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
719 DEL RAY DRIVE Kissimmee, FL This home was recently improved & is priced to sell! Kitchen has been fully remodeled, in...	3 beds \| 2 baths \| 1,167 sq.ft.	$259,000	Airbnb cash on cash: 7.61% Traditional cash on cash: 4.68% Airbnb Rental Income: $3314 Traditional Rental Income: $1857 Airbnb ROI: 7.61% Traditional ROI: 4.68%
2205 Eagles Landing Way Kissimmee, FL From the moment you pull through the gates of Ashley Reserve, 2205 Eagles Landing Way feel...	4 beds \| 4 baths \| 3,541 sq.ft.	$775,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 3.71% Airbnb Rental Income: $3682 Traditional Rental Income: $4554 Airbnb ROI: 1.4% Traditional ROI: 3.71%
99 AUBURN DRIVE Kissimmee, FL Under contract-accepting backup offers. Beautifully maintained home in Solivita. Gorgeous ...	2 beds \| 2 baths \| 1,491 sq.ft.	$269,900	Airbnb cash on cash: 3.91% Traditional cash on cash: 4.3% Airbnb Rental Income: $2758 Traditional Rental Income: $2209 Airbnb ROI: 3.91% Traditional ROI: 4.3%
167 CASTAWAY BEACH WAY Kissimmee, FL Discover your dream home tucked inside the beautifully maintained community of Terre Verde...	4 beds \| 2 baths \| 1,940 sq.ft.	$385,000	Airbnb cash on cash: 4.5% Traditional cash on cash: 3.82% Airbnb Rental Income: $3682 Traditional Rental Income: $2634 Airbnb ROI: 4.5% Traditional ROI: 3.82%
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.	$255,000	Airbnb cash on cash: 5.67% Traditional cash on cash: 2.4% Airbnb Rental Income: $3314 Traditional Rental Income: $1787 Airbnb ROI: 5.67% Traditional ROI: 2.4%
4577 ALBERTO CIRCLE 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: 4.51% Traditional cash on cash: 3.18% Airbnb Rental Income: $3682 Traditional Rental Income: $2406 Airbnb ROI: 4.51% Traditional ROI: 3.18%
2452 SWEETWATER CLUB CIRCLE #27 Kissimmee, FL Your Disney-Themed Fairytale Awaits! Discover this turnkey, fully furnished, Disney-themed...	3 beds \| 2 baths \| 1,220 sq.ft.	$229,900	Airbnb cash on cash: 6.74% Traditional cash on cash: 3.44% Airbnb Rental Income: $3314 Traditional Rental Income: $1855 Airbnb ROI: 6.74% Traditional ROI: 3.44%
3827 BAY CLUB CIR #204 Kissimmee, FL Turnkey Kissimmee Condo â Minutes from Disney! Spacious 2-bedroom, 2-bath condo in the ...	2 beds \| 2 baths \| 910 sq.ft.	$195,000	Airbnb cash on cash: 6.4% Traditional cash on cash: 4.18% Airbnb Rental Income: $2758 Traditional Rental Income: $1698 Airbnb ROI: 6.4% Traditional ROI: 4.18%
3055 ASHLAND LANE N Kissimmee, FL Welcome to 3055 Ashland Lane Nâan oversized 3-bedroom, 2.5-bathroom townhome offering ne...	3 beds \| 3 baths \| 1,957 sq.ft.	$320,000	Airbnb cash on cash: 5.26% Traditional cash on cash: 5.09% Airbnb Rental Income: $3314 Traditional Rental Income: $2523 Airbnb ROI: 5.26% Traditional ROI: 5.09%
2721 N POINCIANA BOULEVARD #163 Kissimmee, FL One or more photo(s) has been virtually staged. Discover the perfect blend of convenience,...	3 beds \| 2 baths \| 1,287 sq.ft.	$205,000	Airbnb cash on cash: 7.29% Traditional cash on cash: 4.33% Airbnb Rental Income: $3314 Traditional Rental Income: $1997 Airbnb ROI: 7.29% Traditional ROI: 4.33%
