One human settlement, one gay main street — at a price and insurance cost that filters the buyer pool.
Status: PUBLISHED · reviewed 2026-09-20 · prices 2026-08Key West sits in Florida: No statewide law for housing and No statewide law for public accommodations. No state income tax; homestead exemption; rising insurance costs. Local ordinance status: yes (see source in the sidebar). Verify current status via the Movement Advancement Project before relying on it — state law is moving.
Anchor institution: Key West Business Guild. Long-established LGBTQ+ retiree base. HIV/LGBTQ-competent care: AH of Monroe County.
Climate: tropical, about 90° July highs and 66° January lows (1991–2020 normals from the nearest NOAA station). County-level FEMA risk ratings of Relatively High or Very High: coastal flooding; hurricane; lightning.As of Sep 2026 · NOAA normals · FEMA
Getting here: EYW — Key West International Airport.As of Sep 2026 · eyw.com
Walkability: fully walkable.
Who holds office right now and what recent action looks like, with sources. We report facts and leave the conclusions to you; party is shown only where a source states it.
| Office | Who holds it | Source |
|---|---|---|
| Governor | Ron DeSantis (Republican) | As of May 2026 · flgov.com · NCSL |
| Legislature — Senate | Republican majority · 27 R, 12 D, 1 other | As of May 2026 · NCSL |
| Legislature — House | Republican majority · 84 R, 34 D, 2 vacant | As of May 2026 · NCSL |
| Local leadership | Sam Kaufman (party not confirmed by the sources we checked) | As of Aug 2026 · cityofkeywest-fl.gov · cityofkeywest-fl.gov (2) · keysnews.com |
Each listing links to the place's own page. Each showed activity in 2026 when we checked in Sep 2026; hours and ownership change, so check before you go.
Month comes from each organizer's own page (checked Sep 2026). Exact dates change every year, so confirm with the organizer.
Recent local headlines. Each links to the outlet's own page; we don't republish articles, and a link is not an endorsement.
Dated changes to laws, events and institutions affecting this place. Each links to its source.
Key West is the most concentrated version of this on the whole list — one small island, one visible gay main street — and the price tag and insurance costs reflect exactly how few people that's realistic for. If the number works for you, the tradeoff is total immersion in a place that's also genuinely exposed to hurricane risk and a shrinking pool of full-time locals versus tourists.
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