The Tryall Club Jamaica Dazzles Caribbean Jetsetters with Two New Luxury Villas

Dragonfly villa

From the seven-bedroom dragonfly to the four-bedroom Tradewinds on the Sea, The Tryall Club invites travelers to discover Caribbean travel at its finest

The Tryall Club in Montego Bay, Jamaica has unveiled two new luxury villas, the striking seven-bedroom dragonfly, and the oceanfront four-bedroom Tradewinds on the Sea. Both villas are outfitted with the most desired amenities and provide a dedicated team to deliver truly one-of-a-kind getaways to luxury jetsetters.

Travelers enjoy the best of both worlds when taking residence in dragonfly and Tradewinds on the Sea – the seclusion of a private villa and the amenities and service of a luxury resort with its own chef and attentive household team. Guests can enjoy a variety of memorable experiences at the Tryall Club, including a recently renovated championship golf course, award-winning tennis club and private beach club. A perfect complement to in-villa dining, luxury travelers can enjoy an array of culinary delights The Beach Restaurant, Organic Garden, and The Great House.

dragonfly | Bedrooms: 7 | Household Staff: 7 | Weekly rates start at: $22,000

Perched atop Garden Hill, dragonfly showcases the best of Jamaica’s tropical landscape, boasting views of the Caribbean Sea to its left and lush mountainside to its right. Its distinct architectural layout allows guests to feel as if they are always outside, with floor-to-ceiling sliding glass doors across the living room and dining room, as well as an eye-catching two-story balcony gazebo at its center. Off the dining room, guests can enjoy indulging in craft cocktails or trying their hand at a game of poker at dragonfly’s stylish bar. Those interested in mixing business and pleasure can head to the villa’s glassed in boardroom, which beats a day in the office.

With seven spacious bedrooms, the villa is fantastic for multi-generational travel, group getaways and executive retreats. Each bedroom features a private balcony or terrace, as well as a full-bathroom complete with dual-rainfall showers, vanity area and plunge bathtub. The master suite provides an escape of its own, featuring a private living area and an intimate terrace with a hot tub.

Outside, the poolside veranda invites travelers to soak up the sun with amenities including a 100-foot infinity pool, swim-up bar and grill with plush lounge area, as well as an expansive wraparound terrace ideal for sunbathing or entertaining. Directly off the veranda, the game room features the best in analog and digital entertainment with access to an impressive collection of board games, pool and chess table, full movie theatre and Xbox console for gaming. Active travelers can also enjoy access to the villa’s wellness amenities, including a private gym and a full-sized basketball court.

Tradewinds on the Sea villa

Tradewinds on the Sea | Bedrooms: 4 | Household Staff: 5 | Weekly rates start at: $11,450

Positioned directly on the shoreline, Tradewinds on the Sea offers enviable ocean views from every bedroom. This newly renovated villa features four bedrooms, each with spacious en-suite bathrooms with walk-in showers. Three of the bedrooms also boast their own private outdoor shower.

A new heated, walk-in infinity pool with an integrated hot tub that spills into the sea complements the villa’s spacious veranda and outdoor terrace. Guests can choose to lounge at the villa’s private beach or relax by the pool area to soak up the Caribbean sun.

As residents of Tradewinds, guests can enjoy access to two golf carts to easily hop over to the Club’s golf course, tennis club, and Beach Club. Outfitted with the latest technologies, travelers will enjoy amenities including SONOS sound systems and flat screen SMART televisions throughout the villa.

A household staff of a butler, chef, laundress, housekeeper, and gardener support in delivering an exceptional stay and showing travelers how Tradewinds on the Sea is the epitome of beachfront living.

For more information on either villa or to make reservations at The Tryall Club, please call 800.238.5290 or visit

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