Montego Bay Holiday Villas, Jamaica
Montego Bay
9 br, 11 ba (9 Ensuite)
Expect touches of art and glamour at this sleek luxury getaway, one of our most impressive Jamaica villa rentals. Owned by one of the world’s premier Jamaican art collectors, Hanover Grange’s interiors and expansive grounds are decorated with pieces from the owner’s collection.
10 br, 6 ba (6 Ensuite)
Silent Waters villa is a superb location for a family reunion, corporate retreat, destination wedding (seating 54 guests) or just a small group of friends seeking a most unusual holiday experience. Nestled in the hills of Jamaica, overlooking pristine forests and the spectacular turquoise waters of Montego Bay sits this truly remarkable private Jamaica resort property.
7 br, 7.5 ba (7 Ensuite)
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. Enjoying one of the finest views in the entire Tryall Club, the property is nestled on 7 acres of tropical splendor, over 350 feet above sea level.
8 br, 8 ba (6 Ensuite), Pool
Brilliant views of the Caribbean Sea set the backdrop for the largest private villa at the world-famous Tryall Club. This 12,000 sq ft villa, styled in British Colonial architecture, has 8 charming bedrooms, 3 of which are master suites.
7 br, 7 ba (7 Ensuite)
Sugar Hill is situated on a gorgeous three-acre property atop Barnes Hill at the magnificent Tryall Club. There is a spacious four-bedroom villa and three-bedroom guesthouse.
5 br, 7 ba (5 Ensuite), Pool
Trinity Villa, located within the exclusive 2,200 acre Tryall Club, is situated high above the Caribbean Sea with breathtaking views of the ocean, tropical forests and Tryall's award-winning golf course. Designed by the prestigious international architect Thomas Reed, Trinity Villa is an ultra-luxurious paradise.
6 br, 6.5 ba (6 Ensuite)
This contemporary 6-bedroom villa is an elegant mix of Caribbean architecture and European style with modern amenities and technology that will please even the most discriminating tastes.
As you enter the luxuriously appointed living room with its soaring cathedral ceiling, you are immediately presented with Anticipation's spectacular view.
5 br, 14 ba (5 Ensuite)
This elegant retreat nestled in the prestigious Spring Farm gated community is the ideal setting for a large gathering. At 18,000 square feet it perfectly accommodates five couples, with additional bedding available for groups of up to 17 guests.
6 br, 6 ba (6 Ensuite), Pool
Following Seas is a one-of-a-kind vacation hideaway offering the ultimate in luxury, comfort and breathtaking décor. The casual elegance seamlessly balances original artwork with classic Jamaican architecture, inviting the outside in through large windows and open air verandas.
5 br, 5.5 ba (5 Ensuite), Pool
Mahogany Hill is a beautiful 3 level, 5 bedroom deluxe villa situated on eleven acres of land that overlooks the world famous Tryall Golf Club, the ocean and Montego Bay in the distance. Ingenious architectural design combines Asia, Africa, and Caribbean influence to fashion a truly spectacular villa.
6 br, 9 ba (6 Ensuite)
Rose Cottage, is a 6-bedroom villa that sits quietly yet dramatically within the world-renowned Tryall Club, on a plateau affording exceptional mountain and ocean views. Designed by Nancy D.
6 br, 6 ba (6 Ensuite)
On 6 beautifully landscaped acres, Villa Viviana sits in a serene and enchanting location at the world-famous Tryall Club. This beautiful villa offers the finest balance of sophisticated luxury and private comfort: elegant and cozy, majestic and inviting.
5 br, 5 ba (5 Ensuite), Pool
Designed by one of Jamaica’s best known architects, Bougainvillea House is built in classic Caribbean Georgian style but discreetly includes every 21st century luxury. It covers more than 8,000 square feet and sits in a panoramic location with 180 degree sea views.
5 br, 5 ba (5 Ensuite)
Infinity is a spectacular 5-bedroom recent addition to the Tryall Club family of villas. The property's spacious rooms and open living spaces represent the finest traditions of Jamaican architecture.
5 br, 5.5 ba (5 Ensuite)
It's been said, "There's no place like home." After visiting Sea Salt, you may choose to differ.
5 br, 5 ba (5 Ensuite)
Sundance is a stunning five bedroom, traditional Palladian style villa extending to 6,000 square feet and occupying a quiet two-acre site, off Mahogany Drive, with views of the Caribbean. Antique brick and Italian tiled terraces, pathways and extensive planted areas create a magnificent setting for this beautifully furnished house with its mahogany floors and porcelain tiled bathrooms.
5 br, 5 ba (5 Ensuite)
Named Villa of the Year in 2009, Lolita is a remarkable architectural achievement designed by noted Chicago architect Tom Reed. A 14,500 sq.
