These 20 Caribbean Resorts Give You a Luxury Summer Vacation With a Boutique Personality

By: - June 19th, 2026
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round hill jamaica
Round Hill in Jamaica.

Round Hill, Jamaica

Round Hill’s charm comes from its heritage — a timeless enclave of villas and suites set along a peninsula with views that sweep across the water. The villas are individually designed, many by noted tastemakers, giving each its own personality while retaining the resort’s signature sense of grace. The rooms are designed by someone you may have heard of: Ralph Lauren, who is actually a co-owner. The layout encourages exploration: small pathways, secluded gardens, and spaces that feel untouched by the outside world.

Amenities include a renowned spa, open-air fitness experiences and a series of terraces and verandas that capture the soft glow of the late afternoon. Dining is refined but relaxed, celebrating Jamaica’s flavors with menus that change throughout the week. The beach stays peaceful, with calm water and long afternoons spent moving between loungers, snorkeling spots and shaded nooks.


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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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