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
4662 CHEYENNE POINT TRAIL Kissimmee, FL Welcome to this stunning pool home situated on a spacious corner lot in a prime location! ...	5 beds \| 3 baths \| 1,778 sq.ft.	$460,000	Airbnb cash on cash: 6.78% Traditional cash on cash: 4.56% Airbnb Rental Income: $4967 Traditional Rental Income: $2994 Airbnb ROI: 6.78% Traditional ROI: 4.56%
108 AMALFI LANE Kissimmee, FL Upgraded VENETIAN model with Casita with beautiful POND VIEWS in the Bella Viana subdivis...	4 beds \| 5 baths \| 2,917 sq.ft.	$620,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 6.89% Airbnb Rental Income: $3272 Traditional Rental Income: $5394 Airbnb ROI: 1.95% Traditional ROI: 6.89%
3144 WET N WILD COURT Kissimmee, FL Seller may consider buyer concessions if made in an offer ~ Turn key townhome and a rare o...	2 beds \| 2 baths \| 1,052 sq.ft.	$280,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 0.78% Airbnb Rental Income: $2355 Traditional Rental Income: $1706 Airbnb ROI: 1.04% Traditional ROI: 0.78%
4384 CREEKSIDE BOULEVARD Kissimmee, FL Come and see this lovely pool home in the well established Creekside Neighborhood. Lots o...	5 beds \| 4 baths \| 2,399 sq.ft.	$519,900	Airbnb cash on cash: 6.38% Traditional cash on cash: 6.96% Airbnb Rental Income: $4967 Traditional Rental Income: $4233 Airbnb ROI: 6.38% Traditional ROI: 6.96%
4721 FLAGLER BEACH WAY Kissimmee, FL Your dream home awaits less than 10 miles from Disney in the 24-hour GUARD GATED - RESORT ...	3 beds \| 3 baths \| 1,286 sq.ft.	$274,000	Airbnb cash on cash: 4.93% Traditional cash on cash: 5.74% Airbnb Rental Income: $2532 Traditional Rental Income: $2131 Airbnb ROI: 4.93% Traditional ROI: 5.74%
1355 LAKEVIEW AVENUE Kissimmee, FL Under contract-accepting backup offers. Step into a timeless 1923 gem, full of character a...	2 beds \| 2 baths \| 1,690 sq.ft.	$395,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 4.75% Airbnb Rental Income: $2355 Traditional Rental Income: $2436 Airbnb ROI: 2.96% Traditional ROI: 4.75%
2835 MIDDLETON CIRCLE Kissimmee, FL Welcome to your dream home! This stunning 3-bedroom, 2-bathroom residence boasts a spaciou...	3 beds \| 2 baths \| 1,852 sq.ft.	$415,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 4.89% Airbnb Rental Income: $2532 Traditional Rental Income: $2842 Airbnb ROI: 2.52% Traditional ROI: 4.89%
2108 SHANNON LAKES BOULEVARD Kissimmee, FL Looking for a perfect home in an ideal location? Look no further! This 4-bedroom, 2-bath c...	4 beds \| 2 baths \| 1,842 sq.ft.	$379,899	Airbnb cash on cash: 4.53% Traditional cash on cash: 4.5% Airbnb Rental Income: $3272 Traditional Rental Income: $2527 Airbnb ROI: 4.53% Traditional ROI: 4.5%
2649 CROWN COURT #2649 Kissimmee, FL Welcome to this stunning 3-bedroom, 3-bathroom, two-story condo located just 15 minutes fr...	3 beds \| 3 baths \| 1,350 sq.ft.	$248,999	Airbnb cash on cash: 4.08% Traditional cash on cash: 5.72% Airbnb Rental Income: $2532 Traditional Rental Income: $2306 Airbnb ROI: 4.08% Traditional ROI: 5.72%
1928 COMMANDER WAY Kissimmee, FL BLACK FRIDAY DEAL OF A LIFETIME! Don't miss out on the ultimate Black Friday sale! We're...	3 beds \| 2 baths \| 1,322 sq.ft.	$324,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 3.73% Airbnb Rental Income: $2532 Traditional Rental Income: $1991 Airbnb ROI: 3.5% Traditional ROI: 3.73%
2716 BUSHMAN DRIVE Kissimmee, FL Highly Motivated Seller due to medical reasons!! This beautiful 3-bedroom, 3-bathroom town...	3 beds \| 3 baths \| 1,440 sq.ft.	$322,500	Airbnb cash on cash: 2.22% Traditional cash on cash: 3.19% Airbnb Rental Income: $2532 Traditional Rental Income: $2215 Airbnb ROI: 2.22% Traditional ROI: 3.19%
8050 KING PALM CIRCLE 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.	$519,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 2.58% Airbnb Rental Income: $3272 Traditional Rental Income: $2578 Airbnb ROI: 2.5% Traditional ROI: 2.58%
2800 BOAT COVE CIRCLE Kissimmee, FL Welcome to PARADISE! Take a Look at this Fully Furnished Sunning WATERFRONT 2-Story Home l...	5 beds \| 4 baths \| 3,591 sq.ft.	$749,000	Airbnb cash on cash: 3.18% Traditional cash on cash: 4.23% Airbnb Rental Income: $4967 Traditional Rental Income: $4687 Airbnb ROI: 3.18% Traditional ROI: 4.23%
