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 Charming and well-maintained home located in the desirable community of Poinciana Villages...	3 beds \| 2 baths \| 1,057 sq.ft.	$265,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 4.75% Airbnb Rental Income: $1472 Traditional Rental Income: $1857 Airbnb ROI: 1.47% Traditional ROI: 4.75%
1831 WINDWARD OAKS COURT Kissimmee, FL Price just LOWERED!!!!!! Welcome to your dream home in the beautiful BellaLago community!...	5 beds \| 3 baths \| 2,813 sq.ft.	$569,990	Airbnb cash on cash: 0.01% Traditional cash on cash: 3.75% Airbnb Rental Income: $2156 Traditional Rental Income: $3601 Airbnb ROI: 0.01% Traditional ROI: 3.75%
3834 Golden Feather Way Kissimmee, FL COME CHECK OUT THIS BEAUTIFUL HOME THIS SUNDAY! Welcome to Bellalago! When entering youâ...	4 beds \| 3 baths \| 2,413 sq.ft.	$428,999	Airbnb cash on cash: 0.02% Traditional cash on cash: 3.49% Airbnb Rental Income: $1735 Traditional Rental Income: $2654 Airbnb ROI: 0.02% Traditional ROI: 3.49%
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.	$238,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 4.64% Airbnb Rental Income: $1472 Traditional Rental Income: $2235 Airbnb ROI: -0.68% Traditional ROI: 4.64%
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.	$299,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 1.96% Airbnb Rental Income: $1472 Traditional Rental Income: $1717 Airbnb ROI: -0.45% Traditional ROI: 1.96%
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: 4.09% Airbnb Rental Income: $1735 Traditional Rental Income: $2729 Airbnb ROI: -0.04% Traditional ROI: 4.09%
1469 SWAN PLACE 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: 1.46% Traditional cash on cash: 6.19% Airbnb Rental Income: $1472 Traditional Rental Income: $2128 Airbnb ROI: 1.46% Traditional ROI: 6.19%
950 Marcello Blvd Kissimmee, FL Get in and take a look at this gorgeous 4 bed, 3 bath home with stunning lake view on the ...	4 beds \| 3 baths \| 1,647 sq.ft.	$455,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 1.55% Airbnb Rental Income: $1735 Traditional Rental Income: $2085 Airbnb ROI: -0.39% Traditional ROI: 1.55%
5108 Adelaide Dr Kissimmee, FL Dream Disney Vacation Townhouse Brand New never lived in located in the gated Compass Bay ...	4 beds \| 3 baths \| 1,637 sq.ft.	$375,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 3.41% Airbnb Rental Income: $1735 Traditional Rental Income: $1967 Airbnb ROI: 1.39% Traditional ROI: 3.41%
1822 TROPHY BASS WAY Kissimmee, FL Under contract-accepting backup offers. Waterfront home in Shingle Creek Reserve, where Fl...	4 beds \| 3 baths \| 2,798 sq.ft.	$489,450	Airbnb cash on cash: -0.24% Traditional cash on cash: 3.8% Airbnb Rental Income: $1735 Traditional Rental Income: $3105 Airbnb ROI: -0.24% Traditional ROI: 3.8%
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.	$219,900	Airbnb cash on cash: -0.12% Traditional cash on cash: 4.98% Airbnb Rental Income: $1472 Traditional Rental Income: $2100 Airbnb ROI: -0.12% Traditional ROI: 4.98%
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.	$188,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 4.67% Airbnb Rental Income: $1341 Traditional Rental Income: $1752 Airbnb ROI: 0.06% Traditional ROI: 4.67%
1230 Wright Cir #308 Kissimmee, FL DIRECT WATERFRONT, Fully Furnished!! Great lock and leave unit with access to the Award Wi...	2 beds \| 2 baths \| 1,345 sq.ft.	$424,000	Airbnb cash on cash: -3.21% Traditional cash on cash: 1.15% Airbnb Rental Income: $1341 Traditional Rental Income: $2661 Airbnb ROI: -3.21% Traditional ROI: 1.15%
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: -0.44% Traditional cash on cash: 3.92% Airbnb Rental Income: $1472 Traditional Rental Income: $2148 Airbnb ROI: -0.44% Traditional ROI: 3.92%
2033 Royal Bay Blvd #51 Kissimmee, FL Whether this is your primary residence, vacation home or investment property, you will enj...	3 beds \| 2 baths \| 1,350 sq.ft.	$230,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 4.32% Airbnb Rental Income: $1472 Traditional Rental Income: $1777 Airbnb ROI: 0.93% Traditional ROI: 4.32%
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.	$124,900	Airbnb cash on cash: -7.32% Traditional cash on cash: 11.08% Airbnb Rental Income: $678 Traditional Rental Income: $2589 Airbnb ROI: -7.32% Traditional ROI: 11.08%
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.	$399,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 4.83% Airbnb Rental Income: $1735 Traditional Rental Income: $2872 Airbnb ROI: 0.51% Traditional ROI: 4.83%
2178 N Stewart St Kissimmee, FL Come see this Beautiful Mediterranean Style Home in a lovely neighborhood on an acre lot w...	4 beds \| 2 baths \| 2,424 sq.ft.	$514,900	Airbnb cash on cash: 1.09% Traditional cash on cash: 3.53% Airbnb Rental Income: $1735 Traditional Rental Income: $2434 Airbnb ROI: 1.09% Traditional ROI: 3.53%
2239 SANTA LUCIA STREET Kissimmee, FL Short Sale. Centrally located and move-in ready, this 3 bedroom, 2 bath home features an o...	3 beds \| 2 baths \| 1,059 sq.ft.	$320,497	Airbnb cash on cash: 0.83% Traditional cash on cash: 4.96% Airbnb Rental Income: $1472 Traditional Rental Income: $2284 Airbnb ROI: 0.83% Traditional ROI: 4.96%
