Hotel El Convento, San Juan $$$$
Concierge.com's insider take:
One of the Historic Hotels of America, the Hotel El Convento is a thoroughly renovated 17th-century Carmelite convent. The small boutique hotel has 58 rooms and sits in the heart of Old San Juan. Rooms have preserved their period grandeur, with high ceilings, huge windows, Andalusian tile, and exposed mahogany beams. Guests who regret the distance from the beach can get a tropical fix in the rooftop pool. An elegant alternative to the sprawling, modern hotels of San Juan, El Convento is worth a visit even if you're staying elsewhere; come for breakfast or lunch in the courtyard, and then a stroll through its dramatic vaulted arcade.