I would recommend arriving in Key West during the week if you can, I did and was luck to find street parking, but it is extremely difficult to find, even on a wednesday, if you can't you will have to pay $14 a day for parking. Make sure that you do not park in the resident spaces, it will be marked on the pavement.
During high season or any major event, parking can be almost non-existent near Duval Street even if you have a reservation at the Bed & Breakfast or small motel-hotel.
Don't even think about parking in a resident's zone unless you have specific permission.
There are parking garages, meters and some free side-street parking but again, if there is something going on in Key West (which seems to be most every weekend), then parking may be both expensive and limited.
Be cautious driving on the one-way streets, the narrow streets and the streets where either the conch train operates.
Because Key West is such a small place, with narrow streets, parking is a problem. So the city assesses fines for parking illegally.
Please NOTE: The residents of Key West have just as much trouble as the visitors do, and therefore in some areas there are spaces which are designated as RESIDENTAL. Not only is it selfish to park your car in one of those spaces for the entire length of your stay, but you will get a ticket.
Do NOT ignore the markings on these parking places (see photo) which are painted on the street and will fade in the hot Key West sun.
Violations must be paid within 10 calendar days or an additional late charge of $5.00 will be assessed. After 20 days, an additional late charge of $5.00 will be assessed - total late fee of $10.00 per ticket. Parking violations will be considered delinquent after 30 days and sent to a collection agency.
OTH Vehicle parked on public right-of-way facing oncoming traffic $35.00
SID Vehicle parked on sidewalk on a public right-of-way $35.00
FIR Vehicle illegally parked near a fire hydrant (within 15 feet) $175.00
DES Failure to park vehicle within authorized parking space $35.00
NPZ Parked in a designated no parking zone $35.00
RV RV/Oversize vehicle parked illegally on a public right-of-way $75.00
HAN Unauthorized use of handicapped parking space $250.00
OTH Other parking violations to wit: $35.00
FLN Parked in designated fire lane $175.00
Parking can get pricey in the downtown areas of Key West. Some lots and garages charge $4 per hour and a maximum of $32 for a day. If you are going for a short period, the hourly lots may be a good choice for you, but if it's all day/night you plan to hang out, I suggest a lot with a flat rate (most go for about $15 or so and are privately owned by the locals, some in lots next to their homes).
This picture was taken from the car while driving along the beach. There is one RV parked as far as possible under the palms, and you can see another one reflected in the side mirror.
There are two hazards with parking. One is the sun. Vehicles get very hot in the sun, and shade is at a premium.
Second is parking. Overnight parking of RVs is prohibited. The streets are narrow with little place available to turn.
The following is a notice on the Key West website:
"A Note For RV'ers From The City Of Key West
"More and more often recreational vehicle owners traveling in South Florida are opting to experience the scenic beauty available along U.S.1 and drive to Key West. Unlike other areas of the United States, campgrounds and waste-pumpout stations are limited in Key West. One popular campground along the city’s historic seaport has been sold and the grounds will eventually be the location of a hotel, limiting the already short supply of campground space on the island.
"..RVers planning on an overnight stay should make reservations ahead of time, since most of the season the few campgrounds in the Lower Keys are often sold out - especially on weekends and holidays.
"City ordinances forbid overnight parking on city streets, parks and beaches [Emphasis added]. It also forbids RVs in excess of 20 feet in length or seven feet in width from parking on city streets; these vehicles may park in designated parking lots, but not for overnight. Signs have been placed along U.S.1 advising RVers of the parking prohibition.."
The second picture in the series has several signs in it. The sign on the right points to the Sigsbee RV park (military only). The military has RV sites on Sigsbee, Trumbo and Truman Annex. Except for Sigsbee, these are 'dry' sites - no water or electricity connections. The Sigsbee site has a waiting list and you can only occupy the site for 2 weeks and then you have to go back to a dry site.
The sign with red lettering beyond it says
This scene shows a relatively calm day at one of the major intersections in Key West. It is Bike Week in Daytona and there are a lot of motorcycles in town (although there aren't any in this picture). Plus it is the beginning of Spring Break (cf shirtless fellow on the moped). You can also see a trolley tour vehicle and one of the three wheeled scooters. But there aren't any cruise ships in town and most of the RVers have left so the streets aren't as enthronged as they can be.
Traffic in Key West can be complete gridlock. The sensible way to avoid sitting in traffic is to walk, take the city bus for $1.00 or ride a bicycle. Key West in general is very bicycle friendly, with bike paths along the upper end of the island (parallel to Roosevelt Blvd) and the traffic in the old part of the city doesn't move much faster than a bike.
However you should be aware that there is now an ordinance in Key West that bicycles that are chained to city property (like parking meters, street signs or lamp posts) or anything other than a designated bike rack will be impounded.
I warn folks planning to take a trip to the Keys to be sure and take along two things: several thousand dollars for bail money and the phone number of a good lawyer. I lost 5 vehicles to the Monroe County/ City of Key West towing scam in the 5 years I lived there. The way it works is this: they have an obscure ordinance on the books, (one of thousands) which prohibits the parking of any vehicle for over 24 hours in the same spot. Cops go around with a piece of chalk and mark your tire to see if you have moved your car. If it hasn't moved by the next day you will come out of where you are staying, (unless it is one of the millionaire-resorts with valet parking-imagine that) and discover your car is missing. When you call the police they will NOT tell you they towed it away. They will have you fill out a stolen vehicle report, After several days , when your towing bill is in the hundreds of dollars, you will find out your car is in one of the towing company storage yards. You either pay them what they charge or lose your car. They like the cars the towing company can re-sell quickly, especially convertibles. Another scam is they will pull you over for some excuse, then claim the car you are driving has been reported stolen. Mostly they just tow your car, but sometimes they haul you in to their new jail which the locals call the "Stock Island Hilton". You will be there over the weekend until Monday morning when they let you see the judge. You don't have to be guilty of doing anything, they just take whoever they choose to jail. There is no accountability because the people in charge get a percentage of each car they have towed. Try to take at least one friend along, because the cops don't like witnesses. Don't travel at night, and watch out on Fridays and Saturdays because that's when they like to fill the jail up. The government pays them for every day you are in there. There is a slogan you hear down there: "Arrived on vacation, Left on probation." BE CAREFUL, or take your vacation somewhere decent.