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
660 EGRET PLACE DRIVE Winter Garden, FL "What if your next home wasnât just a house â but a complete lifestyle upgrade?" Welc...	4 beds \| 3 baths \| 2,647 sq.ft.	$548,500	Airbnb cash on cash: 5.89% Traditional cash on cash: 4.33% Airbnb Rental Income: $5064 Traditional Rental Income: $3234 Airbnb ROI: 5.89% Traditional ROI: 4.33%
2018 BAY CLOVER DRIVE Winter Garden, FL SELLER CONTRIBUTION OF $10,000 TOWARDS NEW ROOF!! This beautiful 4-bedroom, 2-bathroom ho...	4 beds \| 2 baths \| 2,526 sq.ft.	$580,000	Airbnb cash on cash: 5.36% Traditional cash on cash: 2.73% Airbnb Rental Income: $5064 Traditional Rental Income: $2610 Airbnb ROI: 5.36% Traditional ROI: 2.73%
706 GRANDHAVEN WAY Winter Garden, FL Welcome to 706 Grandhaven Way, a beautifully updated home in the heart of Winter Gardenâ...	4 beds \| 3 baths \| 1,904 sq.ft.	$535,000	Airbnb cash on cash: 6.04% Traditional cash on cash: 3.29% Airbnb Rental Income: $5064 Traditional Rental Income: $2655 Airbnb ROI: 6.04% Traditional ROI: 3.29%
13609 GLYNSHEL DRIVE Winter Garden, FL Stunning Executive Home in Gated Glynwood â One-of-a-Kind Custom Renovation! This modern...	4 beds \| 3 baths \| 2,923 sq.ft.	$879,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 2.58% Airbnb Rental Income: $5064 Traditional Rental Income: $3783 Airbnb ROI: 2.88% Traditional ROI: 2.58%
14815 DRIFTWATER DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to 14815 Driftwater Driveâan upd...	4 beds \| 3 baths \| 1,997 sq.ft.	$450,000	Airbnb cash on cash: 5.76% Traditional cash on cash: 2.57% Airbnb Rental Income: $5064 Traditional Rental Income: $2686 Airbnb ROI: 5.76% Traditional ROI: 2.57%
14955 SPEER LAKE DRIVE Winter Garden, FL WATER VIEW - Bring your Boat!! Welcome home to this incredible home in sought after Signa...	4 beds \| 4 baths \| 2,722 sq.ft.	$650,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 3.7% Airbnb Rental Income: $5064 Traditional Rental Income: $3645 Airbnb ROI: 4.34% Traditional ROI: 3.7%
14645 SCOTT KEY DRIVE Winter Garden, FL PRICE REDUCED...Welcome to Watermark built by Meritage homes, a luxury resort style commun...	4 beds \| 4 baths \| 3,427 sq.ft.	$887,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 1.93% Airbnb Rental Income: $5064 Traditional Rental Income: $3797 Airbnb ROI: 2.21% Traditional ROI: 1.93%
213 W TILDEN STREET Winter Garden, FL One of a kind home located in the heart of DOWNTOWN WINTER GARDEN!! This...	4 beds \| 2 baths \| 2,100 sq.ft.	$795,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 1.54% Airbnb Rental Income: $5064 Traditional Rental Income: $2722 Airbnb ROI: 3.3% Traditional ROI: 1.54%
14815 TULLAMORE LOOP Winter Garden, FL BACK ON MARKET, BUYER'S FINANCING FELL THROUGH. Don't miss the chance to own this 4 Bedroo...	4 beds \| 2 baths \| 2,314 sq.ft.	$595,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 2.27% Airbnb Rental Income: $5064 Traditional Rental Income: $2563 Airbnb ROI: 4.91% Traditional ROI: 2.27%
6238 MANUSCRIPT STREET Winter Garden, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 4 baths \| 2,759 sq.ft.	$599,000	Airbnb cash on cash: 4.23% Traditional cash on cash: 3.72% Airbnb Rental Income: $5064 Traditional Rental Income: $3744 Airbnb ROI: 4.23% Traditional ROI: 3.72%
5755 NEW INDEPENDENCE PARKWAY Winter Garden, FL Under contract-accepting backup offers. Rare 4-bedroom, 2.5-bathroom townhome offering ove...	4 beds \| 3 baths \| 2,061 sq.ft.	$418,000	Airbnb cash on cash: 7.25% Traditional cash on cash: 3.98% Airbnb Rental Income: $5064 Traditional Rental Income: $2752 Airbnb ROI: 7.25% Traditional ROI: 3.98%
6578 CALAMONDIN DRIVE Winter Garden, FL This luxury 4bd/3ba townhouse is located in the highly sought-after Hamlin Reserve at Wint...	4 beds \| 3 baths \| 1,853 sq.ft.	$427,000	Airbnb cash on cash: 6.16% Traditional cash on cash: 2.62% Airbnb Rental Income: $5064 Traditional Rental Income: $2616 Airbnb ROI: 6.16% Traditional ROI: 2.62%
