What the drive involves
The Florida Keys tourism council describes the Overseas Highway from Key Largo to Key West as 125 miles with 42 bridges. Its quick facts place Key West about 159 driving miles from Miami International Airport. The miles of narrow islands, bridges, Atlantic Ocean, and Gulf of Mexico make the remoteness and exposure of the Keys impossible to ignore. Traffic, crashes, weather, and peak travel periods can materially change travel time, so avoid planning a tight same-day flight or tour connection.
Parking changes the calculation
The City of Key West lists the Old Town Parking Garage at 301 Grinnell Street as open 24 hours except during evacuation. The posted rate is $6 per hour plus tax or $48 per day plus tax. Overnight parking is allowed, and the 300 spaces are available on a first-come, first-served basis. Special-event rates may apply.
Can visitors park on the street for free?
Yes, but only in a legal unmarked space. The City says unmarked spaces in historic neighborhoods are available to everyone. Spaces marked “Residential” require a valid residential permit. A visitor who parks in a marked residential space without one faces a $65 citation under the City’s 2026 fine schedule.
Read every sign and pavement marking before leaving the car. The City requires all vehicles parked on the street to be moved within 72 hours. Boats, trailers, RVs, and vehicles over 20 feet long cannot park on the street or in municipal lots. A legal unmarked space can be difficult to find, particularly during busy periods, so free street parking should be treated as a possibility rather than the basis of the trip budget.
Legal does not always mean considerate
Residents of historic neighborhoods rely on the same limited curb space, including unmarked spaces when resident-only spaces are occupied. Local parking discussions have specifically identified vehicles searching for parking as a source of congestion and long-term vehicle storage in free spaces as a burden on residents. A visitor using an unmarked space briefly is following the rules. Leaving a car in front of someone’s home for most of a three-day stay may still create understandable frustration.
For a better experience, use lodging parking, a municipal lot, or the Old Town Garage when the car will remain unused for long periods. Do not spend vacation time circling residential blocks simply to avoid a parking charge. Once parked, walking, bicycling, and local transportation are often more practical than repeatedly moving the car.
Bringing a bicycle can improve the stay
Travelers arriving by car or RV can bring bicycles inside the vehicle or on a suitable rack, and visitors without their own bicycles can rent them in Key West. Old Town's compact scale makes bicycling useful for seeing side streets, houses, gardens, waterfronts, and neighborhood changes that are easy to miss from a car.
Bicycling is not equally comfortable for everyone. Heat and humidity can be draining, traffic can feel close, and pavement is uneven on some streets. Choose routes and riding times that match your confidence, avoid assuming every street will feel relaxed, and consider early morning riding when heat and traffic are often easier to tolerate.