12 bedroom, 12 bathroom luxury mansion in Montego Bay. Located in one of the most prestigious neighbours in Montego Bay, Jamaica lies your fantasy escape. The Golden Castle Golf & Spa will host you with consummate elegance in our lush, tropical and exquisite ambiance. Nestled on the majestic...

Twin Palms is perhaps the most amazing feat of architecture and design achieved in the Caribbean in decades. Fit for a king and remarkable for entertaining, the villa is designed to accommodate families and friends in extraordinary comfort and exquisite style. Unparalleled architecture and design...

This 14 bedroom Exclusively Elegant Boutique Villa is, surrounded by lush, green, beautifully manicured gardens with spectacular breathtaking views of the Caribbean Sea. Features spacious and tastefully decorated suites, private balcony, outdoor infinity pool, outdoor hot tub, pool deck bar and...

Coastal chic meets laid-back comfort in Villa 7. Newly renovated, this villa boasts a main house, guesthouse and sparkling pool situated on a beautifully terraced tropical landscape. Tucked into the hillside for privacy, expect magnificent views of the bay from each room on the upper level - with...

An exquisite, superbly welcoming villa, Haystack furnishes you with a vacation experience unmatched in elegance and serenity. Brilliant views of the Caribbean Sea set the backdrop for this lovely villa styled in British Colonial architecture under a sunny Jamaican influence. Classic black and white...

Sundance is a stunning 5 bedroom, traditional Palladian style villa completed in 2006, extending to 6,000 square feet and occupying a quiet 2 acre site with views of the Caribbean. Antique brick and Italian tiled terraces, pathways and extensive planted areas create a magnificant setting for this...

Xanadu is superior villa perched on top of Barnes Hill, commanding spectacular views of the green fairways and sparkling Caribbean Sea beyond. The villa is spacious and features tasteful interiors. An expansive living area has cathedral ceilings, a library, music area complete with Steinway grand...

The newest member to the Tryall Club; Harmony Hill is a private, seven bedroom villa combining Jamaica’s rich architectural tradition with today’s modern amenities. Nestled over 350 feet above sea level, this exclusive, and seven acre oasis enjoys breathtaking panoramic views of the Caribbean Sea,...

Entertaining in style, this dramatic seaside villa has a large covered terrace as well as an open circular pool deck. the dining area, living room and all four bedrooms open onto the pool deck. the master suite features a walk-in shower and magnificent mirrored bath with tub for two inside a walled...

Silent Waters is a spectacular villa at Montego Bay along the northwest shore of Jamaica. With its private heli-pad and ample space for cocktail or dinner parties, the villa forms an enchanting venue for special occasions; while resort-like features including a tennis court and fabulous pool make...

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. Opened in 2010, this...

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. Once you drive in through the palm tree-lined...

Flower Hill - This breathtaking and luxurious 18,000 sq. ft. villa completed in the summer of 2012 is located in the Montego Bay, Spring Farm villas overlooking the Half Moon Resort golf course and the Caribbean Sea. The 6-bedroom 14-bathroom villas was constructed using the finest materials and...

The guiding hand of Greatview’s creator and the commitment of its staff are evident in the upscale décor and careful attention to detail. Each of the 5 large bed-and-bath combination suites in the main house has its signature motif and character. Living areas have been thoughtfully designed to meet...

Silent Waters is a spectacular villa at Montego Bay along the northwest shore of Jamaica. With its private heli-pad and ample space for cocktail or dinner parties, the villa forms an enchanting venue for special occasions; while resort-like features including a tennis court and fabulous pool make...

Sugar Hill Villas are situated on a gorgeous three-acre property atop Barnes Hill at the magnificent Tryall Club in Sandy Bay, Jamaica. There is a spacious four-bedroom villa and three-bedroom guesthouse. Every room boasts spectacular views of the glittering Caribbean Sea, curvaceous northwest...

