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.
429 community guides below, organized by town. Start with the interactive Neighborhood Finder if you'd rather browse the whole map.
Key West (85)
Key Largo (89)
Marathon (101)
Big Pine Key (28)
Cudjoe Key (9)
Summerland Key (8)
Duck Key (10)
Stock Island (10)
Plantation Key (34)
Lower Matecumbe (18)
Big Coppitt (10)
Sugarloaf Key (8)
Little Torch Key (5)
Key Colony (14)
Straight answers
Can I short-term rental a home in the Florida Keys?
It depends heavily on the jurisdiction - Key West, Marathon, Islamorada, and unincorporated Monroe each have their own vacation-rental rules, and many areas require a minimum 28-day rental. Confirm the exact rental license and zoning for the specific address before you buy for income.
Why are building permits (ROGO) a factor in the Keys?
Monroe County's Rate of Growth Ordinance strictly caps new building permits, so a buildable vacant lot or an existing legal dwelling carries real scarcity value. Confirm the permit and legal-unit status before offering on land or a teardown.
How bad is insurance and flood risk in the Keys?
Most of the chain is low-elevation coral rock in high-velocity wind and flood zones, so wind, flood, and elevation certificates drive both insurance cost and financing. Confirm the flood zone, base flood elevation, and any prior claims before you write an offer.
