Key West vs Milwaukee

Florida Restricted | Wisconsin 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
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.

Permits & Licensing

Key West charges $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee for STR licensing, while Milwaukee charges $110 annual license + $300 one-time pre-inspection fee. Key West renewal is annual, and Milwaukee renewal is annual. Overall, Milwaukee 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 Milwaukee, hosts pay 5% state sales + 3% county room tax + 7% city room tax (15% combined). 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 Milwaukee, violations can result in $150–$500 first offense; steeper fines and permit revocation for repeat offenses. 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 →

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.

Contact: Dept. of Neighborhood Services — (414) 286-2268

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. Overall, Milwaukee has a more host-friendly regulatory environment.
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).
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. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Key West and Milwaukee have day limits for Airbnb?
Key West has no annual day limit. Milwaukee has no annual day limit.
Which city is better for first-time Airbnb hosts — Key West or Milwaukee?
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. Milwaukee charges $110 annual license + $300 one-time pre-inspection fee with 5% state sales + 3% county room tax + 7% city room tax (15% combined). Automatic tax collection in Key West and Milwaukee makes compliance easier for beginners.