3101 SWINGLE DRIVE Kissimmee, FL Welcome to this Spacious 3 Bed Home located on a Large Corner Lot in the quiet Gated Commu...	3 beds \| 2 baths \| 2,161 sq.ft.	$387,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 4.35% Airbnb Rental Income: $2532 Traditional Rental Income: $2534 Airbnb ROI: 2.66% Traditional ROI: 4.35%
2785 ALMATON LOOP #202 Kissimmee, FL Priced to SELL! This amazing 2 bedroom 2 bathroom second floor condo is sold fully furnish...	2 beds \| 2 baths \| 1,081 sq.ft.	$279,500	Airbnb cash on cash: 2.64% Traditional cash on cash: 2.83% Airbnb Rental Income: $2355 Traditional Rental Income: $1826 Airbnb ROI: 2.64% Traditional ROI: 2.83%
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.	$399,998	Airbnb cash on cash: 1.96% Traditional cash on cash: 2.4% Airbnb Rental Income: $3272 Traditional Rental Income: $2700 Airbnb ROI: 1.96% Traditional ROI: 2.4%
3634 NORTHWOODS DRIVE Kissimmee, FL AMAZING HOME IN BELLALAGO 3 BEDROOM 2 BATHROOM. Kitchen features a breakfast bar with nice...	3 beds \| 2 baths \| 1,687 sq.ft.	$380,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 2.69% Airbnb Rental Income: $2532 Traditional Rental Income: $2184 Airbnb ROI: 1.96% Traditional ROI: 2.69%
2545 Renshaw Street Kissimmee, FL Discover the perfect blend of comfort and convenience with this fully furnished 3-bedroom,...	3 beds \| 3 baths \| 1,440 sq.ft.	$384,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 2.53% Airbnb Rental Income: $2532 Traditional Rental Income: $1792 Airbnb ROI: 2.88% Traditional ROI: 2.53%
164 OCEAN BLUFF DRIVE Kissimmee, FL Under contract-accepting backup offers. BRAND NEW CARPET ** Seller willing to contribu...	3 beds \| 2 baths \| 1,245 sq.ft.	$190,000	Airbnb cash on cash: 6.11% Traditional cash on cash: 5.9% Airbnb Rental Income: $2532 Traditional Rental Income: $1884 Airbnb ROI: 6.11% Traditional ROI: 5.9%
927 CAMBRIDGE COURT Kissimmee, FL Welcome to 927 Cambridge Court in Kissimmee, Florida, where comfort and convenience blend ...	4 beds \| 2 baths \| 2,088 sq.ft.	$330,000	Airbnb cash on cash: 5.6% Traditional cash on cash: 4.39% Airbnb Rental Income: $3272 Traditional Rental Income: $2163 Airbnb ROI: 5.6% Traditional ROI: 4.39%
153 Pompano Beach Drive Kissimmee, FL Discover this exquisite 3-bedroom, 2.5-bathroom townhouse, offering 1,286 square feet of w...	3 beds \| 3 baths \| 1,286 sq.ft.	$340,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 4.33% Airbnb Rental Income: $2532 Traditional Rental Income: $2150 Airbnb ROI: 3.61% Traditional ROI: 4.33%
8702 KNIGHTSBRIDGE COURT #D Kissimmee, FL Attention Investors The Villas at Island Club has a 3BD/2BA second floor condo with a ...	3 beds \| 2 baths \| 1,357 sq.ft.	$270,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 5.21% Airbnb Rental Income: $2532 Traditional Rental Income: $2068 Airbnb ROI: 4.63% Traditional ROI: 5.21%
2758 SUN KEY PLACE Kissimmee, FL Discover your dream getaway in the stunning Emerald Island Resort! This townhouse is locat...	3 beds \| 3 baths \| 1,291 sq.ft.	$315,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 4.05% Airbnb Rental Income: $2532 Traditional Rental Income: $2182 Airbnb ROI: 3.17% Traditional ROI: 4.05%
1130 Sabine Lane Kissimmee, FL This home is not only beautiful but move-in ready! This 2017 home has 3 bedrooms and 2 bat...	3 beds \| 2 baths \| 1,487 sq.ft.	$299,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 5.68% Airbnb Rental Income: $2532 Traditional Rental Income: $2154 Airbnb ROI: 4.85% Traditional ROI: 5.68%
4577 YORKSHIRE LANE Kissimmee, FL If your looking for somewhere to call Home? You've found it within sought out Community. ...	3 beds \| 2 baths \| 2,005 sq.ft.	$359,000	Airbnb cash on cash: 3.52% Traditional cash on cash: 5.49% Airbnb Rental Income: $2532 Traditional Rental Income: $2585 Airbnb ROI: 3.52% Traditional ROI: 5.49%
2090 CYPRESS BAY BOULEVARD Kissimmee, FL Stunning Townhouse Situated on a Corner Lot! This spacious home features three bedrooms, t...	3 beds \| 3 baths \| 1,807 sq.ft.	$319,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 4.69% Airbnb Rental Income: $2532 Traditional Rental Income: $2443 Airbnb ROI: 2.95% Traditional ROI: 4.69%
4004 SANTA MARIA DRIVE #105 Kissimmee, FL If you're looking for an absolutely adorable Florida Condo to use as your primary residenc...	3 beds \| 2 baths \| 1,296 sq.ft.	$260,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 2.92% Airbnb Rental Income: $2532 Traditional Rental Income: $1972 Airbnb ROI: 2.71% Traditional ROI: 2.92%
