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
2018 BAY CLOVER DRIVE Winter Garden, FL SELLER WILL REPLACE ROOF PRIOR CLOSING WITH AN ACCEPTABLE OFFER!! This beautiful 4-bedroo...	4 beds \| 2 baths \| 2,526 sq.ft.	$578,000	Airbnb cash on cash: 5.38% Traditional cash on cash: 2.75% Airbnb Rental Income: $5064 Traditional Rental Income: $2610 Airbnb ROI: 5.38% Traditional ROI: 2.75%
14488 WHITTRIDGE DRIVE Winter Garden, FL Unique opportunity in highly desired Independence (Winter Garden)! This corner, end-unit t...	4 beds \| 3 baths \| 2,159 sq.ft.	$474,000	Airbnb cash on cash: 6.2% Traditional cash on cash: 3.66% Airbnb Rental Income: $5064 Traditional Rental Income: $2907 Airbnb ROI: 6.2% Traditional ROI: 3.66%
111 LAKEVIEW RESERVE BOULEVARD Winter Garden, FL Move-in ready! From the extra wide paver driveway, Bahama shutters, modern sculptures, th...	4 beds \| 3 baths \| 2,882 sq.ft.	$634,900	Airbnb cash on cash: 4.97% Traditional cash on cash: 3.64% Airbnb Rental Income: $5064 Traditional Rental Income: $3244 Airbnb ROI: 4.97% Traditional ROI: 3.64%
15261 HONEYBELL DRIVE Winter Garden, FL Welcome to this professionally designed and fully remodeled two-story home in the highly s...	4 beds \| 4 baths \| 3,084 sq.ft.	$829,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 2.56% Airbnb Rental Income: $5064 Traditional Rental Income: $3838 Airbnb ROI: 2.81% Traditional ROI: 2.56%
7448 POMELO GROVE DRIVE Winter Garden, FL Welcome to 7448 Pomelo Grove Drive â a beautifully curated 4-bedroom, 3-bath pool home i...	4 beds \| 3 baths \| 2,683 sq.ft.	$809,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 2.21% Airbnb Rental Income: $5064 Traditional Rental Income: $3588 Airbnb ROI: 2.79% Traditional ROI: 2.21%
213 W TILDEN STREET Winter Garden, FL Located in the heart of DOWNTOWN WINTER GARDEN!! This beautifully renova...	4 beds \| 2 baths \| 2,100 sq.ft.	$789,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 1.56% Airbnb Rental Income: $5064 Traditional Rental Income: $2722 Airbnb ROI: 3.34% Traditional ROI: 1.56%
15852 SHOREBIRD LANE Winter Garden, FL Stunning 2-Story Home in Winter Garden â 4 Bedrooms, Solar Panels, and Exceptional Featu...	4 beds \| 5 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%
15594 HAMLIN BLOSSOM AVENUE Winter Garden, FL Immaculate 4-bedroom, 2 1/2 bathroom home available for immediate move-in in the highly so...	4 beds \| 3 baths \| 3,091 sq.ft.	$779,900	Airbnb cash on cash: 3.25% Traditional cash on cash: 2.06% Airbnb Rental Income: $5064 Traditional Rental Income: $3168 Airbnb ROI: 3.25% Traditional ROI: 2.06%
8256 BAYVIEW CROSSING DRIVE Winter Garden, FL POOL HOME â UPGRADED! Welcome to this 4-bed, 3.5-bath retreat in the highly sought-afte...	4 beds \| 4 baths \| 2,557 sq.ft.	$699,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 2.38% Airbnb Rental Income: $5064 Traditional Rental Income: $3546 Airbnb ROI: 3.12% Traditional ROI: 2.38%
14602 WINTER STAY DRIVE Winter Garden, FL Fantastic opportunity to own this exceptional home in the highly sought-after WATERMARK co...	4 beds \| 4 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%
15060 STUTTGART ALLEY Winter Garden, FL Beautiful 2 story house in desirable Watermark in Winter Garden. This house includes stain...	4 beds \| 3 baths \| 1,696 sq.ft.	$490,000	Airbnb cash on cash: 5.96% Traditional cash on cash: 2.39% Airbnb Rental Income: $5064 Traditional Rental Income: $2395 Airbnb ROI: 5.96% Traditional ROI: 2.39%
11018 HANLON TERRACE ALLEY Winter Garden, FL Beautiful 2019 built townhome located in sought after Winding Bay Preserve. Located just 1...	4 beds \| 3 baths \| 2,037 sq.ft.	$400,000	Airbnb cash on cash: 7.37% Traditional cash on cash: 4.45% Airbnb Rental Income: $5064 Traditional Rental Income: $2937 Airbnb ROI: 7.37% Traditional ROI: 4.45%
