Honolulu vs Key West

Hawaii Restricted | Florida Restricted

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

Honolulu, Hawaii
Status Restricted
Permit Fee $1,000 initial registration; $500 annual renewal
Tax Rate ~18.5% combined (11% state TAT + 3% county TAT surcharge + 4.5% GET)
Day Limit No limit
Renewal Annual
Platform Tax No
Max Fine $10,000/day for recurring violations; $5,000 initial fine
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

Both cities have comparable STR regulatory environments.

Permits & Licensing

Honolulu charges $1,000 initial registration; $500 annual renewal for STR licensing, while Key West charges $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee. Honolulu renewal is annual, and Key West renewal is annual. Both cities share a similar regulatory stance, classified as "Restricted."

Tax Obligations

In Honolulu, hosts pay ~18.5% combined (11% state TAT + 3% county TAT surcharge + 4.5% GET). In Key West, hosts pay 12.5% combined (5% county tourist dev. + 7.5% state sales). A key difference: platforms like Airbnb automatically collect taxes in Key West, but hosts in Honolulu 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 Honolulu face penalties including $10,000/day for recurring violations; $5,000 initial fine. In Key West, violations can result in Up to $5,000/violation and 60 days imprisonment; each day is separate. Both cities actively enforce their STR regulations, so securing proper licensing before listing is essential in either market.

Honolulu Overview

STRs limited to resort-zoned and eligible apartment-zoned areas. Hosts must register as B&B (owner-occupied, max 2 guest rooms) or TVU (whole-home in eligible zones). Registrations are non-transferable.

Contact: Dept. of Planning and Permitting — (808) 768-7887

Full Honolulu guide →

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 →

Frequently Asked Questions

Is it easier to Airbnb in Honolulu or Key West?
Honolulu is classified as "Restricted" while Key West is "Restricted." Honolulu's permit fee is $1,000 initial registration; $500 annual renewal compared to $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee in Key West. Both cities have comparable regulatory frameworks.
Which city has higher STR taxes — Honolulu or Key West?
Honolulu charges ~18.5% combined (11% state TAT + 3% county TAT surcharge + 4.5% GET), while Key West charges 12.5% combined (5% county tourist dev. + 7.5% state sales). Notably, Key West benefits from automatic platform tax collection, while hosts in Honolulu must handle taxes themselves.
Which city has stricter fines for illegal short-term rentals?
Honolulu: $10,000/day for recurring violations; $5,000 initial fine. Key West: Up to $5,000/violation and 60 days imprisonment; each day is separate. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Honolulu and Key West have day limits for Airbnb?
Honolulu has no annual day limit. Key West has no annual day limit.
Which city is better for first-time Airbnb hosts — Honolulu or Key West?
For new hosts, consider the total cost of entry: Honolulu charges $1,000 initial registration; $500 annual renewal for permits with ~18.5% combined (11% state TAT + 3% county TAT surcharge + 4.5% GET) in taxes. Key West charges $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee with 12.5% combined (5% county tourist dev. + 7.5% state sales). Automatic tax collection in Key West makes compliance easier for beginners.