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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1204 Cumbrian Lakes Ct Kissimmee, FL Welcome to your dream home, where luxury and serenity harmoniously blend within a charming...	4 beds \| 3 baths \| 2,636 sq.ft.	$485,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 6.4% Airbnb Rental Income: $1735 Traditional Rental Income: $4284 Airbnb ROI: -0.28% Traditional ROI: 6.4%
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.	$380,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 3.18% Airbnb Rental Income: $1735 Traditional Rental Income: $2406 Airbnb ROI: -0.04% Traditional ROI: 3.18%
1053 Oak Pond Dr #302 Kissimmee, FL Welcome to Celebration! Third level condo in an elevator building with covered balcony and...	3 beds \| 2 baths \| 1,430 sq.ft.	$449,900	Airbnb cash on cash: -2.21% Traditional cash on cash: -0.6% Airbnb Rental Income: $1472 Traditional Rental Income: $1715 Airbnb ROI: -2.21% Traditional ROI: -0.6%
1469 Swan Pl Kissimmee, FL One or more photo(s) has been virtually staged. Welcome home to this well maintained 3-bed...	3 beds \| 2 baths \| 1,202 sq.ft.	$244,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 5.57% Airbnb Rental Income: $1472 Traditional Rental Income: $1930 Airbnb ROI: 1.7% Traditional ROI: 5.57%
1822 Trophy Bass Way Kissimmee, FL Waterfront home in Shingle Creek Reserve, where Florida living meets comfort and convenien...	4 beds \| 3 baths \| 2,798 sq.ft.	$514,900	Airbnb cash on cash: -0.28% Traditional cash on cash: 4.03% Airbnb Rental Income: $1735 Traditional Rental Income: $3354 Airbnb ROI: -0.28% Traditional ROI: 4.03%
1230 Wright Cir #308 Kissimmee, FL Enter a storybook lifestyle in the town that Disney built, with this rare top-floor retrea...	2 beds \| 2 baths \| 1,345 sq.ft.	$450,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 2.19% Airbnb Rental Income: $1760 Traditional Rental Income: $2073 Airbnb ROI: 0.31% Traditional ROI: 2.19%
5004 Laguna Bay Cir #47 Kissimmee, FL Experience the ultimate Central Florida lifestyle with this exceptional and fully furnishe...	3 beds \| 2 baths \| 1,220 sq.ft.	$269,999	Airbnb cash on cash: -0.41% Traditional cash on cash: 2.19% Airbnb Rental Income: $1472 Traditional Rental Income: $1701 Airbnb ROI: -0.41% Traditional ROI: 2.19%
225 Celebration Pl #129 Kissimmee, FL 1 Bedroom, 1 Bathroom condo suite located in the heart of Celebration and just minutes fro...	1 beds \| 1 baths \| 754 sq.ft.	$139,900	Airbnb cash on cash: 3.9% Traditional cash on cash: 4.29% Airbnb Rental Income: $2379 Traditional Rental Income: $1847 Airbnb ROI: 3.9% Traditional ROI: 4.29%
2031 PIEDMONT LANE Kissimmee, FL Under contract-accepting backup offers. Welcome home to this SPACIOUS 4-bedroom, 3.5-bath ...	4 beds \| 4 baths \| 1,760 sq.ft.	$275,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 6.97% Airbnb Rental Income: $1735 Traditional Rental Income: $2721 Airbnb ROI: 1.33% Traditional ROI: 6.97%
911 Lake Berkley Dr Kissimmee, FL Welcome to 911 Lake Berkley, a beautifully maintained home located in the highly desirable...	4 beds \| 3 baths \| 1,542 sq.ft.	$399,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 4.02% Airbnb Rental Income: $1735 Traditional Rental Income: $2571 Airbnb ROI: 0.51% Traditional ROI: 4.02%
2023 GRAND OAK DRIVE Kissimmee, FL Under contract-accepting backup offers. Short Sale. Short Sale Approved This stunning ...	4 beds \| 4 baths \| 1,760 sq.ft.	$270,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 4.95% Airbnb Rental Income: $1735 Traditional Rental Income: $2238 Airbnb ROI: 1.1% Traditional ROI: 4.95%
2239 Santa Lucia St Kissimmee, FL Centrally located and move-in ready, this 3 bedroom, 2 bath home features an open floor pl...	3 beds \| 2 baths \| 1,059 sq.ft.	$326,497	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.86% Airbnb Rental Income: $1472 Traditional Rental Income: $1982 Airbnb ROI: 0.79% Traditional ROI: 3.86%
4743 Vero Beach Pl Kissimmee, FL Escape to 4743 Vero Beach Place, a beautifully refreshed three-bedroom, two-and-a-half-bat...	3 beds \| 2 baths \| 1,286 sq.ft.	$294,950	Airbnb cash on cash: 0.42% Traditional cash on cash: 3.74% Airbnb Rental Income: $1472 Traditional Rental Income: $1960 Airbnb ROI: 0.42% Traditional ROI: 3.74%
