Florida Keys neighborhoods, Key Largo to Key West. Know what matters before you buy.

The Florida Keys are a single 113-mile island chain along US-1 in Monroe County, and the market splits by mile marker: Key West and its old-town/condo core at the end of the road, the Upper Keys resort and second-home corridor from Key Largo through Islamorada, and the quieter Middle and Lower Keys around Marathon and Big Pine. Nearly everything trades on water access, elevation, and whether short-term rental is allowed.

What decides a Keys purchase is the vacation-rental rules, which vary sharply by city and by the county's ROGO building-permit system, plus wind and flood insurance and real hurricane and surge exposure on low coral-rock lots. The guides state the rental posture, the flood-zone and elevation reality, and whether a dock or canal access conveys.

430 community guides, organized by town — the largest towns show their most active communities here, with every community on the town page. Start with the interactive Neighborhood Finder if you'd rather browse the whole map.