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
427 Tierra Verde Ln Winter Garden, FL Virtually Staged. Welcome to this beautifully maintained custom home located in the gated ...	4 beds \| 3 baths \| 2,368 sq.ft.	$849,988	Airbnb cash on cash: 1.89% Traditional cash on cash: 1.31% Airbnb Rental Income: $4271 Traditional Rental Income: $2908 Airbnb ROI: 1.89% Traditional ROI: 1.31%
7179 Spring Park Dr Winter Garden, FL Located in the vibrant Lakeview Pointe community within Horizon West, this model-like 4-be...	4 beds \| 2 baths \| 2,272 sq.ft.	$535,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 2.15% Airbnb Rental Income: $4271 Traditional Rental Income: $2467 Airbnb ROI: 3.96% Traditional ROI: 2.15%
14704 Seton Creek Blvd Winter Garden, FL Welcome to resort-style living in the highly sought-after Watermark community of Winter Ga...	4 beds \| 2 baths \| 1,877 sq.ft.	$505,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 2.34% Airbnb Rental Income: $4271 Traditional Rental Income: $2625 Airbnb ROI: 3.86% Traditional ROI: 2.34%
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.	$505,000	Airbnb cash on cash: 4.57% Traditional cash on cash: 4.11% Airbnb Rental Income: $4271 Traditional Rental Income: $3154 Airbnb ROI: 4.57% Traditional ROI: 4.11%
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.	$515,000	Airbnb cash on cash: 3.94% Traditional cash on cash: 1.87% Airbnb Rental Income: $4271 Traditional Rental Income: $2376 Airbnb ROI: 3.94% Traditional ROI: 1.87%
20 E Division St Winter Garden, FL Appraisal in hand! Welcome to one of Winter Garden's most remarkable custom transformation...	4 beds \| 3 baths \| 2,729 sq.ft.	$995,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 1.49% Airbnb Rental Income: $4271 Traditional Rental Income: $3262 Airbnb ROI: 1.6% Traditional ROI: 1.49%
932 Lost Grove Cir Winter Garden, FL A home that's finally been paid attention to. Four bedrooms, two-and-a-half baths, 2,891 s...	4 beds \| 2 baths \| 2,891 sq.ft.	$619,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 2.46% Airbnb Rental Income: $4271 Traditional Rental Income: $3064 Airbnb ROI: 2.99% Traditional ROI: 2.46%
13527 Fox Glove St Winter Garden, FL Some photos are virtually staged. Video tour available. This home has a full-home SOLAR ...	4 beds \| 3 baths \| 3,255 sq.ft.	$699,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 1.84% Airbnb Rental Income: $4271 Traditional Rental Income: $3132 Airbnb ROI: 2.21% Traditional ROI: 1.84%
16968 Hamlin Oasis Loop Winter Garden, FL Welcome to this beautiful like-new residence in the highly desirable Hamlin Pointe communi...	4 beds \| 3 baths \| 2,088 sq.ft.	$570,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.82% Airbnb Rental Income: $4271 Traditional Rental Income: $3128 Airbnb ROI: 4.28% Traditional ROI: 3.82%
13043 Serene Glade Rd Winter Garden, FL Virtually Staged. Welcome to your Newbury model home! This Dream Finders Home is a 4-bedro...	4 beds \| 3 baths \| 2,083 sq.ft.	$569,000	Airbnb cash on cash: 4.41% Traditional cash on cash: 3.35% Airbnb Rental Income: $4271 Traditional Rental Income: $2800 Airbnb ROI: 4.41% Traditional ROI: 3.35%
1906 SHERBOURNE Street Winter Garden, FL Experience luxury living in one of Winter Garden's most desirable areas. This beautifully ...	4 beds \| 3 baths \| 2,029 sq.ft.	$477,000	Airbnb cash on cash: 5.64% Traditional cash on cash: 4.53% Airbnb Rental Income: $4271 Traditional Rental Income: $2873 Airbnb ROI: 5.64% Traditional ROI: 4.53%
2549 Balforn Tower Way Winter Garden, FL Welcome to Stoneybrook West-a one-of-a-kind community in Winter Garden! This premier neigh...	4 beds \| 3 baths \| 3,279 sq.ft.	$689,000	Airbnb cash on cash: 3% Traditional cash on cash: 2.63% Airbnb Rental Income: $4271 Traditional Rental Income: $3131 Airbnb ROI: 3% Traditional ROI: 2.63%
1075 CHASE Drive Winter Garden, FL Zoned for the Golf Cart District! Welcome to 1075 Chase Drive-located in downtown Winter G...	4 beds \| 2 baths \| 2,125 sq.ft.	$625,000	Airbnb cash on cash: 4.1% Traditional cash on cash: 3.87% Airbnb Rental Income: $4271 Traditional Rental Income: $3231 Airbnb ROI: 4.1% Traditional ROI: 3.87%
17418 Honeybell Tangelo Ct Winter Garden, FL Under Construction. Near Walt Disney World Theme Parks! Welcome to the Eliot plan, a luxur...	4 beds \| 3 baths \| 3,041 sq.ft.	$829,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 2.1% Airbnb Rental Income: $4271 Traditional Rental Income: $2814 Airbnb ROI: 2.82% Traditional ROI: 2.1%
