Homes for sale in Kissimmee include regular family homes and townhomes in the city, plus thousands of vacation homes in resort communities a few miles from the Disney parks. If you want to rent by the night, the address matters more than the house: in Osceola County, short-term rentals are only allowed in zones set aside for them, and the HOA must allow it too. Prices are lower than in South Florida, and buyers currently have room to negotiate. Rui Cunha's office is in Deerfield Beach, and he works with clients across Florida, including the Kissimmee area.
What it's like to live in Kissimmee
Kissimmee is the seat of Osceola County, just south of Orlando, on the shore of Lake Tohopekaliga. Florida's Office of Economic and Demographic Research estimated the city's population at 84,958 as of April 2024, up 2.9% in a year (Florida EDR).
There are really two Kissimmees. One is the city where people live and work, with older neighborhoods near the lakefront and newer subdivisions. The other is the tourist area along the US-192 corridor and toward Disney: the local tourism office counts more than 30,000 vacation home properties in the Kissimmee area, 2 to 10 miles from the Disney parks, managed by more than 100 rental companies (Experience Kissimmee). Many of those homes are in unincorporated Osceola County, not inside city limits.
Vacation homes: what the rules actually say
This is the most important part of buying a vacation home here, so check it before you fall in love with a house.
Zoning. In unincorporated Osceola County, a property must be inside the county's short-term rental overlay zone to qualify, and the county has a dedicated Short Term Rental Planned Development (STRPD) district for this kind of housing. Subdivisions and planned developments may add their own restrictions (Osceola County). Inside Kissimmee city limits, check with the city's planning division whether the property can be rented for under 30 days.
Licenses. You need a state vacation rental license from the DBPR's Division of Hotels and Restaurants and a Local Business Tax Receipt from the Osceola County Tax Collector. Rentals inside city limits may also need a city license (Osceola Tax Collector).
Tourist tax. Osceola County charges a 6% tourist development tax on stays under six months. The county says it is not contracted with Airbnb, VRBO or other platforms, so owners or their managers must collect and pay it themselves (Osceola Tax Collector).
HOA rules. Vacation-home communities usually have an HOA with its own rules and fees. Read the HOA documents and confirm that short-term rentals are allowed before you make an offer.
Rental income is never guaranteed. Thousands of similar homes compete for the same guests, and occupancy depends on the house, the management and the season.
Kissimmee market snapshot
Momentum Realty's analysis of Florida MLS data puts Kissimmee's median sale price at about $388,000, down 2.6% from a year earlier. Homes took about 62 days to go under contract, and there were about 6.6 months of supply (Momentum Realty, October 2026), which tilts things toward buyers.
For the wider metro area (Orange, Osceola, Seminole and Lake counties), Florida Realtors reported a median single-family price of $439,000 in August 2026 (Florida Realtors). A family home in the city and a furnished vacation home in a resort community are different markets, so ask Rui for recent sales of the kind of property you want.
Practical notes: flood, taxes and condos
Flood. Kissimmee is inland, but it sits on a chain of lakes. Hurricane Ian caused catastrophic flooding and rescues in Kissimmee in 2022 (Central Florida Public Media). Check the flood zone and get real insurance quotes. Citizens policyholders must carry flood coverage as that requirement phases in through 2027 (News4JAX).
Property taxes. Only a primary residence qualifies for homestead. Osceola County notes that a proposed property tax amendment on the November 2026 ballot would raise the homestead exemption but would not apply to second homes or vacation rentals; it would instead lower the yearly assessment cap for non-homestead properties from 10% to 5% (Osceola County). Check the outcome after the vote, and ask a CPA how it affects you.
Condos and townhomes. Buildings of three or more stories fall under Florida's condo safety laws, with milestone inspections and funded structural reserves (SB 154, 2023; Rimkus). Ask for the reserve study and assessment history.
Schools
Kissimmee is served by the School District of Osceola County. Confirm the assigned schools for any address with the district and check school grades with the Florida Department of Education.
Getting around
US-192, Florida's Turnpike and I-4 connect Kissimmee to Orlando, the parks and Orlando International Airport. Traffic near the parks can be heavy, so test your routes at busy times.
Working with Rui in Kissimmee
Rui has worked in Florida real estate since 2003, as a mortgage broker, a broker and a licensed General Contractor, which helps when you're checking a vacation home's condition, HOA rules or a rental budget. He can help you buy a home, look into an ITIN mortgage or, if you live abroad, understand the steps for international buyers. Use the mortgage calculator to include taxes, insurance and HOA fees, and compare with Orlando.
FAQ
Can I rent my Kissimmee home on Airbnb?
Only if the property is in a zone that allows short-term rentals and the HOA permits it. In unincorporated Osceola County that means the short-term rental overlay. You also need a state vacation rental license, a county business tax receipt and to pay the 6% county tourist tax yourself.
What is the median home price in Kissimmee?
Momentum Realty's analysis of Florida MLS data put it at about $388,000 as of October 2026, down 2.6% from a year earlier. Furnished vacation homes in resort communities can price differently from regular family homes.
Does Airbnb collect Osceola County's tourist tax?
According to the Osceola County Tax Collector, the county is not contracted with Airbnb, VRBO or other platforms, so the owner or manager must collect and pay the 6% tourist tax.
Can I buy in Kissimmee without a Social Security number?
Many buyers use an ITIN mortgage, subject to lender approval. See our ITIN mortgage guide or contact Rui.
Talk to Rui
Thinking about a home or a vacation rental near Kissimmee? Ask Rui to check the zoning, HOA rules and recent sales first.