Boston vs Key West
Massachusetts Legal but Limited | Florida Restricted
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Boston, Massachusetts | Key West, Florida |
|---|---|---|
| Legality Status | Legal but Limited | Restricted |
| Permit Fee | $25 registration fee | $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee |
| Tax Rate | 6.5% state excise + 6% city convention center tax | 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 | Yes | Yes |
| Max Fine Example | $300/day for unregistered listing | Up to $5,000/violation and 60 days imprisonment; each day is separate |
| Verdict | Boston has more favorable STR regulations overall. | |
Boston, Massachusetts
Status Legal but Limited
Permit Fee $25 registration fee
Tax Rate 6.5% state excise + 6% city convention center tax
Day Limit No limit
Renewal Annual
Platform Tax Yes
Max Fine $300/day for unregistered listing
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
Boston has more favorable STR regulations overall.
Boston Overview
Only primary-residence units may be listed as STRs. Investor-owned (non-owner-occupied) short-term rentals are prohibited. Must register with the city and carry $1M liability insurance.
Full Boston 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 Boston or Key West?
Boston is classified as "Legal but Limited" while Key West is "Restricted." Boston's permit fee is $25 registration fee compared to $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee in Key West.
Which city has higher STR taxes — Boston or Key West?
Boston charges 6.5% state excise + 6% city convention center tax, 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?
Boston: $300/day for unregistered listing. Key West: Up to $5,000/violation and 60 days imprisonment; each day is separate.