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%
16512 SEA GLASS STREET Winter Garden, FL Under contract-accepting backup offers. Welcome to 16512 Sea Glass Street, a beautifully u...	4 beds \| 4 baths \| 2,472 sq.ft.	$599,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 3.26% Airbnb Rental Income: $5064 Traditional Rental Income: $3537 Airbnb ROI: 4.14% Traditional ROI: 3.26%
15058 SAWGRASS BLUFF DRIVE Winter Garden, FL Welcome to your move-in ready haven in Winter Garden's highly desirable Johns Lake Pointe ...	4 beds \| 3 baths \| 2,626 sq.ft.	$630,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 2.74% Airbnb Rental Income: $5064 Traditional Rental Income: $3031 Airbnb ROI: 4.45% Traditional ROI: 2.74%
2540 BLACK LAKE BOULEVARD Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to a beautifully updated home that...	4 beds \| 3 baths \| 3,070 sq.ft.	$699,000	Airbnb cash on cash: 3.32% Traditional cash on cash: 2.39% Airbnb Rental Income: $5064 Traditional Rental Income: $3425 Airbnb ROI: 3.32% Traditional ROI: 2.39%
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.	$500,000	Airbnb cash on cash: 5.82% Traditional cash on cash: 2.32% Airbnb Rental Income: $5064 Traditional Rental Income: $2395 Airbnb ROI: 5.82% Traditional ROI: 2.32%
13041 INKWELL ALLEY Winter Garden, FL This extraordinary residence is located in the charming neighborhood of Storey Grove. Almo...	4 beds \| 3 baths \| 2,042 sq.ft.	$529,000	Airbnb cash on cash: 5.97% Traditional cash on cash: 3.28% Airbnb Rental Income: $5064 Traditional Rental Income: $2700 Airbnb ROI: 5.97% Traditional ROI: 3.28%
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.	$445,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 3.91% Airbnb Rental Income: $5064 Traditional Rental Income: $2937 Airbnb ROI: 6.53% Traditional ROI: 3.91%
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.	$465,000	Airbnb cash on cash: 5.5% Traditional cash on cash: 3.63% Airbnb Rental Income: $5064 Traditional Rental Income: $3218 Airbnb ROI: 5.5% Traditional ROI: 3.63%
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.	$699,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 4.36% Airbnb Rental Income: $5064 Traditional Rental Income: $3731 Airbnb ROI: 4.82% Traditional ROI: 4.36%
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.	$659,900	Airbnb cash on cash: 4.5% Traditional cash on cash: 3.37% Airbnb Rental Income: $5064 Traditional Rental Income: $3338 Airbnb ROI: 4.5% Traditional ROI: 3.37%
12216 ENCORE AT OVATION WAY Winter Garden, FL Welcome to 12216 Encore at Ovation Wayâa dream home for families who want it all: luxury...	4 beds \| 3 baths \| 2,889 sq.ft.	$679,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 3.05% Airbnb Rental Income: $5064 Traditional Rental Income: $3807 Airbnb ROI: 3.41% Traditional ROI: 3.05%
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%
3227 BUOY CIRCLE Winter Garden, FL Under contract-accepting backup offers. Welcome to this MOVE-IN READY one-story 4 bed/3 Ba...	4 beds \| 3 baths \| 2,070 sq.ft.	$629,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 2.66% Airbnb Rental Income: $5064 Traditional Rental Income: $3164 Airbnb ROI: 4.14% Traditional ROI: 2.66%
13200 PEACEFUL MELODY DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. Anna Maria A on Lot 115 offers 4 Bedrooms....	4 beds \| 3 baths \| 2,235 sq.ft.	$649,990	Airbnb cash on cash: 4.33% Traditional cash on cash: 2.21% Airbnb Rental Income: $5064 Traditional Rental Income: $2744 Airbnb ROI: 4.33% Traditional ROI: 2.21%
