This is the tallest building in Key West. Ernest Hemingway paid homage to the hotel in To Have or Have Not and Tennessee Williams finished A Streetcar Named Desire during his stay in 1946.The hotelâ€™s fortunes have risen and fallen in tandem with the island but the bar on the top floor has never gone out of style.
This building holds the dual distinction of being one of the oldest commercial structures in Key West and the oldest remaining drug store building. Dr. John Maloney opened the Key West Drug Company in 1903. In 1908 he purchased the adjacent building at 532 Fleming and opened the first public hospital. In 1911 he acquired 504 Simonton connecting the buildings with a raised walkway .
Originally a four room house built on Whitehead Street in the late 1820â€™s by Richard Cussans a shipâ€™s carpenter. The structure was moved to its current location in 1829 and expanded for Captain Francis Watlington to accommodate his wife and nine daughters. The Captainâ€™s descendants lived in the house until the 1970â€™s. This is considered the oldest house in South Florida.
William Wall came to Key West in 1824 as a shipwreck victim. Seven years later he had amassed a substantial fortune as a pioneer in the islandâ€™s burgeoning cigar industry. Behind the building were docks and â€œcoaling stationsâ€ used to supply steam-powered ships. The warehouse was converted into Naval Station #2 and became a vital supply link for the United States Navy during the Spanish American War in 1898.