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: -0.89% Traditional cash on cash: 4.15% Airbnb Rental Income: $1275 Traditional Rental Income: $1690 Airbnb ROI: -0.89% Traditional ROI: 4.15%
719 Del Ray Dr 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: 1.37% Traditional cash on cash: 4.86% Airbnb Rental Income: $1429 Traditional Rental Income: $1857 Airbnb ROI: 1.37% Traditional ROI: 4.86%
1831 Windward Oaks Ct Kissimmee, FL Price just LOWERED!!!!!! Welcome to your dream home in the beautiful BellaLago community!...	5 beds \| 3 baths \| 2,813 sq.ft.	$549,900	Airbnb cash on cash: 2.41% Traditional cash on cash: 4.27% Airbnb Rental Income: $3399 Traditional Rental Income: $3601 Airbnb ROI: 2.41% Traditional ROI: 4.27%
3251 Pinewood Ct Kissimmee, FL Explore this stunning property featuring three bedrooms and two bathrooms. Located at the ...	3 beds \| 2 baths \| 2,404 sq.ft.	$449,900	Airbnb cash on cash: 0.34% Traditional cash on cash: 4.35% Airbnb Rental Income: $1429 Traditional Rental Income: $2690 Airbnb ROI: 0.34% Traditional ROI: 4.35%
202 Woodson Ct Kissimmee, FL Welcome to this stunning 3,744 square foot residence located on a quiet cul de sac within ...	5 beds \| 3 baths \| 3,744 sq.ft.	$595,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 6.73% Airbnb Rental Income: $3399 Traditional Rental Income: $4904 Airbnb ROI: 2.66% Traditional ROI: 6.73%
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: 1.25% Traditional cash on cash: 4.43% Airbnb Rental Income: $2021 Traditional Rental Income: $2129 Airbnb ROI: 1.25% Traditional ROI: 4.43%
5004 Laguna Bay Cir #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.	$229,900	Airbnb cash on cash: -0.84% Traditional cash on cash: 4.83% Airbnb Rental Income: $1429 Traditional Rental Income: $2235 Airbnb ROI: -0.84% Traditional ROI: 4.83%
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.	$298,900	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.96% Airbnb Rental Income: $1429 Traditional Rental Income: $1717 Airbnb ROI: -0.58% Traditional ROI: 1.96%
4577 Alberto Cir 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.	$345,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 4.59% Airbnb Rental Income: $2021 Traditional Rental Income: $2729 Airbnb ROI: 0.79% Traditional ROI: 4.59%
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: 0.17% Traditional cash on cash: 1.55% Airbnb Rental Income: $2021 Traditional Rental Income: $2085 Airbnb ROI: 0.17% Traditional ROI: 1.55%
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.	$200,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 5.56% Airbnb Rental Income: $1429 Traditional Rental Income: $2100 Airbnb ROI: -0.22% Traditional ROI: 5.56%
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: -0.25% Traditional cash on cash: 4.67% Airbnb Rental Income: $1275 Traditional Rental Income: $1752 Airbnb ROI: -0.25% Traditional ROI: 4.67%
2739 N Poinciana Blvd #71 Kissimmee, FL It's here, the condo you've been waiting for! Whether you are looking for a short-term ren...	3 beds \| 2 baths \| 1,287 sq.ft.	$175,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 4.56% Airbnb Rental Income: $1429 Traditional Rental Income: $1697 Airbnb ROI: 0.39% Traditional ROI: 4.56%
5004 Laguna Bay Cir #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: -0.58% Traditional cash on cash: 3.92% Airbnb Rental Income: $1429 Traditional Rental Income: $2148 Airbnb ROI: -0.58% Traditional ROI: 3.92%
604 Chadbury Way Kissimmee, FL Fully furnished Ranch style luxury south facing pool home located in Remington golf commun...	4 beds \| 3 baths \| 1,719 sq.ft.	$439,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 2.75% Airbnb Rental Income: $2021 Traditional Rental Income: $2102 Airbnb ROI: 1.27% Traditional ROI: 2.75%
2239 Santa Lucia St 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.	$318,497	Airbnb cash on cash: 0.72% Traditional cash on cash: 5% Airbnb Rental Income: $1429 Traditional Rental Income: $2284 Airbnb ROI: 0.72% Traditional ROI: 5%
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: 0.51% Traditional cash on cash: 2.87% Airbnb Rental Income: $2021 Traditional Rental Income: $2729 Airbnb ROI: 0.51% 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: 0.95% Traditional cash on cash: 5.56% Airbnb Rental Income: $2021 Traditional Rental Income: $3738 Airbnb ROI: 0.95% 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: -0.82% Traditional cash on cash: 2.26% Airbnb Rental Income: $2021 Traditional Rental Income: $2922 Airbnb ROI: -0.82% 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: -0.81% Traditional cash on cash: 2.02% Airbnb Rental Income: $2021 Traditional Rental Income: $2654 Airbnb ROI: -0.81% Traditional ROI: 2.02%
