—Short-term rental rules · Key West
Key West restricts whole-home STRs of less than 30 days to specific certified properties, with transient rental licenses tightly capped. Here is the local context and a tuned rules angle.
Last reviewed against current municipal sources on 2026-05-20.
01The Key West context
Florida’s vacation-rental preemption law is layered with Key West’s own transient rental licensing — only properties with the right certification can rent on a less-than-30-day basis as whole-home stays. Most condos in Key West cannot.
Monroe County applies on top for properties outside the city limits. The market is small, scrutinized, and chronically enforcement-active around party-house complaints.
Local rules change — confirm current requirements with your city before you list. This page is a market-context summary and a house-rules starting point, not a legal source or a substitute for Key West's own Florida guidance.
02The house-rules angle
A Key West host should be specific about the property’s license type, occupancy limits, and the no-event posture. Sound carries far on the island; neighbors are often year-round residents. A signed acknowledgment maps the listing’s strict framing onto each guest individually.
Pet policies, cruise-day parking advisories, and quiet-hours rules are the items that show up most often in complaints. Document each one specifically.
These are starting points to adapt — not legal advice, and not specific to any one Florida ordinance. Edit the wording and any amounts to your property and what your platform and city allow.
03Put the rules on the file
A house-rules block in your listing is disclosure — it proves the rule existed. It does not prove the guest who booked your Key West place ever saw that specific rule or agreed to it. What sits in the file as evidence after an incident, and what shows good-faith compliance in a regulated market, is acknowledgment: the guest confirming each rule and each fee individually, with a timestamp, before check-in.
PreArrive turns the tuned rules above into a packet the guest signs in about ninety seconds. They tap each rule and each fee to acknowledge it, draw a signature, and you get a PDF certificate — disclosure and acknowledgment in one file, with a two-event audit trail and a content hash. It is evidence, not a verdict: it does not litigate a dispute or decide a code question for you, but it puts a traceable record behind every stay.
Build a packet from these rules once, send it on every reservation. Free covers one property. No credit card.
04Verify with the source
This page is a plainspoken summary. The municipal sources below are where the actual rules live. If something here disagrees with the source, the source is right — let us know and we'll re-review.
Page reviewed 2026-05-20.
05Other regulated markets
The same disclosure-versus-acknowledgment gap shows up across every active STR market. Each city below has a plain-language local summary and a house-rules angle tuned to that market.
Want all of them in one place? See PreArrive for regulated-market hosts.
06Keep reading