20+ Osceola County transactions since 2017
Kissimmee, FL Real Estate & STR Investment — Tony Ubaldini
Kissimmee is one of the strongest short-term rental markets in the country because of its zoning proximity to Walt Disney World. Tony has closed 20+ transactions in Osceola County — from turnkey Airbnb condos in Storey Lake and Windsor Hills to primary residences in St. Cloud. He knows which HOAs allow nightly rentals and which will get you fined.
Kissimmee neighborhoods Tony works in
- Storey Lake
- Windsor Hills
- Windsor at Westside
- Reunion
- ChampionsGate
- Emerald Island
- Solara Resort
- Poinciana
Kissimmee market snapshot
- ›STR-approved condos start around $250K; single-family STR homes $450K–$900K+.
- ›Occupancy for well-managed 4–6 bed themed homes is commonly 60–75%.
- ›HOA fees on resort communities range $350–$750/mo and materially impact cash flow.
- ›Not every Kissimmee neighborhood allows short-term rentals — verify zoning before writing.
Kissimmee FAQ
Kissimmee real estate questions
Should I buy a short-term rental near Disney?
- It can be a strong cash-flow play if the zoning, HOA, and financing all line up. Tony pulls actual AirDNA numbers, verifies the community allows nightly rentals, and shows you a real net-of-expenses projection before you write an offer.
Which Kissimmee communities are approved for Airbnb?
- Storey Lake, Windsor Hills, Windsor at Westside, Reunion, ChampionsGate, Emerald Island, and Solara are all STR-approved. Many surrounding subdivisions are not — always confirm current HOA rules on the specific unit.
How much does it cost to run an Airbnb in Osceola County?
- Budget roughly 25–35% of gross revenue for management, cleaning, utilities, and supplies, plus HOA and property taxes. Tony can share a real operating pro-forma from active clients.
Nearby areas Tony also serves
All areas served: Orlando, Kissimmee, Lake Nona, Winter Park, Oviedo, Winter Garden.