Jamaican Holiday Villas (Caribbean)

Seven Seas is a secluded holiday paradise – a private 5000 sq. ft.

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.

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.

The newest member to the Tryall Club; 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. Nestled over 350 feet above sea level on seven acres of tropical splendor, the seven bedroom villa enjoys inspirational panoramic views of the Caribbean Sea, deep valleys and golf course.

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 open air verandas.

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.

A most serene and enchanting location, Viviana is the ideal place to re-discover the secret to falling in love with nature and with life. This beautiful villa offers the finest balance of sophisticated luxury and private comfort – elegant and cozy, majestic and inviting.

Rose Cottage, a six-bedroom new villa to Tryall, sits quietly yet dramatically on a plateau affording exceptional mountain and ocean views. Designed by Nancy D.

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. Trinity Villa is an ultra-luxurious paradise.

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.

Nestled among the villas of the historic Tryall plantation, Sea Salt, part of the exclusive Tryall Club, is one of the most relaxed, premier private homes that grace the northern cost of this Caribbean paradise. Sea Salt features classic Jamaican architecture with vaulted ceilings and 7,700 sq.

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.

You will see at once how Greatview Villa got its name. An easy 10-minute drive from Montego Bay’s international airport, step into its peaceful and secluded gardens – then take in the spectacular view of ocean and mountains beyond.

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.

A sprawling complex of six beautiful private bedrooms as well as large living, dining and family spaces serve as your exquisitely decorated quarters. There is a media lounge equipped with stereo sound system and cable television.

Villa Lolita is 14,000 square feet of dramatically design. You will be greeted by a professional, experienced staff of seven, that will provide unmatched personalized service.

The most discerning travelers choose our Royal Villas and enjoy superior levels of personal service, luxury amenities, and a staff of three to cater to every need. Sumptuous meals are prepared to order by your personal chef, and the butler is available to assist in any social or sporting arrangements required.

Breathtaking views from No Le Hace will be etched forever in your mind. This five bedroom villa provides almost every amenity for comfort and relaxation.

A recent renovation, and the addition of a new wing, has served to enhance an already spectacular villa. Situated directly on the Caribbean Sea, steps from the first tee, club beach and beach bar, Phoenix is ideally located to take advantage of all The Tryall Club has to offer.

The most discerning travelers choose our Royal Villas and enjoy superior levels of personal service, luxury amenities, and a staff of three to cater to every need. Sumptuous meals are prepared to order by your personal chef, and the butler is available to assist in any social or sporting arrangements required.

The most discerning travelers choose our Royal Villas and enjoy superior levels of personal service, luxury amenities, and a staff of three to cater to every need. Sumptuous meals are prepared to order by your personal chef, and the butler is available to assist in any social or sporting arrangements required.

A visit to Mahogany Hill awakens the realization that you have finally landed in paradise. Set on a luxurious eight-acre estate, Mahogany Hill is captivating with blooms of dewy island flowers in rolling, intimate gardens.

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.

A massive inside-outside renovation in 2006 has created a lovely, tasteful, comfortable vacation villa named “Nutmeg” in the upscale residential neighborhood of Spring Farm, just 5 minutes from three world-class golf courses, designer shops, bars, restaurants and beaches. Through carved entrance doors with antique brass fittings, the magnificent view is immediately apparent.

On the east side of vibrant Montego Bay lies Fairway Manor, 7000 sq. feet of private luxury.

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. The entrance foyer is a celebration of exotic ferns with pleasing tropical flowers brought in fresh from the gardens in anticipation of your arrival.

From its high perch atop Barnes Hill, this recently remodeled luxury villa commands a truly breathtaking view over emerald lawns, an infinity pool and the broad expanse of Tryall Club's legendary golf course. To complete this magical picture are infinite views of the turquoise Caribbean Sea.

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.

Heron Cove is dramatically situated on a lush two-acre property overlooking the sea with a perfect vantage point for sunset viewing. All rooms in this villa have magical water views.

The most discerning travelers choose our Royal Villas and enjoy superior levels of personal service, luxury amenities, and a staff of three to cater to every need. Sumptuous meals are prepared to order by your personal chef, and the butler is available to assist in any social or sporting arrangements required.

Welcome to Calypso Shores, a stunning, fully staffed, waterfront villa with private beach and pool 10 minutes from the Sangster airport in beautiful Montego Bay. Located in a lovely gated community with 24 hr.

A lovely five-bedroom villa overlooking the premier tee of the resort’s Robert Trent Jones’ championship course. Its large verandah runs the length of the villa and overlooks panoramic scenes of the green fairways and the sea beyond.

Villa Rococo captures the allures of Western Jamaica sharing an ideal spanning of hundreds of acres of lush forestation and swirling vista valley. Perched atop the spectacular Content Estate in the heart of paradise this exquisite home rises to complement the splendid landscape and embraces mountainous backdrop, and partial ocean and city view.

Hillside Villa is a four-bedroom private home, located within the famous Round Hill resort, ten miles west of Montego Bay ..

Star Apple House is a luxurious staffed private home, a comfortable retreat situated high above the Caribbean Sea sitting within it's own fully landscaped, private, secluded 6 acre grounds. The house offers superior accommodation and service for up to six guests and is a 25 minute drive west of Montego Bay and 7 miles from the international airport.

This 5000+ sq. ft.

The elegant living room with wet bar, PC, and stereo boasts breathtaking views of the Bay and the famous Negril sunsets. The covered patio, private pool with jacuzzi, and personal dining gazebo grace your front lawn steps from the sand.

Azure has the finest “play room” in Negril. Perfect for family relaxing, large parties, or wedding receptions.

Located on the beach, Dream Walk is 3500 sq ft of luxury. The 50' living room features large screen TV, stereo, computer, and a stocked bar.

Perfect for smaller families, Satin Sunrise is a well-appointed, two-bedroom, two bath villa with lots of outdoor space. The living room features a plasma TV on the wall and ample room for everyone.

Our 'honeymoon villa", lives up its name, and then some. This 1500 sq ft home on one level is romantic and spectacular.

There truly is no place just like Rio Chico, an ultra-luxurious and private villa paradise set on 14 private acres of landscaped, seaside land just outside of Ocho Rios. Its lush gardens hide 20 elegant rooms, private coral beaches, secret waterfalls and every sumptuous amenity you could imagine right at your fingertips in one exotic location all your own.

Roaring Pavilion Villa and Spa is located on a beachfront estate where the Roaring River meets the Caribbean Sea in St. Ann’s Bay, Jamaica, just a few minutes outside of Ocho Rios.

Limited Time Promotion: Stay for 7 nights, pay for only 6. Applicable for travel from now until further notice.