26 Historic Hotels in the Caribbean Where You Step Back in Time

By: - October 19th, 2025
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pool at jamaica round hill villa
A pool at one of the villas at Round HIll.

Round Hill Hotel and Villas — Montego Bay, Jamaica

Round Hill has been a benchmark of Caribbean elegance since 1953. Built on a former estate overlooking the sea, it’s a place of manicured lawns, gingerbread trim, and sea breezes that drift in through louvered shutters. Its understated style has attracted generations of travelers — including some of the world’s most celebrated names — who come not for flash but for its quiet, graceful sense of place. The villas, many designed by Ralph Lauren, maintain their timeless character, blending heritage with light, breezy luxury.

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About the author

Guy Britton is the managing editor of Caribbean Journal. With more than four decades of experience traveling the Caribbean, he is one of the world's foremost experts covering the region.
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