212 SOLIVITA BOULEVARD Kissimmee, FL **NEW PRICE** Remodeled and Updated, Lake views from front porch and all front windows...	2 beds \| 2 baths \| 1,317 sq.ft.	$265,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 4.39% Airbnb Rental Income: $2355 Traditional Rental Income: $2062 Airbnb ROI: 3.23% Traditional ROI: 4.39%
2482 SWEETWATER CLUB CIRCLE #86 Kissimmee, FL Welcome to a pristine property where each interior detail has been tailored to perfection....	3 beds \| 2 baths \| 1,220 sq.ft.	$240,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 4.01% Airbnb Rental Income: $2532 Traditional Rental Income: $1965 Airbnb ROI: 3.82% Traditional ROI: 4.01%
3159 LINTON ROAD Kissimmee, FL Welcome to your dream home located in the vibrant heart of Kissimmee. This stunning two-st...	4 beds \| 3 baths \| 2,254 sq.ft.	$435,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 4.82% Airbnb Rental Income: $3272 Traditional Rental Income: $2749 Airbnb ROI: 4.3% Traditional ROI: 4.82%
2812 TOWER ROCK STREET Kissimmee, FL Back on the market with a new Roof, Picture yourself in a stunning kitchen with Corian cou...	3 beds \| 2 baths \| 1,915 sq.ft.	$385,000	Airbnb cash on cash: 3.18% Traditional cash on cash: 4.87% Airbnb Rental Income: $2532 Traditional Rental Income: $2533 Airbnb ROI: 3.18% Traditional ROI: 4.87%
3331 WHITESTONE CIRCLE #303 Kissimmee, FL This three-bedroom, two-bathroom apartment, located in Kissimmee, is in a prime location, ...	3 beds \| 2 baths \| 1,433 sq.ft.	$275,000	Airbnb cash on cash: 4.8% Traditional cash on cash: 5.56% Airbnb Rental Income: $2532 Traditional Rental Income: $2118 Airbnb ROI: 4.8% Traditional ROI: 5.56%
8406 CRYSTAL COVE LOOP Kissimmee, FL LOCATION,LOCATION,LOCATION !!! Amazing 3 bedroom 2 1/2 bathroom townhouse in the most soug...	3 beds \| 3 baths \| 1,291 sq.ft.	$300,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 4.49% Airbnb Rental Income: $2532 Traditional Rental Income: $2163 Airbnb ROI: 3.63% Traditional ROI: 4.49%
2573 HUNLEY LOOP Kissimmee, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	3 beds \| 3 baths \| 2,416 sq.ft.	$429,999	Airbnb cash on cash: 2.63% Traditional cash on cash: 4.87% Airbnb Rental Income: $2532 Traditional Rental Income: $2824 Airbnb ROI: 2.63% Traditional ROI: 4.87%
2721 N POINCIANA BOULEVARD #167 Kissimmee, FL Welcome to your dream investment opportunity, vacation retreat, or personal residence in t...	3 beds \| 2 baths \| 1,287 sq.ft.	$229,900	Airbnb cash on cash: 2.54% Traditional cash on cash: 3.08% Airbnb Rental Income: $2532 Traditional Rental Income: $2038 Airbnb ROI: 2.54% Traditional ROI: 3.08%
732 AMERICANA COURT Kissimmee, FL Back on the market. Financing fell through. Property appraised asking price. This 3-bedroo...	3 beds \| 2 baths \| 1,835 sq.ft.	$337,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 4.86% Airbnb Rental Income: $2532 Traditional Rental Income: $2448 Airbnb ROI: 3.2% Traditional ROI: 4.86%
2664 HORSESHOE BAY DRIVE Kissimmee, FL #3D Virtual Tour Available* Location is everything, and this residence boasts an enviable...	4 beds \| 3 baths \| 1,959 sq.ft.	$395,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 4.79% Airbnb Rental Income: $3272 Traditional Rental Income: $2807 Airbnb ROI: 4.06% Traditional ROI: 4.79%
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.	$285,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 5.28% Airbnb Rental Income: $2355 Traditional Rental Income: $2079 Airbnb ROI: 4.14% Traditional ROI: 5.28%
1739 SAINT TROPEZ COURT Kissimmee, FL Sought out Kissimmee Bay Country Club. Experience the Monaco Villages on a established gol...	3 beds \| 3 baths \| 2,104 sq.ft.	$379,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 5.31% Airbnb Rental Income: $2532 Traditional Rental Income: $2925 Airbnb ROI: 2.48% Traditional ROI: 5.31%
3133 QUEEN ALEXANDRIA DRIVE Kissimmee, FL Welcome to your dream home in the desirable gated community of Raintree at Springlake, loc...	4 beds \| 2 baths \| 1,956 sq.ft.	$420,000	Airbnb cash on cash: 4.23% Traditional cash on cash: 4.06% Airbnb Rental Income: $3272 Traditional Rental Income: $2472 Airbnb ROI: 4.23% Traditional ROI: 4.06%

