Caroline Street is an iconic and historically significant local road on the island of Key West, Florida. It extends approximately 0.5 miles (0.80 km) northeastward to Grinnell Street from Whitehead Street at its southwest end. One of the oldest roads on the island, Caroline Street is surrounded by many old houses, inns, and historic landmarks, which are known for their seclusion from the street by dense landscaping. From its mostly residential origins between Whitehead and Elizabeth streets, Caroline becomes more commercial, punctuated by numerous businesses. Situated within the historic "Old Town" district, Caroline Street was part of the original infrastructural layout of the island at the time of its 1829 mapping by William Whitehead. Other than changes to both its termini, the majority