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: 0.42% Traditional cash on cash: 4.15% Airbnb Rental Income: $1530 Traditional Rental Income: $1690 Airbnb ROI: 0.42% 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.	$260,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 4.86% Airbnb Rental Income: $1682 Traditional Rental Income: $1857 Airbnb ROI: 2.23% Traditional ROI: 4.86%
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: 3% Traditional cash on cash: 4.08% Airbnb Rental Income: $3852 Traditional Rental Income: $3601 Airbnb ROI: 3% Traditional ROI: 4.08%
1024 Banks Rose St Kissimmee, FL Located in Celebration, this 3-bedroom, 2.5-bathroom home backs up to a permanent conserva...	3 beds \| 2 baths \| 1,987 sq.ft.	$779,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 0.66% Airbnb Rental Income: $1682 Traditional Rental Income: $2284 Airbnb ROI: -0.81% Traditional ROI: 0.66%
202 WOODSON COURT Kissimmee, FL Welcome to this stunning 3,744 square foot residence located on a quiet cul de sac within ...	5 beds \| 4 baths \| 3,744 sq.ft.	$623,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 6.38% Airbnb Rental Income: $3852 Traditional Rental Income: $4904 Airbnb ROI: 3.14% Traditional ROI: 6.38%
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.	$210,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 4.43% Airbnb Rental Income: $2186 Traditional Rental Income: $2129 Airbnb ROI: 1.94% Traditional ROI: 4.43%
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.	$235,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 4.71% Airbnb Rental Income: $1682 Traditional Rental Income: $2235 Airbnb ROI: 0.11% Traditional ROI: 4.71%
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: 1.01% Traditional cash on cash: 4.09% Airbnb Rental Income: $2186 Traditional Rental Income: $2729 Airbnb ROI: 1.01% Traditional ROI: 4.09%
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: 0.25% Traditional cash on cash: 3.92% Airbnb Rental Income: $1682 Traditional Rental Income: $2148 Airbnb ROI: 0.25% Traditional ROI: 3.92%
513 HEARTWELL DR Kissimmee, FL This beautifully maintained 2 BED, 2 BATH home in the premiere 55+ resort community of Sol...	2 beds \| 2 baths \| 1,488 sq.ft.	$275,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 3.73% Airbnb Rental Income: $1530 Traditional Rental Income: $1991 Airbnb ROI: 0.24% Traditional ROI: 3.73%
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.	$319,497	Airbnb cash on cash: 1.42% Traditional cash on cash: 4.98% Airbnb Rental Income: $1682 Traditional Rental Income: $2284 Airbnb ROI: 1.42% Traditional ROI: 4.98%
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.	$560,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 2.87% Airbnb Rental Income: $2186 Traditional Rental Income: $2729 Airbnb ROI: 0.78% Traditional ROI: 2.87%
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: 1.23% Traditional cash on cash: 5.56% Airbnb Rental Income: $2186 Traditional Rental Income: $3738 Airbnb ROI: 1.23% Traditional ROI: 5.56%
8050 King Palm Cir 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: -0.53% Traditional cash on cash: 2.26% Airbnb Rental Income: $2186 Traditional Rental Income: $2922 Airbnb ROI: -0.53% Traditional ROI: 2.26%
8928 Cuban Palm Rd Kissimmee, FL RESORT AMENITIES !! PRIVATE POOL !! WATER VIEWS !! FULLY RENOVATED !! Welcome to Paradise ...	4 beds \| 3 baths \| 1,902 sq.ft.	$438,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 2.02% Airbnb Rental Income: $2186 Traditional Rental Income: $2654 Airbnb ROI: -0.47% Traditional ROI: 2.02%
8859 Candy Palm Rd Kissimmee, FL MUST SEE! Water view. Own a piece of paradise with this stunning, fully furnished waterfro...	4 beds \| 3 baths \| 1,902 sq.ft.	$339,900	Airbnb cash on cash: -0.34% Traditional cash on cash: 3.25% Airbnb Rental Income: $2186 Traditional Rental Income: $2779 Airbnb ROI: -0.34% Traditional ROI: 3.25%
2785 Almaton Loop #202 Kissimmee, FL Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo located in the highly s...	2 beds \| 2 baths \| 1,081 sq.ft.	$240,000	Airbnb cash on cash: -1.8% Traditional cash on cash: 1.46% Airbnb Rental Income: $1530 Traditional Rental Income: $1826 Airbnb ROI: -1.8% Traditional ROI: 1.46%
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: -0.86% Traditional cash on cash: 3.12% Airbnb Rental Income: $1530 Traditional Rental Income: $1969 Airbnb ROI: -0.86% 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: -0.98% Traditional cash on cash: 1.87% Airbnb Rental Income: $1682 Traditional Rental Income: $2332 Airbnb ROI: -0.98% Traditional ROI: 1.87%
7920 GOLDEN POND CIRCLE Kissimmee, FL Under contract-accepting backup offers. Proven Income. Prime Location. Move-In Ready Inves...	4 beds \| 3 baths \| 2,040 sq.ft.	$475,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 3.2% Airbnb Rental Income: $2186 Traditional Rental Income: $2565 Airbnb ROI: 1.1% Traditional ROI: 3.2%
