This narrow barrier island nestled between Venice and Siesta Key feels like a well-protected secret. Grand properties span from Gulf to Bay, nestled behind privacy walls and natural dunes on a flawless white sand beach. Aquamarine views stretch forever. There are no high-rises, traffic lights, or commercial activity to disturb the peace. To the south is the public beach of Nokomis, and easy Gulf access for boaters and fishermen. At the north end, however, the key is totally private property.

Named for Captain John Charles Casey—a West Point classmate of General Robert E. Lee—the bulk of this rarified island is a conservation district. When residents arrive by boat or cross the one-lane swing bridge from the mainland, they leave the mundane world behind and enter Paradise.

While home to many titans of industry, secret celebrities (and one author named Stephen King), the glamour and glitz of the finance, entertainment, and business worlds fade away on Casey Key. Residents seek out the rarified quiet and unpretentious pleasures of authentic island living. Socializing might mean sharing a glass of wine on the terrace or a sunset stroll with like-minded neighbors who also prize discretion as much as unspoiled nature.

Modest beach cottages have largely given way to opulent waterfront estate homes that can command eight-figure prices. Affluent owners may have multiple homes in their portfolios, but few can offer Casey Key’s formula of lazy days spent swimming, shell collecting, boating, fishing, picnicking, and bird watching in luxurious privacy. For more active pursuits, sophisticated dining, and an infusion of culture, Sarasota is an easy, 15-mile drive north.