Villas on the Bay was originally part of the St. Francis Barracks, built between 1864 and 1867. It was built as a Union Military Hospital, but largely used to house wounded Confederate troops as they returned to their homes from the Civil War.

In the early 1900s, the U.S. military sold the building to a local boatbuilder and his family. He moved the building across the street to its present location on the bayfront. At that time, there was a railway from our property out to deep water for handling boats in the Matanzas Bay.

The property was bought out of foreclosure in 1921, and converted to an apartment house. The spacious waterfront accommodations housed many generals, officers and families, and remained in use as an upscale apartment house.

Villas on the Bay was lovingly renovated in 1996, creating a unique option for short term bayfront rentals in St. Augustine's historic downtown area.