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 COURT Kissimmee, FL Welcome to your dream home, where luxury and serenity harmoniously blend within a charming...	4 beds \| 4 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%
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: -0.71% Traditional cash on cash: 2.4% Airbnb Rental Income: $1472 Traditional Rental Income: $1787 Airbnb ROI: -0.71% 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: -0.04% Traditional cash on cash: 3.18% Airbnb Rental Income: $1735 Traditional Rental Income: $2406 Airbnb ROI: -0.04% Traditional ROI: 3.18%
1469 SWAN PLACE Kissimmee, FL Seller is offering a $2,000 CLOSING COSTS CREDIT to the qualified buyer at closing! Welcom...	3 beds \| 2 baths \| 1,202 sq.ft.	$282,000	Airbnb cash on cash: 2.09% Traditional cash on cash: 5.44% Airbnb Rental Income: $1472 Traditional Rental Income: $1930 Airbnb ROI: 2.09% Traditional ROI: 5.44%
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.	$525,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 3.98% Airbnb Rental Income: $1735 Traditional Rental Income: $3354 Airbnb ROI: -0.29% Traditional ROI: 3.98%
5004 LAGUNA BAY CIRCLE #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 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: -6.77% Traditional cash on cash: 3.2% Airbnb Rental Income: $678 Traditional Rental Income: $1724 Airbnb ROI: -6.77% 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: 0.89% Traditional cash on cash: 4.5% Airbnb Rental Income: $1735 Traditional Rental Income: $2527 Airbnb ROI: 0.89% Traditional ROI: 4.5%
911 LAKE BERKLEY DRIVE Kissimmee, FL Welcome to 911 Lake Berkley, a beautifully maintained home located in the highly desirable...	4 beds \| 3 baths \| 1,542 sq.ft.	$405,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 3.95% Airbnb Rental Income: $1735 Traditional Rental Income: $2571 Airbnb ROI: 0.49% Traditional ROI: 3.95%
3561 S ORANGE BLOSSOM TRAIL Kissimmee, FL Under contract-accepting backup offers. Thus property is a fantastic opportunity for inves...	2 beds \| 1 baths \| 1,160 sq.ft.	$480,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 2.02% Airbnb Rental Income: $1341 Traditional Rental Income: $1767 Airbnb ROI: 0.16% Traditional ROI: 2.02%
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 STREET 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.	$330,497	Airbnb cash on cash: 0.77% Traditional cash on cash: 3.81% Airbnb Rental Income: $1472 Traditional Rental Income: $1982 Airbnb ROI: 0.77% Traditional ROI: 3.81%
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: 0.42% Traditional cash on cash: 3.74% Airbnb Rental Income: $1472 Traditional Rental Income: $1960 Airbnb ROI: 0.42% Traditional ROI: 3.74%
2703 MANESTY LANE 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%
8962 CUBAN PALM ROAD 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 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.	$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: 0.37% Traditional cash on cash: 4.53% Airbnb Rental Income: $1341 Traditional Rental Income: $1853 Airbnb ROI: 0.37% Traditional ROI: 4.53%
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.	$455,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 2.77% Airbnb Rental Income: $1735 Traditional Rental Income: $2746 Airbnb ROI: -0.73% Traditional ROI: 2.77%
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.	$398,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 3.89% Airbnb Rental Income: $1735 Traditional Rental Income: $2369 Airbnb ROI: 0.91% Traditional ROI: 3.89%
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.	$319,900	Airbnb cash on cash: -0.42% Traditional cash on cash: 2.87% Airbnb Rental Income: $1735 Traditional Rental Income: $2246 Airbnb ROI: -0.42% Traditional ROI: 2.87%
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.	$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 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: -1.02% Traditional cash on cash: 3.06% Airbnb Rental Income: $1341 Traditional Rental Income: $2136 Airbnb ROI: -1.02% Traditional ROI: 3.06%
4715 FLAGLER BEACH WAY Kissimmee, FL Welcome to this beautifully updated 3-bedroom, 2.5-bathroom townhome located in the sought...	3 beds \| 3 baths \| 1,286 sq.ft.	$309,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 3.85% Airbnb Rental Income: $1472 Traditional Rental Income: $2045 Airbnb ROI: 0.39% Traditional ROI: 3.85%
3331 WHITESTONE CIRCLE #201 Kissimmee, FL One or more photo(s) has been virtually staged. Spacious and well-maintained 3-bedroom, 2-...	3 beds \| 2 baths \| 1,495 sq.ft.	$255,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 4.66% Airbnb Rental Income: $1472 Traditional Rental Income: $2246 Airbnb ROI: -0.36% Traditional ROI: 4.66%
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: 0.96% Traditional cash on cash: 4.18% Airbnb Rental Income: $1472 Traditional Rental Income: $2002 Airbnb ROI: 0.96% Traditional ROI: 4.18%
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.	$278,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 6.17% Airbnb Rental Income: $1472 Traditional Rental Income: $2154 Airbnb ROI: 1.91% Traditional ROI: 6.17%
3208 OLIVIA BREEZE DRIVE 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%
4004 SANTA MARIA DRIVE #105 Kissimmee, FL Motivated Seller. Welcome to this beautifully renovated two-story townhouse-style condomin...	3 beds \| 2 baths \| 1,296 sq.ft.	$260,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 2.89% Airbnb Rental Income: $1472 Traditional Rental Income: $1972 Airbnb ROI: -0.92% Traditional ROI: 2.89%
2611 GALA ROAD N #105 Kissimmee, FL Welcome to Seven Dwarfs Community and your new two-story townhouse-style condominium. This...	3 beds \| 2 baths \| 1,296 sq.ft.	$265,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 0.57% Airbnb Rental Income: $1472 Traditional Rental Income: $1421 Airbnb ROI: -0.97% Traditional ROI: 0.57%
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 DRIVE 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.	$289,000	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 #306 Kissimmee, FL Priced to sell !! Rare & Exquisite Remodeled Partially FURNISHED 2-Bedroom 2 bath Condo in...	2 beds \| 2 baths \| 1,048 sq.ft.	$220,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 3.5% Airbnb Rental Income: $1341 Traditional Rental Income: $1715 Airbnb ROI: -0.27% Traditional ROI: 3.5%
4722 VERO BEACH PLACE Kissimmee, FL OWNER MOTIVATED â INCOME-GENERATING Townhome in Terra Verde Resort â Just Minutes from...	3 beds \| 3 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%
1990 MAJORCA DRIVE Kissimmee, FL Opportunity knocks - Act FAST - this amazing townhome is not going to last!! HUD Case #094...	4 beds \| 4 baths \| 2,102 sq.ft.	$390,000	Airbnb cash on cash: -1.55% Traditional cash on cash: 4.54% Airbnb Rental Income: $1735 Traditional Rental Income: $3484 Airbnb ROI: -1.55% Traditional ROI: 4.54%
2774 ALMATON LOOP #402 Kissimmee, FL Magic vacation home, fully furnished and well decorated. Conveniently located near Disney ...	2 beds \| 2 baths \| 1,081 sq.ft.	$279,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 2.21% Airbnb Rental Income: $1341 Traditional Rental Income: $1715 Airbnb ROI: -0.79% Traditional ROI: 2.21%
1516 RESOLUTE STREET Kissimmee, FL Situated on quiet mew in Celebrationâs Spring Lake neighborhood, this move-in-ready town...	2 beds \| 3 baths \| 1,655 sq.ft.	$499,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 2.48% Airbnb Rental Income: $1341 Traditional Rental Income: $2455 Airbnb ROI: -0.79% Traditional ROI: 2.48%
2732 OAKWATER DRIVE #101 Kissimmee, FL Welcome to this beautiful 2bedroom and 2 bathroom condo turn key fully furnished. REDUCED ...	2 beds \| 2 baths \| 1,015 sq.ft.	$260,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 3.82% Airbnb Rental Income: $1341 Traditional Rental Income: $2079 Airbnb ROI: -0.87% Traditional ROI: 3.82%
2161 QUEENSTOWN DRIVE Kissimmee, FL PRICE REDUCTION! Prepare to be enchanted by this turnkey, immaculately maintained three-be...	3 beds \| 2 baths \| 1,904 sq.ft.	$349,500	Airbnb cash on cash: 0.76% Traditional cash on cash: 4.84% Airbnb Rental Income: $1472 Traditional Rental Income: $2379 Airbnb ROI: 0.76% Traditional ROI: 4.84%
3050 PIRATES RETREAT COURT #207 Kissimmee, FL Welcome to your perfect getaway! This beautifully furnished 2-bedroom, 2-bath condo offers...	2 beds \| 2 baths \| 1,445 sq.ft.	$215,000	Airbnb cash on cash: -2.11% Traditional cash on cash: 3.44% Airbnb Rental Income: $1341 Traditional Rental Income: $2060 Airbnb ROI: -2.11% Traditional ROI: 3.44%
411 MANITOBA DRIVE Kissimmee, FL Seller offering SPECIAL FINANCING OPTION 30 year mortgage with preferred lender. Looking f...	3 beds \| 3 baths \| 2,230 sq.ft.	$314,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 5.87% Airbnb Rental Income: $1472 Traditional Rental Income: $2565 Airbnb ROI: 0.7% Traditional ROI: 5.87%