2300 Eagle Talon Ct Kissimmee, FL Beautiful Mediterranean Style Home (4 bedroom 3.5 bath) nestled away in the highly sought ...	4 beds \| 3 baths \| 3,591 sq.ft.	$475,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 3.39% Airbnb Rental Income: $2021 Traditional Rental Income: $2764 Airbnb ROI: 0.53% Traditional ROI: 3.39%
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: -0.77% Traditional cash on cash: 3.25% Airbnb Rental Income: $2021 Traditional Rental Income: $2779 Airbnb ROI: -0.77% 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.	$220,000	Airbnb cash on cash: -2.9% Traditional cash on cash: 1.67% Airbnb Rental Income: $1275 Traditional Rental Income: $1826 Airbnb ROI: -2.9% Traditional ROI: 1.67%
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: -1.81% Traditional cash on cash: 3.12% Airbnb Rental Income: $1275 Traditional Rental Income: $1969 Airbnb ROI: -1.81% 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: -1.52% Traditional cash on cash: 1.87% Airbnb Rental Income: $1429 Traditional Rental Income: $2332 Airbnb ROI: -1.52% 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: 0.79% Traditional cash on cash: 3.2% Airbnb Rental Income: $2021 Traditional Rental Income: $2565 Airbnb ROI: 0.79% Traditional ROI: 3.2%
4504 Alberto Cir Kissimmee, FL Get $2,000 toward closing costs when you finance with our preferred lender. Act now and mo...	3 beds \| 2 baths \| 1,295 sq.ft.	$299,999	Airbnb cash on cash: -0.81% Traditional cash on cash: 3.38% Airbnb Rental Income: $1429 Traditional Rental Income: $2184 Airbnb ROI: -0.81% Traditional ROI: 3.38%
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.	$309,900	Airbnb cash on cash: 1.3% Traditional cash on cash: 5.42% Airbnb Rental Income: $1429 Traditional Rental Income: $2202 Airbnb ROI: 1.3% Traditional ROI: 5.42%
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: -1.52% Traditional cash on cash: 2.99% Airbnb Rental Income: $1429 Traditional Rental Income: $2296 Airbnb ROI: -1.52% 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: -1.44% Traditional cash on cash: 3.4% Airbnb Rental Income: $1429 Traditional Rental Income: $2144 Airbnb ROI: -1.44% Traditional ROI: 3.4%
2950 Lucayan Harbour Cir #105 Kissimmee, FL Discover your perfect getaway in the desirable Lucaya Village Resort, where convenience, e...	4 beds \| 3 baths \| 1,694 sq.ft.	$309,900	Airbnb cash on cash: 0.41% Traditional cash on cash: 3.3% Airbnb Rental Income: $2021 Traditional Rental Income: $2337 Airbnb ROI: 0.41% Traditional ROI: 3.3%
2634 Corvette Ln Kissimmee, FL Discover Your Dream Getaway in Regal Oaks! This stunning and fully furnished 2-bedroom t...	2 beds \| 2 baths \| 1,350 sq.ft.	$285,000	Airbnb cash on cash: -2.05% Traditional cash on cash: 3.18% Airbnb Rental Income: $1275 Traditional Rental Income: $2279 Airbnb ROI: -2.05% Traditional ROI: 3.18%
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: 1.78% Traditional cash on cash: 5.72% Airbnb Rental Income: $2021 Traditional Rental Income: $2861 Airbnb ROI: 1.78% Traditional ROI: 5.72%
2918 Sunset Vista Blvd Kissimmee, FL Come see this beautiful 4 bedroom, 2 bathroom pool home in a gated community! This home co...	4 beds \| 2 baths \| 1,701 sq.ft.	$399,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 5.01% Airbnb Rental Income: $2021 Traditional Rental Income: $2787 Airbnb ROI: 1.56% Traditional ROI: 5.01%
4715 Flagler Beach Way Kissimmee, FL PRICED BELOW MARKET VALUE â MOTIVATED SELLER â EXCELLENT INVESTMENT OPPORTUNITY Wel...	3 beds \| 2 baths \| 1,286 sq.ft.	$279,900	Airbnb cash on cash: -1.07% Traditional cash on cash: 3.89% Airbnb Rental Income: $1429 Traditional Rental Income: $2310 Airbnb ROI: -1.07% Traditional ROI: 3.89%
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: -0.77% Traditional cash on cash: 4.98% Airbnb Rental Income: $1275 Traditional Rental Income: $1857 Airbnb ROI: -0.77% 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: -5.57% Traditional cash on cash: 3.34% Airbnb Rental Income: $1275 Traditional Rental Income: $2648 Airbnb ROI: -5.57% 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 \| 2 baths \| 1,286 sq.ft.	$304,900	Airbnb cash on cash: -0.43% Traditional cash on cash: 3.07% Airbnb Rental Income: $1429 Traditional Rental Income: $2005 Airbnb ROI: -0.43% Traditional ROI: 3.07%
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: -1.06% Traditional cash on cash: 4.32% Airbnb Rental Income: $1429 Traditional Rental Income: $2124 Airbnb ROI: -1.06% Traditional ROI: 4.32%