7 br, 8 ba (7 Ensuite)
This stunning seven bedroom villa was completed in 2006, built to take advantage of its prestigious Spring Farm neighborhood of Montego Bay and the extensive landscaped grounds include an infinity edged pool, a Jacuzzi, and tennis court overlooking the ocean. With a full staff of 5 to take care of your every need- all you have to do is sit back and enjoy.
6 br, 8 ba (6 Ensuite)
Inside, the house is a perfect blend of beauty with comfort. The guiding hand of Greatview’s creator and the commitment of its staff are evident in the upscale décor and careful attention to detail.
7 br, 7.5 ba (7 Ensuite), Pool
Situated directly on the Caribbean Sea, steps from the first tee, beach club and beach bar, Phoenix is ideally located to take advantage of all The Tryall Club has to offer. The large, open, airy rooms and verandas are quintessentially Jamaican in feel and function.
6 br, 6 ba (6 Ensuite)
Karma Bay is a unique fusion of Asia-Caribbean styles on a spectacular waterfront location in the historic Tryall Club. The villa is a series of pavilions with separate living room/dining room and bedrooms, all connected by covered walkways lined with spectacular art and landscaping.
5 br, 6 ba (5 Ensuite)
No Le Hace is located at the Tryall Club, an exclusive Caribbean destination with club-like atmosphere, spread out over a lush 2,200-acre property on the quiet, pristine north coast of Jamaica. It contains five bedrooms.
7 br, 8 ba (7 Ensuite)
Refurbishment Note: Please note that this villa will be undergoing refurbishments. Please enquire with one of our Villa Specialists for further details.
5 br, 4.5 ba (4 Ensuite)
Newly-built Allamanda Villa is one of our most family-friendly Jamaica villa rentals. Located 15 minutes from the lively town of Montego Bay on two acres of manicured grounds, this fully-staffed villa includes beach club membership at the exclusive Round Hill resort.
4 br, 5 ba (4 Ensuite)
Offering some of the most dramatic views in the Caribbean, Destiny overlooks the Great River Valley, the Caribbean Sea, and Montego Bay. The entrance leading up to Destiny is lined with hibiscus and flowering trees and the cobblestone courtyard features a symbol of the sun laid out in black stone.
9 br, 9 ba (9 Ensuite)
Situated in the Springfarm area of Montego Bay, Summerhill Villa boasts 3 storeys and 10,000 square feet of brightly painted, charming space. The villa is inspired by Spanish architecture, complete with cathedral and vaulted ceilings and meticulously polished wood and marble floors.
5 br, 5 ba (5 Ensuite)
EXCLUSIVE OFFER: 2 FREE NIGHTS
Stay 7 nights for the price of 5. This promotion is not valid during the weeks of Thanksgiving, Christmas or New Year’s Day.
4 br, 4.5 ba (4 Ensuite)
Hillside Villa was built with a vision of joyful family gatherings, romantic getaways and friends celebrating the complete vacation experience. The large living room opens to a spacious verandah overlooking the pool and 10-mile stretch of sea that separates Round Hill from the town of Montego Bay.
5 br, 7.5 ba (5 Ensuite), Pool
Set on over four and one-half acres of gently sloping land and surrounded by well manicured lawns Great River House commands sweeping views of the sea. The property features mature trees including fine citrus and pimento trees together with flowering plants, shrubs and royal palms gently lit in the evening to create a private, secluded, romantic environment.
6 br, 6 ba (6 Ensuite)
Serendipity: "The faculty or phenomenon of finding delightful, pleasant or valuable, things not sought for, while having the wisdom to discern it."
Whether you are coming to Jamaica in search of real relaxation, complete escape, natural beauty, or exhilarating adventure, you will find these and many other unpredictable and delightfully pleasant discoveries at Serendipity.
5 br, 8 ba (5 Ensuite)
Nestled on the hills of the prestigious Rose Hall Estate this luxurious villa offers spectacular view of the turquoise waters of the Caribbean Sea and surrounding hills.
Take a dip in our sparkling fresh water swimming pool or heated jetted bathtub.
4 br, 4 ba (4 Ensuite)
Welcome to Calypso Shores, a fully staffed waterfront villa with private beach and pool 10 minutes from the Sangster airport in beautiful Montego Bay. The villa is located in a lovely gated community with 24 hr.
3 br, 3 ba (3 Ensuite)
Star Apple House is a luxurious, fully-staffed private home situated high above the Caribbean Sea sitting within its own fully landscaped, private, secluded 6 acre grounds. Located in the hills above Great River overlooking the Bay of Montego in what's arguably the best location on the "Jamaican Riviera", the villa is conveniently just a 20-minute drive west of Montego Bay and 7 miles from the international airport.



































