Jamaica Villa Rentals
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.
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.
4 bedroom 4 bath Jamaica villa in Montego Bay
Tradewinds was completely renovated and refurbished in January 2018. This amazing sea front 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.
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.
6 bedroom 6.5 bath Jamaica villa in Runaway Bay
Located on a wide sandy beach, Sweet Spot is like a pretty jewel box next to the sea. Its remarkable location is the best of all worlds ... a 6,000-square-foot private home with a huge lawn and beach.
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.
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!
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!
8 bedroom 6 bath Jamaica villa in Montego Bay
Silent Waters is one of the most glamorous private homes in the Caribbean. It is distinguished by world-class architecture and design, breathtaking location, and exquisite accommodations and service.
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.
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 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.
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.
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.
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 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.
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.
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.
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 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.
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.
8 bedroom 8.5 bath Jamaica villa in Ocho Rios
MALATAI has just undergone a Fabulous renovation, with 8 newly renovated bedrooms and bathrooms, a beachfront, and a top-rated chef, directly on the translucent waters of Mammee Bay, near Ocho Rios. While privately located, Malatai is only minutes from Dolphin Cove, famous Dunn‘s River Falls, and lively Ocho Rios with its wide selection of duty-free shopping, excursions, and music.
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.
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.
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.
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 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.
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.
10 bedroom 10 bath Jamaica villa in Montego Bay
Villa Indigo at HALF MOON is one of the undisputed finest private homes in this collection.
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.
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.
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.
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
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.
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 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.
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
