Airbnb Properties for Sale in Winter Springs, FL

Looking for a vacation rental investment in Winter Springs, FL with high ROI ?

Explore a range of newly added short-term rental homes in Winter Springs, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Winter Springs, FL

Q: How many Airbnb properties are available for sale in Winter-springs?

There are 28 Airbnb properties available for sale in Winter-springs

Q: How to get Winter-springs, FL Airbnb data?

Airbnb data on vacation rentals in Winter-springs, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winter-springs, FL market insights, guest information and booking details, seasonality trends and historical Winter-springs, FL Airbnb performance data .

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
627 CLEARN Court Winter Springs, FL Welcome to this beautifully updated home, with it's own IN-LAW SUITE, tucked away on a qui...	5 beds \| 4 baths \| 1,986 sq.ft.	$469,000	Airbnb cash on cash: 5.89% Traditional cash on cash: 3.61% Airbnb Rental Income: $4737 Traditional Rental Income: $2759 Airbnb ROI: 5.89% Traditional ROI: 3.61%
758 N GRETNA Court Winter Springs, FL Welcome to this versatile and beautifully updated 4-bedroom, 3-bathroom home offering both...	4 beds \| 3 baths \| 2,150 sq.ft.	$379,000	Airbnb cash on cash: 6.45% Traditional cash on cash: 5.44% Airbnb Rental Income: $4125 Traditional Rental Income: $2892 Airbnb ROI: 6.45% Traditional ROI: 5.44%
226 BENNETT Street Winter Springs, FL NO HOA. NO RULES. NO MONTHLY FEES. JUST YOUR HOME, YOUR WAY. Imagine owning a home in Wint...	3 beds \| 2 baths \| 1,050 sq.ft.	$310,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 3.37% Airbnb Rental Income: $2523 Traditional Rental Income: $1761 Airbnb ROI: 3.9% Traditional ROI: 3.37%
3600 BISCAYNE Drive Winter Springs, FL Welcome to 3600 Biscayne Drive in the delightful Hollowbrook neighborhood of Winter Spring...	4 beds \| 2 baths \| 2,498 sq.ft.	$430,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 4.24% Airbnb Rental Income: $4125 Traditional Rental Income: $2757 Airbnb ROI: 5.46% Traditional ROI: 4.24%
201 BURGESS Drive Winter Springs, FL Welcome Home to charming FRONT PORCH LIVING in the sought-after GATED community of AVERY P...	4 beds \| 3 baths \| 3,046 sq.ft.	$635,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 2.51% Airbnb Rental Income: $4125 Traditional Rental Income: $3124 Airbnb ROI: 2.72% Traditional ROI: 2.51%
702 GLASGOW Court Winter Springs, FL Reduced! Amazing value for this immaculate property! Picture-perfect 4 bedroom townhouse w...	4 beds \| 3 baths \| 1,878 sq.ft.	$297,490	Airbnb cash on cash: 7.13% Traditional cash on cash: 5.13% Airbnb Rental Income: $4125 Traditional Rental Income: $2691 Airbnb ROI: 7.13% Traditional ROI: 5.13%
268 TAVESTOCK Loop Winter Springs, FL New Price 268 Tavestock Loop, Winter Springs, FL 32708 Perfectly situated in the heart...	4 beds \| 3 baths \| 2,415 sq.ft.	$557,900	Airbnb cash on cash: 3.97% Traditional cash on cash: 3.36% Airbnb Rental Income: $4125 Traditional Rental Income: $2933 Airbnb ROI: 3.97% Traditional ROI: 3.36%
811 MAPLE LEAF Loop Winter Springs, FL Explore 811 Maple Leaf Loop, recently enhanced with fresh interior paint. The kitchen incl...	5 beds \| 3 baths \| 2,852 sq.ft.	$515,000	Airbnb cash on cash: 5.59% Traditional cash on cash: 4.04% Airbnb Rental Income: $4737 Traditional Rental Income: $3013 Airbnb ROI: 5.59% Traditional ROI: 4.04%
429 SHEOAH Boulevard #9 Winter Springs, FL Welcome to this beautifully maintained 3-bedroom, 2-bath condominium nestled in the highly...	3 beds \| 2 baths \| 1,187 sq.ft.	$199,000	Airbnb cash on cash: 4.98% Traditional cash on cash: 4.33% Airbnb Rental Income: $2523 Traditional Rental Income: $1790 Airbnb ROI: 4.98% Traditional ROI: 4.33%
1389 PONCE DE LEON Boulevard Winter Springs, FL BACK ON THE MARKET!!PRICE TO SELL. LOCATION, LOCATION, LOCATION! Beautifully remodeled hom...	4 beds \| 2 baths \| 2,056 sq.ft.	$499,000	Airbnb cash on cash: 5.19% Traditional cash on cash: 3.99% Airbnb Rental Income: $4125 Traditional Rental Income: $2685 Airbnb ROI: 5.19% Traditional ROI: 3.99%
1015 ANTELOPE Trail Winter Springs, FL Seller is willing to contribute towards Buyers closing costs with reasonable offer. Welcom...	5 beds \| 3 baths \| 2,523 sq.ft.	$600,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 3.96% Airbnb Rental Income: $4737 Traditional Rental Income: $3261 Airbnb ROI: 4.85% Traditional ROI: 3.96%
