TEK TIME is Jamaican patois for advice that almost all of us need: TAKE TIME to slow down and take in all that’s good and beautiful around us. Living in a glamorous villa with a staff of six who pamper their guests without ever intruding makes it easy to heed that advice.

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.

Three Little Birds is a newly renovated four-bedroom villa with a warm and inviting feel, inclusive of every amenity you may need. Located high on the hillside of Copperwood Ridge it enjoys fabulous sea and golf course views and is a perfect location for easy access to all of Tryall Club’s amenities including beach pool access, golf, and tennis.

Timbuktu is a brand-new villa built on the incredible coastline of Boscobel (not far from Oracabessa). Interiors are beautifully decorated with traces of Timbuktu, the Middle East, and Asia - all set in a beautiful tropical background.

Tradewinds was completely renovated and refurbished in January 2018. This amazing sea front property sits on two acres at the famous Tryall Club – directly on the Caribbean Sea. 300 feet of waterfront from the north perimeter of the property, and it is one of the newest premier villas at The Tryall Club.

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.

Trinity is a recently renovated luxury villa that boasts breathtaking views, features two expansive swimming pools, offers opulent furnishings and accessories, incorporates a Sonos music system throughout, and is staffed by a team of professionally trained individuals dedicated to ensuring your vacation is unforgettable.

Trinity is a recently renovated luxury villa that boasts breathtaking views, features two expansive swimming pools, offers opulent furnishings and accessories, incorporates a Sonos music system throughout, and is staffed by a team of professionally trained individuals dedicated to ensuring your vacation is unforgettable.

Occupying a commanding elevated location, Villa Amana offers magnificent ocean views and a backdrop of deeply forested hills.

Set on the historic Rose Hall Estate, Villa Christina welcomes couples, families, and friends to Caribbean luxury in a remarkable 10,000 sq. ft. well-appointed Tuscan style villa located in the Greens at Rose Hall - a private gated-community on the Cinnamon Hill Golf Course.

Villa Indigo at HALF MOON is one of the undisputed finest private homes in this collection.

Lido is a fabulous brand-new contemporary beach house, constructed in 2021. Situated right on the white sand, half-moon beach at Old Fort Bay. Beautifully designed and finished, incorporating family heirlooms and a chic modern vibe. Music, it’s history & it’s relevance today are foremost in its concept.