SPECIAL OFFER FOR BOOKINGS FROM NOW THROUGH DEC. 15th 2017: $1,500 Concierge Credit for new bookings (minimum 7 night stay). Guests may apply to any additional services not included in the rental, such as groceries, tours, staff, transportation… Roaring Pavilion THEE Divine Villa is a one of a...

Silent Waters Villa won the Caribbean World Travel Awards Best Villa of the Year for 2004, 2005, 2006, & 2007! Silent Waters is a spectacular private home located on 18 acres on one of the highest mountaintops overlooking Montego Bay. Glamour, romance and flair define this remarkable vacation site,...

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...

An exclusively elegant villa, 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 traditional or gourmet...

Villa Point of View at the Tryall Club on Jamaica is a gorgeous five-bedroom home with elegant classical furnishings that blend seamlessly with modern amenities and the breathtaking natural environment. This villa offers an outstanding point of view as the name implies. Set at the very highest...

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...

More than an island retreat, the four-bedroom Panorama Villa, once frequented by Audrey Hepburn, is a renovated contemporary residence set on an acre of naturally landscaped gardens that offer stunning views of the Caribbean Sea, Portland’s Coastline, and the enchanting silhouette of the Blue...

Round Hill Villa 21 Jamaica. If the idea of a secluded and ultra-luxurious villa in a mature and manicured garden setting appeals to you, then the Round Hill Villa 21 is one to consider. Part of the exclusive Round Hill resort, it is located in the Montego Bay area of Jamaica and offers you a bevy...

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...

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...

Welcome to Canoe Cove on the Beach on Old Fort Bay, a contemporary 7 bedroom beachfront villa perched on 3 private beachfront acres. This luxurious beachfront Jamaican villa is a paradise for a large family vacation or a gathering among close friends. There’s something for everyone to enjoy at...

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...

In the 1950s, Jamaican attorney Clinton Hart happened onto this remarkable three-acre oceanfront location and built a simple beach cottage for his family. Since then, Canoe Cove has been a virtually unembellished and beloved family home for generations. Recently, Hart’s grandson replaced the worn...

Sundown Villa epitomizes what an exquisite, vacation villa should be. This beautiful, totally renovated in 2012, nine-bedroom villa nestled in the secluded Discovery Bay, on Jamaica's North Coast, is spread across 5.500 square feet of gorgeous, Caribbean-styled living. From four-poster, Mahogany...

3 Waterfront villas with 4 luxury bedrooms + a 3 bedroom luxury villa for a total of 15 bedrooms! Great for weddings, family reunions, special events! Newly refurbished waterfront luxury villas! Enjoy the luxury and peaceful surroundings of these four luxury villas with your own beachfront, sea...

Sundown is an exquisite staffed home on a private white sand beach next to the turquoise waters of Discovery Bay. Interiors are beautifully decorated in rich fabrics on dark wicker and mahogany. Living and dining room floors are marble. Five bedrooms are in the Main House. The old two-bedroom Guest...

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,...

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...

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...

7 bedrooms, 7 bathrooms, spectacular sea views!!! 4 minutes golf cart ride to the beach. Hummingbird House, is the newly refurbished Premier villa with 7 luxury bedrooms! Hummingbird House is one of the finest villas located within the world renowned Tryall Club estate. Located on four acres of...

Welcome to Fortlands Point on the Beach, one of the world's most exquisite and luxurious 7 bedroom beachfront mansions located on a private promontory with its own private beach, swimming pool extensive gardens. Set amongst stunning landscaped gardens with tropical flowers Fortlands Point is...

9 bedrooms in this luxury beachfront Jamaican villa - Spectacular beach front home with commanding views of the Caribbean Sea. 3 private beaches. A magical property. Flortlands Point, Jamaica villa -This is a most stunning and newly built property located at the peninsula of Discovery Bay....

Renting 8 bedrooms of this 9 bedroom Luxury Villa -Spectacular beach front home with commanding views of the Caribbean Sea. 3 private beaches. A magical property. Flortlands Point, Jamaica villa -This is a most stunning and newly built property located at the peninsula of Discovery Bay. Fortlands...

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...

Jamaica's most spectacular contemporary beachfront villa, Canoe Cove is located on 200 feet of white sandy beachfront - a very rare asset to be found! Located on three private acres of beachfront property, this fabulous villa is a one of a kind that gives first class service, with a staff of 9, and...

Jamaica’s Northern coast is home to some of the world’s most sought-after beachfront vacation homes, and with its lengthy list of satisfied A-list clientele, Frankfort has established itself among the best of the best. This converted eighteenth-century plantation has hosted Winston Churchill,...

Brand new half million dollar renovation! Restored 17th Century fortress! Unique to this villa is situated within the Prospect Plantation. Please read about the Plantation's features. Frankfort is one of Jamaica's most famous 17th Century fortress which has been resorted with over half a million...

Frankfort is possibly the most desirable property in Jamaica. The secluded white sand beach is an attraction that has been enjoyed by some of the greatest luminaries of the 20th century including: Sir Winston Churchill, Dr. Henry Kissinger, Mr. Pierre Trudeau as well as royalty and other prime...

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...

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...

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...

NEW FOR 2017: 2 bedroom rates available at luxury spa villa Roaring Pavilion! SPECIAL OFFER FOR BOOKINGS FROM NOW THROUGH DEC. 15th 2017: $1,500 Concierge Credit for new bookings (minimum 7 night stay). Guests may apply to any additional services not included in the rental, such as groceries,...

The Fleming Villa at GoldenEye on Jamaica is an oceanside Ocho Rios retreat with a celebrated history. Known as the home where Ian Fleming conjured up his James Bond character, The Fleming Villa continues to attract writers, artists and others who cherish their privacy and rejoice in the inspiring...

Round Hill Villa 18 Jamaica. Richly decorated and designed for groups, the stunning Round Hill Villa 18 is a fabulous island retreat for families or friends. Sitting in a large and private garden, the five-bedroom property offers a wealth of services and amenities in addition to those available on...

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...

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...

7 bedrooms, 7 bathrooms, spectacular sea views!!! 4 minutes golf cart ride to the beach. Hummingbird House, is the newly refurbished Premier villa with 7 luxury bedrooms! Hummingbird House is one of the finest villas located within the world renowned Tryall Club estate. Located on four acres of...

Located in Discovery Bay and built in 2000, Amanoka Villa (Aman-oka or 'peaceful home' in Indonesian) is living proof that imagination when it is executed to perfection can produce magical results. All materials are of the finest quality and many of the authentic design elements were imported from...

Find a Bali-inspired hideaway tucked into a lush garden at Amanoka on Discovery Bay. Rooted in East Asian architecture and named after the Indonesian word for “peaceful home,” this Jamaica vacation rental draws on traditions from around the world—and a location on a private white-sand beach—to...

Malatai Villa is one of the most deluxe luxury villas in picturesque Ocho Rios. Newly built, the glamorous villa offers eight deluxe bedrooms, exuding pure luxury on the seaside!! The luxury villa Jamaica has a delightful stretch of white sandy beach, great for morning or evening walks! An...

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...