Key West vs Maui County

Florida Restricted | Hawaii Effectively Banned

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
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

Key West 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 Maui County charges Set by annual budget ordinance — contact Planning Dept for current amount. Key West renewal is annual, and Maui County renewal is annual. Overall, Key West has a more permissive regulatory environment (Restricted) compared to Maui County (Effectively Banned).

Tax Obligations

In Key West, hosts pay 12.5% combined (5% county tourist dev. + 7.5% state sales). In Maui County, hosts pay ~18% combined (11% state TAT + 3% county MCTAT + 4% GET). A key difference: platforms like Airbnb automatically collect taxes in Key West, 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 Key West face penalties including Up to $5,000/violation and 60 days imprisonment; each day is separate. In Maui County, violations can result in $20,000 first offense; $10,000/day thereafter. 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 →

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 →

Frequently Asked Questions

Is it easier to Airbnb in Key West or Maui County?
Key West is classified as "Restricted" while Maui County is "Effectively Banned." Key West's permit fee is $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee compared to Set by annual budget ordinance — contact Planning Dept for current amount in Maui County. Overall, Key West has a more host-friendly regulatory environment.
Which city has higher STR taxes — Key West or Maui County?
Key West charges 12.5% combined (5% county tourist dev. + 7.5% state sales), while Maui County charges ~18% combined (11% state TAT + 3% county MCTAT + 4% GET). Notably, Key West 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?
Key West: Up to $5,000/violation and 60 days imprisonment; each day is separate. Maui County: $20,000 first offense; $10,000/day thereafter. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Key West and Maui County have day limits for Airbnb?
Key West has no annual day limit. Maui County has no annual day limit.
Which city is better for first-time Airbnb hosts — Key West or Maui County?
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. Maui County charges Set by annual budget ordinance — contact Planning Dept for current amount with ~18% combined (11% state TAT + 3% county MCTAT + 4% GET). Automatic tax collection in Key West makes compliance easier for beginners.