Boston vs Maui County

Massachusetts Legal but Limited | Hawaii Effectively Banned

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
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.

Permits & Licensing

Boston charges $25 registration fee for STR licensing, while Maui County charges Set by annual budget ordinance — contact Planning Dept for current amount. Boston renewal is annual, and Maui County renewal is annual. Overall, Boston has a more permissive regulatory environment (Legal but Limited) compared to Maui County (Effectively Banned).

Tax Obligations

In Boston, hosts pay 6.5% state excise + 6% city convention center tax. In Maui County, hosts pay ~18% combined (11% state TAT + 3% county MCTAT + 4% GET). A key difference: platforms like Airbnb automatically collect taxes in Boston, but hosts in Maui County must collect and remit taxes themselves — a significant operational burden.

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 Maui County, violations can result in $20,000 first offense; $10,000/day thereafter. 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 →

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.

Contact: Planning Dept., Current Planning Division — (808) 270-8205

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. Overall, Boston has a more host-friendly regulatory environment.
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). Notably, Boston benefits from automatic platform tax collection, while hosts in Maui County must handle taxes themselves.
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. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Boston and Maui County have day limits for Airbnb?
Boston has no annual day limit. Maui County has no annual day limit.
Which city is better for first-time Airbnb hosts — Boston or Maui County?
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. Maui County charges Set by annual budget ordinance — contact Planning Dept for current amount with ~18% combined (11% state TAT + 3% county MCTAT + 4% GET). Automatic tax collection in Boston makes compliance easier for beginners.