The bottom line is that, while in Key West, you are better off not having a car. Chances are that you are staying in or close to the Historic Downtown district on the western part of the island. If this is the case for you, walking is the ideal means of transportation as all the great restaurants, bars, shops and activity locations are in this area. If you are staying a little further out on the eastern part of the town, grabbing a cheap taxi ride to where you need to go is the smartest way to go. You can also rent bikes or scooters at several locations throughout the island. There is a pretty decent bus system in Key West with unlimited one-day passes running for the affordable price of $3.
But if you really want to bring a car down to Key West, you have to come prepared with knowledge on where to park, where not to park, and how much you should expect parking to cost you. Parking is very limited in Key West, especially during the frequent weekend-long or week-long events that take place on the island. Driving and traffic can also prove tricky with small, narrow streets creating congested and slow-moving traffic.
The City of Key West provides three well-guarded parking lots in several prime locations. The Mallory Square parking lot, located on the corner of Front and Wall Streets, allows parking from 7AM to midnight, at a rate of $4 per hour, with a $32 maximum (a total of 8 hours). The Key West Bight lot, on the corner of Margaret and Caroline, has a rate of $2.50 per hour, with a maximum stay of 6.5 hours ($16.25). The Old Town Garage offers a park'n'ride service on the corner of Grinnell and Caroline at $2 per hour or $13 a day maximum. This lot also offers a monthly pass for $99.75. All three of these garages are in the historic downtown district, just a few blocks from the historic and famous Duval Street where most of the action in Key West takes place. Also be aware that some of the rates do go up during special events, such as the weekend of Fantasy Fest.
Another popular option for parking in Key West is street parking. Typically you find metered parking along many side streets and they are enforced normally enforced Mondays through Saturdays from 8AM to Midnight and Noon to Midnight on Sundays. Some of the street parking, however, is strictly residential parking and you should definitely not park here as you will definitely get ticketed. Make sure that the area you are parking is completely legal, as some ticket fines can reach as high as $175 (for parking in a designated fire lane, for instance).
Basically, if you choose to bring your car or a rental car down to Key West, make sure you are well aware of the potential stress and expenses associated with driving and parking on the island. If you plan ahead and well, in addition to familiarizing yourself with the streets, various parking options, and the parking laws, you will definitely be able to navigate your way successfully throughout the island and find decent parking spots.