225 CELEBRATION PLACE #233 Kissimmee, FL Located in Celebration, the picturesque Disney-styled town with shops, dining, and grocery...	1 beds \| 1 baths \| 751 sq.ft.	$141,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 3.2% Airbnb Rental Income: $2286 Traditional Rental Income: $1724 Airbnb ROI: 3.15% Traditional ROI: 3.2%
2108 SHANNON LAKES BOULEVARD Kissimmee, FL Just Listed â 4 Bed \| 2 Bath \| Corner Lot! Looking for space, style, and a great locati...	4 beds \| 2 baths \| 1,842 sq.ft.	$375,000	Airbnb cash on cash: 5.5% Traditional cash on cash: 4.5% Airbnb Rental Income: $3682 Traditional Rental Income: $2527 Airbnb ROI: 5.5% Traditional ROI: 4.5%
1958 COMMANDER WAY Kissimmee, FL Welcome to this 3-bedroom, 2-bathroom home nestled in Shingle Creek Reserve at The Oaks co...	3 beds \| 2 baths \| 1,636 sq.ft.	$335,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 4.2% Airbnb Rental Income: $3314 Traditional Rental Income: $2242 Airbnb ROI: 5.25% Traditional ROI: 4.2%
1010 LAS FUENTES DRIVE Kissimmee, FL Welcome to Bella Vida Resort Living! This beautifully maintained 3-bedroom, 2.5-bath townh...	3 beds \| 3 baths \| 1,295 sq.ft.	$310,000	Airbnb cash on cash: 4.2% Traditional cash on cash: 2.75% Airbnb Rental Income: $3314 Traditional Rental Income: $2150 Airbnb ROI: 4.2% Traditional ROI: 2.75%
3561 S Orange Blossom Trail Kissimmee, FL Thus property is a fantastic opportunity for investors or first-time buyers! This charming...	2 beds \| 1 baths \| 1,160 sq.ft.	$600,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 1.43% Airbnb Rental Income: $2758 Traditional Rental Income: $1767 Airbnb ROI: 2.04% Traditional ROI: 1.43%
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: 7.47% Traditional cash on cash: 4.95% Airbnb Rental Income: $3682 Traditional Rental Income: $2238 Airbnb ROI: 7.47% Traditional ROI: 4.95%
123 Moss Bluff Road Kissimmee, FL This inviting 3-bedroom, 2-bathroom home is tucked away in the peaceful community of Count...	3 beds \| 2 baths \| 1,547 sq.ft.	$384,900	Airbnb cash on cash: 4.82% Traditional cash on cash: 3.73% Airbnb Rental Income: $3314 Traditional Rental Income: $2178 Airbnb ROI: 4.82% Traditional ROI: 3.73%
2649 CROWN COURT #2649 Kissimmee, FL Back on the Market!!! Motivated Seller!!! Priced at Appraised Value! Don't miss this secon...	3 beds \| 3 baths \| 1,350 sq.ft.	$189,900	Airbnb cash on cash: 9.23% Traditional cash on cash: 7.75% Airbnb Rental Income: $3314 Traditional Rental Income: $2306 Airbnb ROI: 9.23% Traditional ROI: 7.75%
4743 VERO BEACH PLACE Kissimmee, FL Escape to 4743 Vero Beach Place, a beautifully refreshed three-bedroom, two-and-a-half-bat...	3 beds \| 3 baths \| 1,286 sq.ft.	$294,950	Airbnb cash on cash: 5.95% Traditional cash on cash: 3.74% Airbnb Rental Income: $3314 Traditional Rental Income: $1960 Airbnb ROI: 5.95% Traditional ROI: 3.74%
8063 KING PALM CIRCLE Kissimmee, FL This fully furnished, 3-bedroom, 2-bathroom home is an ideal investment opportunity or vac...	3 beds \| 2 baths \| 1,664 sq.ft.	$415,000	Airbnb cash on cash: 3.55% Traditional cash on cash: 3.26% Airbnb Rental Income: $3314 Traditional Rental Income: $2463 Airbnb ROI: 3.55% Traditional ROI: 3.26%