6982 Twilight Bay Dr Winter Garden, FL Welcome to 6982 Twilight Bay Drive, a beautifully maintained two-story townhome located in...	4 beds \| 2 baths \| 1,860 sq.ft.	$475,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 3.96% Airbnb Rental Income: $4271 Traditional Rental Income: $3110 Airbnb ROI: 4.54% Traditional ROI: 3.96%
13184 Dendy Way Winter Garden, FL $5,000 Buyer Credit toward Closing Costs or an Interest Rate Buy-Down! Experience exceptio...	4 beds \| 2 baths \| 2,211 sq.ft.	$649,900	Airbnb cash on cash: 3.64% Traditional cash on cash: 3.59% Airbnb Rental Income: $4271 Traditional Rental Income: $3336 Airbnb ROI: 3.64% Traditional ROI: 3.59%
5679 ORANGE ORCHARD Drive Winter Garden, FL Move-In Ready Home Near Hamlin Town Center with Open Layout and Private Backyard. Built in...	4 beds \| 3 baths \| 2,235 sq.ft.	$649,900	Airbnb cash on cash: 3.09% Traditional cash on cash: 3.07% Airbnb Rental Income: $4271 Traditional Rental Income: $3357 Airbnb ROI: 3.09% Traditional ROI: 3.07%
884 Klondike St Winter Garden, FL Welcome to Historic Winter Garden, Florida. NO HOA! Where small-town charm, community, and...	4 beds \| 2 baths \| 1,485 sq.ft.	$372,500	Airbnb cash on cash: 7.09% Traditional cash on cash: 5.51% Airbnb Rental Income: $4271 Traditional Rental Income: $2819 Airbnb ROI: 7.09% Traditional ROI: 5.51%
680 Dunbar Ave Winter Garden, FL Pre-Construction. To be built. This is a pre-construction opportunity in partnership with ...	4 beds \| 2 baths \| 1,713 sq.ft.	$465,000	Airbnb cash on cash: 6.35% Traditional cash on cash: 5.36% Airbnb Rental Income: $4271 Traditional Rental Income: $2939 Airbnb ROI: 6.35% Traditional ROI: 5.36%
5413 New Independence Pkwy Winter Garden, FL Beautiful 4-bedroom, 2.5-bathroom townhouse located in the desirable Winter Garden area. T...	4 beds \| 2 baths \| 2,131 sq.ft.	$488,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 3.72% Airbnb Rental Income: $4271 Traditional Rental Income: $3198 Airbnb ROI: 4.09% Traditional ROI: 3.72%
14006 Frasier St Winter Garden, FL Stunning Corner Lot Home Welcome to this beautifully designed, home situated on a desirabl...	4 beds \| 2 baths \| 2,098 sq.ft.	$655,500	Airbnb cash on cash: 2.92% Traditional cash on cash: 1.99% Airbnb Rental Income: $4271 Traditional Rental Income: $2797 Airbnb ROI: 2.92% Traditional ROI: 1.99%
11243 Pixie Mandarin Ct Winter Garden, FL Stunning Home in Winter Garden - Prime Location! Welcome to this beautiful and meticulousl...	4 beds \| 3 baths \| 2,122 sq.ft.	$849,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 1.46% Airbnb Rental Income: $4271 Traditional Rental Income: $2966 Airbnb ROI: 1.97% Traditional ROI: 1.46%
16185 Taliesin St Winter Garden, FL Virtually Staged. Beautifully maintained 4-bedroom, 3-bathroom two-story home located in t...	4 beds \| 3 baths \| 2,372 sq.ft.	$649,990	Airbnb cash on cash: 3.25% Traditional cash on cash: 2.6% Airbnb Rental Income: $4271 Traditional Rental Income: $2975 Airbnb ROI: 3.25% Traditional ROI: 2.6%
7030 Twilight Bay Dr Winter Garden, FL Short Sale. Great home, great shape, let's talk	4 beds \| 3 baths \| 1,920 sq.ft.	$469,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 4.1% Airbnb Rental Income: $4271 Traditional Rental Income: $3151 Airbnb ROI: 4.6% Traditional ROI: 4.1%
11165 Green Citron Aly Winter Garden, FL Welcome to this stunning, nearly new home, just two years old and thoughtfully designed fo...	4 beds \| 3 baths \| 2,043 sq.ft.	$646,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 2.01% Airbnb Rental Income: $4271 Traditional Rental Income: $2810 Airbnb ROI: 2.94% Traditional ROI: 2.01%
11036 Robert Frost Dr Winter Garden, FL Amazing Single Family, 4 bedrooms and 3 full bathrooms with fenced backyard for privacy an...	4 beds \| 3 baths \| 2,136 sq.ft.	$599,990	Airbnb cash on cash: 2.93% Traditional cash on cash: 1.95% Airbnb Rental Income: $4271 Traditional Rental Income: $2809 Airbnb ROI: 2.93% Traditional ROI: 1.95%
6316 Manuscript St Winter Garden, FL Such a Charming, Family-Friendly 4 Bedroom 2.5 Bath Home in Beautiful Winter Garden. The b...	4 beds \| 2 baths \| 2,608 sq.ft.	$585,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 2.34% Airbnb Rental Income: $4271 Traditional Rental Income: $2978 Airbnb ROI: 3.04% Traditional ROI: 2.34%
