Do I need to rent a car in Key West?

Usually not, and often you're better off without one. Old Town is famously walkable and golf-cart small, so in town you may barely need a car. Where a driver earns it is the journey to and from the mainland, and the marinas and dinners at the island's edges.

Between Key West International Airport (EYW) and neighborhoods like Old Town, Duval Street, the waterfront, a private captain on call covers everything a rental would, minus the counter, the parking, and the return. You ride, someone else drives.