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You don't absolutely need a car to enjoy all of Key West. It's a long walk to many highlights but a bike really makes it enjoyable. Rent right at the Galleon but do some price shopping first. You can also rent every other means of conveyance like scooters, electric cars, etc. If golf or fishing are your game, or if you would like to experience the best lunch or dinner of your life at Little Palm Island on Little Torch Key then a car is necessary. You can rent short term on the island.