2711 Star Grass Cir Kissimmee, FL FOR SALE: - SELLER GIVING CONCESSION TOWARDS CLOSING COST. PLEASE CONTACT FOR MORE DETAILS...	4 beds \| 2 baths \| 2,528 sq.ft.	$420,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 4.1% Airbnb Rental Income: $1735 Traditional Rental Income: $3109 Airbnb ROI: -0.6% Traditional ROI: 4.1%
3523 Forest Park Dr Kissimmee, FL Experience elevated living in this beautifully upgraded two-story home in the prestigious,...	4 beds \| 2 baths \| 2,123 sq.ft.	$580,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 2.42% Airbnb Rental Income: $1735 Traditional Rental Income: $2553 Airbnb ROI: 0.02% Traditional ROI: 2.42%
2703 Manesty Ln Kissimmee, FL Explore this beautifully furnished, updated and Disney themed home in the sought-after Win...	4 beds \| 4 baths \| 1,824 sq.ft.	$590,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 3.09% Airbnb Rental Income: $1735 Traditional Rental Income: $3059 Airbnb ROI: -0.18% Traditional ROI: 3.09%
2660 BREAKER LANE Kissimmee, FL Under contract-accepting backup offers. Rare Waterfront Opportunity with Private Dock and ...	4 beds \| 4 baths \| 2,660 sq.ft.	$560,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 4.61% Airbnb Rental Income: $1735 Traditional Rental Income: $3772 Airbnb ROI: -0.2% Traditional ROI: 4.61%
8962 Cuban Palm Rd Kissimmee, FL REDUCED! Welcome to Paradise! This fully furnished, turnkey 4-bedroom, 3-bathroom, two-st...	4 beds \| 3 baths \| 1,902 sq.ft.	$389,995	Airbnb cash on cash: -1.46% Traditional cash on cash: 2.48% Airbnb Rental Income: $1735 Traditional Rental Income: $2700 Airbnb ROI: -1.46% Traditional ROI: 2.48%
7671 Comrow St #304 Kissimmee, FL Welcome to this beautifully decorated and fully furnished 3-bedroom condo, ideally located...	3 beds \| 2 baths \| 1,450 sq.ft.	$315,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 4.18% Airbnb Rental Income: $1472 Traditional Rental Income: $2046 Airbnb ROI: 0.78% Traditional ROI: 4.18%
2310 Silver Palm Dr #104 Kissimmee, FL The Royal Retreat at Windsor Palms: Your Ultimate Orlando Oasis! Prepare to be captivated ...	2 beds \| 2 baths \| 1,022 sq.ft.	$234,900	Airbnb cash on cash: -1.57% Traditional cash on cash: 2.6% Airbnb Rental Income: $1341 Traditional Rental Income: $1853 Airbnb ROI: -1.57% Traditional ROI: 2.6%
230 Grouper Ct Kissimmee, FL Welcome to this 4 bedroom 2 bath , beautiful home, where spacious living meets thoughtful ...	4 beds \| 2 baths \| 1,850 sq.ft.	$322,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 5.17% Airbnb Rental Income: $2403 Traditional Rental Income: $2261 Airbnb ROI: 3.69% Traditional ROI: 5.17%
8204 Fan Palm Way Kissimmee, FL Upgraded home located in the resort community of Windsor Palms , a few short miles to Disn...	3 beds \| 2 baths \| 1,664 sq.ft.	$395,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 1.88% Airbnb Rental Income: $1472 Traditional Rental Income: $2050 Airbnb ROI: -0.82% Traditional ROI: 1.88%
141 Marabella Loop Kissimmee, FL See the FULL-LENGTH VIDEO on Tour Link 1.â¦ Enjoy the GREAT LOCATION & CONVENIENCE of...	3 beds \| 2 baths \| 1,786 sq.ft.	$299,999	Airbnb cash on cash: 2.43% Traditional cash on cash: 5.95% Airbnb Rental Income: $2193 Traditional Rental Income: $2631 Airbnb ROI: 2.43% Traditional ROI: 5.95%
235 Goldenrain Dr #102 Kissimmee, FL RARE FIND!!! GORGEOUS 1ST FLOOR NEWLY UPDATED 3-BEDROOM, 3-BATHROOM CORNER UNIT STEPS AWAY...	3 beds \| 3 baths \| 1,612 sq.ft.	$424,990	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.65% Airbnb Rental Income: $1472 Traditional Rental Income: $2435 Airbnb ROI: 0.14% Traditional ROI: 3.65%
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.	$314,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 2.96% Airbnb Rental Income: $1341 Traditional Rental Income: $2136 Airbnb ROI: -1.13% Traditional ROI: 2.96%
1400 Celebration Ave #102 Kissimmee, FL This is your chance to live in this amazing Community Artisan Park. Welcome to your future...	2 beds \| 2 baths \| 1,210 sq.ft.	$370,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 2.55% Airbnb Rental Income: $1760 Traditional Rental Income: $1878 Airbnb ROI: 0.82% Traditional ROI: 2.55%
