Puerto Rican fashion designer—and former Esquire editor—Nono Maldonado is behind the twelve grand suites at the new Chateau Cervantes (from $300), in the heart of Old San Juan. Look for Art Deco interiors behind the hotel’s sumptuous baroque façade, with tiny gated balconies overlooking the historic quarter's cobblestone calles. There’s a 40-seat restaurant, too.
Buddha Bar designer Stephane Dupoux has given a much-needed dose of contemporary cool to the historic El San Juan hotel (from $229) in the leafy—yet megaresort-filled—Isla Verde neighborhood. A sleek new pool, with its podlike chaise lounges and aqua t'ai chi classes, anchors the resort's redo, and no fewer than eight restaurants (including New York steakhouse, the Palm) compete for diners.
In leafy, old-monied Ocean Park, Numero Uno on the Beach (from $115, including continental breakfast) is a sleepy alternative to the Isla Verde big shots, with a mere fourteen rooms (all recently renovated, many with balconies), swimming pool, and a prime slice of sandy beach with free lounge chairs and umbrellas. Pamela's, the attached Nuevo Latino restaurant, is well worth its own visit for chef Esteban Torres's multiculti menu.