Key West vs Portland
Florida Restricted | Oregon Legal but Limited
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Key West, Florida | Portland, Oregon |
|---|---|---|
| Legality Status | Restricted | Legal but Limited |
| Permit Fee | $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee | $65 (Type A single dwelling); $105 (Type A multi-dwelling) |
| Tax Rate | 12.5% combined (5% county tourist dev. + 7.5% state sales) | 11.5% Transient Lodging Tax (6% city + 5.5% county) + 3% TID + 1.5% state |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Every 2 years |
| Platform Remits Taxes | Yes | Yes |
| Max Fine Example | Up to $5,000/violation and 60 days imprisonment; each day is separate | Up to $26,201 across five violation types; permit revocation with 2-year ban |
| Verdict | Portland has more favorable STR regulations overall. | |
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.
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.
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.
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.
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. Compare the full breakdown in the table above.
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.