Property Management in Winter Garden, FL — Airbnb & Short-Term Rentals

Short-term rental and Airbnb management in Winter Garden

Winter Garden has two kinds of rental homes. Inside city limits, homes sit around the historic downtown on Plant Street. To the south, Horizon West is a planned area of five villages and a town center in southwest Orange County, and the county describes it as part of unincorporated Orange County. A Winter Garden mailing address alone does not settle which government’s rules apply there.

So property management in Winter Garden begins with a jurisdiction check. A home on a city street and a home in a Horizon West village can look alike and still face different rules for short-term rental management. Once that is settled, we set the home up as an Airbnb, a furnished mid-term rental or an annual lease, whichever its zoning allows.

Where guests come from

Downtown is the draw. The Garden Theatre at 160 West Plant Street opened in 1935 as a single-screen cinema, was restored and reopened in 2008, and has been run directly by the city since 2024. It hosts plays, musicals, concerts and films. The city’s calendar lists the Winter Garden Farmers Market and downtown events such as Fridays on the Plaza.

Outdoor guests come for Lake Apopka and the trails. The Clermont/Minneola Trail, which the City of Clermont says has been connected to the West Orange Trail, links Winter Garden’s trail network with the lakes to the west. The city’s new Tucker Ranch park and botanical garden adds another reason to stay close to downtown.

Visitors fly into Orlando International Airport (MCO).

Winter Garden short-term rental rules

Inside the city, Code §118-1310 says an accessory dwelling unit may be rented on a standard residential lease and that short-term rentals under 30 days are prohibited. A garage apartment or guest cottage can be a long-term rental, never an Airbnb. For the main house, we found no separate vacation rental chapter in the city code as published on Municode, so we confirm the parcel’s zoning with the city’s planning staff before listing.

In Horizon West and other unincorporated areas, Orange County’s rules apply. The county’s zoning FAQ permits short-term rental, which Code §38-1 defines as a stay of 179 days or less, only in commercial and industrial districts or in planned developments that expressly permit it. Single-family stays under 30 days are permitted only in R-3. Single-family districts other than R-3 are not on that list, so a house in one of them is suited to a mid-term or annual lease instead.

Any home rented for under 30 days more than three times a year also needs a state license under §509.241, and HOA rules apply on top of zoning.

Taxes on Winter Garden vacation rentals

Stays of six months or less carry Florida’s 6% sales tax under §212.03 and Orange County’s 0.5% surtax on the DR-15DSS for 2026.

Orange County’s 6% tourist development tax is listed on the state’s DR-15TDT chart as collected by the county, so it is filed with Orange County, separately from the state return.

How Florida Hosts manages Winter Garden rentals

In Winter Garden we sort out the city-or-county question first, then run the home as a vacation rental where zoning allows, or as a furnished mid-term stay or an annual lease where it does not.

For Airbnb management we handle pricing, listings, the state license and tax filings, and 24/7 guest communication, with our own cleaning and maintenance staff. We charge 18–25% of booking revenue for short-term rental management in Winter Garden, and you get the figure in writing. Mid-term and long-term rentals are managed with licensed brokers for the leasing, and a free rental projection arrives within one business day.