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: What is the average Airbnb occupancy rate in Winter-garden, FL?

In June 2026, the average Airbnb occupancy rate in Winter-garden is 78%.

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
2200 ROMANUM DRIVE Winter Garden, FL Come see 2200 Romanum Dr, recently updated with fresh interior paint and partial flooring ...	4 beds \| 4 baths \| 2,561 sq.ft.	$560,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 3.4% Airbnb Rental Income: $5064 Traditional Rental Income: $3451 Airbnb ROI: 4.51% Traditional ROI: 3.4%
897 LANDRUM DRIVE Winter Garden, FL Under contract-accepting backup offers. Welcome to one of Winter Garden's most coveted add...	4 beds \| 4 baths \| 3,012 sq.ft.	$899,900	Airbnb cash on cash: 2.73% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3383 Airbnb ROI: 2.73% Traditional ROI: 1.96%
14776 MAGNOLIA RIDGE LOOP Winter Garden, FL Discover Your Dream Home in the Exclusive Orchard Hills Community! This stunning reside...	4 beds \| 4 baths \| 2,876 sq.ft.	$880,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 1.79% Airbnb Rental Income: $5064 Traditional Rental Income: $3622 Airbnb ROI: 2.28% Traditional ROI: 1.79%
7558 BISHOP SQUARE DRIVE Winter Garden, FL Virtually Staged. Move-in-ready 4-bedroom-plus-office home with a rare, unobstructed fount...	4 beds \| 2 baths \| 1,952 sq.ft.	$554,900	Airbnb cash on cash: 4.77% Traditional cash on cash: 2.93% Airbnb Rental Income: $5064 Traditional Rental Income: $3076 Airbnb ROI: 4.77% Traditional ROI: 2.93%
7266 DESERT MANDARIN STREET Winter Garden, FL Great investment opportunity! Welcome to this beautifully maintained home built in 2018, f...	4 beds \| 3 baths \| 2,365 sq.ft.	$595,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 2.29% Airbnb Rental Income: $5064 Traditional Rental Income: $2890 Airbnb ROI: 4.34% Traditional ROI: 2.29%
14755 MASTHEAD LANDING CIRCLE Winter Garden, FL Located in the highly desirable Stoneybrook West community, this beautifully maintained 4-...	4 beds \| 2 baths \| 2,258 sq.ft.	$580,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 1.47% Airbnb Rental Income: $5064 Traditional Rental Income: $2492 Airbnb ROI: 4.31% Traditional ROI: 1.47%
1701 E BAY STREET Winter Garden, FL Welcome to this beautifully renovated 2-bedroom, 2-bath home in the heart of Winter Garden...	2 beds \| 2 baths \| 825 sq.ft.	$295,000	Airbnb cash on cash: 4.15% Traditional cash on cash: 3.87% Airbnb Rental Income: $2340 Traditional Rental Income: $1685 Airbnb ROI: 4.15% Traditional ROI: 3.87%
1112 JUNIPER HAMMOCK COURT Winter Garden, FL Virtually Staged. Welcome to this beautiful and spacious 4-bedroom, 2-bath home located in...	4 beds \| 2 baths \| 2,545 sq.ft.	$515,000	Airbnb cash on cash: 5.83% Traditional cash on cash: 4.01% Airbnb Rental Income: $5064 Traditional Rental Income: $3154 Airbnb ROI: 5.83% Traditional ROI: 4.01%
1061 PORTMOOR WAY Winter Garden, FL Welcome to 1061 Portmoor Way, a single-story 4-bedroom, 2-bathroom home located in the hig...	4 beds \| 2 baths \| 1,804 sq.ft.	$535,000	Airbnb cash on cash: 5.07% Traditional cash on cash: 1.76% Airbnb Rental Income: $5064 Traditional Rental Income: $2376 Airbnb ROI: 5.07% Traditional ROI: 1.76%
20 E DIVISION STREET Winter Garden, FL Welcome to one of Winter Garden's most remarkable custom transformations. This wasn't a fl...	4 beds \| 3 baths \| 2,729 sq.ft.	$1,149,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 1.34% Airbnb Rental Income: $5064 Traditional Rental Income: $3262 Airbnb ROI: 2.06% Traditional ROI: 1.34%
15058 SAWGRASS BLUFF DRIVE Winter Garden, FL Under contract-accepting backup offers. Accepting Backup Offers! Location! Location! Loc...	4 beds \| 3 baths \| 2,626 sq.ft.	$579,900	Airbnb cash on cash: 4.85% Traditional cash on cash: 3.43% Airbnb Rental Income: $5064 Traditional Rental Income: $3262 Airbnb ROI: 4.85% Traditional ROI: 3.43%
1431 VISCAYA COVE BOULEVARD Winter Garden, FL Welcome to this beautifully designed 2022-built home freshly painted, move in ready and lo...	4 beds \| 3 baths \| 2,030 sq.ft.	$515,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 2.98% Airbnb Rental Income: $5064 Traditional Rental Income: $2938 Airbnb ROI: 5.25% Traditional ROI: 2.98%
