Home to some of the most unique and elegant resorts in the Caribbean, this gorgeous island is your ticket to R&R—that's "rest and reggae."

12. Round Hill Hotel and Villas
This gem of a resort in Montego Bay feels more fancy-preppy: Ralph Lauren, who has two villas here, styled the Pineapple House's 36 oceanfront rooms all white, with pops of blue and pink. (Think East Hampton meets the Caribbean). Nothing beats sitting by the double-edge infinity pool overlooking the sea with rum punch in hand.

Rooms from $379; Round Hill Hotel and Villas Photo: Courtesy of Round Hill Hotel and Villas

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