8001 ARROW CREEK ROAD Kissimmee, FL Under contract-accepting backup offers. HUGE PRICE DROP! Welcome to Your Dream Oasis in In...	4 beds \| 3 baths \| 1,791 sq.ft.	$449,900	Airbnb cash on cash: 4.18% Traditional cash on cash: 4.16% Airbnb Rental Income: $3682 Traditional Rental Income: $2869 Airbnb ROI: 4.18% Traditional ROI: 4.16%
8575 BAY LILLY LOOP Kissimmee, FL Welcome to 8575 Bay Lilly Loop, a beautifully maintained townhome located in the highly so...	3 beds \| 3 baths \| 1,295 sq.ft.	$310,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 2.71% Airbnb Rental Income: $3314 Traditional Rental Income: $2133 Airbnb ROI: 4.22% Traditional ROI: 2.71%
8564 BAY LILLY LOOP Kissimmee, FL Under contract-accepting backup offers. Turnkey Investment or Dream Vacation Home! Welcome...	3 beds \| 3 baths \| 1,295 sq.ft.	$275,000	Airbnb cash on cash: 5.05% Traditional cash on cash: 3.57% Airbnb Rental Income: $3314 Traditional Rental Income: $2190 Airbnb ROI: 5.05% Traditional ROI: 3.57%
2785 ALMATON LOOP #202 Kissimmee, FL Great opportunity to get in to the Windsor Hills community! This 2-bedroom 2-bathroom cond...	2 beds \| 2 baths \| 1,081 sq.ft.	$277,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 2.87% Airbnb Rental Income: $2758 Traditional Rental Income: $1826 Airbnb ROI: 3.95% Traditional ROI: 2.87%
8962 CUBAN PALM ROAD Kissimmee, FL Welcome to Paradise! This fully furnished, turnkey 4-bedroom, 3-bathroom, two-story townho...	4 beds \| 3 baths \| 1,902 sq.ft.	$399,995	Airbnb cash on cash: 2.87% Traditional cash on cash: 2.4% Airbnb Rental Income: $3682 Traditional Rental Income: $2700 Airbnb ROI: 2.87% Traditional ROI: 2.4%
7671 Comrow Street #304 Kissimmee, FL Welcome to this beautifully decorated and fully furnished 3-bedroom condo, ideally located...	3 beds \| 2 baths \| 1,450 sq.ft.	$329,000	Airbnb cash on cash: 5.67% Traditional cash on cash: 3.97% Airbnb Rental Income: $3314 Traditional Rental Income: $2046 Airbnb ROI: 5.67% Traditional ROI: 3.97%
4504 ALBERTO CIRCLE Kissimmee, FL Get $2,000 toward closing costs when you finance with our preferred lender. Act now and mo...	3 beds \| 3 baths \| 1,295 sq.ft.	$360,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 2.35% Airbnb Rental Income: $3314 Traditional Rental Income: $2079 Airbnb ROI: 3.81% Traditional ROI: 2.35%
8118 FAN PALM WAY Kissimmee, FL Welcome to your turnkey investment opportunity in the highly sought-after guard gated reso...	4 beds \| 2 baths \| 1,567 sq.ft.	$415,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.12% Airbnb Rental Income: $3682 Traditional Rental Income: $2426 Airbnb ROI: 4.28% Traditional ROI: 3.12%
2787 LIDO KEY DRIVE Kissimmee, FL This gorgeous and fully-furnished home is ready for you to live the resort lifestyle full-...	4 beds \| 3 baths \| 1,960 sq.ft.	$460,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 2.73% Airbnb Rental Income: $3682 Traditional Rental Income: $2746 Airbnb ROI: 3.04% Traditional ROI: 2.73%
4708 Vero Beach Place Kissimmee, FL Welcome to your dream getaway or income-producing gem in the heart of resort-style living!...	4 beds \| 3 baths \| 1,636 sq.ft.	$416,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 3.68% Airbnb Rental Income: $3682 Traditional Rental Income: $2369 Airbnb ROI: 4.99% Traditional ROI: 3.68%
