Real Estate Investment Properties for Sale in Kissimmee, FL

Looking for investment property in Kissimmee, FL with high ROI ?

Explore a variety of short-term homes & houses in Kissimmee, FL. Invest wisely with VRBO & Kissimmee, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Kissimmee, FL

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3016 Parkway Blvd #204 Kissimmee, FL Location, Location, Location! 2/2 totally renovated, water view, minutes away from Disney,...	2 beds \| 2 baths \| 937 sq.ft.	$170,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 4.15% Airbnb Rental Income: $2090 Traditional Rental Income: $1690 Airbnb ROI: 3.3% Traditional ROI: 4.15%
719 Del Ray Dr Kissimmee, FL Charming and well-maintained home located in the desirable community of Poinciana Villages...	3 beds \| 2 baths \| 1,057 sq.ft.	$260,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 4.86% Airbnb Rental Income: $2503 Traditional Rental Income: $1857 Airbnb ROI: 5.02% Traditional ROI: 4.86%
1831 Windward Oaks Ct Kissimmee, FL LARGE PRICE REDUCTION and Buyer bonus of one free year of pool service included with accep...	5 beds \| 3 baths \| 2,813 sq.ft.	$539,900	Airbnb cash on cash: 5.01% Traditional cash on cash: 4.37% Airbnb Rental Income: $4939 Traditional Rental Income: $3601 Airbnb ROI: 5.01% Traditional ROI: 4.37%
3251 Pinewood Ct Kissimmee, FL Are you ready to fall in love? Look no further, your beautiful home awaits. Your new home ...	3 beds \| 2 baths \| 2,404 sq.ft.	$449,900	Airbnb cash on cash: 2.45% Traditional cash on cash: 4.33% Airbnb Rental Income: $2503 Traditional Rental Income: $2690 Airbnb ROI: 2.45% Traditional ROI: 4.33%
725 Mabbette St Kissimmee, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Se...	3 beds \| 2 baths \| 1,488 sq.ft.	$315,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 5.25% Airbnb Rental Income: $2503 Traditional Rental Income: $2254 Airbnb ROI: 4.04% Traditional ROI: 5.25%
202 Woodson Ct Kissimmee, FL Welcome to this stunning 3,744 square foot residence located on a quiet cul de sac within ...	5 beds \| 3 baths \| 3,744 sq.ft.	$595,000	Airbnb cash on cash: 4.97% Traditional cash on cash: 6.73% Airbnb Rental Income: $4939 Traditional Rental Income: $4904 Airbnb ROI: 4.97% Traditional ROI: 6.73%
5004 LAGUNA BAY Circle #54 Kissimmee, FL Fabulous condo for sale fully furnished! 3 beds and 2 baths condo located just a few minut...	3 beds \| 2 baths \| 1,220 sq.ft.	$229,900	Airbnb cash on cash: 3.28% Traditional cash on cash: 4.83% Airbnb Rental Income: $2503 Traditional Rental Income: $2235 Airbnb ROI: 3.28% Traditional ROI: 4.83%
4558 Ada Ln Kissimmee, FL Formerly the model home for Park Square Homes. Beautiful fully furnished 3 bedroom town ho...	3 beds \| 2 baths \| 1,295 sq.ft.	$298,900	Airbnb cash on cash: 2.6% Traditional cash on cash: 1.96% Airbnb Rental Income: $2503 Traditional Rental Income: $1717 Airbnb ROI: 2.6% Traditional ROI: 1.96%
4577 Alberto Cir Kissimmee, FL Welcome to Bellavida Resort. This home features 4 bedrooms with 3 full baths and one of th...	4 beds \| 3 baths \| 1,636 sq.ft.	$345,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 4.59% Airbnb Rental Income: $3036 Traditional Rental Income: $2729 Airbnb ROI: 3.4% Traditional ROI: 4.59%
