Key West vs Milwaukee
Florida Restricted | Wisconsin Legal with Permit
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Key West, Florida | Milwaukee, Wisconsin |
|---|---|---|
| Legality Status | Restricted | Legal with Permit |
| Permit Fee | $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee | $110 annual license + $300 one-time pre-inspection fee |
| Tax Rate | 12.5% combined (5% county tourist dev. + 7.5% state sales) | 5% state sales + 3% county room tax + 7% city room tax (15% combined) |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Annual |
| Platform Remits Taxes | Yes | Yes |
| Max Fine Example | Up to $5,000/violation and 60 days imprisonment; each day is separate | $150–$500 first offense; steeper fines and permit revocation for repeat offenses |
| Verdict | Milwaukee 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
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
Milwaukee 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 →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 →Frequently Asked Questions
Is it easier to Airbnb in Key West or Milwaukee?
Key West is classified as "Restricted" while Milwaukee is "Legal with Permit." Key West's permit fee is $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee compared to $110 annual license + $300 one-time pre-inspection fee in Milwaukee.
Which city has higher STR taxes — Key West or Milwaukee?
Key West charges 12.5% combined (5% county tourist dev. + 7.5% state sales), while Milwaukee charges 5% state sales + 3% county room tax + 7% city room tax (15% combined). 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. Milwaukee: $150–$500 first offense; steeper fines and permit revocation for repeat offenses.