Round Hill Hotel and Villas

Round Hill opened in 1953 on a green headland west of Montego Bay and quickly became the Caribbean address for a certain kind of guest; Noel Coward, the Kennedys and a long list of others kept villas here. Many of those villas are still privately owned and let out when their owners are away.

The twenty-seven villas climb the hillside, each with staff, a pool and a cook who makes breakfast on the terrace. Below them, the thirty-six-room Pineapple House sits on the beach with interiors designed by Ralph Lauren in a crisp white and dark-mahogany scheme.

The beach is small but well tended, and there is a spa in an eighteenth-century plantation house, tennis, watersports and an exceptionally loyal staff. It remains one of the few Jamaican hotels that feels genuinely historic rather than themed.