3523 FOREST PARK DRIVE Kissimmee, FL NOW YOU CAN RENT-TO-OWN THIS beautifully upgraded two-story home in the prestigious, guard...	4 beds \| 3 baths \| 2,123 sq.ft.	$577,990	Airbnb cash on cash: 0.03% Traditional cash on cash: 2.75% Airbnb Rental Income: $1735 Traditional Rental Income: $2729 Airbnb ROI: 0.03% Traditional ROI: 2.75%
2521 JASMINE TRACE DRIVE Kissimmee, FL Absolutely stunning and thoughtfully designed, this exceptional home offers the perfect bl...	4 beds \| 3 baths \| 2,658 sq.ft.	$520,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 5.56% Airbnb Rental Income: $1735 Traditional Rental Income: $3738 Airbnb ROI: 0.46% Traditional ROI: 5.56%
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.	$495,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.38% Airbnb Rental Income: $1735 Traditional Rental Income: $2922 Airbnb ROI: -0.22% Traditional ROI: 3.38%
3101 Swingle Dr 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.	$350,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 4.01% Airbnb Rental Income: $1472 Traditional Rental Income: $2241 Airbnb ROI: 0.35% Traditional ROI: 4.01%
8859 CANDY PALM ROAD Kissimmee, FL MUST SEE! Own a piece of paradise with this stunning, fully furnished waterfront townhome ...	4 beds \| 3 baths \| 1,902 sq.ft.	$359,000	Airbnb cash on cash: -1.49% Traditional cash on cash: 3.03% Airbnb Rental Income: $1735 Traditional Rental Income: $2779 Airbnb ROI: -1.49% Traditional ROI: 3.03%
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.	$299,900	Airbnb cash on cash: -1.74% Traditional cash on cash: 1.44% Airbnb Rental Income: $1341 Traditional Rental Income: $1826 Airbnb ROI: -1.74% Traditional ROI: 1.44%
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: -1.57% Traditional cash on cash: 3.12% Airbnb Rental Income: $1341 Traditional Rental Income: $1969 Airbnb ROI: -1.57% 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: -1.43% Traditional cash on cash: 1.87% Airbnb Rental Income: $1472 Traditional Rental Income: $2332 Airbnb ROI: -1.43% Traditional ROI: 1.87%
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.	$310,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 5.94% Airbnb Rental Income: $1735 Traditional Rental Income: $2417 Airbnb ROI: 1.96% Traditional ROI: 5.94%
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.	$279,999	Airbnb cash on cash: 1.68% Traditional cash on cash: 6.09% Airbnb Rental Income: $1472 Traditional Rental Income: $2202 Airbnb ROI: 1.68% Traditional ROI: 6.09%
2727 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.	$304,900	Airbnb cash on cash: 0.03% Traditional cash on cash: 4.41% Airbnb Rental Income: $1472 Traditional Rental Income: $2296 Airbnb ROI: 0.03% Traditional ROI: 4.41%
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.	$285,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 3.89% Airbnb Rental Income: $1341 Traditional Rental Income: $2279 Airbnb ROI: -1.14% Traditional ROI: 3.89%
1426 Pacific Rd Kissimmee, FL Beautiful and spacious townhome in sought after Tuscany Preserve Community. Beautiful orig...	4 beds \| 2 baths \| 2,110 sq.ft.	$295,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 4.72% Airbnb Rental Income: $1735 Traditional Rental Income: $2224 Airbnb ROI: 1.24% Traditional ROI: 4.72%
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.	$349,000	Airbnb cash on cash: -2.96% Traditional cash on cash: 1.91% Airbnb Rental Income: $1341 Traditional Rental Income: $2525 Airbnb ROI: -2.96% Traditional ROI: 1.91%
4715 FLAGLER BEACH WAY Kissimmee, FL PRICED BELOW MARKET VALUE â MOTIVATED SELLER â EXCELLENT INVESTMENT OPPORTUNITY Wel...	3 beds \| 3 baths \| 1,286 sq.ft.	$298,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 4.97% Airbnb Rental Income: $1472 Traditional Rental Income: $2310 Airbnb ROI: 0.44% Traditional ROI: 4.97%
3032 PARKWAY BOULEVARD #305 Kissimmee, FL Welcome to this beautifully remodeled 2-bedroom, 2-bathroom condo located in the heart of ...	2 beds \| 2 baths \| 937 sq.ft.	$210,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 4.14% Airbnb Rental Income: $1341 Traditional Rental Income: $1857 Airbnb ROI: -0.52% Traditional ROI: 4.14%
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: -5.29% Traditional cash on cash: 3.34% Airbnb Rental Income: $1341 Traditional Rental Income: $2648 Airbnb ROI: -5.29% Traditional ROI: 3.34%
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: 2.06% Traditional cash on cash: 5.49% Airbnb Rental Income: $1735 Traditional Rental Income: $2368 Airbnb ROI: 2.06% Traditional ROI: 5.49%
3086 White Horse Ct Kissimmee, FL Under contract-accepting backup offers. Welcome home to this fantastic Eastham II floor pl...	4 beds \| 3 baths \| 2,166 sq.ft.	$575,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 2.41% Airbnb Rental Income: $1735 Traditional Rental Income: $2780 Airbnb ROI: -0.42% Traditional ROI: 2.41%
8101 COCONUT PALM WAY #205 Kissimmee, FL SHORT TERM RENTAL *** Located in a guard-gated resort community in Kissimmee, this propert...	3 beds \| 2 baths \| 1,268 sq.ft.	$238,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 3.93% Airbnb Rental Income: $1472 Traditional Rental Income: $2124 Airbnb ROI: -0.9% Traditional ROI: 3.93%
3196 STONEHURST CIRCLE Kissimmee, FL WATERFRONT If you're looking for an open-floor plan move-in ready home with a waterfro...	3 beds \| 2 baths \| 1,814 sq.ft.	$415,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 4.01% Airbnb Rental Income: $1472 Traditional Rental Income: $2671 Airbnb ROI: -0.19% Traditional ROI: 4.01%

