Airbnb Properties for Sale in Winter Garden, FL

Looking for a vacation rental investment in Winter Garden, FL with high ROI ?

Explore a range of newly added short-term rental homes in Winter Garden, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Winter Garden, FL

Q: How to get Winter-garden, FL Airbnb data?

Airbnb data on vacation rentals in Winter-garden, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winter-garden, FL market insights, guest information and booking details, seasonality trends and historical Winter-garden, FL Airbnb performance data .

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
12456 Westfield Lakes Cir Winter Garden, FL Welcome home to this stunning residence in the highly desirable Westfield Lakes community,...	4 beds \| 3 baths \| 2,180 sq.ft.	$575,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 3.13% Airbnb Rental Income: $5064 Traditional Rental Income: $2747 Airbnb ROI: 5.52% Traditional ROI: 3.13%
373 Eron Way #47 Winter Garden, FL Short Sale. MOVE-IN READY and quietly positioned within a well-established Winter Garden c...	2 beds \| 2 baths \| 840 sq.ft.	$169,999	Airbnb cash on cash: 5.22% Traditional cash on cash: 4.64% Airbnb Rental Income: $2340 Traditional Rental Income: $1667 Airbnb ROI: 5.22% Traditional ROI: 4.64%
14645 Scott Key Dr Winter Garden, FL Beautifully updated single-family home featuring NEW EXTERIOR PAINT AND NEW FLOORING THROU...	4 beds \| 3 baths \| 3,427 sq.ft.	$977,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 1.81% Airbnb Rental Income: $5064 Traditional Rental Income: $3797 Airbnb ROI: 2.07% Traditional ROI: 1.81%
15852 Shorebird Ln Winter Garden, FL Stunning 2-Story Home in Winter Garden â 4 Bedrooms, Solar Panels, and Exceptional Featu...	4 beds \| 4 baths \| 2,766 sq.ft.	$899,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 1.78% Airbnb Rental Income: $5064 Traditional Rental Income: $3857 Airbnb ROI: 1.99% Traditional ROI: 1.78%
15372 Gilligan Ct Winter Garden, FL Stunning One-Story Home in the Heart of Horizon West â Beautifully Renovated and Move-In...	4 beds \| 3 baths \| 2,781 sq.ft.	$884,500	Airbnb cash on cash: 2.75% Traditional cash on cash: 2.34% Airbnb Rental Income: $5064 Traditional Rental Income: $3697 Airbnb ROI: 2.75% Traditional ROI: 2.34%
5531 Cypress Hill Rd Winter Garden, FL Exquisitely upgraded 4-bedroom, 3-bath smart home in the highly sought-after Orchard Hills...	4 beds \| 3 baths \| 2,204 sq.ft.	$625,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $2827 Airbnb ROI: 4.02% Traditional ROI: 1.96%
8256 Bayview Crossing Dr Winter Garden, FL PRICE IMPROVEMENT....UPGRADED POOL HOME in Horizon West! Welcome to this 4-bed, 3.5-bath,...	4 beds \| 3 baths \| 2,557 sq.ft.	$675,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.5% Airbnb Rental Income: $5064 Traditional Rental Income: $3546 Airbnb ROI: 3.27% Traditional ROI: 2.5%
634 Foster Ave Winter Garden, FL Charming bungalow that's been completely renovated and is now move-in ready! Rebuilt down ...	2 beds \| 1 baths \| 696 sq.ft.	$285,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 2.86% Airbnb Rental Income: $2340 Traditional Rental Income: $1483 Airbnb ROI: 3.9% Traditional ROI: 2.86%
14602 Winter Stay Dr Winter Garden, FL Fantastic opportunity to own this exceptional home in the highly sought-after WATERMARK co...	4 beds \| 3 baths \| 3,433 sq.ft.	$780,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 3.24% Airbnb Rental Income: $5064 Traditional Rental Income: $4026 Airbnb ROI: 3.25% Traditional ROI: 3.24%