3331 Whitestone Cir #201 Kissimmee, FL One or more photo(s) has been virtually staged. PRICE REDUCED FOR A NEW OWNER TO START ENJ...	3 beds \| 2 baths \| 1,495 sq.ft.	$240,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 5.01% Airbnb Rental Income: $1472 Traditional Rental Income: $2246 Airbnb ROI: -0.32% Traditional ROI: 5.01%
225 Celebration Pl #117 Kissimmee, FL Welcome to Your Home Away from Home! This perfect retreat is a lovely fully furnished 2 B...	2 beds \| 2 baths \| 1,265 sq.ft.	$210,000	Airbnb cash on cash: -4.1% Traditional cash on cash: -0.55% Airbnb Rental Income: $1627 Traditional Rental Income: $1874 Airbnb ROI: -4.1% Traditional ROI: -0.55%
720 BASIN DRIVE Kissimmee, FL One or more photo(s) has been virtually staged. Wake up to breathtaking sunsets and embrac...	3 beds \| 3 baths \| 2,491 sq.ft.	$950,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 2.44% Airbnb Rental Income: $1472 Traditional Rental Income: $3533 Airbnb ROI: -0.38% Traditional ROI: 2.44%
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.	$319,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 4.18% Airbnb Rental Income: $1472 Traditional Rental Income: $2002 Airbnb ROI: 0.96% Traditional ROI: 4.18%
404 Rio Grande Ct Kissimmee, FL Beautiful 4-bedroom, 2-bathroom home is now available for sale in Poinciana! Featuring stu...	4 beds \| 2 baths \| 1,871 sq.ft.	$345,000	Airbnb cash on cash: 3.78% Traditional cash on cash: 5.09% Airbnb Rental Income: $2403 Traditional Rental Income: $2236 Airbnb ROI: 3.78% Traditional ROI: 5.09%
3208 Olivia Breeze Dr Kissimmee, FL Welcome to Concorde Estates â where comfort meets convenience! Step inside this bright a...	3 beds \| 2 baths \| 2,037 sq.ft.	$345,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 3.75% Airbnb Rental Income: $1472 Traditional Rental Income: $2476 Airbnb ROI: -0.69% Traditional ROI: 3.75%
763 Rolfe St Kissimmee, FL Located in an established Kissimmee neighborhood, this 3-bedroom, 2-bath single-family hom...	3 beds \| 2 baths \| 1,088 sq.ft.	$256,500	Airbnb cash on cash: 1.74% Traditional cash on cash: 5.43% Airbnb Rental Income: $1472 Traditional Rental Income: $1933 Airbnb ROI: 1.74% Traditional ROI: 5.43%
4004 Santa Maria Dr #105 Kissimmee, FL Beautiful 3-bedroom, 2-bath townhome- located in the guard-gated community of Venetian Bay...	3 beds \| 2 baths \| 1,296 sq.ft.	$225,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 3.64% Airbnb Rental Income: $1472 Traditional Rental Income: $1972 Airbnb ROI: -0.74% Traditional ROI: 3.64%
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.	$274,900	Airbnb cash on cash: 1.72% Traditional cash on cash: 5.41% Airbnb Rental Income: $1472 Traditional Rental Income: $1995 Airbnb ROI: 1.72% Traditional ROI: 5.41%
2472 WINFIELD DRIVE Kissimmee, FL Under contract-accepting backup offers. Beautiful 4-Bedroom Pool Home in Kissimmee! Step i...	4 beds \| 2 baths \| 2,023 sq.ft.	$390,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 5.72% Airbnb Rental Income: $1735 Traditional Rental Income: $2904 Airbnb ROI: 1.22% Traditional ROI: 5.72%
145 Pompei Dr Kissimmee, FL JUST REDUCED â $289,000 \| Priced to Move Quickly This is the opportunity savvy buyers h...	3 beds \| 2 baths \| 1,438 sq.ft.	$279,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 5.04% Airbnb Rental Income: $1472 Traditional Rental Income: $2174 Airbnb ROI: 0.87% Traditional ROI: 5.04%
8917 LEGACY COURT #17 306 Kissimmee, FL Under contract-accepting backup offers. Priced to sell !! Rare & Exquisite Remodeled Parti...	2 beds \| 2 baths \| 1,048 sq.ft.	$220,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 2.69% Airbnb Rental Income: $1341 Traditional Rental Income: $1715 Airbnb ROI: -1.09% Traditional ROI: 2.69%
225 Celebration Pl #427 Kissimmee, FL ***NEW UPDATED, MODERN FURNITURE PACKAGE*** This stunning, fully furnished 2-bedroom, ...	2 beds \| 2 baths \| 1,206 sq.ft.	$245,897	Airbnb cash on cash: -3.07% Traditional cash on cash: 0.56% Airbnb Rental Income: $1627 Traditional Rental Income: $2009 Airbnb ROI: -3.07% Traditional ROI: 0.56%
4722 Vero Beach Pl Kissimmee, FL OWNER MOTIVATED â INCOME-GENERATING Townhome in Terra Verde Resort â Just Minutes from...	3 beds \| 2 baths \| 1,286 sq.ft.	$314,900	Airbnb cash on cash: 0.39% Traditional cash on cash: 3.81% Airbnb Rental Income: $1472 Traditional Rental Income: $2051 Airbnb ROI: 0.39% Traditional ROI: 3.81%