Real Estate investment in Kissimmee, FL

There are 3,669 properties for sale in the city of Kissimmee . The median list price in Kissimmee is $360,000 and the average price per square foot is $179. In May 2026, the average monthly cash on cash return in Kissimmee is 4.00%. The average monthly rental income in Kissimmee is $2,338.

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

There are 3,669 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 $1,472.

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 | 1,057 sq.ft.

$265,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 4.75%

Airbnb Rental Income: $1472

Traditional Rental Income: $1857

Airbnb ROI: 1.47%

Traditional ROI: 4.75%

1831 WINDWARD OAKS COURT

Kissimmee, FL

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

$569,990

Airbnb cash on cash: 0.01%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $2156

Traditional Rental Income: $3601

Airbnb ROI: 0.01%

Traditional ROI: 3.75%

3834 Golden Feather Way

Kissimmee, FL

4 beds | 3 baths | 2,413 sq.ft.

$428,999

Airbnb cash on cash: 0.02%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $1735

Traditional Rental Income: $2654

Airbnb ROI: 0.02%

Traditional ROI: 3.49%

5004 LAGUNA BAY CIRCLE #54

Kissimmee, FL

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

$238,000

Airbnb cash on cash: -0.68%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $1472

Traditional Rental Income: $2235

Airbnb ROI: -0.68%

Traditional ROI: 4.64%

4558 Ada Ln

Kissimmee, FL

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

$299,000

Airbnb cash on cash: -0.45%

Traditional cash on cash: 1.96%

Airbnb Rental Income: $1472

Traditional Rental Income: $1717

Airbnb ROI: -0.45%

Traditional ROI: 1.96%

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: 4.09%

Airbnb Rental Income: $1735

Traditional Rental Income: $2729

Airbnb ROI: -0.04%

Traditional ROI: 4.09%

1469 SWAN PLACE

Kissimmee, FL

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

$244,000

Airbnb cash on cash: 1.46%

Traditional cash on cash: 6.19%

Airbnb Rental Income: $1472

Traditional Rental Income: $2128

Airbnb ROI: 1.46%

Traditional ROI: 6.19%

950 Marcello Blvd

Kissimmee, FL

4 beds | 3 baths | 1,647 sq.ft.

$455,000

Airbnb cash on cash: -0.39%

Traditional cash on cash: 1.55%

Airbnb Rental Income: $1735

Traditional Rental Income: $2085

Airbnb ROI: -0.39%