Quick Summary:
- Use City parking garages near Old Town for reliable overnight stays.
- Park on signed residential streets only where overnight parking is explicitly allowed.
- Avoid “Resident Permit” and street-cleaning windows, towing is fast.
- Reduce theft near Duval by emptying the car and choosing lit areas.
If you are driving down from Miami on a car hire and spending the night in Key West, parking can feel like the hardest part of the trip. Old Town is compact, many streets are resident-permit controlled, and towing is common when a sign is missed or misunderstood. The good news is that there are dependable, legal options that do not require a local permit, as long as you match the spot to the area you are staying in and you read every sign panel on the post.
This guide focuses on practical, area-by-area choices for overnight parking, common sign traps that catch visitors, and simple ways to reduce theft risk when you are walking Duval Street. For planning your wider Florida drive, Hola Car Rentals has location pages such as Miami, Florida car hire that can help you compare pick-up areas and vehicle types before you head south.
First, know what “no permit required” really means in Key West
Key West has three broad categories of places you might park overnight: City garages and lots, metered or time-limited street spaces, and residential streets with permit zones. “Without resident permits” usually means you want either a City facility that is open to everyone, or a street that is signed for public parking overnight. Many residential streets are not “no parking” in the everyday sense, but they are restricted to permit holders in certain hours, often overnight.
Also, do not assume that a space that was legal at 6pm is legal at 2am. Overnight restrictions, street cleaning windows, and special event rules can kick in later. If you are new to the island on car hire, build a habit: read the entire sign, front and back, and check for smaller supplementary plates below the main one.
Best overnight options in Old Town, near Duval Street
Old Town is where parking is most competitive and where many visitors most want to leave the car and walk. If you want to minimise towing risk, choose structured parking or established public lots rather than hunting for a residential street space.
City parking garages (most reliable)
Garages are typically the safest choice for an overnight stay because the rules are clearer, access is controlled, and you avoid permit-zoned streets. They are also convenient for Duval Street, Mallory Square, and the historic district. Expect to pay, and keep your ticket safe. If you are staying out late, note any closing or “no overnight” language at the entrance signage, although City garages commonly support overnight parking.
Public lots (good, but read the posted terms)
Lots can be excellent when they clearly state 24-hour rules and payment instructions. The trap is assuming a lot is municipal because it is busy, some are private and enforce their own rules. At the pay station or entrance, look for: hours of operation, how overnight is charged, and whether you must display a receipt.
Limited street parking (possible, but highest sign-risk)
Some Old Town streets have non-permit parking, but spaces are scarce and the signs can be layered. If you find a spot, do a full check: is it a metered space that stops enforcing at night, or does it revert to permit-only overnight? Are there loading zones that change by time? If anything is unclear, pick a garage instead, the cost is usually less than a tow.
If your trip starts in Miami and you are deciding where to collect your vehicle, pages like Dollar car hire Downtown Miami can be useful for comparing locations close to hotels or public transport before the drive to the Keys.
Parking in Bahama Village and the south-west edge of Old Town
Bahama Village sits close to the action but has more residential blocks, which is where visitors get towed when they park late and miss a permit notice. Here, the best approach is to use public facilities at the edge and walk in, rather than pushing into narrow streets with mixed rules.
What tends to work
Look for clearly signed public parking areas serving the historic district. If you are within a few minutes’ walk of Duval, that usually means demand is high and enforcement is active. Pay attention to corners, hydrants, and “no parking to corner” rules, which are enforced even when a car seems to fit.
What to avoid
Do not assume that because other vehicles are parked on a residential street, it is safe for non-residents overnight. Residents may have permits, and a visitor can still be cited or towed. If a sign includes “Resident Permit” with hours, treat it as off-limits during that time.
New Town and the areas away from Duval
If you are happy to be a short taxi or rideshare from Duval, New Town areas can be easier for overnight parking, especially at larger hotels or properties built with car access in mind. If you are staying in a hotel, your simplest legal option is often the hotel’s own parking. Confirm whether it is included, whether it is gated, and whether overnight requires a hangtag or registration at reception.
For travellers in larger groups, choosing a vehicle that fits your luggage without advertising it is important. Hola Car Rentals also offers options such as minivan rental in Miami, which can reduce the temptation to leave bags visible in a smaller boot.
Common Key West sign traps that lead to towing
Key West signage is not impossible, but it is easy to misread when you are tired after the Overseas Highway drive. These are the most common pitfalls:
1) Permit zones with time windows
A sign might allow public parking in the daytime but switch to permit-only overnight. If you arrive in the evening, you might miss that the restriction begins at a specific hour.
