City Watch — Islamorada
Pending STR legislation and regulatory rating tracking for Islamorada.
City portrait · J. Hamilton Studio
- pre-2011 grandfathered hard cap on vacation-rental licenses (331 village-wide)
- 7-day minimum stay in residential zoning classifications
- vacation rentals excluded from Residential Medium (R-1) except ~25 grandfathered legacy properties
- mandatory annual village vacation-rental license ($1,325) + life-safety inspection
- limited license availability (cap effectively closed; waitlist dynamics)
Based on: Village of Islamorada Land Development Regulations Ch. 30, Art. 30-VI, Div. 30-VI-6 Vacation Rentals (§§30-1291 through
“VERBATIM §30-1295: 'The annual registration shall allow up to a total of 331 single-family and multifamily vacation rental units.' Original enactment Ord. No. 01-12, § 1(5), 7-24-2001 (pre-2011-06-01); amended through Ord. 23-04 (2023, added assessed-value criteria).”— Village of Islamorada Land Development Regulations Ch. 30, Art. 30-VI, Div. 30-VI-6 Vacation Rentals (§§30-1291 through
View the ordinance source ↗✓ Verified
Last reviewed Sep 21, 2026 · Sources · Report an error
Pending legislation
Monitoring Islamorada · system last checked Sep 21, 2026
City Watch tracks changes from public sources (council agendas, state bills, local news) as coverage is activated for this market — not a complete legal compendium.
A city permit is not the whole picture — HOA, condominium, deed, or lease rules may be stricter.
City Watch provides good-faith summaries of publicly available information as of the review date shown. Rules, enforcement, and permit availability can change, and summaries may contain errors or omissions. Ratings describe the general regulatory environment; they do not establish whether a particular property or stay is permitted. This is general information, not legal advice. Before buying, listing, or hosting, verify applicable requirements with the responsible authorities and review any HOA, condominium, deed, or lease restrictions.