Boston vs Orlando
Massachusetts Legal but Limited | Florida Restricted
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Boston, Massachusetts | Orlando, Florida |
|---|---|---|
| Legality Status | Legal but Limited | Restricted |
| Permit Fee | $25 registration fee | $100 city permit + state DBPR license |
| Tax Rate | 6.5% state excise + 6% city convention center tax | 12.5% (6% state + 6% county tourist dev. + 0.5% city) |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Annual (city); Biennial (state) |
| Platform Remits Taxes | Yes | Yes |
| Max Fine Example | $300/day for unregistered listing | $250–$500/day for code violations |
| 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
Orlando, Florida
Status Restricted
Permit Fee $100 city permit + state DBPR license
Tax Rate 12.5% (6% state + 6% county tourist dev. + 0.5% city)
Day Limit No limit
Renewal Annual (city); Biennial (state)
Platform Tax Yes
Max Fine $250–$500/day for code violations
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 →Orlando Overview
STRs are prohibited in most single-family residential zoning districts. Allowed in tourist-commercial zones and some mixed-use areas. Florida state law preempts local bans enacted after June 2011, creating a complex legal landscape.
Full Orlando guide →Frequently Asked Questions
Is it easier to Airbnb in Boston or Orlando?
Boston is classified as "Legal but Limited" while Orlando is "Restricted." Boston's permit fee is $25 registration fee compared to $100 city permit + state DBPR license in Orlando.
Which city has higher STR taxes — Boston or Orlando?
Boston charges 6.5% state excise + 6% city convention center tax, while Orlando charges 12.5% (6% state + 6% county tourist dev. + 0.5% city). Compare the full breakdown in the table above.
Which city has stricter fines for illegal short-term rentals?
Boston: $300/day for unregistered listing. Orlando: $250–$500/day for code violations.