OLV Fifty Five Hotel, Puerto Rico The sexiest place to stay in the Caribbean is the brainchild of the innovative team of Loisse Herger and Fernando Davila, who have created the hottest hotspot in San Juan with this stunning 26-room property on the edge of the Condado Lagoon. The food is outstanding, the service on point and, most importantly, it’s home to a truly mesmerizing pool deck (and a rooftop hot tub to boot).