Parking: Ok the car may be a great way to see the Florida Keys Islands on your way to Key West. Once in Key West the car may become a pain to deal with it. Parking in the Old Town area can be limited. If you park along the residential streets, watch the sidewalk and painted street signage. There is “Resident Only” parking area, and if you park there, the resident will call to have your car towed, and they will do it. (We have seen people walking around the sidewalks saying they are sure they parked their car there. But it had been towed away.) Also parking fines range from $35 to $175. On my first KW visit I was lucky to find a free spot 4 blocks away from the B&B we were staying. After I moved the car, my only option was a paid parking lot at $16.25 a day. Most of the time we stay for 7 days and the car usually sits. We have found to find a place to stay that offers onsite parking.
If you are in need of parking, there are paid parking around the area. Old Town Garage on Grinnell & Caroline, $2 hour or $13 a day. Key West Bright Lot on Margaret & Caroline at $2.50 hour or $16.25 at 6 hours max. Around Mallory Square the parking rates are higher at $4 hr and $32 max for 8 hours. Remember key West is not all that big and walking is a fun way to see the sights.
So enjoy your stay but be cautious of where you park. The Parking signage and paid parking lot rules are taken seriously, and you may be making a donation to the City if you do not follow the rules.