In 1960, alarmed that many of Key West's most valued architectural treasures would be lost to neglect or to growing development pressures, concerned local citizens formed the not-for-profit Old Island Restoration Foundation to promote the preservation and restoration of historically significant buildings.That same year, it established Old Island Days, a six-month series of events celebrating the island city's cultural heritage.

Over the years, Old Island has raised and granted hundreds of thousands of dollars to many historical buildings in Key West. It also administers and maintains the Wreckers Museum in the Oldest House and Mallory Museum at the Hospitality House. Each spring, it sponsors the Conch Shell Blowing Contest.

Old Island's activities are funded by its member contributions, its annual house and garden tours, several fundraisers held throughout the year, and rental of the beautiful gardens behind the Oldest House for weddings and other events.