Round Hill occupies a 110-acre peninsula in Montego Bay, Jamaica, and has welcomed guests since 1953. Three Har-Tru clay courts and one hard court anchor the tennis, with a director of tennis, visiting clinicians and four pickleball courts alongside. Ralph Lauren designed the rooms in Pineapple House, and the private villas run from two to six bedrooms, each with dedicated staff.
Caribbean & Latin America · LXV
Round Hill began in the early 1950s, when John Pringle turned a former pineapple and coconut plantation into a resort where friends built private villas and placed them in the rental pool. Noel Coward and Adele Astaire were among the first owners, and the Kennedys honeymooned in Villa 10. Ralph Lauren, a villa owner, designed the rooms…
Three Har-Tru clay courts and one hard court sit under palms with the sea below. A director of tennis and in-house professionals teach privately and in clinics, and visiting players such as Bianca Andreescu have led sessions. Lessons start at $45 for thirty minutes and an hour with the director is…
Ocean-view rooms in Pineapple House were designed by Ralph Lauren, with four-poster beds and cathedral ceilings on the upper level. The villas run from two to six bedrooms, most with private pools, and each comes with dedicated staff and breakfast prepared in the villa. One-bedroom suites have…
The spa occupies a restored 1753 plantation house on the oceanfront, with an open-air yoga pavilion and a fitness centre nearby. The treatment menu includes a recovery session for racquet players aimed at the muscles tennis and pickleball work hardest, and a separate reset for swimmers and…
Seaside Terrace · The Grille · Cocktail Bar (designed by Ralph Lauren) · Beach Bar · Pool Bar · Afternoon Tea Lounge
Round Hill Tennis and Pickleball (3 Har-Tru clay courts, 1 hard court, 4 pickleball courts) · Tennis Pro Shop · Private lessons, clinics and visiting pros · Spa in a restored 1753 plantation house · Infinity pool · Private beach · Fitness centre · Watersports · Pineapple Club and 7-Up Club for children
December - April
The dry season brings the most reliable court days. Visiting tennis professionals are scheduled for late February and March, and the resort runs its Fantasy Week in early June.
Play the upper courts after dark. They are the dual tennis and pickleball courts, they are lit, and the resort takes court bookings from 7am to 8pm. The clinic mornings also include a 30-minute lesson that guests can add.
Reservations from North America: 1-800-972-2159. Helicopter transfers and Club Mobay airport service are booked through the concierge.
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