2950 LUCAYAN HARBOUR CIRCLE #105 Kissimmee, FL Discover your perfect getaway in the desirable Lucaya Village Resort, where convenience, e...	4 beds \| 3 baths \| 1,694 sq.ft.	$329,900	Airbnb cash on cash: 4.79% Traditional cash on cash: 2.75% Airbnb Rental Income: $3682 Traditional Rental Income: $2246 Airbnb ROI: 4.79% Traditional ROI: 2.75%
3 TROPHY LANE Kissimmee, FL ?? VA Eligible â Kissimmee Cottage Near Shopping, Dining & Healthcare Step into this ...	4 beds \| 2 baths \| 1,578 sq.ft.	$255,000	Airbnb cash on cash: 9.32% Traditional cash on cash: 6.79% Airbnb Rental Income: $3682 Traditional Rental Income: $2270 Airbnb ROI: 9.32% Traditional ROI: 6.79%
235 Goldenrain Drive #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.	$439,990	Airbnb cash on cash: 3.83% Traditional cash on cash: 3.49% Airbnb Rental Income: $3314 Traditional Rental Income: $2435 Airbnb ROI: 3.83% Traditional ROI: 3.49%
3156 Via Palma Lane Kissimmee, FL Turnkey 4BR/3.5BA corner townhouse in gated Villa Sol, offered fully furnishedâincluding...	4 beds \| 3 baths \| 1,980 sq.ft.	$379,000	Airbnb cash on cash: 4.27% Traditional cash on cash: 3.03% Airbnb Rental Income: $3682 Traditional Rental Income: $2436 Airbnb ROI: 4.27% Traditional ROI: 3.03%
2634 CORVETTE LANE Kissimmee, FL Discover Your Dream Getaway in Regal Oaks! This stunning and fully furnished 2-bedroom t...	2 beds \| 3 baths \| 1,350 sq.ft.	$314,000	Airbnb cash on cash: 2.97% Traditional cash on cash: 3.06% Airbnb Rental Income: $2758 Traditional Rental Income: $2136 Airbnb ROI: 2.97% Traditional ROI: 3.06%
720 BASIN DRIVE Kissimmee, FL Experience LAKE FRONT living and the ultimate Florida lifestyle in this stunning 3-bedroom...	3 beds \| 3 baths \| 2,491 sq.ft.	$980,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 2.37% Airbnb Rental Income: $3314 Traditional Rental Income: $3533 Airbnb ROI: 1.32% Traditional ROI: 2.37%
4717 FLAGLER BEACH WAY Kissimmee, FL Amenities amenities amenities! Stunning home in the immaculate Terra Verde Resort. This mo...	3 beds \| 3 baths \| 1,286 sq.ft.	$319,000	Airbnb cash on cash: 6.08% Traditional cash on cash: 4.18% Airbnb Rental Income: $3314 Traditional Rental Income: $2002 Airbnb ROI: 6.08% Traditional ROI: 4.18%
4529 ORCHARD GROVE ROAD Kissimmee, FL Welcome to this beautifully maintained 4-bedroom, 2-bath home in the heart of St. Cloudâ...	4 beds \| 2 baths \| 1,707 sq.ft.	$380,000	Airbnb cash on cash: 5.55% Traditional cash on cash: 3.97% Airbnb Rental Income: $3682 Traditional Rental Income: $2317 Airbnb ROI: 5.55% Traditional ROI: 3.97%
8702 KNIGHTSBRIDGE COURT #D Kissimmee, FL Welcome to 8702 Knightsbridge Court, Unit? D. With 1,357 square feet this bright and airy ...	3 beds \| 2 baths \| 1,357 sq.ft.	$250,000	Airbnb cash on cash: 6.97% Traditional cash on cash: 4.83% Airbnb Rental Income: $3314 Traditional Rental Income: $2068 Airbnb ROI: 6.97% Traditional ROI: 4.83%
1130 Sabine Lane Kissimmee, FL Welcome to this beautiful move-in ready home with 3 bedrooms and 2 bathrooms. This spectac...	3 beds \| 2 baths \| 1,487 sq.ft.	$289,000	Airbnb cash on cash: 7.13% Traditional cash on cash: 5.59% Airbnb Rental Income: $3314 Traditional Rental Income: $2154 Airbnb ROI: 7.13% Traditional ROI: 5.59%

