Every Kissimmee listing graded A through F based on cash flow, cap rate, and ROI. Free to use. Updated daily.
Kissimmee is Osceola County's Airbnb capital — and one of the top short-term rental investment markets in the United States. Located 10 minutes from Walt Disney World, Kissimmee properties near US-192 and Celebration average $4,500–$8,000/month gross STR revenue in peak season. Median prices near $310K with strong cash flows from vacation rental management make Kissimmee ideal for investors targeting the Orlando tourism corridor. Long-term rental demand from theme park employees and construction workers provides a fallback income strategy when STR regulations tighten. Cap rates on LTR strategies run 5.8–6.5%, while STR investors often achieve 10–14% cash-on-cash returns. SpillDeals grades every Kissimmee listing with both LTR and STR cash flow projections, updated daily with live Airbnb market data.
Our system updates deals throughout the day. Search all Florida deals to find investment properties near Kissimmee.
Expand to All Florida DealsKissimmee, Florida remains a strong market for real estate investors in 2026. With a growing population, strong rental demand, and no state income tax, investors can find cash-flowing properties across multiple price points. SpillDeals analyzes every listing in Kissimmee and grades them A through F so you can instantly identify the best deals.
Rental yields in Kissimmee vary by neighborhood and property type. SpillDeals calculates cap rate, cash-on-cash return, and monthly cashflow for every property so you can compare deals side by side.
SpillDeals pulls live listing data from multiple sources across Florida, including Kissimmee. Every property is automatically analyzed for cash flow, cap rate, cash-on-cash return, and DSCR using current mortgage rates and local rental estimates. Properties are then graded A through F — A being exceptional investment potential and F being negative cashflow. This analysis runs continuously so you always see the latest deals.