2727 Sun Key Pl Kissimmee, FL Discover your dream getaway in the stunning Emerald Island Resort! This townhouse is locat...	3 beds \| 2 baths \| 1,291 sq.ft.	$304,900	Airbnb cash on cash: -0.78% Traditional cash on cash: 2.99% Airbnb Rental Income: $1682 Traditional Rental Income: $2296 Airbnb ROI: -0.78% Traditional ROI: 2.99%
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.	$249,500	Airbnb cash on cash: -0.55% Traditional cash on cash: 3.4% Airbnb Rental Income: $1682 Traditional Rental Income: $2144 Airbnb ROI: -0.55% Traditional ROI: 3.4%
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: -0.56% Traditional cash on cash: 3.89% Airbnb Rental Income: $1530 Traditional Rental Income: $2279 Airbnb ROI: -0.56% Traditional ROI: 3.89%
4490 SPRING BLOSSOM LANE Kissimmee, FL Under contract-accepting backup offers. Beautiful and maintained 3,266 sq. ft. two-story h...	4 beds \| 3 baths \| 3,266 sq.ft.	$370,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 5.72% Airbnb Rental Income: $2186 Traditional Rental Income: $2861 Airbnb ROI: 2.18% Traditional ROI: 5.72%
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: -2.48% Traditional cash on cash: 1.91% Airbnb Rental Income: $1530 Traditional Rental Income: $2525 Airbnb ROI: -2.48% Traditional ROI: 1.91%
3032 Parkway Blvd #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.	$180,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 4.98% Airbnb Rental Income: $1530 Traditional Rental Income: $1857 Airbnb ROI: 0.48% Traditional ROI: 4.98%
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: -4.5% Traditional cash on cash: 3.34% Airbnb Rental Income: $1530 Traditional Rental Income: $2648 Airbnb ROI: -4.5% Traditional ROI: 3.34%
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.	$304,900	Airbnb cash on cash: 1.66% Traditional cash on cash: 4.42% Airbnb Rental Income: $1682 Traditional Rental Income: $2005 Airbnb ROI: 1.66% Traditional ROI: 4.42%
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.	$219,900	Airbnb cash on cash: -0.05% Traditional cash on cash: 4.32% Airbnb Rental Income: $1682 Traditional Rental Income: $2124 Airbnb ROI: -0.05% Traditional ROI: 4.32%
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: 0.26% Traditional cash on cash: 4.01% Airbnb Rental Income: $1682 Traditional Rental Income: $2671 Airbnb ROI: 0.26% 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.	$159,900	Airbnb cash on cash: 4.48% Traditional cash on cash: 11.04% Airbnb Rental Income: $1682 Traditional Rental Income: $2214 Airbnb ROI: 4.48% Traditional ROI: 11.04%
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: 1.31% Traditional cash on cash: 5.32% Airbnb Rental Income: $1682 Traditional Rental Income: $2310 Airbnb ROI: 1.31% 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.	$387,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 6.76% Airbnb Rental Income: $2186 Traditional Rental Income: $3673 Airbnb ROI: 1.14% Traditional ROI: 6.76%
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: 2.39% Traditional cash on cash: 4.87% Airbnb Rental Income: $2186 Traditional Rental Income: $2310 Airbnb ROI: 2.39% Traditional ROI: 4.87%
2657 Oneida Loop Kissimmee, FL Welcome to this beautifully maintained, fully furnished 4-bedroom, 3-bath pool home in the...	4 beds \| 3 baths \| 1,791 sq.ft.	$479,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 4.14% Airbnb Rental Income: $2186 Traditional Rental Income: $3014 Airbnb ROI: 1.05% Traditional ROI: 4.14%
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.	$339,000	Airbnb cash on cash: -3.76% Traditional cash on cash: -1.11% Airbnb Rental Income: $1530 Traditional Rental Income: $1931 Airbnb ROI: -3.76% Traditional ROI: -1.11%
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.	$215,887	Airbnb cash on cash: -3.75% Traditional cash on cash: 3.57% Airbnb Rental Income: $1530 Traditional Rental Income: $2582 Airbnb ROI: -3.75% Traditional ROI: 3.57%
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: 0.22% Traditional cash on cash: 4.51% Airbnb Rental Income: $2186 Traditional Rental Income: $3540 Airbnb ROI: 0.22% Traditional ROI: 4.51%
2774 ALMATON LOOP #402 Kissimmee, FL PRICE IMPROVED! Highly successful vacation rental with strong occupancy history in Windsor...	2 beds \| 2 baths \| 1,081 sq.ft.	$269,000	Airbnb cash on cash: -1.63% Traditional cash on cash: 1.58% Airbnb Rental Income: $1530 Traditional Rental Income: $1900 Airbnb ROI: -1.63% Traditional ROI: 1.58%
3410 OAKMONT COURT Kissimmee, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	3 beds \| 3 baths \| 2,741 sq.ft.	$484,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.76% Airbnb Rental Income: $1682 Traditional Rental Income: $3146 Airbnb ROI: -0.51% Traditional ROI: 3.76%