Real Estate investment in Kissimmee, FL

There are 3,781 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 $172. In August 2026, the average monthly cash on cash return in Kissimmee is 4.00%. The average monthly rental income in Kissimmee is $2,319.

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

There are 3,781 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 $2,319.

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: -0.89%

Traditional cash on cash: 4.15%

Airbnb Rental Income: $1275

Traditional Rental Income: $1690

Airbnb ROI: -0.89%

Traditional ROI: 4.15%

719 Del Ray Dr

Kissimmee, FL

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

$260,000

Airbnb cash on cash: 1.37%

Traditional cash on cash: 4.86%

Airbnb Rental Income: $1429

Traditional Rental Income: $1857

Airbnb ROI: 1.37%

Traditional ROI: 4.86%

1831 Windward Oaks Ct

Kissimmee, FL

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

$549,900

Airbnb cash on cash: 2.41%

Traditional cash on cash: 4.27%

Airbnb Rental Income: $3399

Traditional Rental Income: $3601

Airbnb ROI: 2.41%

Traditional ROI: 4.27%

3251 Pinewood Ct

Kissimmee, FL

3 beds | 2 baths | 2,404 sq.ft.

$449,900

Airbnb cash on cash: 0.34%

Traditional cash on cash: 4.35%

Airbnb Rental Income: $1429

Traditional Rental Income: $2690

Airbnb ROI: 0.34%

Traditional ROI: 4.35%

202 Woodson Ct

Kissimmee, FL

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

$595,000

Airbnb cash on cash: 2.66%

Traditional cash on cash: 6.73%

Airbnb Rental Income: $3399

Traditional Rental Income: $4904

Airbnb ROI: 2.66%

Traditional ROI: 6.73%

2219 SAN VITTORINO CIRCLE #107

Kissimmee, FL

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

$210,000

Airbnb cash on cash: 1.25%

Traditional cash on cash: 4.43%

Airbnb Rental Income: $2021

Traditional Rental Income: $2129

Airbnb ROI: 1.25%

Traditional ROI: 4.43%

5004 Laguna Bay Cir #54

Kissimmee, FL

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

$229,900

Airbnb cash on cash: -0.84%

Traditional cash on cash: 4.83%

Airbnb Rental Income: $1429

Traditional Rental Income: $2235

Airbnb ROI: -0.84%

Traditional ROI: 4.83%

4558 Ada Ln

Kissimmee, FL

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

$298,900

Airbnb cash on cash: -0.58%

Traditional cash on cash: 1.96%

Airbnb Rental Income: $1429

Traditional Rental Income: $1717

Airbnb ROI: -0.58%