Milwaukee vs Portland
Wisconsin Legal with Permit | Oregon Legal but Limited
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Milwaukee, Wisconsin | Portland, Oregon |
|---|---|---|
| Legality Status | Legal with Permit | Legal but Limited |
| Permit Fee | $110 annual license + $300 one-time pre-inspection fee | $65 (Type A single dwelling); $105 (Type A multi-dwelling) |
| Tax Rate | 5% state sales + 3% county room tax + 7% city room tax (15% combined) | 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 | $150–$500 first offense; steeper fines and permit revocation for repeat offenses | Up to $26,201 across five violation types; permit revocation with 2-year ban |
| Verdict | Milwaukee has more favorable STR regulations overall. | |
Milwaukee, Wisconsin
Status Legal with Permit
Permit Fee $110 annual license + $300 one-time pre-inspection fee
Tax Rate 5% state sales + 3% county room tax + 7% city room tax (15% combined)
Day Limit No limit
Renewal Annual
Platform Tax Yes
Max Fine $150–$500 first offense; steeper fines and permit revocation for repeat offenses
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
Milwaukee has more favorable STR regulations overall.
Milwaukee Overview
Tourist Rooming House license required for rentals under one month. Properties must pass safety inspection for building code and fire safety compliance before license is issued.
Full Milwaukee 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 Milwaukee or Portland?
Milwaukee is classified as "Legal with Permit" while Portland is "Legal but Limited." Milwaukee's permit fee is $110 annual license + $300 one-time pre-inspection fee compared to $65 (Type A single dwelling); $105 (Type A multi-dwelling) in Portland.
Which city has higher STR taxes — Milwaukee or Portland?
Milwaukee charges 5% state sales + 3% county room tax + 7% city room tax (15% combined), 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?
Milwaukee: $150–$500 first offense; steeper fines and permit revocation for repeat offenses. Portland: Up to $26,201 across five violation types; permit revocation with 2-year ban.