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.
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.
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 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
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.
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.
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.
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.
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.
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.
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!
4 bedroom 4 bath Jamaica villa in Montego Bay
Windsong is an exquisite and very private home just minutes from Round Hill. 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 of Round Hill, the sea and the sunset.
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 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.
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.
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
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.
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.
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.
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 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 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.
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.
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.
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
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.
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.
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 4.5 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.
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.
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.
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.
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.
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.
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.
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 nearby membership at Round Hill.
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.
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 5 bath Jamaica villa in Ocho Rios
SCOTCH ON THE ROCKS is a charming turquoise villa overlooking the Caribbean Sea.
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 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.
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 6.5 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.
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.
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.
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
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.
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 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.
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.
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