Key West vs Portland

Florida Restricted | Oregon 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
Portland, Oregon
Status Legal but Limited
Permit Fee $65 (Type A single dwelling); $105 (Type A multi-dwelling)
Tax Rate 11.5% Transient Lodging Tax (6% city + 5.5% county) + 3% TID + 1.5% state
Day Limit No limit
Renewal Every 2 years
Platform Tax Yes
Max Fine Up to $26,201 across five violation types; permit revocation with 2-year ban

Portland 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 Portland charges $65 (Type A single dwelling); $105 (Type A multi-dwelling). Key West renewal is annual, and Portland renewal is every 2 years. Overall, Portland 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 Portland, hosts pay 11.5% Transient Lodging Tax (6% city + 5.5% county) + 3% TID + 1.5% state. 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 Portland, violations can result in Up to $26,201 across five violation types; permit revocation with 2-year ban. 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 →

Portland Overview

Only accessory (hosted) short-term rentals allowed; resident must occupy the dwelling at least 270 days/year. Type A permits allow up to 2 bedrooms and 5 guests. Whole-home unhosted rentals are prohibited.

Contact: Portland Permitting & Development — (503) 823-2633

Full Portland guide →

Frequently Asked Questions

Is it easier to Airbnb in Key West or Portland?
Key West is classified as "Restricted" while Portland is "Legal but Limited." Key West's permit fee is $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee compared to $65 (Type A single dwelling); $105 (Type A multi-dwelling) in Portland. Overall, Portland has a more host-friendly regulatory environment.
Which city has higher STR taxes — Key West or Portland?
Key West charges 12.5% combined (5% county tourist dev. + 7.5% state sales), while Portland charges 11.5% Transient Lodging Tax (6% city + 5.5% county) + 3% TID + 1.5% state.
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. Portland: Up to $26,201 across five violation types; permit revocation with 2-year ban. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Key West and Portland have day limits for Airbnb?
Key West has no annual day limit. Portland has no annual day limit.
Which city is better for first-time Airbnb hosts — Key West or Portland?
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. Portland charges $65 (Type A single dwelling); $105 (Type A multi-dwelling) with 11.5% Transient Lodging Tax (6% city + 5.5% county) + 3% TID + 1.5% state. Automatic tax collection in Key West and Portland makes compliance easier for beginners.