16012 MICELLI DRIVE Winter Garden, FL Welcome to this beautifully designed 2021-built 4-bedroom, 3-bathroom plus a bonus room co...	4 beds \| 3 baths \| 2,428 sq.ft.	$684,000	Airbnb cash on cash: 3.87% Traditional cash on cash: 2.98% Airbnb Rental Income: $5064 Traditional Rental Income: $3463 Airbnb ROI: 3.87% Traditional ROI: 2.98%
17059 HARBOR OAK PARKWAY Winter Garden, FL Welcome to this beautiful, well-maintained home located in the Waterside Community at 1705...	4 beds \| 3 baths \| 2,692 sq.ft.	$630,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 2.87% Airbnb Rental Income: $5064 Traditional Rental Income: $3433 Airbnb ROI: 3.88% Traditional ROI: 2.87%
5040 BREEZY ACRES STREET Winter Garden, FL Virtually Staged. BETTER THAN NEW WITH FULLY PAID-OFF SOLAR PANELS AND WHOLE-HOME WATER FI...	4 beds \| 4 baths \| 2,724 sq.ft.	$680,000	Airbnb cash on cash: 4.05% Traditional cash on cash: 3.83% Airbnb Rental Income: $5064 Traditional Rental Income: $3891 Airbnb ROI: 4.05% Traditional ROI: 3.83%
8906 DODDINGTON WAY Winter Garden, FL ***This house comes with a REDUCED RATE through the seller's preferred lender. This is a l...	4 beds \| 3 baths \| 2,352 sq.ft.	$550,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 3.73% Airbnb Rental Income: $5064 Traditional Rental Income: $3488 Airbnb ROI: 4.78% Traditional ROI: 3.73%
8878 BISMARCK PALM DRIVE Winter Garden, FL Welcome to a beautifully upgraded residence in Lakeshore Preserve, one of Horizon West pre...	4 beds \| 4 baths \| 2,581 sq.ft.	$656,500	Airbnb cash on cash: 3.01% Traditional cash on cash: 1.94% Airbnb Rental Income: $5064 Traditional Rental Income: $3376 Airbnb ROI: 3.01% Traditional ROI: 1.94%
214 S WOODLAND STREET Winter Garden, FL Coming Soon! Awesome Opportunity to own in Historic Winter Garden. LOT parcels in the fr...	4 beds \| 2 baths \| 2,868 sq.ft.	$800,000	Airbnb cash on cash: 3.98% Traditional cash on cash: 3.27% Airbnb Rental Income: $5064 Traditional Rental Income: $3503 Airbnb ROI: 3.98% Traditional ROI: 3.27%
1906 SHERBOURNE STREET Winter Garden, FL Experience luxury living in one of Winter Gardenâs most desirable areas. This beautifull...	4 beds \| 3 baths \| 2,029 sq.ft.	$477,000	Airbnb cash on cash: 7.12% Traditional cash on cash: 4.53% Airbnb Rental Income: $5064 Traditional Rental Income: $2873 Airbnb ROI: 7.12% Traditional ROI: 4.53%
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: 3.51% Airbnb Rental Income: $5064 Traditional Rental Income: $3516 Airbnb ROI: 4.51% Traditional ROI: 3.51%
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.	$599,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 3.45% Airbnb Rental Income: $5064 Traditional Rental Income: $3739 Airbnb ROI: 3.97% Traditional ROI: 3.45%
1075 CHASE DRIVE Winter Garden, FL Welcome to 1075 Chase Drive-located in downtown Winter Garden, just minutes from the charm...	4 beds \| 2 baths \| 2,125 sq.ft.	$625,000	Airbnb cash on cash: 5.24% Traditional cash on cash: 3.87% Airbnb Rental Income: $5064 Traditional Rental Income: $3231 Airbnb ROI: 5.24% Traditional ROI: 3.87%
8220 BAYVIEW CROSSING DRIVE Winter Garden, FL Virtually Staged. Welcome home, to the highly sought-after Waterleigh community in Winter ...	4 beds \| 4 baths \| 2,477 sq.ft.	$550,000	Airbnb cash on cash: 4.4% Traditional cash on cash: 3.1% Airbnb Rental Income: $5064 Traditional Rental Income: $3363 Airbnb ROI: 4.4% Traditional ROI: 3.1%
11045 BOSTWICK ALLEY Winter Garden, FL SELLER MOTIVATED AND PRICE IS INCLUDING TRANSFERRABLE SOLAR PANELS PAID BY THE SELLER! Thi...	4 beds \| 4 baths \| 2,292 sq.ft.	$575,000	Airbnb cash on cash: 4.27% Traditional cash on cash: 3.38% Airbnb Rental Income: $5064 Traditional Rental Income: $3557 Airbnb ROI: 4.27% Traditional ROI: 3.38%
7363 MEZZANO LANE Winter Garden, FL Welcome to your chance to own one of the most desirable residences in this vibrant communi...	4 beds \| 4 baths \| 1,920 sq.ft.	$469,999	Airbnb cash on cash: 6.02% Traditional cash on cash: 4.18% Airbnb Rental Income: $5064 Traditional Rental Income: $3220 Airbnb ROI: 6.02% Traditional ROI: 4.18%
15075 TEA TREE DRIVE 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.	$829,347	Airbnb cash on cash: 3% Traditional cash on cash: 2.9% Airbnb Rental Income: $5064 Traditional Rental Income: $3955 Airbnb ROI: 3% Traditional ROI: 2.9%