12114 STONELEIGH ALLEY Winter Garden, FL Move-in ready and nearly new, this beautifully upgraded Wekiva floor plan offers a thought...	4 beds \| 4 baths \| 2,789 sq.ft.	$650,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 3.67% Airbnb Rental Income: $5064 Traditional Rental Income: $3304 Airbnb ROI: 4.87% Traditional ROI: 3.67%
16061 BAYOU CREST DRIVE Winter Garden, FL Welcome to Your Own Slice of Paradise in Waterleigh! Offering 4 spacious bedrooms and 3 fu...	4 beds \| 3 baths \| 2,117 sq.ft.	$749,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 1.8% Airbnb Rental Income: $5064 Traditional Rental Income: $3135 Airbnb ROI: 3.08% Traditional ROI: 1.8%
1034 HUNTSPOINT STREET Winter Garden, FL Under contract-accepting backup offers. Welcome to 1034 Huntspoint Street, a charming and ...	4 beds \| 4 baths \| 2,219 sq.ft.	$780,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 2.04% Airbnb Rental Income: $5064 Traditional Rental Income: $3024 Airbnb ROI: 3.43% Traditional ROI: 2.04%
16250 FIREDRAGON DRIVE Winter Garden, FL Seller's loss buyers gain this property has now been reduced below market value hurry befo...	4 beds \| 3 baths \| 2,128 sq.ft.	$499,999	Airbnb cash on cash: 6.23% Traditional cash on cash: 3.46% Airbnb Rental Income: $5064 Traditional Rental Income: $2739 Airbnb ROI: 6.23% Traditional ROI: 3.46%
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.	$1,282,000	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%
275 VIRGINIA DRIVE Winter Garden, FL Located in the coveted "golf cart district" of downtown Winter Garden, this original owner...	4 beds \| 3 baths \| 2,004 sq.ft.	$484,900	Airbnb cash on cash: 6.54% Traditional cash on cash: 3.83% Airbnb Rental Income: $5064 Traditional Rental Income: $2803 Airbnb ROI: 6.54% Traditional ROI: 3.83%
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.	$2,199,999	Airbnb cash on cash: 0.43% Traditional cash on cash: -0.26% Airbnb Rental Income: $5064 Traditional Rental Income: $2631 Airbnb ROI: 0.43% Traditional ROI: -0.26%
322 APOPKA STREET Winter Garden, FL *OPPORTUNITY KNOCKS* Come see this STUNNING 4-bedroom 2.5-bathroom POOL HOME nestled i...	4 beds \| 3 baths \| 1,579 sq.ft.	$709,000	Airbnb cash on cash: 4.39% Traditional cash on cash: 3.18% Airbnb Rental Income: $5064 Traditional Rental Income: $3231 Airbnb ROI: 4.39% Traditional ROI: 3.18%
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.	$694,000	Airbnb cash on cash: 3.98% Traditional cash on cash: 2.75% Airbnb Rental Income: $5064 Traditional Rental Income: $3239 Airbnb ROI: 3.98% Traditional ROI: 2.75%
10038 VERSE ALLEY Winter Garden, FL EXCLUSIVE PARK-FRONT LIVING AWAITS Cherish memorable moments with your loved ones while ad...	4 beds \| 4 baths \| 2,486 sq.ft.	$550,000	Airbnb cash on cash: 5.09% Traditional cash on cash: 4.53% Airbnb Rental Income: $5064 Traditional Rental Income: $3744 Airbnb ROI: 5.09% Traditional ROI: 4.53%
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%
2019 WINTERMERE POINTE DRIVE Winter Garden, FL SELLER OFFERING $1000.00 CREDIT ON THIS PROPERTY TO A BUYER THAT IS UNDER CONTRACT BEFORE ...	4 beds \| 3 baths \| 2,455 sq.ft.	$539,900	Airbnb cash on cash: 5.22% Traditional cash on cash: 4.39% Airbnb Rental Income: $5064 Traditional Rental Income: $3613 Airbnb ROI: 5.22% Traditional ROI: 4.39%
15531 WATERLEIGH COVE DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. We just dropped the price to $620K. Take a...	4 beds \| 3 baths \| 2,295 sq.ft.	$620,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 2.62% Airbnb Rental Income: $5064 Traditional Rental Income: $2892 Airbnb ROI: 4.59% Traditional ROI: 2.62%
1005 CHASE DRIVE Winter Garden, FL Under contract-accepting backup offers. Please read: Seller has a quote for $52,000 for fu...	4 beds \| 3 baths \| 2,319 sq.ft.	$610,000	Airbnb cash on cash: 4.76% Traditional cash on cash: 2.59% Airbnb Rental Income: $5064 Traditional Rental Income: $2793 Airbnb ROI: 4.76% Traditional ROI: 2.59%