Real Estate investment in Kissimmee, FL

There are 1,536 properties for sale in the city of Kissimmee . The median list price in Kissimmee is $366,500 and the average price per square foot is $202. In September 2025, the average monthly cash on cash return in Kissimmee is 4.00%. The average monthly rental income in Kissimmee is $2,414.

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

There are 1,536 investment properties available for sale in Kissimmee.

In 2025, 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 $3,314.

Your search for investment property begins and ends here

Investment Property for Sale in Kissimmee, FL

719 DEL RAY DRIVE

Kissimmee, FL

3 beds | 2 baths | 1,167 sq.ft.

$259,000

Airbnb cash on cash: 7.61%

Traditional cash on cash: 4.68%

Airbnb Rental Income: $3314

Traditional Rental Income: $1857

Airbnb ROI: 7.61%

Traditional ROI: 4.68%

2205 Eagles Landing Way

Kissimmee, FL

4 beds | 4 baths | 3,541 sq.ft.

$775,000

Airbnb cash on cash: 1.4%

Traditional cash on cash: 3.71%

Airbnb Rental Income: $3682

Traditional Rental Income: $4554

Airbnb ROI: 1.4%

Traditional ROI: 3.71%

99 AUBURN DRIVE

Kissimmee, FL

2 beds | 2 baths | 1,491 sq.ft.

$269,900

Airbnb cash on cash: 3.91%

Traditional cash on cash: 4.3%

Airbnb Rental Income: $2758

Traditional Rental Income: $2209

Airbnb ROI: 3.91%

Traditional ROI: 4.3%

167 CASTAWAY BEACH WAY

Kissimmee, FL

4 beds | 2 baths | 1,940 sq.ft.

$385,000

Airbnb cash on cash: 4.5%

Traditional cash on cash: 3.82%

Airbnb Rental Income: $3682

Traditional Rental Income: $2634

Airbnb ROI: 4.5%

Traditional ROI: 3.82%

5004 LAGUNA BAY CIRCLE #54

Kissimmee, FL

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

$255,000

Airbnb cash on cash: 5.67%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $3314

Traditional Rental Income: $1787

Airbnb ROI: 5.67%

Traditional ROI: 2.4%

4577 ALBERTO CIRCLE

Kissimmee, FL

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

$380,000

Airbnb cash on cash: 4.51%

Traditional cash on cash: 3.18%

Airbnb Rental Income: $3682

Traditional Rental Income: $2406

Airbnb ROI: 4.51%

Traditional ROI: 3.18%

2452 SWEETWATER CLUB CIRCLE #27

Kissimmee, FL

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

$229,900

Airbnb cash on cash: 6.74%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $3314

Traditional Rental Income: $1855

Airbnb ROI: 6.74%

Traditional ROI: 3.44%

3827 BAY CLUB CIR #204

Kissimmee, FL

2 beds | 2 baths | 910 sq.ft.

$195,000

Airbnb cash on cash: 6.4%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $2758

Traditional Rental Income: $1698

Airbnb ROI: 6.4%