9814 AMBER CHESTNUT WAY Winter Garden, FL Expect to be impressed with this 4BR home in the desirable Watermark community. Room for e...	4 beds \| 4 baths \| 2,303 sq.ft.	$450,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 3.79% Airbnb Rental Income: $5064 Traditional Rental Income: $3218 Airbnb ROI: 5.72% Traditional ROI: 3.79%
17117 HEARTWOOD LOOP Winter Garden, FL Welcome to your very own slice of Winter Garden paradise! This impressive 5.3-acre, high-a...	4 beds \| 4 baths \| 3,265 sq.ft.	$1,299,900	Airbnb cash on cash: 1.35% Traditional cash on cash: 1.14% Airbnb Rental Income: $5064 Traditional Rental Income: $3785 Airbnb ROI: 1.35% Traditional ROI: 1.14%
10386 ATWATER BAY DRIVE Winter Garden, FL Experience the best of resort-style living in the desirable Waterleigh community of Winter...	4 beds \| 3 baths \| 2,117 sq.ft.	$699,900	Airbnb cash on cash: 3.37% Traditional cash on cash: 1.49% Airbnb Rental Income: $5064 Traditional Rental Income: $2805 Airbnb ROI: 3.37% Traditional ROI: 1.49%
634 BURCH AVENUE Winter Garden, FL Welcome to your dream home in the heart of Downtown Winter Gardenâs golf cart districtâ...	4 beds \| 4 baths \| 2,448 sq.ft.	$664,000	Airbnb cash on cash: 5.13% Traditional cash on cash: 4.64% Airbnb Rental Income: $5064 Traditional Rental Income: $3731 Airbnb ROI: 5.13% Traditional ROI: 4.64%
15452 FIRELIGHT DRIVE 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.	$649,900	Airbnb cash on cash: 4.58% Traditional cash on cash: 3.44% Airbnb Rental Income: $5064 Traditional Rental Income: $3338 Airbnb ROI: 4.58% Traditional ROI: 3.44%
12216 ENCORE AT OVATION WAY Winter Garden, FL Under contract-accepting backup offers. Welcome to 12216 Encore at Ovation Wayâa dream h...	4 beds \| 3 baths \| 2,889 sq.ft.	$650,000	Airbnb cash on cash: 3.6% Traditional cash on cash: 3.23% Airbnb Rental Income: $5064 Traditional Rental Income: $3807 Airbnb ROI: 3.6% Traditional ROI: 3.23%
15349 MURCOTT HARVEST LOOP Winter Garden, FL This two story house featuring 4 bedrooms, 3 baths with Orange County National Golf court ...	4 beds \| 3 baths \| 2,469 sq.ft.	$680,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 2.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3392 Airbnb ROI: 3.97% Traditional ROI: 2.96%
312 ENGLISH LAKE DRIVE Winter Garden, FL Under contract-accepting backup offers. Living beautifully in a Winter Garden neighborhood...	4 beds \| 3 baths \| 2,833 sq.ft.	$895,000	Airbnb cash on cash: 2.45% Traditional cash on cash: 1.2% Airbnb Rental Income: $5064 Traditional Rental Income: $2986 Airbnb ROI: 2.45% Traditional ROI: 1.2%
9182 HOLLISTON CREEK PLACE Winter Garden, FL Discover Your New Home in Winter Garden! Are you searching for the perfect home for your f...	4 beds \| 4 baths \| 2,733 sq.ft.	$890,000	Airbnb cash on cash: 2.3% Traditional cash on cash: 1.67% Airbnb Rental Income: $5064 Traditional Rental Income: $3509 Airbnb ROI: 2.3% Traditional ROI: 1.67%
68 WINDTREE LANE #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: 5.19% Traditional cash on cash: 4.66% Airbnb Rental Income: $2340 Traditional Rental Income: $1654 Airbnb ROI: 5.19% Traditional ROI: 4.66%
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.	$1,280,000	Airbnb cash on cash: 1.79% Traditional cash on cash: 0.98% Airbnb Rental Income: $5064 Traditional Rental Income: $3063 Airbnb ROI: 1.79% Traditional ROI: 0.98%
1674 VICTORIA WAY Winter Garden, FL Beautifully updated POOL home in the desirable Tuscany community! Major updates include a ...	4 beds \| 3 baths \| 2,239 sq.ft.	$675,000	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%
1136 BRICK RD Winter Garden, FL Donât miss this rare opportunity to own almost 5 acres in the heart of downtown Winter G...	4 beds \| 3 baths \| 2,535 sq.ft.	$1,899,999	Airbnb cash on cash: 0.65% Traditional cash on cash: -0.14% Airbnb Rental Income: $5064 Traditional Rental Income: $2631 Airbnb ROI: 0.65% Traditional ROI: -0.14%
