The Florida Keys were inhabited by Indigenous peoples long before Spanish explorers began charting the islands in the 16th century. During the 19th century, Key West developed into an important maritime and commercial center, with wrecking and salvage, cigar manufacturing, fishing, shipping, and naval activity contributing to its economy. Henry Flagler’s Overseas Railway reached Key West in 1912, creating a direct rail connection to mainland Florida; after portions of the railway were destroyed by the 1935 Labor Day hurricane, its route helped form the basis for the Overseas Highway. During the 20th century, Key West became closely associated with writers, artists, musicians, and other creative figures, including Ernest Hemingway, Tennessee Williams, and later Jimmy Buffett. Today, the Florida Keys combine maritime history, distinctive architecture, tourism, environmental conservation, boating, fishing, arts, and an island culture shaped by generations of residents and visitors.
Are short-term rentals allowed in Key West and the Florida Keys?
Short-term rental rules vary significantly by municipality, neighborhood, zoning district, property type, licensing, and association rules.
Key West permits transient rentals only where applicable zoning and licensing requirements are satisfied, while regulations elsewhere in the Florida Keys differ by jurisdiction.
Verify current requirements for the specific property and address.