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John Pringle Dr., Montego Bay, , Jamaica

A west shore institution, Round Hill is one of the places that put Jamaican tourism on the map. Over the years, many a famous name has slept here, from presidents and prime ministers to movie stars and professional athletes. The 36 white-on-white rooms are spread between the two-story Pineapple House overlooking the infinity pool and beach, and 27 private villas (most with their own pools) scattered among the property’s coconut, pineapple, and allspice groves. The 18th-century great house is now a luxury spa, the cocktail lounge and piano bar were designed by Ralph Lauren, and culinary maestro Martin Maginley oversees one of the best resort kitchens on the island.

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Round Hill Hotel & Villas

A west shore institution, Round Hill is one of the places that put Jamaican tourism on the map. Over the years, many a famous name has slept here, from presidents and prime ministers to movie stars and professional athletes. The 36 white-on-white rooms are spread between the two-story Pineapple House overlooking the infinity pool and beach, and 27 private villas (most with their own pools) scattered among the property’s coconut, pineapple, and allspice groves. The 18th-century great house is now a luxury spa, the cocktail lounge and piano bar were designed by Ralph Lauren, and culinary maestro Martin Maginley oversees one of the best resort kitchens on the island.