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 April 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
12456 WESTFIELD LAKES CIRCLE Winter Garden, FL Welcome home to this stunning residence in the highly desirable Westfield Lakes community,...	4 beds \| 3 baths \| 2,180 sq.ft.	$549,000	Airbnb cash on cash: 5.83% Traditional cash on cash: 3.32% Airbnb Rental Income: $5064 Traditional Rental Income: $2747 Airbnb ROI: 5.83% Traditional ROI: 3.32%
337 SUNSET OAKS RD Winter Garden, FL This exceptional home is ideally located in the desirable Golf Cart District, offering par...	4 beds \| 3 baths \| 2,186 sq.ft.	$599,900	Airbnb cash on cash: 4.61% Traditional cash on cash: 4.05% Airbnb Rental Income: $5064 Traditional Rental Income: $3717 Airbnb ROI: 4.61% Traditional ROI: 4.05%
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%
213 W TILDEN STREET Winter Garden, FL Located in DOWNTOWN WINTER GARDEN!! This beautifully renovated single story home combi...	4 beds \| 2 baths \| 2,151 sq.ft.	$765,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 2.24% Airbnb Rental Income: $5064 Traditional Rental Income: $3152 Airbnb ROI: 3.47% Traditional ROI: 2.24%
5531 CYPRESS HILL ROAD 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.	$610,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 3.02% Airbnb Rental Income: $5064 Traditional Rental Income: $3393 Airbnb ROI: 4.14% Traditional ROI: 3.02%
1112 JUNIPER HAMMOCK COURT Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to this beautiful and spacious 4-b...	4 beds \| 2 baths \| 2,545 sq.ft.	$520,000	Airbnb cash on cash: 5.77% Traditional cash on cash: 3.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3154 Airbnb ROI: 5.77% Traditional ROI: 3.96%
15058 SAWGRASS BLUFF DRIVE Winter Garden, FL Location! Location! Located just 10 minutes from historic downtown Winter Garden and adjac...	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%
10043 SEQUEL ALLEY Winter Garden, FL About 10 minutes to Disney. Corner lot facing open green space. Main floor primary suite w...	4 beds \| 4 baths \| 2,502 sq.ft.	$569,000	Airbnb cash on cash: 4.76% Traditional cash on cash: 4.09% Airbnb Rental Income: $5064 Traditional Rental Income: $3675 Airbnb ROI: 4.76% Traditional ROI: 4.09%
15309 HONEYBELL DRIVE Winter Garden, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 4 baths \| 3,094 sq.ft.	$775,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 3.42% Airbnb Rental Income: $5064 Traditional Rental Income: $3976 Airbnb ROI: 3.49% Traditional ROI: 3.42%
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.	$699,000	Airbnb cash on cash: 3.77% Traditional cash on cash: 2.9% Airbnb Rental Income: $5064 Traditional Rental Income: $3463 Airbnb ROI: 3.77% Traditional ROI: 2.9%
15444 LEBEAU LOOP Winter Garden, FL Newer 2024 build, this 4-bedroom home features three full bathrooms plus + a powder bath -...	4 beds \| 4 baths \| 2,415 sq.ft.	$580,000	Airbnb cash on cash: 5.73% Traditional cash on cash: 5.05% Airbnb Rental Income: $5064 Traditional Rental Income: $3663 Airbnb ROI: 5.73% Traditional ROI: 5.05%
14571 BAHAMA SWALLOW BOULEVARD Winter Garden, FL Back on the marketâand now even better. 14571 Bahama Swallow Blvd has just returned wit...	4 beds \| 2 baths \| 2,063 sq.ft.	$519,900	Airbnb cash on cash: 5.1% Traditional cash on cash: 3.28% Airbnb Rental Income: $5064 Traditional Rental Income: $3147 Airbnb ROI: 5.1% Traditional ROI: 3.28%
11187 HANLON TERRACE ALLEY Winter Garden, FL Welcome to this beautifully maintained two-story townhouse in the heart of Winter Garden, ...	4 beds \| 3 baths \| 2,200 sq.ft.	$429,900	Airbnb cash on cash: 6.3% Traditional cash on cash: 4.53% Airbnb Rental Income: $5064 Traditional Rental Income: $3320 Airbnb ROI: 6.3% Traditional ROI: 4.53%
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%
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.	$669,990	Airbnb cash on cash: 4.31% Traditional cash on cash: 4.17% Airbnb Rental Income: $5064 Traditional Rental Income: $3947 Airbnb ROI: 4.31% Traditional ROI: 4.17%
15543 PEBBLE RIDGE STREET Winter Garden, FL Popular Stoneybrook West Subdivision - A gated golf community with 2255 homes. 2 Story, 4 ...	4 beds \| 3 baths \| 3,359 sq.ft.	$645,900	Airbnb cash on cash: 3.79% Traditional cash on cash: 3.04% Airbnb Rental Income: $5064 Traditional Rental Income: $3576 Airbnb ROI: 3.79% Traditional ROI: 3.04%
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: 4.5% Airbnb Rental Income: $5064 Traditional Rental Income: $3297 Airbnb ROI: 6.33% Traditional ROI: 4.5%
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: 2.71% Airbnb Rental Income: $5064 Traditional Rental Income: $3863 Airbnb ROI: 2.95% Traditional ROI: 2.71%
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: 2.89% Airbnb Rental Income: $5064 Traditional Rental Income: $3380 Airbnb ROI: 3.94% Traditional ROI: 2.89%
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.	$629,000	Airbnb cash on cash: 4.47% Traditional cash on cash: 3.4% Airbnb Rental Income: $5064 Traditional Rental Income: $3400 Airbnb ROI: 4.47% Traditional ROI: 3.4%
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%
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.	$599,900	Airbnb cash on cash: 5.48% Traditional cash on cash: 4.56% Airbnb Rental Income: $5064 Traditional Rental Income: $3518 Airbnb ROI: 5.48% Traditional ROI: 4.56%
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%
10031 BEDTIME STORY DRIVE Winter Garden, FL Under contract-accepting backup offers. ***This house comes with a REDUCED RATE through th...	4 beds \| 4 baths \| 2,722 sq.ft.	$669,000	Airbnb cash on cash: 4.8% Traditional cash on cash: 4.73% Airbnb Rental Income: $5064 Traditional Rental Income: $3983 Airbnb ROI: 4.8% Traditional ROI: 4.73%
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.	$549,999	Airbnb cash on cash: 5.74% Traditional cash on cash: 3.75% Airbnb Rental Income: $5064 Traditional Rental Income: $3011 Airbnb ROI: 5.74% Traditional ROI: 3.75%
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%
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.	$590,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.27% Airbnb Rental Income: $5064 Traditional Rental Income: $3557 Airbnb ROI: 4.13% Traditional ROI: 3.27%
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.	$479,999	Airbnb cash on cash: 5.93% Traditional cash on cash: 4.13% Airbnb Rental Income: $5064 Traditional Rental Income: $3220 Airbnb ROI: 5.93% Traditional ROI: 4.13%
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%
5931 FLOWERING CHERRY BEND Winter Garden, FL One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Anna Ma...	4 beds \| 4 baths \| 2,688 sq.ft.	$829,965	Airbnb cash on cash: 2.99% Traditional cash on cash: 2.42% Airbnb Rental Income: $5064 Traditional Rental Income: $3586 Airbnb ROI: 2.99% Traditional ROI: 2.42%
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%
6309 WILD PERSIMMON WAY Winter Garden, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Pr...	4 beds \| 4 baths \| 2,515 sq.ft.	$709,990	Airbnb cash on cash: 3.81% Traditional cash on cash: 3.01% Airbnb Rental Income: $5064 Traditional Rental Income: $3503 Airbnb ROI: 3.81% Traditional ROI: 3.01%
16137 LEYLAND CYPRESS LANE Winter Garden, FL One or more photo(s) has been virtually staged. Pre-Construction. To be built. Welcome to ...	4 beds \| 3 baths \| 2,726 sq.ft.	$895,620	Airbnb cash on cash: 2.64% Traditional cash on cash: 1.45% Airbnb Rental Income: $5064 Traditional Rental Income: $3043 Airbnb ROI: 2.64% Traditional ROI: 1.45%
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%
2543 BALFORN TOWER WAY Winter Garden, FL Beautiful Winter Garden!! Located in Stoneybrook West, the only 24-hour manned, guard-gate...	4 beds \| 2 baths \| 1,980 sq.ft.	$550,000	Airbnb cash on cash: 5.53% Traditional cash on cash: 3.59% Airbnb Rental Income: $5064 Traditional Rental Income: $3036 Airbnb ROI: 5.53% Traditional ROI: 3.59%
6388 TABEBUIA PARKWAY Winter Garden, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 3 baths \| 1,770 sq.ft.	$455,000	Airbnb cash on cash: 7.33% Traditional cash on cash: 4.69% Airbnb Rental Income: $5064 Traditional Rental Income: $2907 Airbnb ROI: 7.33% Traditional ROI: 4.69%

