Casa Monica Resort & Spa, Autograph Collection

Franklin W. Smith, a Boston businessman with a passion for Spanish and Moorish architecture, designed and built Casa Monica to open on January 1, 1888. St. Augustine, founded by Spanish colonists in 1565, is the oldest continuously occupied European settlement in the continental United States, and Smith intended the hotel's architecture to reflect that heritage — the Moorish towers, arched windows, and ornamental tilework are direct references to the Andalusian and North African influences in Spanish colonial building. Smith used an experimental concrete process incorporating crushed coquina and Portland cement.

Henry Flagler, who had co-founded Standard Oil with John D. Rockefeller and was then building his Florida East Coast Railway and transforming Florida into a winter resort destination, purchased the hotel in May 1888 — only about four months after it opened. He renamed it the Cordova Hotel and incorporated it into his broader development of St. Augustine.

The Depression forced Casa Monica to close in 1932. The building sat largely vacant until 1962, when the St. Johns County Commission voted to acquire it; the property was dedicated as the St. Johns County Courthouse in May 1968 and filled that role until the 1990s — an unglamorous institutional use that preserved the structure through decades when less substantial buildings in the area were demolished. Richard Kessler purchased the building in February 1997 and completed a restoration in less than two years; it reopened as a hotel in December 1999. The hotel was added to the Historic Hotels of America roster and later affiliated with Marriott's Autograph Collection. It appears on the 2025 Historic Hotels of America most-haunted list.