Boston vs Maui County
Massachusetts Legal but Limited | Hawaii Effectively Banned
Disclaimer: General information only — not legal advice. Verify with your local government.
| Requirement | Boston, Massachusetts | Maui County, Hawaii |
|---|---|---|
| Legality Status | Legal but Limited | Effectively Banned |
| Permit Fee | $25 registration fee | Set by annual budget ordinance — contact Planning Dept for current amount |
| Tax Rate | 6.5% state excise + 6% city convention center tax | ~18% combined (11% state TAT + 3% county MCTAT + 4% GET) |
| Annual Day Limit | No limit | No limit |
| Renewal Interval | Annual | Annual |
| Platform Remits Taxes | Yes | No — host must remit |
| Max Fine Example | $300/day for unregistered listing | $20,000 first offense; $10,000/day thereafter |
| 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
Maui County, Hawaii
Status Effectively Banned
Permit Fee Set by annual budget ordinance — contact Planning Dept for current amount
Tax Rate ~18% combined (11% state TAT + 3% county MCTAT + 4% GET)
Day Limit No limit
Renewal Annual
Platform Tax No
Max Fine $20,000 first offense; $10,000/day thereafter
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 →Maui County Overview
Ordinance 5909 (signed Dec 2025) phases out all apartment-zoned vacation rentals — STR use must cease by Jan 1, 2029 in West Maui and Jan 1, 2031 elsewhere. Existing STRH and B&B permits remain but are capped. Legal challenges are pending.
Full Maui County guide →Frequently Asked Questions
Is it easier to Airbnb in Boston or Maui County?
Boston is classified as "Legal but Limited" while Maui County is "Effectively Banned." Boston's permit fee is $25 registration fee compared to Set by annual budget ordinance — contact Planning Dept for current amount in Maui County.
Which city has higher STR taxes — Boston or Maui County?
Boston charges 6.5% state excise + 6% city convention center tax, while Maui County charges ~18% combined (11% state TAT + 3% county MCTAT + 4% GET). Compare the full breakdown in the table above.
Which city has stricter fines for illegal short-term rentals?
Boston: $300/day for unregistered listing. Maui County: $20,000 first offense; $10,000/day thereafter.