The Florida Keys business market is small, strange, and moves fast - and most of what is "for sale" never makes the front page of a listing site. Here is what is actually on the market right now, and how to watch it without refreshing five sites a day.
What's listed right now (late October 2026)
A sampling from the public listing sites this week: an Upper Keys fishing charter with forward bookings and the boat included, asking $199,000. A rare free-standing restaurant building in Key Largo at $995,000. A Key West deep-sea charter in the $65,000-$100,000 range. Dons' Place bar in Key West. A Marathon hotel, a Big Pine short-term-rental portfolio, a Monroe County liquor license, and on the biggest end an Islamorada waterfront restaurant with real estate at $23 million. Commercial space moves too: 1,000-4,600 square feet on Duval Street is offered around $65 per square foot NNN.
Why listings disappear fast here
Monroe County inventory is capped by geography and permitting, so anything priced right - especially charters with bookings and anything with a liquor license - draws buyers from the whole state. The listing sites also bury Keys results inside "South Florida," so good ones are easy to miss.
A radar instead of a search
We run OpsScout, a free live board that tracks Keys (and Southeast) business opportunities in one feed: businesses for sale, commercial leases, vendor events, gigs, and sponsorships - 500+ verified items, each with a direct link and contact. It is updated continually, so the charter that lists on a Tuesday shows up before the weekend buyers see it.
Watch the Keys market free on OpsScout →
Listing prices change and sell quickly - always verify current status with the broker. Nothing here is financial or investment advice.