Real Estate investment in Kissimmee, FL

There are 2,053 properties for sale in the city of Kissimmee . The median list price in Kissimmee is $349,241 and the average price per square foot is $174. In July 2026, the average monthly cash on cash return in Kissimmee is 4.00%. The average monthly rental income in Kissimmee is $2,363.

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

There are 2,053 investment properties available for sale in Kissimmee.

In 2026, 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 $2,363.

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: 0.42%

Traditional cash on cash: 4.15%

Airbnb Rental Income: $1530

Traditional Rental Income: $1690

Airbnb ROI: 0.42%

Traditional ROI: 4.15%

719 DEL RAY DRIVE

Kissimmee, FL

3 beds | 2 baths | 1,057 sq.ft.

$260,000

Airbnb cash on cash: 2.23%

Traditional cash on cash: 4.86%

Airbnb Rental Income: $1682

Traditional Rental Income: $1857

Airbnb ROI: 2.23%

Traditional ROI: 4.86%

1831 WINDWARD OAKS COURT

Kissimmee, FL

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

$569,990

Airbnb cash on cash: 3%

Traditional cash on cash: 4.08%

Airbnb Rental Income: $3852

Traditional Rental Income: $3601

Airbnb ROI: 3%

Traditional ROI: 4.08%

1024 Banks Rose St

Kissimmee, FL

3 beds | 2 baths | 1,987 sq.ft.

$779,000

Airbnb cash on cash: -0.81%

Traditional cash on cash: 0.66%

Airbnb Rental Income: $1682

Traditional Rental Income: $2284

Airbnb ROI: -0.81%

Traditional ROI: 0.66%

202 WOODSON COURT

Kissimmee, FL

5 beds | 4 baths | 3,744 sq.ft.

$623,000

Airbnb cash on cash: 3.14%

Traditional cash on cash: 6.38%

Airbnb Rental Income: $3852

Traditional Rental Income: $4904

Airbnb ROI: 3.14%

Traditional ROI: 6.38%

2219 SAN VITTORINO CIRCLE #107

Kissimmee, FL

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

$210,000

Airbnb cash on cash: 1.94%

Traditional cash on cash: 4.43%

Airbnb Rental Income: $2186

Traditional Rental Income: $2129

Airbnb ROI: 1.94%

Traditional ROI: 4.43%

5004 LAGUNA BAY CIRCLE #54

Kissimmee, FL

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

$235,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: 4.71%

Airbnb Rental Income: $1682

Traditional Rental Income: $2235

Airbnb ROI: 0.11%

Traditional ROI: 4.71%

4577 ALBERTO CIRCLE

Kissimmee, FL

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

$380,000

Airbnb cash on cash: 1.01%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $2186

Traditional Rental Income: $2729

Airbnb ROI: 1.01%