Sugar Hill is a stunning private villa within the Tryall Club on Jamaica's north coast, named by Condé Nast as one of the finest resort destinations in the world. Guests enjoy access to the Tryall's extraordinary amenities, while the villa itself includes a pool, spa, games room, and more. The...

Windrush is a majestic villa within the renowned Tryall Club on Jamaica's north coast. Perched atop Barnes Hill on a five-acre private estate, the villa surveys panoramic views of the resort's lush shoreline and the Caribbean Sea. Special features include an expansive swimming pool, excellent...

This entirely renovated luxury villa is beautifully situated on five acres of lush gardens. It features an air-conditioned master bedroom with a four-poster Jamaican mahogany king-size bed and mahogany floors, en-suite bathroom with separate shower and dressing room. Four more guest bedrooms (two...

Villa Hummingbird House at the Tryall Club on Jamaica is a spectacular 14,000 square foot estate on four beautiful acres. This newly refurbished seven-bedroom villa features traditional English Colonial styling and outstanding interior design. Take advantage of the onsite heliport, then drive...

Phoenix is a fabulous waterfront villa at Tryall Club on Jamaica's north coast, named by Condé Nast as one of the top resort destinations the world. The villa is situated within a short walk of the resort's beach club and championship golf course, while its private estate features a beautiful...

Villa Royale is a 15 bedroom villa, can rent on a per room basis or whole villa. Close to all Montego Bay amenities, great for large functions or family reunions. Villa Royale is a large 15 bedroom villa in Montego Bay, close to Montego Bay amenities, fully secured, clean king bedrooms with...

Greatview is perched on a lush hillside at Montego Bay on the north shore of Jamaica, with majestic, panoramic views of the Caribbean Sea. Practically a private resort unto itself, the villa features two swimming pools and fabulous amenities for dining, relaxation, wellness, and play. The friendly...

Rose Cottage, a six-bedroom villa in Tryall, built in 2008, sits quietly yet dramatically on a plateau affording exceptional mountain and ocean views. Designed by Nancy D. Maffasanti in traditional Jamaican style, the house is decorated in an elegant arrangement of themes influenced by Asia,...

Caribbean charm and five-star luxury are a perfect pairing at Rose Cottage at Tryall Club. In spite of its name, this Jamaica vacation rental is a fully staffed six-bedroom villa that can accommodate parties of up to twelve friends or family members. Reserve this ocean-view property for a special...

Silent Waters is a spectacular villa at Montego Bay along the northwest shore of Jamaica. With its private heli-pad and ample space for cocktail or dinner parties, the villa forms an enchanting venue for special occasions; while resort-like features including a tennis court and fabulous pool make...

Winner of the Caribbean Travel & Living Awards 'Best Luxury Villa of the Year' for 9 straight years! 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....

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. Once you drive in through the palm tree-lined...

OMG! You have found a villa with a VERY SPECIAL OFFER!! COMPLIMENTARY 15 SEATER VAN AND DRIVER FOR WEEKLY BOOKINGS!! Includes complimentary airport transfers, trips to Negril and over to Ocho Rios! Best way to see Jamaica! (Guests responsible for gas and tips to driver) One of the most luxurious...

Following Seas is a one-of-a-kind vacation hideaway offering the ultimate in luxury, comfort and breathtaking décor. Newly renovated in 2007, Following Seas' casual elegance seamlessly balances original artwork with classic Jamaican architecture, inviting the outside in through large windows and...

With incredible ocean views, spacious open-air living, and helpful staff, Following Seas is one of Tryall Club’s most prestigious six-bedroom villas. Located minutes from the golf course, tennis court, and sandy beach, you’ll have no trouble exploring Tryall’s beautiful estate, and you’ll have the...

Bumper's Nest is a deluxe villa located on Mahogany Hill with expansive ocean views. Set in a lush garden, the villa has been professionally decorated and offers the Old World charm of Jamaica. Located on three acres of land, entrance is via a central atrium complete with a fountain in the shape of...