15058 Sawgrass Bluff Dr Winter Garden, FL Location! Location! Located just 10 minutes from historic downtown Winter Garden and adjac...	4 beds \| 2 baths \| 2,626 sq.ft.	$600,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 2.93% Airbnb Rental Income: $5064 Traditional Rental Income: $3031 Airbnb ROI: 4.72% Traditional ROI: 2.93%
500 Teacup Springs Ct Winter Garden, FL Short Sale. An exceptional opportunity for investors, builders, and developersâthis prop...	4 beds \| 3 baths \| 2,397 sq.ft.	$530,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 3.83% Airbnb Rental Income: $5064 Traditional Rental Income: $3060 Airbnb ROI: 5.79% Traditional ROI: 3.83%
13820 Orchard Leaf Way Winter Garden, FL Charming Two-Story Home in Winter Garden â Gated Community with Pool! This beautiful,...	4 beds \| 2 baths \| 1,657 sq.ft.	$399,000	Airbnb cash on cash: 7.35% Traditional cash on cash: 3.21% Airbnb Rental Income: $5064 Traditional Rental Income: $2483 Airbnb ROI: 7.35% Traditional ROI: 3.21%
634 Burch Ave Winter Garden, FL One or more photo(s) has been virtually staged. Seller offering $7,500 towards buyerâs c...	4 beds \| 3 baths \| 2,351 sq.ft.	$650,000	Airbnb cash on cash: 4.67% Traditional cash on cash: 4.18% Airbnb Rental Income: $5064 Traditional Rental Income: $3731 Airbnb ROI: 4.67% Traditional ROI: 4.18%
15452 Firelight Dr Winter Garden, FL Welcome to this stunning 4 bedroom, 3 bathroom home nestled in the highly sought-after gat...	4 beds \| 3 baths \| 2,648 sq.ft.	$639,900	Airbnb cash on cash: 4.67% Traditional cash on cash: 3.51% Airbnb Rental Income: $5064 Traditional Rental Income: $3338 Airbnb ROI: 4.67% Traditional ROI: 3.51%
15309 Honeybell Dr Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to 3,094 sq ft of contemporary liv...	4 beds \| 3 baths \| 3,094 sq.ft.	$789,900	Airbnb cash on cash: 3.41% Traditional cash on cash: 3.09% Airbnb Rental Income: $5064 Traditional Rental Income: $3792 Airbnb ROI: 3.41% Traditional ROI: 3.09%
14571 Bahama Swallow Blvd Winter Garden, FL Welcome to this charming single-story home located in the highly desirable Summerlake comm...	4 beds \| 2 baths \| 2,063 sq.ft.	$539,000	Airbnb cash on cash: 4.88% Traditional cash on cash: 2.74% Airbnb Rental Income: $5064 Traditional Rental Income: $2953 Airbnb ROI: 4.88% Traditional ROI: 2.74%
8906 Doddington Way Winter Garden, FL Discover the ideal blend of modern comfort and family-friendly living in this beautifully ...	4 beds \| 3 baths \| 2,352 sq.ft.	$569,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 2.04% Airbnb Rental Income: $5064 Traditional Rental Income: $2673 Airbnb ROI: 4.59% Traditional ROI: 2.04%
68 Windtree Ln #201 Winter Garden, FL Come and see why this spacious 2 bedrooms, 2 bathrooms second floor open floor plan condo ...	2 beds \| 2 baths \| 918 sq.ft.	$214,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 4.18% Airbnb Rental Income: $2340 Traditional Rental Income: $1654 Airbnb ROI: 4.71% Traditional ROI: 4.18%
11400 LOVERS LANE Winter Garden, FL If you've ever dreamed of country living, but don't want to give up your conveniences, the...	4 beds \| 3 baths \| 2,517 sq.ft.	$1,270,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 0.99% Airbnb Rental Income: $5064 Traditional Rental Income: $3063 Airbnb ROI: 1.81% Traditional ROI: 0.99%
