I’m a lifelong Disney fan, and so are a lot of the Central Virginia families I work with. If you’re dreaming about a vacation home near the parks, whether it’s for your own family trips, for renting to other families, or both, here’s what to sort out before you fall in love with a listing.
Andy Zemon, NMLS 208916, is an NMLS-registered mortgage loan originator, registered to lend in all 50 states. You can verify that on NMLS Consumer Access. My home market is still Charlottesville and Central Virginia; this page is for the clients who ask me about a place in the sunshine too.
Walt Disney World sits across parts of Orange and Osceola counties, and the rental rules on either side of that line are very different. Cities such as Orlando and Kissimmee also set their own rules, so start by confirming the exact jurisdiction for the parcel.
Summarized from official sources as of November 9, 2026. Rules change; confirm for the specific parcel and any HOA before you offer.
Short-term rental (stays of 179 days or less) is permitted only in Commercial C-1, C-2, C-3 and certain Industrial districts, or in Planned Developments where it is expressly permitted. Renting a single-family home for less than 30 days (“single-family transient rental”) is permitted only in the R-3 district. In all other zoning districts, both are prohibited.
Osceola County’s steps: verify that your zoning allows short-term rentals (the county publishes a short-term rental overlay map), get a Florida DBPR Vacation Rental license, then register a Local Business Tax Receipt with the Osceola County Tax Collector. Subdivisions and planned developments may add their own rules. Rentals of less than 180 days are subject to the county’s Tourist Development Tax. Inside city limits, check that city’s rules too.
Sources: Osceola County: STRPD district & STR license steps · Osceola County Tax Collector: Tourist Development Tax
The Florida DBPR Division of Hotels and Restaurants requires a vacation rental license if you rent an entire unit more than three times in a calendar year for periods of less than 30 days or one calendar month, whichever is less, or if it’s advertised or held out as regularly rented to guests.
Florida law generally prevents local governments from prohibiting vacation rentals or regulating how often or how long they’re rented, but local rules adopted on or before June 1, 2011 are grandfathered. That’s part of why rules can change sharply at a county line.
Source: Florida Statutes §509.032
The same rules apply in Florida as in Virginia. Under Fannie Mae’s guidelines, a second home must be occupied by you for part of the year, stay under your exclusive control, not be primarily operated as a rental, and generally can’t use rental income to qualify. Many homes near the parks sit in resort communities with rental programs. A program that controls your calendar can push the loan into investment-property territory, so share any rental or management agreement with me early.
Yes. Andy Zemon, NMLS 208916, is an NMLS-registered mortgage loan originator, registered to lend in all 50 states. The same second-home and investment-property rules apply in Florida as in Virginia: the loan is classified by how you will actually use the home.
In unincorporated Orange County, short-term rental (stays of 179 days or less) is permitted only in Commercial C-1, C-2 and C-3 and certain Industrial districts, or in Planned Developments that expressly permit it. Renting a single-family home for less than 30 days is permitted only in the R-3 district. In all other zoning districts both are prohibited, according to the Orange County Zoning Division.
Osceola County lists three steps: verify that your zoning allows short-term rentals, get a Vacation Rental license from the Florida DBPR Division of Hotels and Restaurants, and register a Local Business Tax Receipt with the Osceola County Tax Collector. Rentals of less than 180 days are also subject to the county’s Tourist Development Tax.
According to the Florida DBPR, you need a vacation rental license if you rent an entire unit more than three times in a calendar year for periods of less than 30 days or one calendar month, whichever is less, or if the unit is advertised or held out to the public as a place regularly rented to guests.
Sometimes. Under Fannie Mae’s guidelines a second home must be occupied by you for part of the year, stay under your exclusive control, not be primarily operated as a rental and not use rental income to qualify. Homes in resort communities with mandatory rental programs, or homes bought mainly to rent, are usually financed as investment properties.
Tell me the town, the property and how you plan to use it. I’ll tell you how a lender is likely to classify it, which local rules to check and what to gather before you make an offer.