12033 Encore At Ovation Way Winter Garden, FL Welcome to 12033 Encore At Ovation Way in Winter Garden, Florida! This new construction ho...	4 beds \| 3 baths \| 2,740 sq.ft.	$749,990	Airbnb cash on cash: 3.09% Traditional cash on cash: 2.59% Airbnb Rental Income: $4271 Traditional Rental Income: $3025 Airbnb ROI: 3.09% Traditional ROI: 2.59%
11031 Jackson Cv Winter Garden, FL Virtually Staged. 2023 CONSTRUCTION - PRIVATE CUL-DE-SAC - FIRST-FLOOR BEDROOM & FULL BATH...	4 beds \| 3 baths \| 2,931 sq.ft.	$700,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 1.61% Airbnb Rental Income: $4271 Traditional Rental Income: $3141 Airbnb ROI: 1.96% Traditional ROI: 1.61%
12523 Gold Honeysuckle St Winter Garden, FL Under Construction. .	4 beds \| 3 baths \| 2,552 sq.ft.	$834,990	Airbnb cash on cash: 1.96% Traditional cash on cash: 1.4% Airbnb Rental Income: $4271 Traditional Rental Income: $2928 Airbnb ROI: 1.96% Traditional ROI: 1.4%
16082 Hampton Crossing Dr Winter Garden, FL ONE-OF-A-KIND IN MARINA BAY AT WATERLEIGH! Custom craftsmanship, incredible energy upgrade...	4 beds \| 3 baths \| 2,240 sq.ft.	$729,900	Airbnb cash on cash: 2.58% Traditional cash on cash: 1.8% Airbnb Rental Income: $4271 Traditional Rental Income: $2839 Airbnb ROI: 2.58% Traditional ROI: 1.8%
13361 Sunny Retreat Ln Winter Garden, FL Better Than New in Del Webb Oasis at Horizon West! Located within this sought after gated,...	4 beds \| 3 baths \| 3,172 sq.ft.	$859,900	Airbnb cash on cash: 1.2% Traditional cash on cash: 1.01% Airbnb Rental Income: $4271 Traditional Rental Income: $3221 Airbnb ROI: 1.2% Traditional ROI: 1.01%
12632 Clear Sapphire Dr Winter Garden, FL BEST PRICE IN FLAMINGO CROSSING AREA IN WINTER GARDEN, THE SELLER WILL CONTRIBUTE UP TO $ ...	4 beds \| 2 baths \| 2,148 sq.ft.	$563,000	Airbnb cash on cash: 4.62% Traditional cash on cash: 3.54% Airbnb Rental Income: $4271 Traditional Rental Income: $2800 Airbnb ROI: 4.62% Traditional ROI: 3.54%
8016 Sweet Orange Ave Winter Garden, FL Virtually Staged. ~Seller may consider buyer concessions if made in an offer~Perfectly sit...	4 beds \| 2 baths \| 2,084 sq.ft.	$514,900	Airbnb cash on cash: 4.15% Traditional cash on cash: 2.93% Airbnb Rental Income: $4271 Traditional Rental Income: $2785 Airbnb ROI: 4.15% Traditional ROI: 2.93%
16495 Point Rock Dr Winter Garden, FL 10 minutes from Disney World & theme parks!!! Built in 2023, this beautifully home offers ...	4 beds \| 2 baths \| 2,216 sq.ft.	$567,900	Airbnb cash on cash: 2.99% Traditional cash on cash: 2.02% Airbnb Rental Income: $4271 Traditional Rental Income: $2851 Airbnb ROI: 2.99% Traditional ROI: 2.02%
301 Valencia Ct Winter Garden, FL Welcome to 301 Valencia Ct., a well maintained 4bedroom 2.5 bath home situated on a large,...	4 beds \| 2 baths \| 2,029 sq.ft.	$750,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 2.91% Airbnb Rental Income: $4271 Traditional Rental Income: $3008 Airbnb ROI: 3.43% Traditional ROI: 2.91%
231 E Lafayette St Winter Garden, FL Brand-New Construction in Winter Garden! Welcome to 231 E Lafayette Street, a beautifully ...	4 beds \| 3 baths \| 1,608 sq.ft.	$479,900	Airbnb cash on cash: 6.04% Traditional cash on cash: 3.85% Airbnb Rental Income: $4271 Traditional Rental Income: $2386 Airbnb ROI: 6.04% Traditional ROI: 3.85%
17802 JEFFERSON Street Winter Garden, FL Virtually Staged. Step into 17802 Jefferson St, a residence presenting a refreshed exterio...	4 beds \| 2 baths \| 1,778 sq.ft.	$433,000	Airbnb cash on cash: 6.08% Traditional cash on cash: 3.84% Airbnb Rental Income: $4271 Traditional Rental Income: $2461 Airbnb ROI: 6.08% Traditional ROI: 3.84%
4981 Coral Bean Aly Winter Garden, FL BETTER THAN NEW - NO CDD FEE! Welcome to this like-new, move-in-ready home in Silverleaf R...	4 beds \| 2 baths \| 2,114 sq.ft.	$569,900	Airbnb cash on cash: 3.95% Traditional cash on cash: 2.92% Airbnb Rental Income: $4271 Traditional Rental Income: $2814 Airbnb ROI: 3.95% Traditional ROI: 2.92%
15081 Masthead Landing Cir Winter Garden, FL Virtually Staged. Welcome to this beautifully renovated golf-front home in the gated commu...	4 beds \| 2 baths \| 2,842 sq.ft.	$625,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 3.23% Airbnb Rental Income: $4271 Traditional Rental Income: $3076 Airbnb ROI: 3.73% Traditional ROI: 3.23%

