Large Groups

Nestled on its own sandy beach by the blue waters of Discovery Bay, A Summer Place is a spacious and playful family home. The design is of typical Caribbean gingerbread style with hand-carved fretwork trimming the length of the house.

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.

On three acres of land with a commanding view of the Caribbean Sea, lush green mountains and golf course, Bumper's Nest was designed by distinguished architect Kasimir Korybut in 1995. A brilliant renovation completed in 2015 has recreated one of the most glamorous homes at the Tryall Club. Here is an extraordinary private home with simply the best of everything.

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.

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.

COCONUT is a very private 5-bedroom cottage nestled into an acre on a gentle hillside that was the original 500-acre plantation of Round Hill Estate. Set in a storybook wooded lot, the villa accommodates couples and families in three bedrooms in the Main House and two more bedrooms in the Cottage just a few yards away.

Built in the 1940‘s by the Duke of Marlborough, Drambuie Estate is a slice of old Jamaica when lively drawing room conversation and gracious service ruled the day in an extraordinary private setting.

One of the most glamorous villas in Jamaica, Endless Summer is a turreted mansion with breathtaking views of the Caribbean Sea.

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.

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.

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.

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.

FOR DECADES, The Fleming Villa has been legend for its illustrious past, its celebrity guests, and the lasting works of literature and film that were penned and shot here. Today, it is just as stunning as ever and still filled with the echoes of the literati, the rich, famous and infamous who gathered here for adventures romantic, intellectual and illicit.

Greatview is one of the most glamorous private homes overlooking the Half Moon golf course and vast ocean vista. Three world-class golf courses (Cinnamon Hill, Half Moon and White Witch) are within a five-minute drive. The view is breathtaking ~ the deep blue sea to the north and magnificent mountains to the south.

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.

Hummingbird House is one of the finest properties within the Tryall Club!

JAMAICAN DREAM is an aptly-named 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.

Located on a private coral cove, this pretty yellow stone villa overlooks one of Jamaica's loveliest bodies of water ~ Discovery Bay.

In the Rose Hall residential expanse of fine homes, Kenyan Sunset Golf Villa is designed for families and golfers. It sits on two acres bordering the famous White Witch golf course and has direct walk-on access to the 4th tee, virtually in your own backyard.

More than 50 years ago, a visionary named John Pringle dreamed of turning a magical Jamaican hillside and waterfront into a luxurious retreat and he named it Round Hill. He sat upon the hill, gazed over the deep blue sea and selected the site for his own home, the genesis of what was to become a renowned resort for guests from around the world. Today, that home is Knockando, distinguished by one of the most breathtaking views in the Caribbean.

This 3-bedroom casual cottage shares a delightful waterfront site with its sister property, Coral Cove 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.

From acres of beautifully landscaped and terraced grounds, Longview Manor commands sweeping views of the Caribbean Sea and blue-green mountain range. Large comfortable verandahs ~ one facing east, the other west ~ are vantage points for memorable sunrises and sunsets.

On seven acres overlooking the Tryall golf course and the Caribbean Sea, Mahogany Hill is among the most beautiful and spacious private homes at the Tryall Club. The unique architecture has situated all bedrooms for maximum privacy.

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.

A paradigm of elegance and style, Noble House on the Beach is an architectural gem, unique in the Caribbean.

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.

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.

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.

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.

On its own sugary white sand beach lapped by the clear turquoise waters of Discovery Bay sits the charming home Sea Grapes. The translucent azure waters here are excellent for swimming and kayaking. Surrounding the swimming pool is a spacious grassy lawn, wonderful for children and games.

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.

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!

6,000-square-foot private villa on 5 acres with magnificent views of the Caribbean Sea. After sunset, the view transforms from brilliant blue water to the mesmerizing beauty of the sea at night, glimmering with reflections of cruise ships and the romantic night lights of Montego Bay nine miles away.

Sundown is an exquisite staffed home on a private white sand beach next to the turquoise waters of Discovery 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.

From the homeowner who created the wonderful villa Keela Wee comes its new sister house, Whispering Waters. Located immediately next door to Keela Wee, this brand new villa offers seven bedrooms and en-suite bathrooms. Whispering Waters overlooks one of Jamaica’s loveliest crystal clear bodies of water, Discovery Bay. On its own private coral cove, this newest property can be rented alone ~ or in combination with any other neighboring villa.

Wild Orchid is a private Jamaican hideaway located on part of a former banana and coconut plantation stretching from mountain to sea.

Premier Villa on Two Acres on Tryall Club’s Chic West End!