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If you rent living quarters or accommodation in Monroe County for a period of six months or less, you have to collect a 5 percent tourist development tax and remit it to the Monroe County Tax Collector. State sales tax applies on top of that, separately. This is the tax that catches people. Not the…

If you own a cottage, conch house, or condo in Key West and rent it out on Airbnb or VRBO, the tax side of that income is more complicated than most owners expect. Between local licensing, county lodging tax, and IRS rules that change depending on how you run the property, it’s easy to get…

Boat slips and dockage are still subject to Florida sales tax. They were specifically carved out of the 2025 commercial rent repeal, so nothing changed for marinas. Charters and tours are more complicated, and the answer depends on how the trip is actually structured. This is the corner of Florida sales tax where Key West…

Whether someone is an employee or a contractor is decided by how much control you have over their work, not by what you call them, not by whether they invoice you, and not by what the agreement they signed says. A written contract is evidence. It is not the answer. This is one of the…

Florida reemployment tax is the state’s version of unemployment insurance tax, paid entirely by the employer. You become liable once you pay $1,500 or more in wages in any calendar quarter, or once you have at least one employee for some part of a day in 20 different weeks in a year. Most states call…

Florida has no personal income tax, but it does have a corporate income tax. Whether your business owes it comes down to one thing: how your entity is taxed federally. C corporations generally owe it. Pass-through entities generally do not. The confusion is understandable. “Florida has no income tax” is repeated so often that owners…

Yes, almost certainly. If you operate a business inside Key West city limits you generally need a business tax receipt from the City of Key West and a separate one from Monroe County. They are two different registrations with two different offices. People still call these occupational licenses out of habit. Florida renamed them years…

No. Florida repealed the sales tax on commercial rent effective October 1, 2025. If your landlord is still adding it to a storefront or office lease, that is an error and you should raise it. This one is worth being precise about, because Florida was the only state in the country that taxed commercial rent,…

A Key West business owner pays into three separate systems: the IRS, the State of Florida, and Monroe County. Florida has no personal income tax, but that does not mean your business owes nothing at the state and local level. Most of the trouble I see comes from owners who assumed “no income tax” meant…

If a storm damages your business, the size of your insurance settlement and your casualty loss deduction will both come down to one thing: whether you can prove what you had and what it was worth. That proof gets built now, in July, while the weather is fine. It cannot be built afterward. Peak season…