1674 Victoria Way Winter Garden, FL Under contract-accepting backup offers. Beautifully updated POOL home in the desirable Tus...	4 beds \| 2 baths \| 2,239 sq.ft.	$679,990	Airbnb cash on cash: 4.27% Traditional cash on cash: 3.82% Airbnb Rental Income: $5064 Traditional Rental Income: $3747 Airbnb ROI: 4.27% Traditional ROI: 3.82%
1556 Coluso Dr Winter Garden, FL One or more photo(s) has been virtually staged. Experience modern Winter Garden living in ...	4 beds \| 2 baths \| 1,916 sq.ft.	$625,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 2.35% Airbnb Rental Income: $5064 Traditional Rental Income: $2611 Airbnb ROI: 4.79% Traditional ROI: 2.35%
14902 Arrena Rd Winter Garden, FL WATERFRONT--2 ACRES--NO HOA 7 Miles west of Disneys' main entrance...Winter Garden addre...	4 beds \| 2 baths \| 3,392 sq.ft.	$650,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 3% Airbnb Rental Income: $5064 Traditional Rental Income: $3239 Airbnb ROI: 4.31% Traditional ROI: 3%
6560 Candied Peel Aly Winter Garden, FL BEAUTIFUL 4 bedrooms and 3 bathrooms townhouse located in new Winter Garden area, the kit...	4 beds \| 3 baths \| 1,902 sq.ft.	$430,000	Airbnb cash on cash: 6.33% Traditional cash on cash: 4.1% Airbnb Rental Income: $5064 Traditional Rental Income: $3136 Airbnb ROI: 6.33% Traditional ROI: 4.1%
2510 BLACK LAKE BOULEVARD Winter Garden, FL Beautifully Updated Corner-Lot Home in Guard-Gated Stoneybrook West! This stylish resid...	4 beds \| 3 baths \| 3,022 sq.ft.	$665,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 2.87% Airbnb Rental Income: $5064 Traditional Rental Income: $3157 Airbnb ROI: 4.28% Traditional ROI: 2.87%
18339 Oliver Twist Way Winter Garden, FL Motivated Seller This 2023 built home has only had One-owner, highly upgraded luxury...	4 beds \| 3 baths \| 2,931 sq.ft.	$748,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 1.73% Airbnb Rental Income: $5064 Traditional Rental Income: $3177 Airbnb ROI: 2.95% Traditional ROI: 1.73%
963 STUCKI TERRACE Winter Garden, FL *** Price Improvement! Cozy Townhome Just Minutes from Downtown Winter Garden. Discover co...	2 beds \| 1 baths \| 761 sq.ft.	$210,000	Airbnb cash on cash: 5.94% Traditional cash on cash: 5.09% Airbnb Rental Income: $2340 Traditional Rental Income: $1592 Airbnb ROI: 5.94% Traditional ROI: 5.09%
14711 Winter Stay Dr Winter Garden, FL This stunning 4-bedroom, 3-bathroom home in Panther View offers the perfect blend of comfo...	4 beds \| 3 baths \| 2,662 sq.ft.	$849,999	Airbnb cash on cash: 2.58% Traditional cash on cash: 1.73% Airbnb Rental Income: $5064 Traditional Rental Income: $3356 Airbnb ROI: 2.58% Traditional ROI: 1.73%
14925 Lebeau Loop Winter Garden, FL Seller offering an $8,000 contribution toward buyer closing costs! Welcome to this stunnin...	4 beds \| 3 baths \| 2,116 sq.ft.	$665,000	Airbnb cash on cash: 3.94% Traditional cash on cash: 1.98% Airbnb Rental Income: $5064 Traditional Rental Income: $2816 Airbnb ROI: 3.94% Traditional ROI: 1.98%
15716 Sweet Lemon Way Winter Garden, FL Beautiful two-story single-family home located in the highly desirable Winter Garden area,...	4 beds \| 3 baths \| 2,945 sq.ft.	$795,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 2.69% Airbnb Rental Income: $5064 Traditional Rental Income: $3840 Airbnb ROI: 2.95% Traditional ROI: 2.69%
3467 BUOY CIRCLE Winter Garden, FL This move-in ready lakeview home offers 4 bedrooms, 3 full bathrooms, and a spacious bonus...	4 beds \| 3 baths \| 2,610 sq.ft.	$649,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 2.37% Airbnb Rental Income: $5064 Traditional Rental Income: $2858 Airbnb ROI: 4.31% Traditional ROI: 2.37%
