A Key West conch house — and the Old Town-vs-New Town decision that shapes everything
Key West is walkable, historic, and deeply regulated on short-term rentals. Old Town vs New Town vs the resort corridor — each is a different Key West.
Key West is a 2-by-4 mile island at the end of the Florida Keys, connected to the mainland by 113 miles of the Overseas Highway. It's got 400 years of Cuban and Bahamian and gay/artist/refugee/Hemingway/Buffett layered history, and one of the most walkable historic downtowns in the American South. It's also one of the most heavily-regulated STR markets in the country — legal Key West rentals require minimum 28-day stays inside city limits, with narrow exceptions in select buildings.
The three practical bases: Old Town (the historic core, Duval Street, walking distance to everything — but STR rules limit shorter stays), New Town (residential east side, less character, more legal supply), and Stock Island / Sunset Key / adjacent islands (Marathon and Big Pine for longer stays if the Key West market is fully permitted-out).
Cards below open Vrbo destination results in a new tab. Commissions accrue on completed stays; you pay the same either way.
Vrbo rentals in Key West
Florida · category picks from Vrbo's own inventory
Vrbo is a member of the Expedia Group family. destination.com earns a commission on completed bookings — it doesn't change what you pay.
Frequently asked
Can I actually rent a Key West Vrbo for less than a month?
Yes, but only in specifically permitted units. Key West requires transient rental licenses for stays under 28 days, and the city has strictly capped new licenses. Legal short-term Vrbo listings will display a license number. Marathon and the Middle Keys have less restrictive rules and are the workaround for shorter stays.
How does Key West compare to Sanibel or the Hamptons?
Key West is denser, more walkable, more historic, and more heavily regulated than Sanibel. It's less mansion-driven and cheaper than the Hamptons. The rental market is more constrained than either — the STR license system is the whole reason to plan Key West trips carefully.
When should Key West rentals be booked?
Peak is January through April (snowbird season, dry, warm). Book 6+ months out. Fantasy Fest (late October) is a real mini-peak — book a year out. Summer (June-September) is hot, buggy, and cheaper but hurricane risk is real. Fall (October-November) is the sleeper for weather-price ratio.