Real Estate investment in Kissimmee, FL

There are 3,869 properties for sale in the city of Kissimmee . The median list price in Kissimmee is $389,000 and the average price per square foot is $197. In February 2026, the average monthly cash on cash return in Kissimmee is 3.00%. The average monthly rental income in Kissimmee is $2,302.

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

There are 3,869 investment properties available for sale in Kissimmee.

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

The ROI for Short-Term is higher than the Long-Term in Kissimmee with average rental income of $1,735.

Your search for investment property begins and ends here

Investment Property for Sale in Kissimmee, FL

1204 Cumbrian Lakes Ct

Kissimmee, FL

4 beds | 3 baths | 2,636 sq.ft.

$485,000

Airbnb cash on cash: -0.28%

Traditional cash on cash: 6.4%

Airbnb Rental Income: $1735

Traditional Rental Income: $4284

Airbnb ROI: -0.28%

Traditional ROI: 6.4%

4577 Alberto Cir

Kissimmee, FL

4 beds | 3 baths | 1,636 sq.ft.

$380,000

Airbnb cash on cash: -0.04%

Traditional cash on cash: 3.18%

Airbnb Rental Income: $1735

Traditional Rental Income: $2406

Airbnb ROI: -0.04%

Traditional ROI: 3.18%

1053 Oak Pond Dr #302

Kissimmee, FL

3 beds | 2 baths | 1,430 sq.ft.

$449,900

Airbnb cash on cash: -2.21%

Traditional cash on cash: -0.6%

Airbnb Rental Income: $1472

Traditional Rental Income: $1715

Airbnb ROI: -2.21%

Traditional ROI: -0.6%

1469 Swan Pl

Kissimmee, FL

3 beds | 2 baths | 1,202 sq.ft.

$244,000

Airbnb cash on cash: 1.7%

Traditional cash on cash: 5.57%

Airbnb Rental Income: $1472

Traditional Rental Income: $1930

Airbnb ROI: 1.7%

Traditional ROI: 5.57%

1822 Trophy Bass Way

Kissimmee, FL

4 beds | 3 baths | 2,798 sq.ft.

$514,900

Airbnb cash on cash: -0.28%

Traditional cash on cash: 4.03%

Airbnb Rental Income: $1735

Traditional Rental Income: $3354

Airbnb ROI: -0.28%

Traditional ROI: 4.03%

1230 Wright Cir #308

Kissimmee, FL

2 beds | 2 baths | 1,345 sq.ft.

$450,000

Airbnb cash on cash: 0.31%

Traditional cash on cash: 2.19%

Airbnb Rental Income: $1760

Traditional Rental Income: $2073

Airbnb ROI: 0.31%

Traditional ROI: 2.19%

5004 Laguna Bay Cir #47

Kissimmee, FL

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

$269,999

Airbnb cash on cash: -0.41%

Traditional cash on cash: 2.19%

Airbnb Rental Income: $1472

Traditional Rental Income: $1701

Airbnb ROI: -0.41%

Traditional ROI: 2.19%

225 Celebration Pl #129

Kissimmee, FL

1 beds | 1 baths | 754 sq.ft.

$139,900

Airbnb cash on cash: 3.9%

Traditional cash on cash: 4.29%

Airbnb Rental Income: $2379

Traditional Rental Income: $1847

Airbnb ROI: 3.9%