16632 Point Rock Dr Winter Garden, FL Short Sale. Located in the sought-after resort-style community of Waterleigh in Winter Gar...	4 beds \| 3 baths \| 2,292 sq.ft.	$550,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 3.23% Airbnb Rental Income: $5064 Traditional Rental Income: $3370 Airbnb ROI: 4.51% Traditional ROI: 3.23%
1606 Malcolm Point Dr Winter Garden, FL *Golf Cart District* Nestled in a serene cul-de-sac in the heart of Winter Garden, Flo...	4 beds \| 3 baths \| 2,455 sq.ft.	$609,900	Airbnb cash on cash: 5.37% Traditional cash on cash: 3.5% Airbnb Rental Income: $5064 Traditional Rental Income: $2966 Airbnb ROI: 5.37% Traditional ROI: 3.5%
17865 Adrift Rd Winter Garden, FL A home full of charm, comfort, and practicality. It features four bedrooms, including a sp...	4 beds \| 3 baths \| 2,484 sq.ft.	$629,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 2.76% Airbnb Rental Income: $5064 Traditional Rental Income: $3454 Airbnb ROI: 3.74% Traditional ROI: 2.76%
17993 GOURD NECK LOOP Winter Garden, FL Come see this exquisite Meritage Home in Winter Gardenâs VERDE PARK, sitting on a 1/4 ac...	4 beds \| 3 baths \| 2,736 sq.ft.	$575,000	Airbnb cash on cash: 5.45% Traditional cash on cash: 3.55% Airbnb Rental Income: $5064 Traditional Rental Income: $3011 Airbnb ROI: 5.45% Traditional ROI: 3.55%
17329 Beachgrass Aly Winter Garden, FL Under Construction. Discover this stunning new construction home located at 17329 Beachgra...	4 beds \| 3 baths \| 2,510 sq.ft.	$574,990	Airbnb cash on cash: 4.61% Traditional cash on cash: 2.66% Airbnb Rental Income: $5064 Traditional Rental Income: $2983 Airbnb ROI: 4.61% Traditional ROI: 2.66%
11045 Bostwick Aly Winter Garden, FL LOCATION, LOCATION, LOCATION!!!PRICE IS INCLUDING TRANSFERRABLE SOLAR PANELS PAID BY THE S...	4 beds \| 3 baths \| 2,292 sq.ft.	$649,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 2.66% Airbnb Rental Income: $5064 Traditional Rental Income: $3419 Airbnb ROI: 3.67% Traditional ROI: 2.66%
16555 Wingspread Loop Winter Garden, FL This stunning 4-bedroom, 3.5-bath residence sits proudly in the highly sought-after Hawksm...	4 beds \| 3 baths \| 3,093 sq.ft.	$791,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 2.72% Airbnb Rental Income: $5064 Traditional Rental Income: $3850 Airbnb ROI: 2.96% Traditional ROI: 2.72%
1085 Chase Dr Winter Garden, FL Highly Motivated Seller! Enjoy the ultimate downtown lifestyleâhop on your golf cart and...	4 beds \| 3 baths \| 2,967 sq.ft.	$619,999	Airbnb cash on cash: 5.23% Traditional cash on cash: 3.95% Airbnb Rental Income: $5064 Traditional Rental Income: $3292 Airbnb ROI: 5.23% Traditional ROI: 3.95%
7363 Mezzano Ln Winter Garden, FL Welcome to your chance to own one of the most desirable residences in this vibrant communi...	4 beds \| 3 baths \| 1,920 sq.ft.	$479,999	Airbnb cash on cash: 5.93% Traditional cash on cash: 4.07% Airbnb Rental Income: $5064 Traditional Rental Income: $3194 Airbnb ROI: 5.93% Traditional ROI: 4.07%
15075 Tea Tree Dr Winter Garden, FL One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity...	4 beds \| 3 baths \| 3,038 sq.ft.	$773,260	Airbnb cash on cash: 3.35% Traditional cash on cash: 2.19% Airbnb Rental Income: $5064 Traditional Rental Income: $3193 Airbnb ROI: 3.35% Traditional ROI: 2.19%