Real Estate investment in Kissimmee, FL

There are 1,449 properties for sale in the city of Kissimmee . The median list price in Kissimmee is $375,000 and the average price per square foot is $205. In December 2024, the average monthly cash on cash return in Kissimmee is 4.00%. The average monthly rental income in Kissimmee is $2,383.

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

There are 1,449 investment properties available for sale in Kissimmee.

In 2024, 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 $2,383.

Your search for investment property begins and ends here

Investment Property for Sale in Kissimmee, FL

4662 CHEYENNE POINT TRAIL

Kissimmee, FL

5 beds | 3 baths | 1,778 sq.ft.

$460,000

Airbnb cash on cash: 6.78%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $4967

Traditional Rental Income: $2994

Airbnb ROI: 6.78%

Traditional ROI: 4.56%

108 AMALFI LANE

Kissimmee, FL

4 beds | 5 baths | 2,917 sq.ft.

$620,000

Airbnb cash on cash: 1.95%

Traditional cash on cash: 6.89%

Airbnb Rental Income: $3272

Traditional Rental Income: $5394

Airbnb ROI: 1.95%

Traditional ROI: 6.89%

3144 WET N WILD COURT

Kissimmee, FL

2 beds | 2 baths | 1,052 sq.ft.

$280,000

Airbnb cash on cash: 1.04%

Traditional cash on cash: 0.78%

Airbnb Rental Income: $2355

Traditional Rental Income: $1706

Airbnb ROI: 1.04%

Traditional ROI: 0.78%

4384 CREEKSIDE BOULEVARD

Kissimmee, FL

5 beds | 4 baths | 2,399 sq.ft.

$519,900

Airbnb cash on cash: 6.38%

Traditional cash on cash: 6.96%

Airbnb Rental Income: $4967

Traditional Rental Income: $4233

Airbnb ROI: 6.38%

Traditional ROI: 6.96%

4721 FLAGLER BEACH WAY

Kissimmee, FL

3 beds | 3 baths | 1,286 sq.ft.

$274,000

Airbnb cash on cash: 4.93%

Traditional cash on cash: 5.74%

Airbnb Rental Income: $2532

Traditional Rental Income: $2131

Airbnb ROI: 4.93%

Traditional ROI: 5.74%

1355 LAKEVIEW AVENUE

Kissimmee, FL

2 beds | 2 baths | 1,690 sq.ft.

$395,000

Airbnb cash on cash: 2.96%

Traditional cash on cash: 4.75%

Airbnb Rental Income: $2355

Traditional Rental Income: $2436

Airbnb ROI: 2.96%

Traditional ROI: 4.75%

2835 MIDDLETON CIRCLE

Kissimmee, FL

3 beds | 2 baths | 1,852 sq.ft.

$415,000

Airbnb cash on cash: 2.52%

Traditional cash on cash: 4.89%

Airbnb Rental Income: $2532

Traditional Rental Income: $2842

Airbnb ROI: 2.52%

Traditional ROI: 4.89%

2108 SHANNON LAKES BOULEVARD

Kissimmee, FL

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

$379,899

Airbnb cash on cash: 4.53%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $3272

Traditional Rental Income: $2527

Airbnb ROI: 4.53%