My top recommendations on where to stay in San Juan include:
Hotel el Convento: Located across from the Catedral de San Juan Bautista, at Calle del Cristo #100 on a pleasant square, this is the perfect hotel. It was opened as a Carmelite convent in 1651. It was closed in 1903 and opened as a hotel in 1962. It has a great deal of old world charm and a lovely center courtyard. The staff could not have been more helpful and friendly. There is a nice room on the third floor with complimentary cocktails from 6-7 pm, and free water, coffee and tea at all times. I liked my room but changed due to street noise from a bar across the street. The second room was equally nice and much quieter. So choose room 103 over 324. The breakfasts in the courtyard were quite good. They have the restaurant Patio del Níspero, and the most recently added Santísimo, for Puerto Rican cuisine and cocktails.
Condado is the upscale neighborhood just east of Old San Juan, along the ocean, where you will find hotels, casinos, restaurants and upscale shopping. I really liked the look of the colorful and contemporary La Concha Resort at 1077 Ashford Avenue. “In December, 1958, La Concha Resort opened to rave reviews, and was hailed as a shining moment in the Tropical Modernism movement’s heyday in Puerto Rico.”