216 TAVESTOCK Loop Winter Springs, FL Enjoy waterfront views and your own private pool in this spacious 5-bedroom, 2-bath home l...	5 beds \| 2 baths \| 2,355 sq.ft.	$605,000	Airbnb cash on cash: 3.99% Traditional cash on cash: 2.77% Airbnb Rental Income: $4737 Traditional Rental Income: $3070 Airbnb ROI: 3.99% Traditional ROI: 2.77%
414 HORIZON Drive Winter Springs, FL Stunningly updated and refreshed single-family home in "The Seasons," located in the highl...	3 beds \| 2 baths \| 1,101 sq.ft.	$299,900	Airbnb cash on cash: 3.56% Traditional cash on cash: 3.41% Airbnb Rental Income: $2523 Traditional Rental Income: $1871 Airbnb ROI: 3.56% Traditional ROI: 3.41%
1610 FOX GLEN COURT Winter Springs, FL Seller is offering up to $10,000 toward buyer's closing costs with an acceptable offer! We...	4 beds \| 3 baths \| 1,992 sq.ft.	$486,900	Airbnb cash on cash: 5.14% Traditional cash on cash: 4.18% Airbnb Rental Income: $4125 Traditional Rental Income: $2811 Airbnb ROI: 5.14% Traditional ROI: 4.18%
699 N ENDEAVOUR Drive Winter Springs, FL Welcome to this spacious 4-bedroom, 2-bathroom home offering 1,931 square feet of living s...	4 beds \| 2 baths \| 1,931 sq.ft.	$515,000	Airbnb cash on cash: 5.1% Traditional cash on cash: 4.18% Airbnb Rental Income: $4125 Traditional Rental Income: $2805 Airbnb ROI: 5.1% Traditional ROI: 4.18%
1230 STONE HARBOUR Road Winter Springs, FL Financing Fell Through so the former Buyers' loss is your gain! Welcome to your Dream Home...	4 beds \| 2 baths \| 2,050 sq.ft.	$589,900	Airbnb cash on cash: 4.19% Traditional cash on cash: 3.22% Airbnb Rental Income: $4125 Traditional Rental Income: $2713 Airbnb ROI: 4.19% Traditional ROI: 3.22%
475 VERANDAH Court Winter Springs, FL Tucked away on a cul-de-sac in the gated community of Barrington, this stunning 4-bedroom,...	4 beds \| 3 baths \| 2,520 sq.ft.	$699,900	Airbnb cash on cash: 2.95% Traditional cash on cash: 2.27% Airbnb Rental Income: $4125 Traditional Rental Income: $2803 Airbnb ROI: 2.95% Traditional ROI: 2.27%
135 CORTEZ Court Winter Springs, FL Virtually Staged. Welcome home to this charming 3-bed/2-bath with an oversized 1-car garag...	3 beds \| 2 baths \| 1,098 sq.ft.	$325,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 3.31% Airbnb Rental Income: $2523 Traditional Rental Income: $1763 Airbnb ROI: 3.81% Traditional ROI: 3.31%
425 S HAWTHORN Circle Winter Springs, FL Three bedrooms, a corner lot and NO HOA in the heart of Winter Springs! This concrete bloc...	3 beds \| 2 baths \| 948 sq.ft.	$250,000	Airbnb cash on cash: 5.36% Traditional cash on cash: 4.81% Airbnb Rental Income: $2523 Traditional Rental Income: $1786 Airbnb ROI: 5.36% Traditional ROI: 4.81%
1354 TARFLOWER Drive Winter Springs, FL Welcome to Hickory Grove, where modern living meets everyday convenience in the heart of W...	4 beds \| 3 baths \| 1,643 sq.ft.	$445,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 2.73% Airbnb Rental Income: $4125 Traditional Rental Income: $2256 Airbnb ROI: 5.12% Traditional ROI: 2.73%
3755 SAINT LUCIE Court Winter Springs, FL Enjoy the best of Florida living at 3755 St. Lucie Court, a four-bedroom, two-bath pool ho...	4 beds \| 2 baths \| 2,341 sq.ft.	$515,000	Airbnb cash on cash: 5.19% Traditional cash on cash: 4.73% Airbnb Rental Income: $4125 Traditional Rental Income: $3027 Airbnb ROI: 5.19% Traditional ROI: 4.73%
1114 DUNCAN Drive Winter Springs, FL DIAMOND IN THE ROUGH IN HIGHLY SOUGHT-AFTER TUSCAWILLA! Situated on a spacious 1/2-ACRE LO...	4 beds \| 3 baths \| 2,147 sq.ft.	$475,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 5.5% Airbnb Rental Income: $4125 Traditional Rental Income: $3229 Airbnb ROI: 5.54% Traditional ROI: 5.5%
1361 SAN DIEGO Court Winter Springs, FL Welcome home to this freshly updated 3-bedroom, 2-bath single-story block home in the Sunr...	3 beds \| 2 baths \| 1,153 sq.ft.	$349,900	Airbnb cash on cash: 4.24% Traditional cash on cash: 4.09% Airbnb Rental Income: $2523 Traditional Rental Income: $1863 Airbnb ROI: 4.24% Traditional ROI: 4.09%
711 THISTLE Place Winter Springs, FL Welcome to Wildwood! This three-bedroom, two-bath home features ceramic tile flooring thro...	3 beds \| 2 baths \| 960 sq.ft.	$269,900	Airbnb cash on cash: 5.21% Traditional cash on cash: 4.5% Airbnb Rental Income: $2523 Traditional Rental Income: $1734 Airbnb ROI: 5.21% Traditional ROI: 4.5%
122 BURGOS Road Winter Springs, FL Winter Springs Fixer-Upper with Great Potential! Welcome to 122 Burgos Road, a 3-bedroom, ...	3 beds \| 2 baths \| 1,178 sq.ft.	$259,000	Airbnb cash on cash: 6.18% Traditional cash on cash: 5.88% Airbnb Rental Income: $2523 Traditional Rental Income: $1841 Airbnb ROI: 6.18% Traditional ROI: 5.88%

