They may not be the biggest, or have the most amenities. They may be brand new, they may be centuries old.

But the coolest hotels in the Caribbean are the ones that have that indescribable x-factor; where, no matter how many times you come back, it feels at once fresh and timeless.

Cool can mean so many things; but for these hotels spread across the Caribbean, it’s about a sense of place, a sense of purpose, and a sense of personality. 

The ninth annual edition of the Cool List spotlights unique, special, one-of-a-kind hotels across the Caribbean. 

They may not be the biggest, or have the most amenities. They may be brand new, they may be centuries old. But the coolest hotels in the Caribbean are the ones that have that indescribable x-factor, the one that keeps you coming back, that can only be explained by actually experiencing it. Cool can mean so many things; but for these hotels spread across the Caribbean, it’s about a sense of place, a sense of purpose, and a sense of personality. 

The ninth annual edition of the Cool List spotlights unique, special, one-of-a-kind hotels across the Caribbean. 

Rockhouse, Jamaica The essence of Caribbean cool. What’s not to love about this cliffside retreat in Negril? The waterside cottages; the sweeping ocean-view suites; the bold, fantastic Pushcart restaurant; and that endlessly feeling that somehow become part of the landscape, even or a few days. There’s a reason after all, that everyone from the Rolling Stones to Bob himself used to come here back in the day.