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
3016 Parkway Blvd #204 Kissimmee, FL Location, Location, Location! 2/2 totally renovated, water view, minutes away from Disney,...	2 beds \| 2 baths \| 937 sq.ft.	$170,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 4.15% Airbnb Rental Income: $1341 Traditional Rental Income: $1690 Airbnb ROI: -0.55% Traditional ROI: 4.15%
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: 0.34% Traditional cash on cash: 4.08% Airbnb Rental Income: $2156 Traditional Rental Income: $3601 Airbnb ROI: 0.34% Traditional ROI: 4.08%
2219 SAN VITTORINO CIRCLE #107 Kissimmee, FL Welcome to your dream getaway, permanent oasis, or high-yield investment property in the p...	4 beds \| 3 baths \| 1,470 sq.ft.	$246,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 3.65% Airbnb Rental Income: $1735 Traditional Rental Income: $2129 Airbnb ROI: -0.1% Traditional ROI: 3.65%
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%
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%
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%
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.	$419,000	Airbnb cash on cash: -3.23% Traditional cash on cash: 1.18% Airbnb Rental Income: $1341 Traditional Rental Income: $2661 Airbnb ROI: -3.23% Traditional ROI: 1.18%
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%
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%
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%
8928 CUBAN PALM ROAD Kissimmee, FL RESORT AMENITIES !! PRIVATE POOL !! WATER VIEWS !! FULLY RENOVATED !! Welcome to Paradise ...	4 beds \| 3 baths \| 1,902 sq.ft.	$450,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 1.94% Airbnb Rental Income: $1735 Traditional Rental Income: $2654 Airbnb ROI: -1.38% Traditional ROI: 1.94%
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%
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%
8474 Crystal Cove Loop Kissimmee, FL Easy to fall in love with this gorgeous vacation home near the most famous theme parks whe...	3 beds \| 2 baths \| 1,263 sq.ft.	$249,000	Airbnb cash on cash: -1.29% Traditional cash on cash: 3.41% Airbnb Rental Income: $1472 Traditional Rental Income: $2144 Airbnb ROI: -1.29% Traditional ROI: 3.41%
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%
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%
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.	$229,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 4.12% Airbnb Rental Income: $1472 Traditional Rental Income: $2124 Airbnb ROI: -0.9% Traditional ROI: 4.12%
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%
763 ROLFE STREET Kissimmee, FL Located in an established Kissimmee neighborhood, this 3-bedroom, 2-bath single-family hom...	3 beds \| 2 baths \| 1,088 sq.ft.	$208,900	Airbnb cash on cash: 2.34% Traditional cash on cash: 8.28% Airbnb Rental Income: $1472 Traditional Rental Income: $2214 Airbnb ROI: 2.34% Traditional ROI: 8.28%
4004 SANTA MARIA DRIVE #105 Kissimmee, FL Under contract-accepting backup offers. Beautiful 3-bedroom, 2-bath townhome- located in t...	3 beds \| 2 baths \| 1,296 sq.ft.	$195,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 4.44% Airbnb Rental Income: $1472 Traditional Rental Income: $1991 Airbnb ROI: -0.71% Traditional ROI: 4.44%
157 POMPANO BEACH DRIVE Kissimmee, FL This stunning furnished townhouse features three spacious bedrooms, two full bathrooms, an...	3 beds \| 3 baths \| 1,286 sq.ft.	$290,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 5.32% Airbnb Rental Income: $1472 Traditional Rental Income: $2310 Airbnb ROI: 0.67% Traditional ROI: 5.32%
2708 PRESTWICK LANE Kissimmee, FL Beautiful 4-bedroom, 3.5-bath pool home located in the highly desirable community of Remin...	4 beds \| 4 baths \| 2,513 sq.ft.	$380,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 6.91% Airbnb Rental Income: $1735 Traditional Rental Income: $3673 Airbnb ROI: 0.13% Traditional ROI: 6.91%
7681 BENJI RIDGE TRAIL Kissimmee, FL Under contract-accepting backup offers. BEAUTIFUL 4 bed 2 full bath corner lot home in Ind...	4 beds \| 2 baths \| 1,602 sq.ft.	$290,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 4.87% Airbnb Rental Income: $1735 Traditional Rental Income: $2310 Airbnb ROI: 1.02% Traditional ROI: 4.87%
2657 ONEIDA LOOP Kissimmee, FL Back on the market after a prior contract did not move forward. Opportunity to own a fully...	4 beds \| 3 baths \| 1,791 sq.ft.	$489,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 4.03% Airbnb Rental Income: $1735 Traditional Rental Income: $3014 Airbnb ROI: 0.19% Traditional ROI: 4.03%
2682 MAYAGUANA STREET Kissimmee, FL Beautiful end-unit Townhome located in a gated Community just 2.5 miles from Walt Disney ...	3 beds \| 3 baths \| 1,595 sq.ft.	$290,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 6% Airbnb Rental Income: $1472 Traditional Rental Income: $2574 Airbnb ROI: 0.37% Traditional ROI: 6%
1410 Celebration Ave #102 Kissimmee, FL Immaculate first floor condo with one car garage, only used as a second home by the owners...	2 beds \| 2 baths \| 1,210 sq.ft.	$360,000	Airbnb cash on cash: -4.07% Traditional cash on cash: -1.1% Airbnb Rental Income: $1341 Traditional Rental Income: $1931 Airbnb ROI: -4.07% Traditional ROI: -1.1%
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.	$217,887	Airbnb cash on cash: -4.48% Traditional cash on cash: 3.53% Airbnb Rental Income: $1341 Traditional Rental Income: $2582 Airbnb ROI: -4.48% Traditional ROI: 3.53%
3129 RIACHUELO LANE Kissimmee, FL Under contract-accepting backup offers. Tile roof. Direct lakefront. Screened pool. Behind...	4 beds \| 3 baths \| 2,338 sq.ft.	$475,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 4.51% Airbnb Rental Income: $1735 Traditional Rental Income: $3540 Airbnb ROI: -0.63% Traditional ROI: 4.51%
2774 ALMATON LOOP #402 Kissimmee, FL Welcome to this fully furnished and well decorated vacation home just minutes from Walt Di...	2 beds \| 2 baths \| 1,081 sq.ft.	$279,000	Airbnb cash on cash: -2.2% Traditional cash on cash: 1.49% Airbnb Rental Income: $1341 Traditional Rental Income: $1900 Airbnb ROI: -2.2% Traditional ROI: 1.49%