2017 Gold Spring Cv Kissimmee, FL This beautiful town home features 3 bedrooms, 2.5 baths, bonus area, ceramic tile througho...	3 beds \| 2 baths \| 2,079 sq.ft.	$325,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 4.31% Airbnb Rental Income: $2503 Traditional Rental Income: $2189 Airbnb ROI: 3.35% Traditional ROI: 4.31%
255 Gardenia Rd Kissimmee, FL Nice and cozy home. Three bedrms., 2 baths. Jacuzzi on the porch. Minutes from Orlando I...	3 beds \| 2 baths \| 1,168 sq.ft.	$339,000	Airbnb cash on cash: 4.4% Traditional cash on cash: 3.86% Airbnb Rental Income: $2503 Traditional Rental Income: $1726 Airbnb ROI: 4.4% Traditional ROI: 3.86%
3048 Seaview Castle Dr Kissimmee, FL Live, work and play in gated Compass Bay, a resort style community in the center of everyt...	4 beds \| 2 baths \| 1,872 sq.ft.	$399,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 2.79% Airbnb Rental Income: $3036 Traditional Rental Income: $2053 Airbnb ROI: 3.56% Traditional ROI: 2.79%
2725 N Poinciana Blvd #147 Kissimmee, FL Investor Alert! Hit the ground running with this stunning, First floor unit located in the...	3 beds \| 2 baths \| 1,287 sq.ft.	$200,000	Airbnb cash on cash: 4.49% Traditional cash on cash: 5.56% Airbnb Rental Income: $2503 Traditional Rental Income: $2100 Airbnb ROI: 4.49% Traditional ROI: 5.56%
3827 Bay Club Cir #204 Kissimmee, FL Investment Opportunity â Tenant in Place Until October 2026! Welcome to this spacious 2...	2 beds \| 2 baths \| 910 sq.ft.	$182,000	Airbnb cash on cash: 3.7% Traditional cash on cash: 4.85% Airbnb Rental Income: $2090 Traditional Rental Income: $1752 Airbnb ROI: 3.7% Traditional ROI: 4.85%
225 Southbridge Cir Kissimmee, FL LOVELY POOL HOME BACKING UP TO THE LAKE...BREAKFAST AREA HAS A VERY COZY DECK..RELAX IN TH...	3 beds \| 2 baths \| 1,284 sq.ft.	$349,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 3.81% Airbnb Rental Income: $2503 Traditional Rental Income: $1906 Airbnb ROI: 3.79% Traditional ROI: 3.81%
604 Chadbury Way Kissimmee, FL Welcome to this beautiful LAKEVIEW POOL HOME with 4 bed/3 bath FURNISHED located in Reming...	4 beds \| 3 baths \| 1,719 sq.ft.	$419,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.66% Airbnb Rental Income: $3036 Traditional Rental Income: $2102 Airbnb ROI: 3.27% Traditional ROI: 2.66%
4647 Cumbrian Lakes Dr Kissimmee, FL Exceptional turnkey opportunity in a highly desirable, gated short-term rental community i...	4 beds \| 3 baths \| 1,830 sq.ft.	$479,999	Airbnb cash on cash: 2.24% Traditional cash on cash: 2.45% Airbnb Rental Income: $3036 Traditional Rental Income: $2435 Airbnb ROI: 2.24% Traditional ROI: 2.45%
7664 Comrow St #202 Kissimmee, FL Fabulous fully furnished luxury Disney area 2-bed, 2-bath Mickey themed condo in the Gated...	2 beds \| 2 baths \| 1,081 sq.ft.	$275,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 0.64% Airbnb Rental Income: $2090 Traditional Rental Income: $1553 Airbnb ROI: 0.64% Traditional ROI: 0.64%
8050 King Palm Cir Kissimmee, FL Welcome to the Guard gated Windsor Palms Resort style Community to escape to paradise. Thi...	4 beds \| 2 baths \| 1,567 sq.ft.	$495,000	Airbnb cash on cash: 1% Traditional cash on cash: 2.26% Airbnb Rental Income: $3036 Traditional Rental Income: $2922 Airbnb ROI: 1% Traditional ROI: 2.26%