Make your home away from home at one of the most exclusive addresses in Jamaica at Bumper’s Nest. Not only is it part of the five-star Tryall Club on the island’s northwest coast, this luxury six-bedroom vacation rental is perched on the top of Mahogany Hill and affords panoramic views of the...

One of the finest villas at Tryall Club, Anticipation has all the inviting atmosphere of an elegant private island home and all the amenities necessary to ensure a successful Caribbean vacation. There are three bedrooms in the main villa and one in a separate cottage a breath away from the pool....

For a taste of paradise where the waves lap the shore and the trade winds caress the palm trees, Karma Bay has all the attributes that make for an unforgettable oceanfront living experience. With six private bedrooms, this magnificent waterfront villa melds influences from Asia and the Caribbean...

Villa Harmony Hill at the Tryall Club, Jamaica.  Harmony Hill is an elegant seven-bedroom estate with the ambiance of an intimate boutique hotel. This very private Montego Bay property blends classic Jamaican styling with all the amenities you desire for a carefree getaway. Enjoy the services...

Located between Lucea and Montego Bay on the northern coast of Jamaica, this beachfront luxury villa is island living at its finest. Situated within The Tryall Club’s estate, Sunset is just a short walk from tennis, restaurants, and Tryall’s oceanside golf course. With five beautiful bedrooms, all...

The Round House is a superior villa located on Copperwood Ridge. Nestled in a tropical paradise, the home offers views of the lush Jamaican mountains and Caribbean Sea beyond. The home is built on two levels and offers traditionally styled interiors with some local artwork. The home boasts seven...

Please note that there is construction near this villa. Please enquire with one of our Villa Specialists for further details. Reward yourself with a true luxury holiday at Karma Bay at Tryall. Set on an incredible beachfront lot on the grounds of the exclusive Tryall Club, this Jamaica vacation...

OMG!! You have found a villa with a free Van an Driver!! SPECIAL OFFER: COMPLIMENTARY VAN AND DRIVER FOR THE WEEK - with Weekly bookings! Includes airport transfers, you can have the driver services for 10 hours of the day! Go to Negril, Montego Bay night life, shopping, Ocho Rios tours, Bob...

Phoenix is a fabulous waterfront villa at Tryall Club on Jamaica's north coast, named by Condé Nast as one of the top resort destinations the world. The villa is situated within a short walk of the resort's beach club and championship golf course, while its private estate features a beautiful...

Among the newest Premier villas 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,...

Villa Infinity at the Tryall Club on Jamaica is a premiere five-bedroom estate with breathtaking views of the Caribbean Sea. Arrive in style on the convenient onsite helipad and discover a full staff including the services of a personal chef, a butler, housekeepers and a laundress. The interior of...

Make countless memories in a gorgeous setting at Infinity at Tryall Club. This luxury Jamaica vacation rental is fully staffed and features incredible outdoor living areas overlooking the lush landscape. Use it to host a family reunion or anniversary celebration, hold a destination wedding on the...

You’ll see at once how Greatview got its name. An easy 10-minute drive from Montego Bay’s international airport, you'll find this oasis of beautiful gardens with spectacular ocean and mountain views. Both secluded and handy to golf, sailing, beach, horseback riding and other adventures, Greatview...

Villa Longview Manor at Round Hill on Jamaica is a stunning 7,500 estate with seven-bedrooms distributed in a main house and a separate private cottage. Located in the upscale area of Round Hill in Montego Bay, Villa Longview Manor offers panoramic views of the lush mountainside and the sparkling...

Rated Premier, the highest rating in the Tryall Club, Pineapple House is an elegant home offering over 6000 square feet of total indulgence your very own Caribbean island private home. The soft, gentle sounds of the waterfall grotto greet you upon arrival...along with the extensive collection of...