Key West vs San Diego

Florida Restricted | California Legal with Permit

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

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
San Diego, California
Status Legal with Permit
Permit Fee Tier 1: $226; Tier 2: $317; Tier 3/4: $1,170 (includes application + license)
Tax Rate 11.75%–13.75% TOT (varies by zone proximity to Convention Center)
Day Limit 20 days/year
Renewal Biennial
Platform Tax Yes
Max Fine $1,000 per violation; criminal misdemeanor charges for continued violations

San Diego has more favorable STR regulations overall.

Permits & Licensing

Key West charges $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee for STR licensing, while San Diego charges Tier 1: $226; Tier 2: $317; Tier 3/4: $1,170 (includes application + license). Key West renewal is annual, and San Diego renewal is biennial. Overall, San Diego has a more permissive regulatory environment (Legal with Permit) compared to Key West (Restricted).

Tax Obligations

In Key West, hosts pay 12.5% combined (5% county tourist dev. + 7.5% state sales). In San Diego, hosts pay 11.75%–13.75% TOT (varies by zone proximity to Convention Center). Both cities benefit from automatic platform tax collection through Airbnb and similar services, simplifying compliance for hosts.

Day Limits & Restrictions

San Diego imposes a 20-night annual limit, while Key West has no annual cap — a significant advantage for high-volume hosts.

Fines & Enforcement

Hosts operating without a permit in Key West face penalties including Up to $5,000/violation and 60 days imprisonment; each day is separate. In San Diego, violations can result in $1,000 per violation; criminal misdemeanor charges for continued violations. Both cities actively enforce their STR regulations, so securing proper licensing before listing is essential in either market.

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 →

San Diego Overview

Four-tier license system with caps: Tier 3 limited to 1% of housing units; Tier 4 (Mission Beach) capped at 30% and at capacity. Only one license per host; licenses are non-transferable.

Contact: STRO Administration, City Treasurer — (619) 615-6120

Full San Diego guide →

Frequently Asked Questions

Is it easier to Airbnb in Key West or San Diego?
Key West is classified as "Restricted" while San Diego is "Legal with Permit." Key West's permit fee is $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee compared to Tier 1: $226; Tier 2: $317; Tier 3/4: $1,170 (includes application + license) in San Diego. Overall, San Diego has a more host-friendly regulatory environment.
Which city has higher STR taxes — Key West or San Diego?
Key West charges 12.5% combined (5% county tourist dev. + 7.5% state sales), while San Diego charges 11.75%–13.75% TOT (varies by zone proximity to Convention Center).
Which city has stricter fines for illegal short-term rentals?
Key West: Up to $5,000/violation and 60 days imprisonment; each day is separate. San Diego: $1,000 per violation; criminal misdemeanor charges for continued violations. Both cities actively enforce STR regulations, so proper licensing is essential.
Do Key West and San Diego have day limits for Airbnb?
Key West has no annual day limit. San Diego limits STRs to 20 nights per year.
Which city is better for first-time Airbnb hosts — Key West or San Diego?
For new hosts, consider the total cost of entry: Key West charges $150 Business Tax Receipt + $110 Transient Manager License + fire inspection fee for permits with 12.5% combined (5% county tourist dev. + 7.5% state sales) in taxes. San Diego charges Tier 1: $226; Tier 2: $317; Tier 3/4: $1,170 (includes application + license) with 11.75%–13.75% TOT (varies by zone proximity to Convention Center). Automatic tax collection in Key West and San Diego makes compliance easier for beginners.