While Water Island might make you think it is a separate landmass, this is not the case. Water Island is a small, extremely private Fire Island beach community comprised of about 50 houses on modest plots of Fire Island real estate. With Davis Park to the East and Barrett Beach to the west, Water Island is far from the Fire Island beach civilization, creating a sense of privacy that is well-appreciated by its residents.

As early as 1878 a restaurant called the Pavilion existed where Water Island is today. It was run by a man named Richard Silsbee. During the 1890s Water Island was home to the prestigious White House Hotel, a pleasant example of beach hotel architecture designed by Edward Ryder and frequented by Theodore Roosevelt and his family. Caldwell Realty opened the areas up to residential development in 1912. The isolation of Water Island made it an ideal destination for rumrunners during the prohibition era.

Many coastal areas on Long Island and Fire Island share in this heritage, and as Fire Island has a legacy of wreckers and land pirates, this was not so great a leap—yet Water Island is perhaps the quintessential example of such an outpost. For a great many years, the residents of Water Island did not have even the most basic services. It was one of the last Fire Island communities to connect to the Long Island Power Authority grid. Prior to that, access to the nearest stores or restaurants required a mile-long hike to either Fire Island Pines or Davis Park. For many years there was no ferry service as well, only private boat access. However now a minimal ferry schedule out of Sayville, NY, finally exists.