Montego Bay Villa Rentals
Jamaica
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.
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.
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.
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.
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 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.
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.
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.
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.
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 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.
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.
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.
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.
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
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.
6 bedroom 6 bath Jamaica villa in Montego Bay
Welcome to the Wheel House Villa!
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.
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!
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.
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.
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.
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.
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.
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 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.
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.
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 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 5.5 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.
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 8 bath Jamaica villa in Montego Bay
Hummingbird House is one of the finest properties within the Tryall Club!
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.
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.
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.
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.
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.
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 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.
4 bedroom 4 bath Jamaica villa in Montego Bay
Windsong is an exquisite and very private home. Designed by noted architect Kasimir Coribut, the site benefits from spectacular views day and night and the most favorable tradewinds. The east view captures the sunrise and Montego Bay ... the west view is an equally lovely vista towards Negril, the sea, and the sunset.
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.
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
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.
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.
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.
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.
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.
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.
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.
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 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.
4 bedroom 4 bath Jamaica villa in Montego Bay
This amazing seafront 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.
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.
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.
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.
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.
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!
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.
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 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.
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.
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 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.
5 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 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.
5 bedroom 5.5 bath Jamaica villa in Montego Bay
Villa Indigo at HALF MOON is one of the undisputed finest private homes in this collection.
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.
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.
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