4 bath Jamaica villa in Montego Bay
Casuarina is a hidden gem and one of the loveliest villas at Tryall. The ocean views are breathtaking while inside there is a magical charm created by a very clever combination of flower-filled gardens, and furniture designed for total comfort.
5 bedroom 5 bath Jamaica villa in Montego Bay
Offering what is undoubtedly the most magnificent ocean view in Tryall from a commanding position atop Garden Hill; Celestial Villa is one of the finest private homes in Jamaica where meticulous attention to detail and designers flourish resulting in the epitome of sophisticated living without compromise.
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!
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.
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 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 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.
1 bedroom 1 bath Jamaica villa in Montego Bay
A beautifully presented one-bedroom villa with outstanding ocean views looking east towards Montego Bay.
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.
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.
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.
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.
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.
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 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 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.
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.
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.
3 bedroom 3 bath Jamaica villa in Montego Bay
Commanding excellent views of the Caribbean Sea and Tryall Club’s golf course, No Problem is a cozy two-story villa.
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.
5 bedroom 5 bath Jamaica villa in Montego Bay
Built on one of the prime sites at Tryall and conveniently located in easy walking distance of the Great House, gym and tennis courts, with total privacy and magnificent landscaping.
5 bedroom 6 bath Jamaica villa in Montego Bay
Pavilion is an exquisite villa privately located at the end of a cul-de-sac with magnificent views of the Caribbean Sea to the north and a tranquil 10-mile view of the mountains to the south. It is spacious, quiet, peaceful and beautiful.
5 bedroom 5.5 bath Jamaica villa in Montego Bay
Pineapple House is a spacious villa located on Copper Ridge with a magnificent 180 degree view of the Caribbean Sea located on Jamaica’s exclusive North Shore
2 bedroom 2 bath Jamaica villa in Montego Bay
Poinciana is an exquisite 2-bedroom Great House Villa with a private plunge pool on a quiet corner of its spacious terrace and with far-reaching views of the Tryall golf course and Caribbean Sea.
5 bedroom 5 bath Jamaica villa in Montego Bay
Located on the highest point at the renowned Tryall Club, Point of View sits on one of the most spectacular sites in the Caribbean … indeed, in the world. From its unique vantage point, a sweeping panorama stretches down the mountain and across the 18-hole championship golf course to the deep blue Caribbean and distant horizon. Breathtaking at every turn.
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.
4 bedroom 4 bath Jamaica villa in Montego Bay
Reef House is the embodiment of oceanfront cottage living. This gorgeous home brings the outside in, bathing the rooms with soft natural light and the irresistible blues of the ocean beyond.
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.
5 bedroom 5 bath Jamaica villa in Ocho Rios
SCOTCH ON THE ROCKS is a charming turquoise villa overlooking the Caribbean Sea.
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.
4 bedroom 4 bath Jamaica villa in Discovery Bay
Located on a private waterfront acre, Sea Haven is a traditional West Indian cottage dressed in charming periwinkle blue and sitting directly on the edge of beautiful Discovery Bay.
4 bedroom 4 bath Jamaica villa in Montego Bay
Seaside was completely renovated & refurbished in 2018. This amazing sea front property is one of the newest premier villas at Round Hill.
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.
1 bedroom 2 bath Jamaica villa in Montego Bay
Stella Marina is a very smart and well-presented one-bedroom villa with stunning ocean and golf course views.
4 bedroom 4 bath Jamaica villa in Runaway Bay
Located on Runaway Bay, Spanish Cove is perched on a beautiful sandy beach nearby the heart of town. Runaway Bay is known for beautiful beaches, coral reefs, excellent scuba diving as well as the well-known Green Grotto Caves. It is also conveniently located and within easy reach of Ocho Rios for restaurants, excursions, and shopping.
5 bedroom 5.5 bath Jamaica villa in Discovery Bay
On its own sugary white sand beach lapped by the turquoise waters of Discovery Bay sits the exquisite home Sugar Bay. Interiors have just been refreshed throughout and are distinguished by elegant custom-designed furniture, gleaming breadnut floors, and fascinating objets d`art from around the world. There has also been an addition of a brand new air conditioned Gym!
4 bedroom 4 bath Jamaica villa in Montego Bay
Summertime at Silver Sands has a wonderful beach vibe, it benefits from cool sea breezes and is a relaxed and unfussy villa located on the renowned Silver Sands Beach Club, a collection of privately owned villas all overlooking the Caribbean sea.
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.
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.
5 bedroom 5 bath Jamaica villa in Montego Bay
Trinity is a recently renovated luxury villa that boasts breathtaking views, features two expansive swimming pools, offers opulent furnishings and accessories, incorporates a Sonos music system throughout, and is staffed by a team of professionally trained individuals dedicated to ensuring your vacation is unforgettable.
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
4 bedroom 4 bath Jamaica villa in Montego Bay
One of the most enviable locations at Tryall atop Barnes Hill, Vista Del Mar is a Jamaican Classic offering charm and spectacular views.
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