Vacation Rentals in Winter Garden

There are 144 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 $615,000 and the average price per square foot is $259. 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 144 Airbnb properties available for sale in Winter Garden.

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

In April 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 CIRCLE

Winter Garden, FL

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

$549,000

Airbnb cash on cash: 5.83%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $5064

Traditional Rental Income: $2747

Airbnb ROI: 5.83%

Traditional ROI: 3.32%

337 SUNSET OAKS RD

Winter Garden, FL

4 beds | 3 baths | 2,186 sq.ft.

$599,900

Airbnb cash on cash: 4.61%

Traditional cash on cash: 4.05%

Airbnb Rental Income: $5064

Traditional Rental Income: $3717

Airbnb ROI: 4.61%

Traditional ROI: 4.05%

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%

213 W TILDEN STREET

Winter Garden, FL

4 beds | 2 baths | 2,151 sq.ft.

$765,000

Airbnb cash on cash: 3.47%

Traditional cash on cash: 2.24%

Airbnb Rental Income: $5064

Traditional Rental Income: $3152

Airbnb ROI: 3.47%

Traditional ROI: 2.24%

5531 CYPRESS HILL ROAD

Winter Garden, FL

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

$610,000

Airbnb cash on cash: 4.14%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $5064

Traditional Rental Income: $3393

Airbnb ROI: 4.14%

Traditional ROI: 3.02%

1112 JUNIPER HAMMOCK COURT

Winter Garden, FL

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

$520,000

Airbnb cash on cash: 5.77%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $5064

Traditional Rental Income: $3154

Airbnb ROI: 5.77%

Traditional ROI: 3.96%

15058 SAWGRASS BLUFF DRIVE

Winter Garden, FL

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%

10043 SEQUEL ALLEY

Winter Garden, FL

4 beds | 4 baths | 2,502 sq.ft.

$569,000

Airbnb cash on cash: 4.76%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $5064

Traditional Rental Income: $3675

Airbnb ROI: 4.76%