6517 SHORE JUNIPER STREET Winter Garden, FL One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity...	4 beds \| 3 baths \| 2,879 sq.ft.	$849,625	Airbnb cash on cash: 2.88% Traditional cash on cash: 1.6% Airbnb Rental Income: $5064 Traditional Rental Income: $3017 Airbnb ROI: 2.88% Traditional ROI: 1.6%
6339 WILD PERSIMMON WAY Winter Garden, FL One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity...	4 beds \| 3 baths \| 2,102 sq.ft.	$591,830	Airbnb cash on cash: 4.94% Traditional cash on cash: 2.79% Airbnb Rental Income: $5064 Traditional Rental Income: $2841 Airbnb ROI: 4.94% Traditional ROI: 2.79%
5937 FLOWERING CHERRY BEND Winter Garden, FL One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity...	4 beds \| 3 baths \| 2,235 sq.ft.	$674,475	Airbnb cash on cash: 4.11% Traditional cash on cash: 2.78% Airbnb Rental Income: $5064 Traditional Rental Income: $3192 Airbnb ROI: 4.11% Traditional ROI: 2.78%
5943 FLOWERING CHERRY BEND Winter Garden, FL One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity...	4 beds \| 4 baths \| 2,688 sq.ft.	$746,650	Airbnb cash on cash: 3.53% Traditional cash on cash: 2.98% Airbnb Rental Income: $5064 Traditional Rental Income: $3648 Airbnb ROI: 3.53% Traditional ROI: 2.98%
15213 MARITIME PINE DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity...	4 beds \| 3 baths \| 2,879 sq.ft.	$899,360	Airbnb cash on cash: 2.62% Traditional cash on cash: 1.57% Airbnb Rental Income: $5064 Traditional Rental Income: $3150 Airbnb ROI: 2.62% Traditional ROI: 1.57%
12554 WESTHAVEN OAK DRIVE Winter Garden, FL This tenant-occupied home, rented for $3,400/month until June 30, 2026, presents an excell...	4 beds \| 4 baths \| 2,743 sq.ft.	$599,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 4.97% Airbnb Rental Income: $5064 Traditional Rental Income: $3713 Airbnb ROI: 5.54% Traditional ROI: 4.97%
9414 EMERALD BERRY DRIVE Winter Garden, FL Beautiful home offered fully furnished, move-in ready. All furniture and dÃ©cor are includ...	4 beds \| 4 baths \| 2,921 sq.ft.	$867,000	Airbnb cash on cash: 3.55% Traditional cash on cash: 3.2% Airbnb Rental Income: $5064 Traditional Rental Income: $3745 Airbnb ROI: 3.55% Traditional ROI: 3.2%
6529 SHORE JUNIPER STREET Winter Garden, FL Virtually Staged. Pre-Construction. To be built. Opportunity in Avalon Woods! ARLINGTON bo...	4 beds \| 3 baths \| 3,108 sq.ft.	$970,460	Airbnb cash on cash: 2.29% Traditional cash on cash: 1.34% Airbnb Rental Income: $5064 Traditional Rental Income: $3169 Airbnb ROI: 2.29% Traditional ROI: 1.34%
16175 LEYLAND CYPRESS LANE Winter Garden, FL Under contract-accepting backup offers. Virtually Staged. Pre-Construction. To be built. O...	4 beds \| 3 baths \| 3,108 sq.ft.	$920,308	Airbnb cash on cash: 2.52% Traditional cash on cash: 1.54% Airbnb Rental Income: $5064 Traditional Rental Income: $3190 Airbnb ROI: 2.52% Traditional ROI: 1.54%
15166 TEA TREE DRIVE Winter Garden, FL Virtually Staged. Pre-Construction. To be built. Opportunity in Avalon Woods! ARLINGTON bo...	4 beds \| 3 baths \| 3,108 sq.ft.	$943,160	Airbnb cash on cash: 2.41% Traditional cash on cash: 1.45% Airbnb Rental Income: $5064 Traditional Rental Income: $3190 Airbnb ROI: 2.41% Traditional ROI: 1.45%
869 BENDING OAK TRAIL Winter Garden, FL Welcome to this beautifully maintained 4-bedroom, 2-bath home located in The Oaks at Brand...	4 beds \| 2 baths \| 1,975 sq.ft.	$520,000	Airbnb cash on cash: 5.85% Traditional cash on cash: 3.88% Airbnb Rental Income: $5064 Traditional Rental Income: $3075 Airbnb ROI: 5.85% Traditional ROI: 3.88%
9723 LOST CREEK DRIVE Winter Garden, FL Beautiful 4-bedroom, 3 bath water view home in Waterleigh, Horizon Westâs Premier Commun...	4 beds \| 3 baths \| 2,117 sq.ft.	$669,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 2.17% Airbnb Rental Income: $5064 Traditional Rental Income: $3333 Airbnb ROI: 3.29% Traditional ROI: 2.17%
15292 MARITIME PINE DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity...	4 beds \| 3 baths \| 3,108 sq.ft.	$971,815	Airbnb cash on cash: 2.29% Traditional cash on cash: 1.36% Airbnb Rental Income: $5064 Traditional Rental Income: $3190 Airbnb ROI: 2.29% Traditional ROI: 1.36%
6315 WILD PERSIMMON WAY Winter Garden, FL One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity...	4 beds \| 3 baths \| 2,102 sq.ft.	$668,990	Airbnb cash on cash: 4.16% Traditional cash on cash: 2.25% Airbnb Rental Income: $5064 Traditional Rental Income: $2837 Airbnb ROI: 4.16% Traditional ROI: 2.25%