2300 Eagle Talon Ct Kissimmee, FL Priced to give the next owner the freedom to walk in and make it exactly what they want, t...	4 beds \| 3 baths \| 3,591 sq.ft.	$450,000	Airbnb cash on cash: 2.12% Traditional cash on cash: 3.13% Airbnb Rental Income: $3036 Traditional Rental Income: $2764 Airbnb ROI: 2.12% Traditional ROI: 3.13%
8859 Candy Palm Rd Kissimmee, FL Under contract-accepting backup offers. MUST SEE! Water view. Own a piece of paradise with...	4 beds \| 3 baths \| 1,902 sq.ft.	$339,900	Airbnb cash on cash: 1.88% Traditional cash on cash: 3.25% Airbnb Rental Income: $3036 Traditional Rental Income: $2779 Airbnb ROI: 1.88% Traditional ROI: 3.25%
2310 Silver Palm Dr #104 Kissimmee, FL PROFESSIONALLY MANAGED with MANY Short Term Rentals! The Royal Retreat at Windsor Palms: Y...	2 beds \| 2 baths \| 1,022 sq.ft.	$234,900	Airbnb cash on cash: 1.24% Traditional cash on cash: 3.12% Airbnb Rental Income: $2090 Traditional Rental Income: $1969 Airbnb ROI: 1.24% Traditional ROI: 3.12%
2545 Renshaw St Kissimmee, FL Discover the perfect blend of comfort and convenience with this fully furnished 3-bedroom,...	3 beds \| 3 baths \| 1,440 sq.ft.	$419,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 1.87% Airbnb Rental Income: $2503 Traditional Rental Income: $2332 Airbnb ROI: 0.76% Traditional ROI: 1.87%
4504 Alberto Cir Kissimmee, FL Get $2,000 toward closing costs when you finance with our preferred lender. Act now and mo...	3 beds \| 2 baths \| 1,295 sq.ft.	$289,999	Airbnb cash on cash: 2.47% Traditional cash on cash: 3.52% Airbnb Rental Income: $2503 Traditional Rental Income: $2184 Airbnb ROI: 2.47% Traditional ROI: 3.52%
639 Mesilla Dr Kissimmee, FL Short term rental approved, no minimum lease period. Are looking for an immaculate home w...	3 beds \| 2 baths \| 2,033 sq.ft.	$309,900	Airbnb cash on cash: 4.37% Traditional cash on cash: 5.42% Airbnb Rental Income: $2503 Traditional Rental Income: $2202 Airbnb ROI: 4.37% Traditional ROI: 5.42%
2727 Sun Key Pl Kissimmee, FL Discover your dream getaway in the stunning Emerald Island Resort! This townhouse is locat...	3 beds \| 2 baths \| 1,291 sq.ft.	$294,900	Airbnb cash on cash: 1.69% Traditional cash on cash: 3.12% Airbnb Rental Income: $2503 Traditional Rental Income: $2296 Airbnb ROI: 1.69% Traditional ROI: 3.12%
2634 Corvette Ln Kissimmee, FL Discover Your Dream Getaway in Regal Oaks! This stunning and fully furnished 2-bedroom t...	2 beds \| 2 baths \| 1,350 sq.ft.	$285,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 3.18% Airbnb Rental Income: $2090 Traditional Rental Income: $2279 Airbnb ROI: 0.48% Traditional ROI: 3.18%
2918 Sunset Vista Blvd Kissimmee, FL Come see this beautiful 4 bedroom, 2 bathroom pool home in a gated community! This home co...	4 beds \| 2 baths \| 1,701 sq.ft.	$399,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 5.01% Airbnb Rental Income: $3036 Traditional Rental Income: $2787 Airbnb ROI: 3.82% Traditional ROI: 5.01%
4715 Flagler Beach Way Kissimmee, FL PRICED BELOW MARKET VALUE â MOTIVATED SELLER â EXCELLENT INVESTMENT OPPORTUNITY Wel...	3 beds \| 2 baths \| 1,286 sq.ft.	$269,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 4.09% Airbnb Rental Income: $2503 Traditional Rental Income: $2310 Airbnb ROI: 2.46% Traditional ROI: 4.09%
