Key West
Old Town historic, New Town everyday — the end of US-1.
The most storied address in the Keys. Key West splits between the historic Old Town (gingerbread Conch houses, Duval, Truman Annex) and New Town (canal homes, schools, and the practical side of island life).
Old Town is walk-everywhere, bike-everywhere, tourist-adjacent. New Town is suburban by Keys standards — grid streets, schools, big-box. Casa Marina and Key Haven-adjacent pockets are their own worlds.
Full-time residents, second-home buyers wanting the ultimate Keys address, and specific VR-permitted investors (very narrow — most of Key West is off-limits for transient rentals).
Historic Old Town conch houses, modern Old Town renovations, Casa Marina estates, New Town single-family, townhomes, and condos.
Oceanfront and harbor-front pockets (Casa Marina, Truman Annex, Sunset Key) command the premium. Canal-front in New Town is the practical waterfront path.
Short-term rental is tightly restricted — most non-commercially-zoned single-family homes require 28+ day minimums. Transient licenses are limited and valuable when legitimately attached.
Key West FAQ
- Can I nightly-rent a Key West home?
- Almost certainly not unless the property carries a grandfathered transient license. Monthly (28+ day) rentals are more broadly allowed. Always verify with the City of Key West Code Compliance.
- Old Town vs. New Town — what's the tradeoff?
- Old Town gives you history, walkability, and resale liquidity. New Town gives you space, parking, schools, and better dollar-for-dollar value. Both are real Key West.
Talk to Gracie
Serious about Key West?
Gracie will hand-curate Key West listings matching your criteria, walk you through the VR rules and insurance math, and set up showings when you're ready.