Vacation Rentals in Winter Garden

There are 174 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 $609,685 and the average price per square foot is $253. The cash on cash return on vacation rentals in Winter Garden is 2.00%. 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 174 Airbnb properties available for sale in Winter Garden.

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

In June 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

2200 ROMANUM DRIVE

Winter Garden, FL

4 beds | 4 baths | 2,561 sq.ft.

$560,000

Airbnb cash on cash: 4.51%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $5064

Traditional Rental Income: $3451

Airbnb ROI: 4.51%

Traditional ROI: 3.4%

897 LANDRUM DRIVE

Winter Garden, FL

4 beds | 4 baths | 3,012 sq.ft.

$899,900

Airbnb cash on cash: 2.73%

Traditional cash on cash: 1.96%

Airbnb Rental Income: $5064

Traditional Rental Income: $3383

Airbnb ROI: 2.73%

Traditional ROI: 1.96%

14776 MAGNOLIA RIDGE LOOP

Winter Garden, FL

4 beds | 4 baths | 2,876 sq.ft.

$880,000

Airbnb cash on cash: 2.28%

Traditional cash on cash: 1.79%

Airbnb Rental Income: $5064

Traditional Rental Income: $3622

Airbnb ROI: 2.28%

Traditional ROI: 1.79%

7558 BISHOP SQUARE DRIVE

Winter Garden, FL

4 beds | 2 baths | 1,952 sq.ft.

$554,900

Airbnb cash on cash: 4.77%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $5064

Traditional Rental Income: $3076

Airbnb ROI: 4.77%

Traditional ROI: 2.93%

7266 DESERT MANDARIN STREET

Winter Garden, FL

4 beds | 3 baths | 2,365 sq.ft.

$595,000

Airbnb cash on cash: 4.34%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $5064

Traditional Rental Income: $2890

Airbnb ROI: 4.34%

Traditional ROI: 2.29%

14755 MASTHEAD LANDING CIRCLE

Winter Garden, FL

4 beds | 2 baths | 2,258 sq.ft.

$580,000

Airbnb cash on cash: 4.31%

Traditional cash on cash: 1.47%

Airbnb Rental Income: $5064

Traditional Rental Income: $2492

Airbnb ROI: 4.31%

Traditional ROI: 1.47%

1701 E BAY STREET

Winter Garden, FL

2 beds | 2 baths | 825 sq.ft.

$295,000

Airbnb cash on cash: 4.15%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $2340

Traditional Rental Income: $1685

Airbnb ROI: 4.15%

Traditional ROI: 3.87%

1112 JUNIPER HAMMOCK COURT

Winter Garden, FL

4 beds | 2 baths | 2,545 sq.ft.

$515,000

Airbnb cash on cash: 5.83%

Traditional cash on cash: 4.01%

Airbnb Rental Income: $5064

Traditional Rental Income: $3154

Airbnb ROI: 5.83%