Kissimmee, FL Rental Market for Investors
An estimated 35% of Kissimmee's active listings could cash-flow as a short-term rental — here's what the numbers say for investors, as of October 2026.
As of October 2026, we analyzed 2,723 active for-sale homes in Kissimmee, Florida. The typical listing is priced at $389,900 and is projected to generate about $41,369 a year as a short-term rental.
After setting aside an estimated 20% for operating costs, an estimated 35.4% of those homes could still cover an investor mortgage payment on short-term-rental income — below the 53.1% median across the 200 major metros we track, ranking Kissimmee #158 of 200 for cash-flow potential.
On market momentum: homes in Kissimmee sit a median of 95 days on the market, and 20% of active listings came on in just the last 30 days — a slower-moving market, which shapes how much room there is to negotiate.
For a DSCR loan — which qualifies on the property's rental income rather than your personal income — Kissimmee runs tighter once operating costs are accounted for: many listings need a below-median price, a stronger short-term-rental setup, or more money down before the income covers the payment. It's a market where running the numbers property-by-property matters.
What actually works in Kissimmee
Cash-flow is the exception rather than the rule in Kissimmee right now: 167 of the 2,308 Kissimmee homes, condos and townhomes we can price confidently clear a DSCR of 1.25. Nine in ten of them are priced under $367,000.
| Price | 1 bed | 2 bed | 3 bed | 4 bed | 5 bed |
|---|---|---|---|---|---|
| $150k–$250k | 8%0.99 | 31%1.11 | 18%1.04 | 10%1.00 | — |
| $250k–$350k | 0%0.83 | 3%0.94 | 9%0.98 | 12%0.96 | — |
| $350k–$500k | — | 0%0.81 | 3%0.93 | 2%0.92 | 5%0.96 |
| $500k+ | — | — | 0%0.63 | 0%0.77 | 1%0.86 |
Darker means a larger share of that group cash-flows. “—” means fewer than 8 active listings — too few to draw a conclusion from.
Kissimmee in full
| Active for-sale homes analyzed | 2,723 |
|---|---|
| Median list price | $389,900 |
| Median projected STR revenue (annual, gross) | $41,369 |
| Median average daily rate (ADR) | $174 |
| Median occupancy | 64% |
| Median beds | 4 |
| Median size | 1,845 sqft |
| Estimated cash-flow-positive share | 35.4% |
| Median days on market | 95 days |
| New listings (last 30 days) | 19.7% of active |
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Estimates for educational purposes. Final terms subject to credit, property & program approval.
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