A Place Where Luxury Feels Natural
Islamorada operates on its own frequency. The alarm clock is the mullet jumping at dawn. The commute is a 15-minute boat ride across the flats. The office view is a turquoise Atlantic stretching to the horizon.
It’s a place where retired executives share bait tips with commercial fishermen, where the best restaurant in town has picnic tables, and where your neighbors are as likely to be a champion fly-fishing guide as a Fortune 500 CEO.
For those who choose to live here, Islamorada isn’t a compromise between nature and comfort — it’s proof that you don’t have to choose.
Where to Eat, Drink & Unwind
Islamorada’s dining scene punches well above its population. From waterfront sunset spots to no-menu raw bars, the food is as fresh as the catch.
Marker 88 & Lorelei
Marker 88 has been setting the standard for Keys cuisine since 1966 — fresh dolphin, snapper, and the best Key lime pie on the island. Lorelei’s outdoor stage and sunset bar draw the sailing crowd nightly.
Theater of the Sea & History of Diving Museum
The History of Diving Museum is world-class — a genuine deep-dive (forgive the pun) into humanity’s obsession with the ocean. Theater of the Sea is a beloved old-Keys institution that hasn’t changed, and that’s the point.
Florida Keys Brewing Co.
A genuine craft brewery doing serious work in a tiny space. Grab a Snook Stout or a Keys Kolsch after a day on the water. The taproom crowd is exactly who you’d want to hear fish stories from.
What You Need to Know
Before You Move Here
Schools
Islamorada is in the Monroe County School District. Plantation Key School (K–8) and Coral Shores High School are both on Upper Matecumbe. Many families supplement with private schooling in Homestead or Miami for secondary education.
Healthcare
Mariners Hospital in Tavernier (MM 91) is the primary facility for upper Keys residents. Fishermen’s Community Hospital is in Marathon. Miami’s Jackson Health and Baptist Health systems are 90 minutes north via US-1 or helicopter.
Flood Insurance & ROGO
Monroe County’s Rate of Growth Ordinance (ROGO) severely limits new construction. This is a feature, not a bug — it preserves property values and keeps density low. NFIP flood insurance is mandatory and varies by elevation certificate. Budget $4,000–$15,000/year depending on structure.
Getting There
Miami International Airport is 75 miles north — roughly 90 minutes in normal traffic. Florida Keys Marathon Airport (MTH) handles charter flights. Many estate owners fly private into MTH or Opa-locka Executive Airport and drive the last stretch of US-1.
Hurricane Preparedness
The Keys are a Zone A evacuation zone for Category 3+ storms. Serious owners build for it: impact glass, concrete construction above BFE+2, whole-house generators, and documented evacuation plans. The right estate handles storms like a ship handles weather — by design.
Property Tax & Homestead
Florida has no state income tax. Monroe County millage rates run roughly 1.1% of assessed value. Homestead exemption applies to primary residences ($50,000 off assessed value + Save Our Homes 3% cap). Non-homestead properties are reassessed at market more aggressively.
A Small Town With a Big Heart — and Bigger Fish Stories
Islamorada’s 6,000 permanent residents form one of the tightest communities in South Florida. There are no degrees of separation here — everyone knows the best guide, the marina that treats you right, and the hardware store guy who’ll open up on Sunday.
The Islamorada Community Cooperative, the Chamber of Commerce, and the annual Redbone Celebrity Tournament bind the community together. The latter raises millions for cystic fibrosis research — and happens to be one of the premier social events in the Keys calendar.