Key West vs Pittsburgh

Florida Restricted | Pennsylvania Legal with Permit

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
Pittsburgh, Pennsylvania
Status Legal with Permit
Permit Fee $35.50/unit ($16 registration + $5.50 inspection + $14 dwelling unit inspection)
Tax Rate 13% combined (7% Allegheny County hotel tax + 6% state hotel occupancy tax)
Day Limit No limit
Renewal Annual
Platform Tax Yes
Max Fine $500/unit/month for operating without permit

Pittsburgh 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 Pittsburgh charges $35.50/unit ($16 registration + $5.50 inspection + $14 dwelling unit inspection). Key West renewal is annual, and Pittsburgh renewal is annual. Overall, Pittsburgh has a more permissive regulatory environment (Legal with Permit) compared to Key West (Restricted).

Tax Obligations

In Key West, hosts pay 12.5% combined (5% county tourist dev. + 7.5% state sales). In Pittsburgh, hosts pay 13% combined (7% Allegheny County hotel tax + 6% state hotel occupancy tax). Both cities benefit from automatic platform tax collection through Airbnb and similar services, simplifying compliance for hosts.

Day Limits & Restrictions

Neither city imposes an annual day limit on short-term rentals, giving hosts year-round flexibility.

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 Pittsburgh, violations can result in $500/unit/month for operating without permit. 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 →

Pittsburgh Overview

Rental Permit Program launched December 2024. No day caps or per-owner unit limits. All rental properties must register and pass inspection.

Contact: Dept. of Permits, Licenses & Inspections — (412) 255-2621

Full Pittsburgh guide →

Frequently Asked Questions

Is it easier to Airbnb in Key West or Pittsburgh?
Key West is classified as "Restricted" while Pittsburgh is "Legal with Permit." Key West's permit fee is $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee compared to $35.50/unit ($16 registration + $5.50 inspection + $14 dwelling unit inspection) in Pittsburgh. Overall, Pittsburgh has a more host-friendly regulatory environment.
Which city has higher STR taxes — Key West or Pittsburgh?
Key West charges 12.5% combined (5% county tourist dev. + 7.5% state sales), while Pittsburgh charges 13% combined (7% Allegheny County hotel tax + 6% state hotel occupancy 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. Pittsburgh: $500/unit/month for operating without permit. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Key West and Pittsburgh have day limits for Airbnb?
Key West has no annual day limit. Pittsburgh has no annual day limit.
Which city is better for first-time Airbnb hosts — Key West or Pittsburgh?
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. Pittsburgh charges $35.50/unit ($16 registration + $5.50 inspection + $14 dwelling unit inspection) with 13% combined (7% Allegheny County hotel tax + 6% state hotel occupancy tax). Automatic tax collection in Key West and Pittsburgh makes compliance easier for beginners.