This guide covers Key West, Florida only. STR rules in these nearby markets are often confused with Key West:
- Marathon: Minimum 7-day rentals, separate city permitting and enforcement.
- Islamorada: Village with its own STR caps and 28-day minimums in most zones.
- Big Pine Key: Unincorporated Monroe County, generally 28-day minimums, county permit required.
- Stock Island: Unincorporated Monroe County, adjacent to Key West, subject to county STR rules.
Legality Verdict
Short-term rentals (STRs) in Key West are legal only with a Transient License, which is capped and tied to specific zoning. Enforcement is strict, with high penalties and active monitoring. Investor entry is highly constrained.
- Legality Status: 2/5
- License Availability: 2/5
- Compliance Cost (% revenue): 3/5
- Regulatory Stability: 4/5
- Enforcement Climate: 2/5
TL;DR
Key West defines STRs as rentals of 28 days or less. A city Business Tax Receipt and Florida DBPR license are required, with a 12.5% total lodging tax. Only properties in eligible zones with a Transient License may operate; new licenses are rarely available. Enforcement is aggressive, with daily fines and license revocation. The single biggest gotcha: most residential zones prohibit STRs entirely, and licenses are capped and non-transferable.
Quick Facts
| Item | Detail |
|---|---|
| STR Definition | Rental of 28 days or less Moving to the Florida Keys |
| Registration Required | Yes — City Business Tax Receipt + Florida DBPR license City of Key West FAQs |
| Permit Cost | [needs verification — no primary source found] |
| Annual Renewal | [needs verification — no primary source found] |
| State License Fee | $230/year (DBPR, single unit) Luxehaus Stays |
| State Sales Tax | 6% Checkmate Rentals |
| County Discretionary Surtax | 1.5% Checkmate Rentals |
| County Tourist Development Tax | 5% Monroe County Tax Collector |
| Total Effective Lodging Tax | 12.5% (state + county) Monroe County Tax Collector |
| City Lodging Tax | Not codified — no separate city lodging tax Monroe County Tax Collector |
| Tax Remittance | Hosts must remit 5% county TDT directly; platforms do not collect Monroe County Tax Collector |
| License Cap | Not codified — no explicit citywide STR license cap in sources reviewed City of Key West FAQs |
| Permitted Zones | Only specific transient-zoned districts (e.g., HRCC-1, HRCC-3, HCT, HNC-1, HNC-3) Holly’s Real Estate |
| Prohibited Zones | Most residential zones Holly’s Real Estate |
| Occupancy Cap | Not codified — Florida Building Code applies City of Key West Code of Ordinances |
| Parking Requirement | Tenant and vehicle registration required City of Key West Code of Ordinances |
| Primary Regulator | Licensing Division, City of Key West; Florida DBPR City of Key West FAQs |
| Transferability | Not codified — DBPR licenses are not transferable MyFloridaLicense.com |
| Enforcement Penalties | Daily fines, license revocation, liens Lanasa Law PLLC |
| Last Updated | August 4, 2026 |
Regulatory Impact Snapshot
Key West’s STR regime is among Florida’s most restrictive. Only properties in specific transient-zoned districts can obtain a license, and new licenses are rarely available. The total tax burden is 12.5%, with hosts responsible for remitting the 5% county Tourist Development Tax directly. State and city licensing fees add to compliance costs. Underwriters should model compliance costs at 13.2% of gross revenue, with median Key West STRs earning $79,211 at an average daily rate of $522 and 45% occupancy. The binding constraint is the scarcity of eligible, licensed properties. Run this market in our Airbnb Calculator →
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Frequently Asked Questions
Basics
What is considered a short-term rental in Key West?
A short-term rental is any rental of 28 days or less within the city limits Moving to the Florida Keys.
Are short-term rentals legal in Key West?
Yes, but only in specific zoning districts and with a valid Transient License Holly’s Real Estate.
Can I operate an STR in any residential area?
No, most residential zones prohibit STRs; only certain transient-zoned districts allow them Holly’s Real Estate.
Licensing
What licenses are required to operate an STR in Key West?
You need a City of Key West Business Tax Receipt and a Florida DBPR vacation rental license City of Key West FAQs.
How much does the state license cost?
The Florida DBPR vacation rental license for a single unit is $230 per year as of 2026 Luxehaus Stays.
Are STR licenses capped in Key West?
No explicit citywide cap is codified, but new licenses are rarely available due to zoning and practical constraints City of Key West FAQs.
Are licenses transferable when selling a property?
DBPR licenses are not transferable; a new owner must apply for a new license MyFloridaLicense.com.
Taxes
What is the total tax rate on STRs in Key West?
The total effective lodging tax is 12.5% (6% state sales tax, 1.5% county surtax, 5% county tourist tax) Monroe County Tax Collector.
Do Airbnb and VRBO collect all required taxes?
No, they collect state and county surtax but not the 5% county Tourist Development Tax; hosts must remit this directly Monroe County Tax Collector.
Do I need to register for tax remittance?
Yes, you must register with both the Florida Department of Revenue and Monroe County Tax Collector Monroe County Tax Collector.
