Investor market data · Florida

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 August 2026.

See what pencils →Run a DSCR

$389,000Median list price2,733 active listings

$40,819Median STR revenue / yrprojected, gross

Homes in Kissimmee that pencil right now

A sample of active Kissimmee listings whose DSCR clears 1.25 using short-term rental income projections we accept as a direct lender. These are spread across the price range, not ranked, and current as of August 2026.

$176,000DSCR 1.61
2 bed · 2 bath · 930 sqft
Townhouse in 34741 · built 1984
STR revenue
$31,028/yr
Est. interest-only payment
$1,285/mo
On the market 11 days · Listed by CHARLES RUTENBERG RLTY ORLANDO
Scout this home & market: 2-bed townhouse in Kissimmee
$219,990DSCR 1.54
3 bed · 2 bath · 1,330 sqft
House in 34758 · built 2001
STR revenue
$38,408/yr
Est. interest-only payment
$1,668/mo
On the market 95 days · Listed by Agent Trust Realty Corporation
Scout this home & market: 3-bed house in Kissimmee
$240,000DSCR 1.28
3 bed · 2 bath · 1,346 sqft
House in 34758 · built 1984
STR revenue
$34,139/yr
Est. interest-only payment
$1,784/mo
On the market 73 days · Listed by National Real Estate
Scout this home & market: 3-bed house in Kissimmee
$259,990DSCR 1.39
2 bed · 2 bath · 952 sqft
Townhouse in 34743 · built 1992
STR revenue
$43,641/yr
Est. interest-only payment
$2,099/mo
On the market 56 days · Listed by Empire Network Realty
Scout this home & market: 2-bed townhouse in Kissimmee
$299,000DSCR 1.34
3 bed · 2 bath · 1,424 sqft
House in 34741 · built 1956
STR revenue
$36,247/yr
Est. interest-only payment
$1,797/mo
On the market 51 days · Listed by IRON VALLEY REAL ESTATE OSCEOLA
Scout this home & market: 3-bed house in Kissimmee
$320,000DSCR 1.29
3 bed · 2 bath · 1,559 sqft
House in 34744 · built 2022
STR revenue
$42,025/yr
Est. interest-only payment
$2,169/mo
On the market 38 days · Listed by Atrium Realty - Orlando
Scout this home & market: 3-bed house in Kissimmee
$334,900DSCR 1.57
3 bed · 2 bath · 1,704 sqft
House in 34743 · built 1999
STR revenue
$49,361/yr
Est. interest-only payment
$2,092/mo
On the market 24 days · Listed by REALTY PROS UNLIMITED INC
Scout this home & market: 3-bed house in Kissimmee
$349,900DSCR 1.31
3 bed · 2 bath · 1,486 sqft
House in 34743 · built 1984
STR revenue
$47,517/yr
Est. interest-only payment
$2,418/mo
On the market 78 days · Listed by Keller Williams Winter Park
Scout this home & market: 3-bed house in Kissimmee
$379,000DSCR 1.38
3 bed · 2 bath · 1,377 sqft
House in 34746 · built 1991
STR revenue
$48,451/yr
Est. interest-only payment
$2,342/mo
On the market 322 days · Listed by Ljl Real Estate, Inc.
Scout this home & market: 3-bed house in Kissimmee

Ask about Kissimmee deals →Run any address yourself

As of August 2026, we analyzed 2,733 active for-sale homes in Kissimmee, Florida. The typical listing is priced at $389,000 and is projected to generate about $40,819 a year as a short-term rental.

After setting aside an estimated 20% for operating costs, an estimated 34.9% of those homes could still cover an investor mortgage payment on short-term-rental income — below the 52.5% median across the 200 major metros we track, ranking Kissimmee #157 of 200 for cash-flow potential.

On market momentum: homes in Kissimmee sit a median of 97 days on the market, and 18% 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: 173 of the 2,319 Kissimmee homes, condos and townhomes we can price confidently clear a DSCR of 1.25. Nine in ten of them are priced under $382,000.

Share of those listings clearing an DSCR of 1.25, by price and bedroom count. The smaller figure is the median DSCR for that group.
Price	1 bed	2 bed	3 bed	4 bed	5 bed
$150k–$250k	8%1.08	31%1.14	20%1.03	9%1.06	—
$250k–$350k	0%0.85	1%0.95	11%0.96	7%0.93	—
$350k–$500k	—	0%0.81	4%0.92	2%0.93	7%0.96
$500k+	—	—	0%0.63	0%0.76	1%0.85

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	2,733
Median list price	$389,000
Median projected STR revenue (annual, gross)	$40,819
Median average daily rate (ADR)	$171
Median occupancy	64%
Median beds	4
Median size	1,840 sqft
Estimated cash-flow-positive share	34.9%
Median days on market	97 days
New listings (last 30 days)	18.1% of active