Vacation Rentals in Winter Garden

There are 264 vacation rental properties available for sale in the city of Winter Garden . The median list price of Airbnb properties available for sale in Winter Garden is $614,995 and the average price per square foot is $253. The cash on cash return on vacation rentals in Winter Garden is 1.00%. The average monthly short term rental income in Winter Garden is $2,390.

Winter Garden, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 264 Airbnb properties available for sale in Winter Garden.

In 2026, the best neighborhood to buy short term rental property is Winter Garden.

In February 2026, the average Airbnb occupancy rate in Winter Garden is 78%.

Airbnb data on vacation rentals in Winter Garden, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winter Garden, FL market insights, guest information and booking details, seasonality trends and historical Winter Garden, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Winter Garden, FL

12456 Westfield Lakes Cir

Winter Garden, FL

4 beds | 3 baths | 2,180 sq.ft.

$575,000

Airbnb cash on cash: 5.52%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $5064

Traditional Rental Income: $2747

Airbnb ROI: 5.52%

Traditional ROI: 3.13%

373 Eron Way #47

Winter Garden, FL

2 beds | 2 baths | 840 sq.ft.

$169,999

Airbnb cash on cash: 5.22%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $2340

Traditional Rental Income: $1667

Airbnb ROI: 5.22%

Traditional ROI: 4.64%

14645 Scott Key Dr

Winter Garden, FL

4 beds | 3 baths | 3,427 sq.ft.

$977,000

Airbnb cash on cash: 2.07%

Traditional cash on cash: 1.81%

Airbnb Rental Income: $5064

Traditional Rental Income: $3797

Airbnb ROI: 2.07%

Traditional ROI: 1.81%

15852 Shorebird Ln

Winter Garden, FL

4 beds | 4 baths | 2,766 sq.ft.

$899,000

Airbnb cash on cash: 1.99%

Traditional cash on cash: 1.78%

Airbnb Rental Income: $5064

Traditional Rental Income: $3857

Airbnb ROI: 1.99%

Traditional ROI: 1.78%

15372 Gilligan Ct

Winter Garden, FL

4 beds | 3 baths | 2,781 sq.ft.

$884,500

Airbnb cash on cash: 2.75%

Traditional cash on cash: 2.34%

Airbnb Rental Income: $5064

Traditional Rental Income: $3697

Airbnb ROI: 2.75%

Traditional ROI: 2.34%

5531 Cypress Hill Rd

Winter Garden, FL

4 beds | 3 baths | 2,204 sq.ft.

$625,000

Airbnb cash on cash: 4.02%

Traditional cash on cash: 1.96%

Airbnb Rental Income: $5064

Traditional Rental Income: $2827

Airbnb ROI: 4.02%

Traditional ROI: 1.96%

8256 Bayview Crossing Dr

Winter Garden, FL

4 beds | 3 baths | 2,557 sq.ft.

$675,000

Airbnb cash on cash: 3.27%

Traditional cash on cash: 2.5%

Airbnb Rental Income: $5064

Traditional Rental Income: $3546

Airbnb ROI: 3.27%

Traditional ROI: 2.5%

634 Foster Ave

Winter Garden, FL

2 beds | 1 baths | 696 sq.ft.

$285,000

Airbnb cash on cash: 3.9%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $2340

Traditional Rental Income: $1483

Airbnb ROI: 3.9%