Honolulu vs Key West
Hawaii Restricted | Florida Restricted
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Honolulu, Hawaii | Key West, Florida |
|---|---|---|
| Legality Status | Restricted | Restricted |
| Permit Fee | $1,000 initial registration; $500 annual renewal | $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee |
| Tax Rate | ~18.5% combined (11% state TAT + 3% county TAT surcharge + 4.5% GET) | 12.5% combined (5% county tourist dev. + 7.5% state sales) |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Annual |
| Platform Remits Taxes | No — host must remit | Yes |
| Max Fine Example | $10,000/day for recurring violations; $5,000 initial fine | Up to $5,000/violation and 60 days imprisonment; each day is separate |
| Verdict | Both cities have comparable STR regulatory environments. | |
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.
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.
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.
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.
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). Compare the full breakdown in the table above.
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.