Boston vs Honolulu

Massachusetts Legal but Limited | Hawaii 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
Honolulu, Hawaii
Status Restricted
Permit Fee $1,000 initial registration; $500 annual renewal
Tax Rate ~18.5% combined (11% state TAT + 3% county TAT surcharge + 4.5% GET)
Day Limit No limit
Renewal Annual
Platform Tax No
Max Fine $10,000/day for recurring violations; $5,000 initial fine

Boston has more favorable STR regulations overall.

Permits & Licensing

Boston charges $25 registration fee for STR licensing, while Honolulu charges $1,000 initial registration; $500 annual renewal. Boston renewal is annual, and Honolulu renewal is annual. Overall, Boston has a more permissive regulatory environment (Legal but Limited) compared to Honolulu (Restricted).

Tax Obligations

In Boston, hosts pay 6.5% state excise + 6% city convention center tax. In Honolulu, hosts pay ~18.5% combined (11% state TAT + 3% county TAT surcharge + 4.5% GET). A key difference: platforms like Airbnb automatically collect taxes in Boston, but hosts in Honolulu 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 Honolulu, violations can result in $10,000/day for recurring violations; $5,000 initial fine. 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 →

Honolulu Overview

STRs limited to resort-zoned and eligible apartment-zoned areas. Hosts must register as B&B (owner-occupied, max 2 guest rooms) or TVU (whole-home in eligible zones). Registrations are non-transferable.

Contact: Dept. of Planning and Permitting — (808) 768-7887

Full Honolulu guide →

Frequently Asked Questions

Is it easier to Airbnb in Boston or Honolulu?
Boston is classified as "Legal but Limited" while Honolulu is "Restricted." Boston's permit fee is $25 registration fee compared to $1,000 initial registration; $500 annual renewal in Honolulu. Overall, Boston has a more host-friendly regulatory environment.
Which city has higher STR taxes — Boston or Honolulu?
Boston charges 6.5% state excise + 6% city convention center tax, while Honolulu charges ~18.5% combined (11% state TAT + 3% county TAT surcharge + 4.5% GET). Notably, Boston benefits from automatic platform tax collection, while hosts in Honolulu must handle taxes themselves.
Which city has stricter fines for illegal short-term rentals?
Boston: $300/day for unregistered listing. Honolulu: $10,000/day for recurring violations; $5,000 initial fine. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Boston and Honolulu have day limits for Airbnb?
Boston has no annual day limit. Honolulu has no annual day limit.
Which city is better for first-time Airbnb hosts — Boston or Honolulu?
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. Honolulu charges $1,000 initial registration; $500 annual renewal with ~18.5% combined (11% state TAT + 3% county TAT surcharge + 4.5% GET). Automatic tax collection in Boston makes compliance easier for beginners.