14902 ARRENA ROAD Winter Garden, FL WATERFRONT--2 ACRES--NO HOA 7 Miles west of Disneys' main entrance...Winter Garden addre...	4 beds \| 3 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 ALLEY Winter Garden, FL BEAUTIFUL 4 bedrooms and 3 bathrooms townhouse located in new Winter Garden area, the kit...	4 beds \| 4 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%
15531 WATERLEIGH COVE DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. Gigantic price drop. Priced to sell fast! ...	4 beds \| 3 baths \| 2,295 sq.ft.	$575,000	Airbnb cash on cash: 5.03% Traditional cash on cash: 2.91% Airbnb Rental Income: $5064 Traditional Rental Income: $2892 Airbnb ROI: 5.03% Traditional ROI: 2.91%
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.	$675,000	Airbnb cash on cash: 4.2% Traditional cash on cash: 2.81% Airbnb Rental Income: $5064 Traditional Rental Income: $3157 Airbnb ROI: 4.2% Traditional ROI: 2.81%
9736 AMBER CHESTNUT WAY Winter Garden, FL Welcome to this beautifully appointed 4 bedroom, 2.5 bath end unit townhome with a front p...	4 beds \| 3 baths \| 1,937 sq.ft.	$449,900	Airbnb cash on cash: 6.75% Traditional cash on cash: 3.6% Airbnb Rental Income: $5064 Traditional Rental Income: $2702 Airbnb ROI: 6.75% Traditional ROI: 3.6%
7833 FREESTYLE LANE Winter Garden, FL Under contract-accepting backup offers. Welcome to a truly exquisite single-story residenc...	4 beds \| 3 baths \| 3,364 sq.ft.	$1,295,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 0.24% Airbnb Rental Income: $5064 Traditional Rental Income: $3243 Airbnb ROI: 0.9% Traditional ROI: 0.24%
16150 Parkwyn Street Winter Garden, FL MUST SEE THIS LUXURIOUS OPEN CONCEPT HOME SWEET HOME! * * * CLICK ON 'VIRTUAL TOUR' AND SE...	4 beds \| 4 baths \| 3,093 sq.ft.	$769,990	Airbnb cash on cash: 3.55% Traditional cash on cash: 3.28% Airbnb Rental Income: $5064 Traditional Rental Income: $3839 Airbnb ROI: 3.55% Traditional ROI: 3.28%
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%
9846 Emerald Berry Drive Winter Garden, FL Beautiful 4-Bedroom Home with Stunning Views and Spectacular Sunsets This immaculate singl...	4 beds \| 3 baths \| 2,072 sq.ft.	$698,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 1.84% Airbnb Rental Income: $5064 Traditional Rental Income: $2750 Airbnb ROI: 3.81% Traditional ROI: 1.84%
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%
459 MILLWOOD PLACE Winter Garden, FL One or more photo(s) has been virtually staged. Just in Time for Summer â A Self-Sustain...	4 beds \| 3 baths \| 2,873 sq.ft.	$675,000	Airbnb cash on cash: 4.44% Traditional cash on cash: 3.53% Airbnb Rental Income: $5064 Traditional Rental Income: $3460 Airbnb ROI: 4.44% Traditional ROI: 3.53%
40 W SMITH STREET Winter Garden, FL Welcome home to 40 W Smith St. Step into a piece of Winter Garden's rich history with thi...	4 beds \| 2 baths \| 2,225 sq.ft.	$750,000	Airbnb cash on cash: 4.41% Traditional cash on cash: 2.77% Airbnb Rental Income: $5064 Traditional Rental Income: $2883 Airbnb ROI: 4.41% Traditional ROI: 2.77%
14711 WINTER STAY DRIVE 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.	$875,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 1.65% Airbnb Rental Income: $5064 Traditional Rental Income: $3356 Airbnb ROI: 2.48% Traditional ROI: 1.65%
14925 LEBEAU LOOP Winter Garden, FL 15,000 seller closing cost contribution! Welcome to this beautiful one-story home nestled...	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%
16489 SILVER BROOK WAY Winter Garden, FL Welcome to your dream home in the heart of Winter Garden! This beautifully designed single...	4 beds \| 3 baths \| 2,080 sq.ft.	$720,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 3.51% Airbnb Rental Income: $5064 Traditional Rental Income: $3482 Airbnb ROI: 4.32% Traditional ROI: 3.51%

