Mile Marker 73–90 · Upper Keys
Islamorada Real Estate
The Village of Islands and the Sport Fishing Capital of the World.
The Village of Islands
Five islands under one incorporated village
Islamorada is the 'Village of Islands' — an incorporated municipality that ties together Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key and Tea Table Key, running from roughly Mile Marker 73 to 90. Like Marathon and Key Colony Beach, it governs itself, so village ordinances rather than county rules shape what you can do with a property here.
Its identity is fishing. Islamorada bills itself as the Sport Fishing Capital of the World, with a charter fleet, backcountry flats and offshore access that anchor a genuinely high-end market. Founders Park, Theater of the Sea, Anne's Beach and the historic Matecumbe communities give it a settled, established feel, and the housing skews toward premium waterfront.
What Buying in Islamorada Actually Involves
Village rules, waterfront premiums, and access
Because Islamorada is its own village, the governing rules — zoning, building, and especially rental regulation — come from the village, and they are among the stricter in the Keys. Any purchase here starts with the village's rulebook and the permit history for the address, not with the county's.
This is a premium waterfront market, so the water is the asset: bay side versus ocean side, the run to open water, and the condition of the dock, lift and seawall. Pair that with the standard Keys diligence — elevation certificate, wind mitigation, firm flood and windstorm quotes — and read the fine print on any property whose value assumes a use the village may restrict.
Renting It Out
The Village of Islamorada regulates vacation rentals tightly, with limited eligibility and a licensing regime that is not open across all residential zones. A high price tag does not imply a short-term-rental right. If your model depends on nightly or weekly rental, confirm the current village ordinance and whether a transferable license exists for the specific property before you commit.
See What’s for Sale in Islamorada
Search active Florida Keys MLS listings, and reach out for anything you want walked in person. We know these islands address by address — what the photos do not show is usually what decides the deal.
Explore the Other Keys
Every island in the chain has its own rules, water and market.