Boston vs Key West

Massachusetts Legal but Limited | Florida Restricted

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

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.

Permits & Licensing

Boston charges $25 registration fee for STR licensing, while Key West charges $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee. Boston renewal is annual, and Key West renewal is annual. Overall, Boston has a more permissive regulatory environment (Legal but Limited) compared to Key West (Restricted).

Tax Obligations

In Boston, hosts pay 6.5% state excise + 6% city convention center tax. In Key West, hosts pay 12.5% combined (5% county tourist dev. + 7.5% state sales). Both cities benefit from automatic platform tax collection through Airbnb and similar services, simplifying compliance for hosts.

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 Boston face penalties including $300/day for unregistered listing. 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.

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.

Contact: Boston Inspectional Services — (617) 635-5300

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.

Contact: Key West Licensing Division — (305) 809-3959

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. Overall, Boston has a more host-friendly regulatory environment.
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).
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. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Boston and Key West have day limits for Airbnb?
Boston has no annual day limit. Key West has no annual day limit.
Which city is better for first-time Airbnb hosts — Boston or Key West?
For new hosts, consider the total cost of entry: Boston charges $25 registration fee for permits with 6.5% state excise + 6% city convention center tax 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 Boston and Key West makes compliance easier for beginners.