These Are the Best Luxury Resorts on the Island of Puerto Rico

By: - November 28th, 2025
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We love this rooftop.

OLV 55
This place just oozes sex appeal. OLV 55 is San Juan’s most design-forward boutique hotel, a 26-suite showpiece on the Condado Lagoon that pairs high-gloss architecture with an intimate urban energy. Suites feature sculptural furnishings, dramatic marble accents, and oversized soaking tubs, many with lagoon-facing terraces that catch the sunset.

On the rooftop, the pool area becomes a social centerpiece with views over Condado’s skyline and a lounge scene that feels more like a private club than a hotel deck. It’s luxury on a smaller scale but delivered with precision, personality, and an unmistakably contemporary Puerto Rican aesthetic. I’ve always loved the O:live portfolio, but this one just might be my favorite. And did I mention the incredible bathrooms?

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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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