Key West vs Washington DC

Florida Restricted | District of Columbia Legal but Limited

Disclaimer: General information only — not legal advice. Verify with your local government.

Key West, Florida
Status Restricted
Permit Fee $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee
Tax Rate 12.5% combined (5% county tourist dev. + 7.5% state sales)
Day Limit No limit
Renewal Annual
Platform Tax Yes
Max Fine Up to $5,000/violation and 60 days imprisonment; each day is separate
Washington DC, District of Columbia
Status Legal but Limited
Permit Fee $104.50 for 2-year license
Tax Rate 14.5% combined (sales tax on accommodations + transient lodging tax)
Day Limit 90 days/year
Renewal Every 2 years
Platform Tax Yes
Max Fine $500 first violation; $2,000 second; $6,000 third + license revocation

Washington DC has more favorable STR regulations overall.

Permits & Licensing

Key West charges $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee for STR licensing, while Washington DC charges $104.50 for 2-year license. Key West renewal is annual, and Washington DC renewal is every 2 years. Overall, Washington DC has a more permissive regulatory environment (Legal but Limited) compared to Key West (Restricted).

Tax Obligations

In Key West, hosts pay 12.5% combined (5% county tourist dev. + 7.5% state sales). In Washington DC, hosts pay 14.5% combined (sales tax on accommodations + transient lodging tax). Both cities benefit from automatic platform tax collection through Airbnb and similar services, simplifying compliance for hosts.

Day Limits & Restrictions

Washington DC imposes a 90-night annual limit, while Key West has no annual cap — a significant advantage for high-volume hosts.

Fines & Enforcement

Hosts operating without a permit in Key West face penalties including Up to $5,000/violation and 60 days imprisonment; each day is separate. In Washington DC, violations can result in $500 first violation; $2,000 second; $6,000 third + license revocation. Both cities actively enforce their STR regulations, so securing proper licensing before listing is essential in either market.

Key West Overview

Moratorium on new transient rental licenses — only grandfathered properties may operate STRs under 28 days. Existing licenses are property-specific and command $400K+ on the secondary market. Florida DBPR state license also required.

Contact: Key West Licensing Division — (305) 809-3959

Full Key West guide →

Washington DC Overview

Primary residence only (must qualify for Homestead Deduction). Hosted stays have no day cap. Vacation rentals (unhosted) capped at 90 nights/year. Must carry $250K liability insurance.

Contact: DC DLCP Short-Term Rental Hotline — (202) 221-8550

Full Washington DC guide →

Frequently Asked Questions

Is it easier to Airbnb in Key West or Washington DC?
Key West is classified as "Restricted" while Washington DC is "Legal but Limited." Key West's permit fee is $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee compared to $104.50 for 2-year license in Washington DC. Overall, Washington DC has a more host-friendly regulatory environment.
Which city has higher STR taxes — Key West or Washington DC?
Key West charges 12.5% combined (5% county tourist dev. + 7.5% state sales), while Washington DC charges 14.5% combined (sales tax on accommodations + transient lodging tax).
Which city has stricter fines for illegal short-term rentals?
Key West: Up to $5,000/violation and 60 days imprisonment; each day is separate. Washington DC: $500 first violation; $2,000 second; $6,000 third + license revocation. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Key West and Washington DC have day limits for Airbnb?
Key West has no annual day limit. Washington DC limits STRs to 90 nights per year.
Which city is better for first-time Airbnb hosts — Key West or Washington DC?
For new hosts, consider the total cost of entry: Key West charges $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee for permits with 12.5% combined (5% county tourist dev. + 7.5% state sales) in taxes. Washington DC charges $104.50 for 2-year license with 14.5% combined (sales tax on accommodations + transient lodging tax). Automatic tax collection in Key West and Washington DC makes compliance easier for beginners.