Gallery Inn at Galería San Juan (San Juan; tel. 787/722-1808): The most whimsically bohemian hotel in the Caribbean sits in the heart of the historic city. Once the home of an aristocratic Spanish family, it is today filled with verdant courtyards and adorned with sculptures, silk screens, and original paintings. Staying in one of the comfortable rooms here is like living in an art gallery.
At Wind Chimes Inn (San Juan; tel. 800/946-3244 or 787/727-4153): This renovated and restored Spanish manor house, a favorite with families, is one of the best guesthouses in the Condado district. The inn offers spacious rooms with kitchens, lies only a short block from Puerto Rico's most famous beach, and also features a pool.
Copamarina Beach Resort (Caña Gorda; tel. 800/468-4553 or 787/821-0505): Near Ponce, this resort was once the private vacation retreat of local cement barons-the de Castro family. Today it's been converted into one of the best beach hotels along Puerto Rico's southern shore. In fact, its beach is one of the best in the area. Set in a palm grove, the resort is handsomely decorated and comfortably furnished, with a swimming pool and two tennis courts.
Lemontree Waterfront Suites (Rincón; tel. 787/823-6452): On a sandy beach at the windsurfing capital of the Caribbean, this colony offers large apartments with kitchenettes, ideal for families who like to prepare some of their own meals.
Hacienda Tamarindo (Vieques; tel. 787/741-8525): On the site of a 1990s nightclub, this expanded inn has style, flair, charm, and a desirable location-just inland from a great white sandy beach. Built around a massive 2-century-old tamarind tree and operated by a couple from Vermont, the inn has comfortable and appealing accommodations, which are often furnished with antiques. The welcome is warm.