3032 Parkway Blvd #305 Kissimmee, FL Welcome to this beautifully remodeled 2-bedroom, 2-bathroom condo at 3032 Parkway Blvd #30...	2 beds \| 2 baths \| 937 sq.ft.	$160,000	Airbnb cash on cash: 3.71% Traditional cash on cash: 5.7% Airbnb Rental Income: $2090 Traditional Rental Income: $1857 Airbnb ROI: 3.71% Traditional ROI: 5.7%
225 Celebration Pl #117 Kissimmee, FL Welcome to Your Home Away from Home! This perfect retreat is a lovely fully furnished 2 Be...	2 beds \| 2 baths \| 1,265 sq.ft.	$210,000	Airbnb cash on cash: -2.16% Traditional cash on cash: 3.34% Airbnb Rental Income: $2090 Traditional Rental Income: $2648 Airbnb ROI: -2.16% Traditional ROI: 3.34%
4717 Flagler Beach Way Kissimmee, FL Amenities amenities amenities! Stunning home in the immaculate Terra Verde Resort. This mo...	3 beds \| 2 baths \| 1,286 sq.ft.	$304,900	Airbnb cash on cash: 2.69% Traditional cash on cash: 3.07% Airbnb Rental Income: $2503 Traditional Rental Income: $2005 Airbnb ROI: 2.69% Traditional ROI: 3.07%
2971 Banana Palm Dr Kissimmee, FL PRICED TO SELL! THEMED BEDROOMS AND EXTENDED DECK! Welcome to Paradise Palms Resort! This ...	4 beds \| 3 baths \| 1,902 sq.ft.	$334,900	Airbnb cash on cash: 2.21% Traditional cash on cash: 3.38% Airbnb Rental Income: $3036 Traditional Rental Income: $2709 Airbnb ROI: 2.21% Traditional ROI: 3.38%
1144 Cambourne Dr Kissimmee, FL TO BE BUILT and UNDER CONSTRUCTION. Looking for a step up without breaking the budget??? W...	4 beds \| 2 baths \| 1,808 sq.ft.	$325,000	Airbnb cash on cash: 5.93% Traditional cash on cash: 5.12% Airbnb Rental Income: $3036 Traditional Rental Income: $2096 Airbnb ROI: 5.93% Traditional ROI: 5.12%
1025 Derbyshire Dr Kissimmee, FL Stop Buy! -Beautiful, move-in ready Pool home settled in almost a quarter of an acre. As y...	3 beds \| 2 baths \| 1,834 sq.ft.	$324,990	Airbnb cash on cash: 3.68% Traditional cash on cash: 6.62% Airbnb Rental Income: $2503 Traditional Rental Income: $2796 Airbnb ROI: 3.68% Traditional ROI: 6.62%
602 Mesilla Dr Kissimmee, FL Buy through Auction.com. This foreclosure property is a great opportunity to invest in thi...	3 beds \| 2 baths \| 1,771 sq.ft.	$289,900	Airbnb cash on cash: 2.23% Traditional cash on cash: 5.85% Airbnb Rental Income: $1684 Traditional Rental Income: $2203 Airbnb ROI: 2.23% Traditional ROI: 5.85%
5148 Adelaide Dr Kissimmee, FL Under Construction - Vacation in the Heart of Central Florida. Townhome features 4 bedroom...	4 beds \| 3 baths \| 1,782 sq.ft.	$364,900	Airbnb cash on cash: 3.8% Traditional cash on cash: 3.72% Airbnb Rental Income: $3036 Traditional Rental Income: $2312 Airbnb ROI: 3.8% Traditional ROI: 3.72%
157 Pompano Beach Dr Kissimmee, FL This stunning furnished townhouse features three spacious bedrooms, two full bathrooms, an...	3 beds \| 2 baths \| 1,286 sq.ft.	$290,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 3.9% Airbnb Rental Income: $2503 Traditional Rental Income: $2310 Airbnb ROI: 2.39% Traditional ROI: 3.9%
5134 Adelaide Dr Kissimmee, FL UNDER CONSTRUCTION. Dream Disney Vacation Townhouse! 4 bedrooms, 3.5 bathrooms & one car g...	4 beds \| 3 baths \| 1,782 sq.ft.	$375,000	Airbnb cash on cash: 3.65% Traditional cash on cash: 3.7% Airbnb Rental Income: $3036 Traditional Rental Income: $2357 Airbnb ROI: 3.65% Traditional ROI: 3.7%

