86. The Island City House

Historic Marker number 86 is located at 411 William Street between Eaton and Fleming Streets.

By the Civil War, Key West was the dominant manufacturing and population center in Florida lasting thru the beginning of the twentieth century. The original structure on this location was a two story private residence built by a wealthy Charleston merchant in the 1880s. Its location was in the middle of town and just two blocks from the historic seaport.

In the early 1900's, South Florida was consumed with meeting the challenge of building the eighth engineering wonder in the World. Henry Flagler had committed his immense fortune and lofty ambitions to extend his railway from Florida's mainland to Key West including a ferry connection to Cuba.

In anticipation of the arrival of the railroad in 1912, the private residence was rebuilt and converted to a hotel.

The footprint of the house was enlarged to cover most of the lot and a third story was added to increase room capacity. The expansive double porticos across the front and side of the structure were designed to capture fresh ocean breezes and take advantage of the subtropical climate.

A decorative homage to the new purpose of the building was created by carpenters on the top portion of the front facade. Notice the wooden silhouette of the railroad's unique bridge spans stretching across the building. By 1912 the building opened as Island City House Hotel.

The hotel was a private venture built to capitalize on the marvel of the Over-Sea Railroad and predates Flagler's grand Casa Marina Hotel built in 1920.