Maui County vs Milwaukee

Hawaii Effectively Banned | Wisconsin Legal with Permit

Disclaimer: General information only — not legal advice. Verify with your local government.

Maui County, Hawaii
Status Effectively Banned
Permit Fee Set by annual budget ordinance — contact Planning Dept for current amount
Tax Rate ~18% combined (11% state TAT + 3% county MCTAT + 4% GET)
Day Limit No limit
Renewal Annual
Platform Tax No
Max Fine $20,000 first offense; $10,000/day thereafter
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

Maui County charges Set by annual budget ordinance — contact Planning Dept for current amount for STR licensing, while Milwaukee charges $110 annual license + $300 one-time pre-inspection fee. Maui County renewal is annual, and Milwaukee renewal is annual. Overall, Milwaukee has a more permissive regulatory environment (Legal with Permit) compared to Maui County (Effectively Banned).

Tax Obligations

In Maui County, hosts pay ~18% combined (11% state TAT + 3% county MCTAT + 4% GET). In Milwaukee, hosts pay 5% state sales + 3% county room tax + 7% city room tax (15% combined). A key difference: platforms like Airbnb automatically collect taxes in Milwaukee, but hosts in Maui County must collect and remit taxes themselves — a significant operational burden.

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 Maui County face penalties including $20,000 first offense; $10,000/day thereafter. 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.

Maui County Overview

Ordinance 5909 (signed Dec 2025) phases out all apartment-zoned vacation rentals — STR use must cease by Jan 1, 2029 in West Maui and Jan 1, 2031 elsewhere. Existing STRH and B&B permits remain but are capped. Legal challenges are pending.

Contact: Planning Dept., Current Planning Division — (808) 270-8205

Full Maui County 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 Maui County or Milwaukee?
Maui County is classified as "Effectively Banned" while Milwaukee is "Legal with Permit." Maui County's permit fee is Set by annual budget ordinance — contact Planning Dept for current amount 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 — Maui County or Milwaukee?
Maui County charges ~18% combined (11% state TAT + 3% county MCTAT + 4% GET), while Milwaukee charges 5% state sales + 3% county room tax + 7% city room tax (15% combined). Notably, Milwaukee benefits from automatic platform tax collection, while hosts in Maui County must handle taxes themselves.
Which city has stricter fines for illegal short-term rentals?
Maui County: $20,000 first offense; $10,000/day thereafter. 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 Maui County and Milwaukee have day limits for Airbnb?
Maui County has no annual day limit. Milwaukee has no annual day limit.
Which city is better for first-time Airbnb hosts — Maui County or Milwaukee?
For new hosts, consider the total cost of entry: Maui County charges Set by annual budget ordinance — contact Planning Dept for current amount for permits with ~18% combined (11% state TAT + 3% county MCTAT + 4% GET) 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 Milwaukee makes compliance easier for beginners.