STR rules · verified 1mo ago
Short-term rental rules in Islamorada, FL
The Village of Islamorada (Florida Keys, Monroe County) operates one of the most restrictive STR regimes in the United States. Vacation rental licenses are CAPPED at 331 village-wide under a grandfathered ordinance that predates June 1, 2011 (preserving the cap against Florida Statute 509.032(7) preemption). The license fee is $1,325 per year and is non-transferable on sale. Minimum assessed-valuation requirements gate eligibility: Residential High / Mixed Use parcels must be assessed at $708,000 (2026), and Residential Conservation / Residential Low / Airport parcels at $1,062,000 (2026). Applicants must hold a Florida DBPR Ch. 509 license, a Monroe County Local Business Tax Receipt, an active Monroe County TDT account, and pass a Village Fire Chief life-safety inspection. Monroe County ROGO further constrains new dwelling units Keys-wide. Tax stack is Monroe County 5% TDT + 1.5% Monroe discretionary surtax + FL 6% state sales tax = ~12.5%.
What's behind the sign-in
- Registration fees — initial + annual renewal cost, per permit type
- Permit caps + waitlists — exact cap values, current waitlist counts
- Owner-occupancy rules — days/year requirement, permit-class splits
- Zoning carve-outs — which districts allow / disallow STR
- Tax stack — TOT, hotel, county + state layers
- Stay limits — min/max nightly, max nights/year
- Operational requirements — parking, insurance, fire inspection, neighbor notice
- Penalties — per-night fines, revocation thresholds
- City-specific gotchas — HOA carve-outs, pending legislation, recent court rulings
- Refresh on demand — re-run the agentic pipeline against the city's current ordinance
Frequently asked
Are short-term rentals legal in Islamorada, FL?
Islamorada is currently restricted for short-term rentals. Permitted but with material constraints — caps, owner-occupancy rules, zoning carve-outs, or active ordinance review. For the actual fees, caps, owner-occupancy rules, and city-specific gotchas, sign in.
Do I need a permit to run an Airbnb in Islamorada?
Almost certainly yes — almost every U.S. city now requires a short-term rental permit, vacation rental permit, or transient lodging permit before you can legally list. The specifics for Islamorada (cost, renewal cycle, required documents) are behind sign-in. You can also read the source ordinance directly: https://www.islamorada.fl.us/315/Vacation-Rental-License-Annual-Registrat.
What happens if I rent without a permit in Islamorada?
Most cities charge per-night fines (a few hundred to a few thousand dollars per violation), escalating to cease-and-desist letters and platform delisting on repeat. Airbnb and Vrbo now share permit-validation feeds with most major cities, so unpermitted listings get blocked at the platform level. Sign in to see the specific penalty schedule for Islamorada.
How current is this data for Islamorada?
This record was verified 1mo ago against the city's published ordinance (.gov or the city's official municipal-code publisher). Cached cities re-verify on a cadence — daily for cities under active legislation, weekly otherwise. Signed-in users can hit Refresh on any city to force a fresh pull. If you're underwriting a deal, always confirm against the city's code-enforcement office before closing.
Can my HOA or condo association ban STRs even if Islamorada allows them?
Yes. City permits authorize you under municipal law, but your HOA, condo association, or co-op board sets contractual rules that override the city for your unit. Many HOAs adopted blanket STR bans between 2018 and 2024 in response to neighbor complaints. Read the CC&Rs, bylaws, and rental addendums before you buy with an STR plan — the city saying yes does not mean your building says yes.