Classically Jamaican, exclusively private, and naturally beautiful, The Tryall Club is a 2,200-acre property in Montego Bay on the northwest Caribbean coast of Jamaica. Tryall features over 90 privately owned villa homes—with over 70 available for rental—ranging from two to ten bedrooms, each with a dedicated staff including butler, chef, housekeeper, laundress and gardener to ensure a seamless stay. Operating since 1957, the resort, just 30 minutes by car from Sangster International Airport in Montego Bay, has attracted discerning travelers year round. Recently, The Livity Spa by Tryall Club, a holistic wellness space dedicated to elevating well-being through treatments, yoga, sound therapy and Jamaican botanical rituals, opened on property. Designed by local architect Nancy Maffessanti in collaboration with her father, it blends traditional Jamaican design with local artisanship. Inspired by the seven chakra colors, the spa offers a yoga and meditation room, four treatment rooms and a shaded terrace.
The Beach Club
New signature treatments include the Bamford Ultimate Signature Massage, personalized facials and 90-minute spa journeys. The resort also recently debuted Ooshan Bar & Restaurant, a restaurant helmed by chef Kevin Betton, open for lunch and dinner daily to villa and outside guests. With an award-winning, Ralph Plummer-designed 18-hole golf course, a dynamic Kids’ Club and nanny program, watersports, nine tennis and four pickleball courts and the Beach Club, The Tryall Club offers a rare blend of luxury, privacy and family-friendly programming.
DuJour spoke with the property’s managing director, Kenton Jones, to discover what makes it so special.
What’s the most requested room at the property?
Dragonfly is hands down one of our most requested villas, because of its combination of sleek, contemporary design and standout amenities.
The Oceana villa
What makes it so special?
What sets Dragonfly apart is its incredible outdoor space. The expansive pool area is perfect for both lounging and entertaining, and the private basketball court adds a fun, active twist.
What is the nightly room rate for this suite?
From $3,000
The main pool
What is your favorite design element on property?
The main house at Oceana stands out, it’s a serene, secluded space that blends luxury with accessibility. Its open, thoughtful design makes it feel like a true retreat. Oceana is one of the few villas at Tryall where you can watch the sunrise over the Caribbean Sea and catch the sunset from the same spot thanks to its unique hilltop location and panoramic layout.
What’s your personal favorite room? Why?
Each villa is distinct, individually designed and thoughtfully curated, so picking one feels like choosing a favorite star in the sky. Every guest can find their perfect fit, whether they crave beachfront seclusion or panoramic hilltop views.
The Oceana villa main pool
What’s an interesting tidbit about the hotel that speaks to its status as an icon?
The Tryall Club is Jamaica’s largest all-villa resort, with over 90 privately owned villas spanning 2,200 lush acres. That scale alone sets us apart from the competition, not to mention our blend of privacy, heritage, and world-class service making the Club a true gem.
What a special perk or amenity do you offer that no one knows about?
One of Tryall’s best-kept secrets is how deeply personalized each stay can be. From private chefs and custom wellness programs to kid-friendly setups and special celebrations, guests have the freedom to tailor every detail, and true luxury is having the power to choose.