Real Estate investment in Kissimmee, FL

There are 2,092 properties for sale in the city of Kissimmee . The median list price in Kissimmee is $390,000 and the average price per square foot is $195. In May 2026, the average monthly cash on cash return in Kissimmee is 4.00%. The average monthly rental income in Kissimmee is $2,390.

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

There are 2,092 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

3016 Parkway Blvd #204

Kissimmee, FL

2 beds | 2 baths | 937 sq.ft.

$170,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: 4.15%

Airbnb Rental Income: $1341

Traditional Rental Income: $1690

Airbnb ROI: -0.55%

Traditional ROI: 4.15%

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: 0.34%

Traditional cash on cash: 4.08%

Airbnb Rental Income: $2156

Traditional Rental Income: $3601

Airbnb ROI: 0.34%

Traditional ROI: 4.08%

2219 SAN VITTORINO CIRCLE #107

Kissimmee, FL

4 beds | 3 baths | 1,470 sq.ft.

$246,000

Airbnb cash on cash: -0.1%

Traditional cash on cash: 3.65%

Airbnb Rental Income: $1735

Traditional Rental Income: $2129

Airbnb ROI: -0.1%

Traditional ROI: 3.65%

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%

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%

1822 TROPHY BASS WAY

Kissimmee, 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%

1230 Wright Cir #308

Kissimmee, FL

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

$419,000

Airbnb cash on cash: -3.23%

Traditional cash on cash: 1.18%

Airbnb Rental Income: $1341

Traditional Rental Income: $2661

Airbnb ROI: -3.23%