Operations
What are the occupancy limits for STRs?
Occupancy must comply with the Florida Building Code; there is no separate city cap City of Key West Code of Ordinances.
Are there parking or registration requirements?
Yes, owners must maintain a tenant and vehicle registration for each unit City of Key West Code of Ordinances.
Can HOAs or condos prohibit STRs?
Not codified — no separate city rule on HOA/condo override identified in sources reviewed City of Key West FAQs.
Enforcement
How is STR compliance enforced in Key West?
The city uses complaint response, platform monitoring, and proactive investigation STR Agent HUB.
What are the penalties for illegal STR operation?
Violations can result in daily fines of hundreds of dollars, license revocation, and liens Lanasa Law PLLC.
What happened in the Truman Annex in 2025–2026?
The city revoked STR licenses after a 20-year agreement expired, requiring medallions to be returned Keys Weekly.
Permit Process
Key West requires a Business Tax Receipt for all residential rentals, including STRs. Transient rentals (28 days or less) also need a Florida DBPR license. The DBPR license costs $230 per year for a single unit as of 2026. Corporations, LLCs, and DBAs must be registered with the state before applying. Monroe County also requires a business tax receipt for STRs City of Key West FAQs.
Zoning
STR eligibility in Key West is strictly tied to zoning. Only properties in designated transient districts (e.g., HRCC-1, HRCC-3, HCT, HNC-1, HNC-3) may obtain a Transient License. Most residential zones prohibit STRs entirely. The city does not codify a citywide cap, but practical availability is extremely limited Holly’s Real Estate.
Taxes and Remittance
Key West STRs are subject to a 6% state sales tax, 1.5% county discretionary surtax, and 5% county Tourist Development Tax, totaling 12.5%. Airbnb and VRBO collect only the state and surtax; hosts must remit the 5% county tax directly. All STR operators must register with both the Florida Department of Revenue and Monroe County Tax Collector Monroe County Tax Collector.
Enforcement and Recent Actions
Key West enforces STR rules aggressively, using complaint-driven and proactive investigations. Daily fines for violations can reach hundreds of dollars, and unresolved fines may result in liens or foreclosure. In 2025–2026, the city revoked licenses in the Truman Annex after a 20-year agreement expired, demonstrating the risk of regulatory change Keys Weekly.
Recent Changes and Pending Legislation
In 2024, Florida’s governor vetoed a bill that would have centralized STR regulation, so Key West’s local rules remain in effect. The city’s enforcement posture remains strict, with no sign of loosening. Legal challenges, such as the Foundry HOA lawsuit, have not overturned the city’s authority Minut.
Comparable Markets
- Marathon, FL: Consider if you want 7-day minimums and a more open permit regime.
- Islamorada, FL: Consider for 28-day minimums and village-level caps.
- Miami Beach, FL: Consider for urban STRs with strict enforcement but more inventory.
- Fort Lauderdale, FL: Consider for a larger metro with more flexible licensing.
Sources
- City of Key West FAQs: https://www.cityofkeywest-fl.gov/Faq.aspx?QID=193
- City of Key West FAQs: https://www.cityofkeywest-fl.gov/FAQ.aspx?QID=194
- City of Key West FAQs: https://www.cityofkeywest-fl.gov/Faq.aspx?QID=196
- City of Key West Code of Ordinances (Municode): https://library.municode.com/FL/Key%20West/CODES/Code_of_Ordinances?nodeId=SPBLADERE_CH122ZO_ARTVSUDIRE_DIV7TRLIACREDW
- Monroe County Tax Collector: https://monroetaxcollector.com/services/tdt/
- Florida DBPR Vacation Rental License (2026): Cost, Requirements & How to Apply: https://www.luxehausstays.com/insights/florida-dbpr-vacation-rental-license/
- MyFloridaLicense.com: https://www2.myfloridalicense.com/hotels-restaurants/licensing/vrtsp-guide/
- Holly’s Real Estate: https://hollysrealestate.com/blog/short-term-or-long-term-rental-strategies-in-key-west
- Moving to the Florida Keys: https://movingtothefloridakeys.com/florida-keys-vacation-rental-license/
- Checkmate Rentals: https://www.checkmaterentals.com/blog/short-term-rental-laws-florida
- STR Agent HUB: https://stragenthub.com/regulations/key-west-fl-airbnb-regulations
- Lanasa Law PLLC: https://lanasalawfirm.com/5-common-code-violations-faced-by-property-owners-in-the-florida-keys-and-how-to-avoid-them/
- Keys Weekly: https://keysweekly.com/42/times-up-for-transient-rentals-in-key-wests-truman-annex/
- Keys News: https://www.keysnews.com/news/local/key-west-moves-to-dismiss-foundry-lawsuit-over-expired-short-term-rental-licenses/article_1ab13263-b006-4fdd-9db6-481c6ed8ec12.html
- Minut: https://www.minut.com/blog/florida-short-term-rental-laws
This page is research, not legal advice. Consult local counsel before acquiring or operating a short-term rental in City of Key West, Monroe County, Florida.
Ready to evaluate Key West as an STR market?
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