Real Estate investment in Kissimmee, FL

There are 3,369 properties for sale in the city of Kissimmee . The median list price in Kissimmee is $349,241 and the average price per square foot is $176. In September 2026, the average monthly cash on cash return in Kissimmee is 3.00%. The average monthly rental income in Kissimmee is $1,989.

Kissimmee, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 3,369 investment properties available for sale in Kissimmee.

In 2026, the best neighborhood to buy investment property is Kissimmee.

The ROI for Long-Term is higher than the Short-Term in Kissimmee with average rental income of $1,989.

Your search for investment property begins and ends here

Investment Property for Sale in Kissimmee, FL

3016 Parkway Blvd #204

Kissimmee, FL

2 beds | 2 baths | 937 sq.ft.

$170,000

Airbnb cash on cash: 3.3%

Traditional cash on cash: 4.15%

Airbnb Rental Income: $2090

Traditional Rental Income: $1690

Airbnb ROI: 3.3%

Traditional ROI: 4.15%

719 Del Ray Dr

Kissimmee, FL

3 beds | 2 baths | 1,057 sq.ft.

$260,000

Airbnb cash on cash: 5.02%

Traditional cash on cash: 4.86%

Airbnb Rental Income: $2503

Traditional Rental Income: $1857

Airbnb ROI: 5.02%

Traditional ROI: 4.86%

1831 Windward Oaks Ct

Kissimmee, FL

5 beds | 3 baths | 2,813 sq.ft.

$539,900

Airbnb cash on cash: 5.01%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $4939

Traditional Rental Income: $3601

Airbnb ROI: 5.01%

Traditional ROI: 4.37%

3251 Pinewood Ct

Kissimmee, FL

3 beds | 2 baths | 2,404 sq.ft.

$449,900

Airbnb cash on cash: 2.45%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $2503

Traditional Rental Income: $2690

Airbnb ROI: 2.45%

Traditional ROI: 4.33%

725 Mabbette St

Kissimmee, FL

3 beds | 2 baths | 1,488 sq.ft.

$315,000

Airbnb cash on cash: 4.04%

Traditional cash on cash: 5.25%

Airbnb Rental Income: $2503

Traditional Rental Income: $2254

Airbnb ROI: 4.04%

Traditional ROI: 5.25%

202 Woodson Ct

Kissimmee, FL

5 beds | 3 baths | 3,744 sq.ft.

$595,000

Airbnb cash on cash: 4.97%

Traditional cash on cash: 6.73%

Airbnb Rental Income: $4939

Traditional Rental Income: $4904

Airbnb ROI: 4.97%

Traditional ROI: 6.73%

5004 LAGUNA BAY Circle #54

Kissimmee, FL

3 beds | 2 baths | 1,220 sq.ft.

$229,900

Airbnb cash on cash: 3.28%

Traditional cash on cash: 4.83%

Airbnb Rental Income: $2503

Traditional Rental Income: $2235

Airbnb ROI: 3.28%

Traditional ROI: 4.83%

4558 Ada Ln

Kissimmee, FL

3 beds | 2 baths | 1,295 sq.ft.

$298,900

Airbnb cash on cash: 2.6%

Traditional cash on cash: 1.96%

Airbnb Rental Income: $2503

Traditional Rental Income: $1717

Airbnb ROI: 2.6%