2) Street cleaning or maintenance hours
Some streets prohibit parking on certain days or times for cleaning. These windows can start early. If you are staying two nights, what was fine yesterday might not be fine tomorrow morning.
3) Loading zones and commercial spaces
Loading zones can look empty and tempting at night. Many remain restricted 24 hours, or they change over at a stated time. If the sign is not explicit that general parking is allowed after hours, do not assume.
4) “No parking” close to intersections, driveways, hydrants
Even if there is no sign, curb markings and general rules apply. If a driveway is even partially blocked, towing can happen quickly.
5) Private lots with strict enforcement
Key West has private lots serving businesses. Parking there overnight without permission can lead to towing even if there is no barrier. Always check whether the lot is “customer parking only” and whether hours are limited.
How to reduce theft risk when parking near Duval Street
Key West is generally visitor-friendly, but theft from cars can happen anywhere busy. Near Duval Street, the risk factor is foot traffic and the ease of quickly trying door handles. These steps meaningfully reduce your exposure:
Choose light and activity, not quiet corners
A well-lit garage level or a lot with obvious pedestrian flow is usually safer than a dark side street, even if the side street feels calmer.
Leave nothing visible, including “cheap” items
Empty the cabin completely. Sunglasses, charging cables, beach bags, and coins can be enough to prompt a break-in. Put items in the boot before you arrive, not after you park, so you are not seen storing valuables.
Lock properly and double-check
With car hire vehicles, travellers sometimes assume the remote lock worked. Listen for the lock sound, check the handle, and confirm windows are fully closed.
Limit paperwork on show
Do not leave rental documents, itineraries, or anything with personal details in the glovebox if it might be accessed during a break-in. Keep essential documents on you.
Park, then walk directly
Lingering while you organise bags can draw attention. Get out, lock up, and head to your accommodation or Duval Street without fuss.
Practical overnight parking strategy by where you are staying
Staying close to Duval Street or Mallory Square
Use a City garage or clearly signed public lot and budget for the cost. It is often cheaper than the time and stress of searching for a street space, and it reduces the chance of permit-related towing.
Staying in a guesthouse on a residential street
Ask your host exactly where guests can park overnight. “On the street” is not enough, you want the street name, which side, and whether a pass is needed. If they offer a dedicated space, take it.
Staying in New Town hotels
Use hotel parking where possible, especially if it is gated or monitored. If overflow parking is mentioned, confirm it is officially approved for overnight guests.
Doing a one-night stop with an early departure
Prioritise speed and certainty. A garage close to your route out of town can save time in the morning, and you avoid trying to interpret signage at dawn.
If you are collecting your vehicle in the Miami area before heading to Key West, you might also compare pick-up points like car hire Airport Doral or neighbourhood locations such as car hire Coral Gables, depending on where you are staying in Miami.
What to do if you are unsure at night
If it is late, you are tired, and signage is confusing, default to the option with the clearest rules. In practice that usually means a garage or a major public lot with a payment machine and posted terms. Take a quick photo of the sign nearest your space so you can confirm the restrictions later. If you are using a paid facility, keep the receipt or app confirmation, and note your bay or level so you are not wandering around late at night.
Finally, remember that Key West is small. Parking slightly farther away and walking ten minutes can dramatically reduce both towing risk and theft temptation, especially if it gets you into a straightforward facility rather than a permit-heavy residential block.
FAQ
Q: Can I park overnight on the street in Key West without a resident permit?
A: Sometimes, yes, but only where signage explicitly allows public parking overnight. Many residential streets switch to permit-only during evening or overnight hours, so a garage or public lot is usually safer.
Q: Are City parking garages the safest option to avoid towing?
A: They are generally the most reliable because rules are posted at entrances and do not change block by block. You still need to follow payment instructions and any stated hours.
Q: What is the fastest way to avoid sign mistakes?
A: Read every panel on the post, including small plates, and check for time windows. If anything mentions permits, loading, or cleaning times, choose a different spot.
Q: How can I reduce break-in risk near Duval Street?
A: Use well-lit parking, remove all visible items, and lock the car carefully. Put valuables in the boot before arriving, and avoid quiet, dark side streets.
Q: If I am staying at a guesthouse, should I rely on host advice?
A: Yes, but ask for specifics: exact street, which side, and whether a pass is required. If they offer an off-street space, it is often the lowest-risk overnight choice.