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 $599,054 and the average price per square foot is $257. 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 $691.

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 October 2026, the average Airbnb occupancy rate in Winter Garden is 25%.

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

427 Tierra Verde Ln

Winter Garden, FL

4 beds | 3 baths | 2,368 sq.ft.

$849,988

Airbnb cash on cash: 1.89%

Traditional cash on cash: 1.31%

Airbnb Rental Income: $4271

Traditional Rental Income: $2908

Airbnb ROI: 1.89%

Traditional ROI: 1.31%

7179 Spring Park Dr

Winter Garden, FL

4 beds | 2 baths | 2,272 sq.ft.

$535,000

Airbnb cash on cash: 3.96%

Traditional cash on cash: 2.15%

Airbnb Rental Income: $4271

Traditional Rental Income: $2467

Airbnb ROI: 3.96%

Traditional ROI: 2.15%

14704 Seton Creek Blvd

Winter Garden, FL

4 beds | 2 baths | 1,877 sq.ft.

$505,000

Airbnb cash on cash: 3.86%

Traditional cash on cash: 2.34%

Airbnb Rental Income: $4271

Traditional Rental Income: $2625

Airbnb ROI: 3.86%

Traditional ROI: 2.34%

1112 JUNIPER HAMMOCK Court

Winter Garden, FL

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

$505,000

Airbnb cash on cash: 4.57%

Traditional cash on cash: 4.11%

Airbnb Rental Income: $4271

Traditional Rental Income: $3154

Airbnb ROI: 4.57%

Traditional ROI: 4.11%

1061 PORTMOOR Way

Winter Garden, FL

4 beds | 2 baths | 1,804 sq.ft.

$515,000

Airbnb cash on cash: 3.94%

Traditional cash on cash: 1.87%

Airbnb Rental Income: $4271

Traditional Rental Income: $2376

Airbnb ROI: 3.94%

Traditional ROI: 1.87%

20 E Division St

Winter Garden, FL

4 beds | 3 baths | 2,729 sq.ft.

$995,000

Airbnb cash on cash: 1.6%

Traditional cash on cash: 1.49%

Airbnb Rental Income: $4271

Traditional Rental Income: $3262

Airbnb ROI: 1.6%

Traditional ROI: 1.49%

932 Lost Grove Cir

Winter Garden, FL

4 beds | 2 baths | 2,891 sq.ft.

$619,000

Airbnb cash on cash: 2.99%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $4271

Traditional Rental Income: $3064

Airbnb ROI: 2.99%

Traditional ROI: 2.46%

13527 Fox Glove St

Winter Garden, FL

4 beds | 3 baths | 3,255 sq.ft.

$699,000

Airbnb cash on cash: 2.21%

Traditional cash on cash: 1.84%

Airbnb Rental Income: $4271

Traditional Rental Income: $3132

Airbnb ROI: 2.21%