Florida runs every kind of STR market at once: urban units in Miami and Tampa, beach houses from Destin to the Keys, and resort communities ringing Orlando. Peak pricing is strong enough to justify real risk-taking, which is exactly why discipline matters here more than anywhere.
The wind problemHurricane and wind coverage is non-negotiable and expensive, with named-storm and wind deductibles commonly set as a percentage of dwelling value that scales with coastal proximity. Flood is almost always excluded from the property policy and has to be bought separately, through the NFIP or private flood markets. After years of carrier exits, a growing share of Florida STRs end up in surplus lines or with the state-backed insurer of last resort, which brings its own limits and assessments. None of this makes a Florida STR uninsurable. It makes the structure of the program the entire game.
Flood-related losses are the single largest denial category, usually because there was no flood policy at all. Hurricane claims are denied on underwriting misstatements about distance to coast or elevation, which is why the application matters as much as the policy. And wind-versus-water disputes, where the carrier attributes damage to excluded storm surge rather than covered wind, are a recurring fight after every major landfall.
Florida sets a statewide floor and lets cities build on it. Every vacation rental must hold a transient rental license from the Department of Business and Professional Regulation under Chapter 509, and most municipalities add their own registration, resort and transient taxes, and a business tax receipt. Several, including Hollywood, now require hosts to show proof of liability coverage, noting that a standard homeowner’s policy may not provide it. Enforcement budgets are real, and some cities have issued five-figure fines. State vacation-rental law keeps moving, so treat this as a starting point: verify the specific city, and confirm your policy meets any stated insurance requirement, before you buy.