Sometimes, and the answer changes at the city line. Short-term rental rules in Naples depend on which side of the municipal boundary your house sits on, and then on what your community documents say. A home three miles inland in unincorporated Collier County can legally take a one-week booking. A house downtown on Third Street cannot, at least not more than three times a year. Buyers get this wrong constantly, because the listing says Naples and the tax bill says Naples and the two properties are governed by completely different rules.
Inside Naples city limits, the answer is 30 days
The City of Naples requires rental terms of 30 days or longer. There is a narrow exception that lets you rent for a shorter period up to three times in a calendar year, and that is the whole allowance. You also cannot advertise the property as available for stays under 30 days, which means a permanent Airbnb listing with a two-night minimum is a problem on its own, separate from whether anyone actually books it.
Three times a year is not a business. If you are buying inside the city with rental income in the underwriting, run the numbers on monthly and seasonal tenants instead. Season here is January through April, and a well-located city home rents by the month at rates that often beat the nightly math anyway.
Unincorporated Collier County: register the property
Most of what people call Naples is not in the city. North Naples, Golden Gate, the Estates, Lely, and everything east of Airport-Pulling is unincorporated Collier County, and the county allows short-term rentals as long as you register.
Ordinance 2021-45 took effect in January 2022. It applies to any habitable space rented for terms of six months or less, the fee is $50 per property, and it does not cover the City of Naples, Marco Island, or Everglades City, which set their own rules. Skipping it is not a paperwork problem. Fines run up to $500 per day for ongoing violations, and code enforcement here responds to neighbor complaints.
Marco Island, Bonita Springs, and Fort Myers all differ
Marco Island passed a voter-approved registration program and then lost it. State legislation passed after Hurricane Ian nullified the ordinance, the city halted the program, and fees were refunded. There is no city registration requirement on Marco today and weekly rentals are common, but zoning still varies by address.
Bonita Springs surprises people. The city requires a rental permit for any rental inside city limits, short term or long term, and the unit has to pass a code enforcement inspection against minimum property maintenance standards before the permit is issued. The fee is $100 per unit and the permit runs three years. The exemption is for units inside complexes of six or more governed by a state-recognized association, which covers most Bonita condos but not a single-family house or a small duplex.
Fort Myers has no city vacation rental ordinance and no local registration program, so there is no city permit to chase. You still need the state license, a Florida Department of Revenue sales tax account, a Lee County tourist development tax account, and business tax receipts from both the city and the county before you take a booking.
Why the rules are such a patchwork
Florida law preempts most of this. Under Florida Statute 509.032(7)(b), a local government cannot prohibit vacation rentals or regulate how long or how often a home is rented. The catch is the grandfather clause: the preemption does not touch any ordinance adopted on or before June 1, 2011. Cities that already had restrictions on the books kept them, and cities that did not can no longer create them. That single date explains why Naples can enforce a 30-day minimum and Fort Myers has nothing at all.
The HOA documents usually decide it before the city does
This is the part that kills more deals than the ordinances. A community can be stricter than the county, and most of them are. Minimum lease terms of 30 days, 90 days, or a cap on the number of leases per year are all common in Naples communities, and some associations require board approval and an application fee for every tenant. Whatever the county allows, the recorded documents control your property.
Ask for the declaration, the rules and regulations, and the most recent amendments before your inspection period closes, and read the leasing article yourself rather than taking a verbal answer. Sellers are frequently wrong about their own rules, usually because they are describing what was true when they bought. On a condo, the same document request also gets you the milestone inspection and reserve study, so ask for all of it at once, and confirm what the dues actually cover before you build a pro forma on them.
The licenses and taxes nobody budgets for
You need a Florida DBPR vacation rental license once the home is rented more than three times in a year for periods of less than 30 days, or advertised that way. That is the state threshold and it is separate from anything local.
Then there is the tax. Collier County levies a 5% tourist development tax on rentals of six months or less, and the state adds 6% sales tax on the same income, so 11% comes off the top of every short stay. Lee County's tourist development tax is also 5%. Airbnb and VRBO collect and remit the Collier bed tax for bookings made through their platforms, VRBO since February 2023. Anything you book privately or through another site, you remit yourself. The Collier Tax Collector's tourist tax department is at 239-252-8171 and they audit rental records.
One more thing that catches investors: renting the home short term can affect your homestead exemption, and that is a conversation to have with the property appraiser before you list it. The exemption is a large part of what you actually pay in property taxes here.
What I check before a client writes the offer
Three things, in this order. Whether the address is in a city or in unincorporated county, which I verify on the property appraiser record rather than the mailing address. What the community documents say about minimum lease terms and approval. And whether the seller has been renting it, because an existing registration, license, and tax account mean the property has a track record you can look at.
If income is part of why you are buying, put those questions in front of the offer. The inspection period is a bad time to find out the community requires 90-day leases.
Have questions about a specific property or neighborhood? Call John at 239-304-6224 or send a message.