Real Estate investment in Kissimmee, FL

There are 1,534 properties for sale in the city of Kissimmee . The median list price in Kissimmee is $355,000 and the average price per square foot is $198. In December 2025, the average monthly cash on cash return in Kissimmee is 4.00%. The average monthly rental income in Kissimmee is $2,316.

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

There are 1,534 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 $1,735.

Your search for investment property begins and ends here

Investment Property for Sale in Kissimmee, FL

1204 CUMBRIAN LAKES COURT

Kissimmee, FL

4 beds | 4 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%

5004 LAGUNA BAY CIRCLE #54

Kissimmee, FL

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

$255,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $1472

Traditional Rental Income: $1787

Airbnb ROI: -0.71%

Traditional ROI: 2.4%

4577 ALBERTO CIRCLE

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%

1469 SWAN PLACE

Kissimmee, FL

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

$282,000

Airbnb cash on cash: 2.09%

Traditional cash on cash: 5.44%

Airbnb Rental Income: $1472

Traditional Rental Income: $1930

Airbnb ROI: 2.09%

Traditional ROI: 5.44%

1822 TROPHY BASS WAY

Kissimmee, FL

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

$525,000

Airbnb cash on cash: -0.29%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $1735

Traditional Rental Income: $3354

Airbnb ROI: -0.29%

Traditional ROI: 3.98%

5004 LAGUNA BAY CIRCLE #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 PLACE #233

Kissimmee, FL

1 beds | 1 baths | 751 sq.ft.

$141,000

Airbnb cash on cash: -6.77%

Traditional cash on cash: 3.2%

Airbnb Rental Income: $678

Traditional Rental Income: $1724

Airbnb ROI: -6.77%

Traditional ROI: 3.2%

2108 SHANNON LAKES BOULEVARD

Kissimmee, FL

4 beds | 2 baths | 1,842 sq.ft.

$375,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $1735

Traditional Rental Income: $2527

Airbnb ROI: 0.89%