Vacation Rentals in Winter Garden

There are 134 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 $599,000 and the average price per square foot is $248. 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 134 Airbnb properties available for sale in Winter Garden.

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

In September 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

660 EGRET PLACE DRIVE

Winter Garden, FL

4 beds | 3 baths | 2,647 sq.ft.

$548,500

Airbnb cash on cash: 5.89%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $5064

Traditional Rental Income: $3234

Airbnb ROI: 5.89%

Traditional ROI: 4.33%

2018 BAY CLOVER DRIVE

Winter Garden, FL

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

$580,000

Airbnb cash on cash: 5.36%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $5064

Traditional Rental Income: $2610

Airbnb ROI: 5.36%

Traditional ROI: 2.73%

706 GRANDHAVEN WAY

Winter Garden, FL

4 beds | 3 baths | 1,904 sq.ft.

$535,000

Airbnb cash on cash: 6.04%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $5064

Traditional Rental Income: $2655

Airbnb ROI: 6.04%

Traditional ROI: 3.29%

13609 GLYNSHEL DRIVE

Winter Garden, FL

4 beds | 3 baths | 2,923 sq.ft.

$879,000

Airbnb cash on cash: 2.88%

Traditional cash on cash: 2.58%

Airbnb Rental Income: $5064

Traditional Rental Income: $3783

Airbnb ROI: 2.88%

Traditional ROI: 2.58%

14815 DRIFTWATER DRIVE

Winter Garden, FL

4 beds | 3 baths | 1,997 sq.ft.

$450,000

Airbnb cash on cash: 5.76%

Traditional cash on cash: 2.57%

Airbnb Rental Income: $5064

Traditional Rental Income: $2686

Airbnb ROI: 5.76%

Traditional ROI: 2.57%

14955 SPEER LAKE DRIVE

Winter Garden, FL

4 beds | 4 baths | 2,722 sq.ft.

$650,000

Airbnb cash on cash: 4.34%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $5064

Traditional Rental Income: $3645

Airbnb ROI: 4.34%

Traditional ROI: 3.7%

14645 SCOTT KEY DRIVE

Winter Garden, FL

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

$887,000

Airbnb cash on cash: 2.21%

Traditional cash on cash: 1.93%

Airbnb Rental Income: $5064

Traditional Rental Income: $3797

Airbnb ROI: 2.21%

Traditional ROI: 1.93%

213 W TILDEN STREET

Winter Garden, FL

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

$795,000

Airbnb cash on cash: 3.3%

Traditional cash on cash: 1.54%

Airbnb Rental Income: $5064

Traditional Rental Income: $2722

Airbnb ROI: 3.3%