Vacation Rentals in Winter Garden

There are 125 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 $603,495 and the average price per square foot is $247. 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 125 Airbnb properties available for sale in Winter Garden.

In 2025, the best neighborhood to buy short term rental property is Winter Garden.

In November 2025, 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

2018 BAY CLOVER DRIVE

Winter Garden, FL

4 beds | 2 baths | 2,526 sq.ft.

$578,000

Airbnb cash on cash: 5.38%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $5064

Traditional Rental Income: $2610

Airbnb ROI: 5.38%

Traditional ROI: 2.75%

14488 WHITTRIDGE DRIVE

Winter Garden, FL

4 beds | 3 baths | 2,159 sq.ft.

$474,000

Airbnb cash on cash: 6.2%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $5064

Traditional Rental Income: $2907

Airbnb ROI: 6.2%

Traditional ROI: 3.66%

111 LAKEVIEW RESERVE BOULEVARD

Winter Garden, FL

4 beds | 3 baths | 2,882 sq.ft.

$634,900

Airbnb cash on cash: 4.97%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $5064

Traditional Rental Income: $3244

Airbnb ROI: 4.97%

Traditional ROI: 3.64%

15261 HONEYBELL DRIVE

Winter Garden, FL

4 beds | 4 baths | 3,084 sq.ft.

$829,000

Airbnb cash on cash: 2.81%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $5064

Traditional Rental Income: $3838

Airbnb ROI: 2.81%

Traditional ROI: 2.56%

7448 POMELO GROVE DRIVE

Winter Garden, FL

4 beds | 3 baths | 2,683 sq.ft.

$809,000

Airbnb cash on cash: 2.79%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $5064

Traditional Rental Income: $3588

Airbnb ROI: 2.79%

Traditional ROI: 2.21%

213 W TILDEN STREET

Winter Garden, FL

4 beds | 2 baths | 2,100 sq.ft.

$789,000

Airbnb cash on cash: 3.34%

Traditional cash on cash: 1.56%

Airbnb Rental Income: $5064

Traditional Rental Income: $2722

Airbnb ROI: 3.34%

Traditional ROI: 1.56%

15852 SHOREBIRD LANE

Winter Garden, FL

4 beds | 5 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%

15594 HAMLIN BLOSSOM AVENUE

Winter Garden, FL

4 beds | 3 baths | 3,091 sq.ft.

$779,900

Airbnb cash on cash: 3.25%

Traditional cash on cash: 2.06%

Airbnb Rental Income: $5064

Traditional Rental Income: $3168

Airbnb ROI: 3.25%