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 .

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
15445 PEBBLE RIDGE STREET Winter Garden, FL Under contract-accepting backup offers. Video Tour Available Welcome to Stoneybrook We...	4 beds \| 2 baths \| 2,375 sq.ft.	$575,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 3.32% Airbnb Rental Income: $5064 Traditional Rental Income: $3245 Airbnb ROI: 4.79% Traditional ROI: 3.32%
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 Under contract-accepting backup offers. Multiple offers! We listened to feed back. We hav...	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%
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 DRIVE Winter Garden, FL Beautifully updated single-family home featuring NEW EXTERIOR PAINT AND NEW FLOORING THROU...	4 beds \| 4 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%
15372 GILLIGAN COURT Winter Garden, FL Stunning One-Story Home in the Heart of Horizon West â Beautifully Renovated and Move-In...	4 beds \| 4 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%
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%
634 FOSTER AVENUE 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 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%
15058 SAWGRASS BLUFF DRIVE Winter Garden, FL NEW PRICE! Welcome to your move-in ready haven in Winter Garden's highly desirable Johns...	4 beds \| 3 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%
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%
500 TEACUP SPRINGS COURT 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%
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.	$448,900	Airbnb cash on cash: 5.73% Traditional cash on cash: 3.8% Airbnb Rental Income: $5064 Traditional Rental Income: $3218 Airbnb ROI: 5.73% Traditional ROI: 3.8%
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 One or more photo(s) has been virtually staged. Seller offering $7,500 towards buyerâs c...	4 beds \| 4 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%
9282 WOODCRANE DRIVE Winter Garden, FL Under contract-accepting backup offers. Welcome to 9282 Woodcrane Drive, a stunning reside...	4 beds \| 4 baths \| 2,650 sq.ft.	$785,000	Airbnb cash on cash: 2.77% Traditional cash on cash: 2.03% Airbnb Rental Income: $5064 Traditional Rental Income: $3494 Airbnb ROI: 2.77% Traditional ROI: 2.03%
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.	$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 DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to 3,094 sq ft of contemporary liv...	4 beds \| 4 baths \| 3,094 sq.ft.	$794,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 3.06% Airbnb Rental Income: $5064 Traditional Rental Income: $3792 Airbnb ROI: 3.39% Traditional ROI: 3.06%
14571 BAHAMA SWALLOW BOULEVARD 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.	$545,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 2.7% Airbnb Rental Income: $5064 Traditional Rental Income: $2953 Airbnb ROI: 4.82% Traditional ROI: 2.7%
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.	$1,270,000	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%
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 Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Gi...	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.	$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%
9736 AMBER CHESTNUT WAY Winter Garden, FL Under contract-accepting backup offers. Welcome to this beautifully appointed 4 bedroom, 2...	4 beds \| 3 baths \| 1,937 sq.ft.	$439,900	Airbnb cash on cash: 6.92% Traditional cash on cash: 3.7% Airbnb Rental Income: $5064 Traditional Rental Income: $2702 Airbnb ROI: 6.92% Traditional ROI: 3.7%
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: 3.38% Traditional cash on cash: 3.11% Airbnb Rental Income: $5064 Traditional Rental Income: $3839 Airbnb ROI: 3.38% Traditional ROI: 3.11%
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 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%
2237 WINTERMERE POINTE DRIVE Winter Garden, FL Under contract-accepting backup offers. Welcome to this one-story 4 bed/2 Bath home, locat...	4 beds \| 2 baths \| 1,950 sq.ft.	$495,000	Airbnb cash on cash: 6.51% Traditional cash on cash: 3.37% Airbnb Rental Income: $5064 Traditional Rental Income: $2574 Airbnb ROI: 6.51% Traditional ROI: 3.37%
17359 BEACHGRASS ALLEY Winter Garden, FL Under Construction. Welcome to this beautiful new construction home located at 17359 Beach...	4 beds \| 4 baths \| 2,780 sq.ft.	$686,990	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.77% Airbnb Rental Income: $5064 Traditional Rental Income: $3705 Airbnb ROI: 4.28% Traditional ROI: 3.77%
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 DRIVE Winter Garden, FL Short Sale. Located in the sought-after resort-style community of Waterleigh in Winter Gar...	4 beds \| 4 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 DRIVE 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 ROAD Winter Garden, FL A home full of charm, comfort, and practicality. It features four bedrooms, including a sp...	4 beds \| 4 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%
10031 BEDTIME STORY DRIVE Winter Garden, FL ***ASSUMABLE VA MORTGAGE OPTION WITH 3.75 INTEREST FIXED RATE. Sellers willing to install ...	4 beds \| 4 baths \| 2,722 sq.ft.	$675,000	Airbnb cash on cash: 4.75% Traditional cash on cash: 4.06% Airbnb Rental Income: $5064 Traditional Rental Income: $3599 Airbnb ROI: 4.75% Traditional ROI: 4.06%
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%
17323 BEACHGRASS ALLEY Winter Garden, FL Under Construction. Discover this stunning new construction home, located at 17323 Beachgr...	4 beds \| 4 baths \| 2,780 sq.ft.	$659,900	Airbnb cash on cash: 3.76% Traditional cash on cash: 3.3% Airbnb Rental Income: $5064 Traditional Rental Income: $3745 Airbnb ROI: 3.76% Traditional ROI: 3.3%
17329 BEACHGRASS ALLEY Winter Garden, FL Under Construction. Discover this stunning new construction home located at 17329 Beachgra...	4 beds \| 3 baths \| 2,510 sq.ft.	$631,990	Airbnb cash on cash: 4.11% Traditional cash on cash: 2.33% Airbnb Rental Income: $5064 Traditional Rental Income: $2983 Airbnb ROI: 4.11% Traditional ROI: 2.33%

Vacation Rentals in Winter Garden

There are 121 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 $599,995 and the average price per square foot is $250. 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 121 Airbnb properties available for sale in Winter Garden.

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

In January 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

15445 PEBBLE RIDGE STREET

Winter Garden, FL

4 beds | 2 baths | 2,375 sq.ft.

$575,000

Airbnb cash on cash: 4.79%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $5064

Traditional Rental Income: $3245

Airbnb ROI: 4.79%

Traditional ROI: 3.32%

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%

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 DRIVE

Winter Garden, FL

4 beds | 4 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%

15372 GILLIGAN COURT

Winter Garden, FL

4 beds | 4 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%

8256 BAYVIEW CROSSING DRIVE

Winter Garden, FL

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%

634 FOSTER AVENUE

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%