A month in Orlando

Florida taxes rentals of six months or less, so a 30-night stay pays the same 12.5% as a weekend in Orange County, and 13.5% in Osceola County. The tax stops only with a written lease for longer than six months, or after six months in the same place with the tax paid.

Since 1 July 2025, occupancy in a hotel, motel or vacation rental is transient unless a written agreement says the unit is the guest's sole residence. Florida's landlord and tenant act does not apply to transient stays, and the operator can ask a guest who has not paid, or has not checked out by the time given in writing, to leave; staying on after that request is a misdemeanour. Under a residential lease the landlord returns a deposit within 15 days, or sends written notice of a claim within 30.

In unincorporated Orange County, a short-term rental is any stay of 179 days or less, allowed only in commercial and industrial districts and in planned developments that permit it. A month in a house or flat in any other district of the county's unincorporated area is not allowed.

The City of Orlando counts less than 30 days as short-term. A whole home rented for 30 days or more is an ordinary residential rental under state and federal housing law, while shorter whole-home rentals are commercial dwelling units, allowed in certain districts only. A home share, where the host lives on site, takes one booking at a time of at most four unrelated people, or two per room if that is fewer. Osceola County's rules for Kissimmee could not be verified as of September 2026, so ask the host which permit covers the stay.

Downtown Orlando suits a month with city services and monthly parking at hand. Winter Park, about 10 km (6 miles) north, suits a quieter month with free timed parking downtown. International Drive and the Disney area suit shorter hotel stays better than a month. These choices are editorial.

The city sells monthly permits downtown: 24-hour access costs USD 165 a month in the Central Boulevard, Jefferson Street and Library garages and USD 105 at the Livingston lot, and weekday permits from USD 70, all plus tax. The city asks for a properly registered vehicle, the driver's licence and the registration, so check with the rental company that its papers will do.

Rental companies bill tolls through their own programmes. The Visitor Toll Pass from Orlando International covers renters flying round trip through the airport, and a SunPass Portable owner can add the rental plate to the account for the rental dates.

Visitors from the 42 Visa Waiver Program countries, among them the UK and 24 of the 27 EU countries (not Bulgaria, Cyprus or Romania), can stay up to 90 days with an ESTA, which costs USD 40.27. The stay cannot be extended, and a side trip to the Bahamas, Canada or Mexico does not restart the 90 days. CBP records each arrival electronically, with an admit-until date that can be checked on its website.

Airbnb calls 28 nights or more a monthly stay: the first month is charged up front, later months 10 days before each period, under a long-term cancellation policy that generally requires 30 days' notice of changes.

Booking a month in a house in unincorporated Orange County outside the permitted districts. The 179-day rule covers it.

Expecting the room taxes to stop after 30 nights. They run for six months unless a written lease for longer is in place.

Leaving a car in a downtown garage past 5:29 a.m. without a permit. The next day's charges start.

Assuming utilities, cleaning or a deposit are included. No official source on local practice was found, so ask in writing.