Rockhouse Hotel, Negril  

There is really no analog for this classic set on the mystical cliffs of Negril, where a tremendous approach to hospitality marries with seriously cool design and a fun, engaging history (the property has been visited by everyone from The Rolling Stones to Bob Dylan to Bob Marley. It’s a different, decidedly chill approach to luxury, and a place you’ll fall in love with immediately. That’s without mentioning the hotel’s marvelous food, anchored by the oceanfront Pushcart restaurant.