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.
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.
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 6.5 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
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.
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.
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 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.
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 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.
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.
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.
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; Quinntessential is one of the finest private homes in Jamaica where meticulous attention to detail and designers flourish result in the epitome of sophisticated living without compromise.
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.
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.
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
Occupying a commanding elevated location, Villa Amana offers magnificent ocean views and a backdrop of deeply forested hills.
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.
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.
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 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.
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.
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.
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 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.
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 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.
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.
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