Vacation Rentals in Winter Springs

There are 28 vacation rental properties available for sale in the city of Winter Springs . The median list price of Airbnb properties available for sale in Winter Springs is $434,763 and the average price per square foot is $257. The cash on cash return on vacation rentals in Winter Springs is 3.00%. The average monthly short term rental income in Winter Springs is $2,523.

Winter Springs, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 28 Airbnb properties available for sale in Winter Springs.

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

In November 2026, the average Airbnb occupancy rate in Winter Springs is 33%.

Airbnb data on vacation rentals in Winter Springs, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winter Springs, FL market insights, guest information and booking details, seasonality trends and historical Winter Springs, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Winter Springs, FL

627 CLEARN Court

Winter Springs, FL

5 beds | 4 baths | 1,986 sq.ft.

$469,000

Airbnb cash on cash: 5.89%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $4737

Traditional Rental Income: $2759

Airbnb ROI: 5.89%

Traditional ROI: 3.61%

758 N GRETNA Court

Winter Springs, FL

4 beds | 3 baths | 2,150 sq.ft.

$379,000

Airbnb cash on cash: 6.45%

Traditional cash on cash: 5.44%

Airbnb Rental Income: $4125

Traditional Rental Income: $2892

Airbnb ROI: 6.45%

Traditional ROI: 5.44%

226 BENNETT Street

Winter Springs, FL

3 beds | 2 baths | 1,050 sq.ft.

$310,000

Airbnb cash on cash: 3.9%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $2523

Traditional Rental Income: $1761

Airbnb ROI: 3.9%

Traditional ROI: 3.37%

3600 BISCAYNE Drive

Winter Springs, FL

4 beds | 2 baths | 2,498 sq.ft.

$430,000

Airbnb cash on cash: 5.46%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $4125

Traditional Rental Income: $2757

Airbnb ROI: 5.46%

Traditional ROI: 4.24%

201 BURGESS Drive

Winter Springs, FL

4 beds | 3 baths | 3,046 sq.ft.

$635,000

Airbnb cash on cash: 2.72%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $4125

Traditional Rental Income: $3124

Airbnb ROI: 2.72%

Traditional ROI: 2.51%

702 GLASGOW Court

Winter Springs, FL

4 beds | 3 baths | 1,878 sq.ft.

$297,490

Airbnb cash on cash: 7.13%

Traditional cash on cash: 5.13%

Airbnb Rental Income: $4125

Traditional Rental Income: $2691

Airbnb ROI: 7.13%

Traditional ROI: 5.13%

268 TAVESTOCK Loop

Winter Springs, FL

4 beds | 3 baths | 2,415 sq.ft.

$557,900

Airbnb cash on cash: 3.97%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $4125

Traditional Rental Income: $2933

Airbnb ROI: 3.97%

Traditional ROI: 3.36%

811 MAPLE LEAF Loop

Winter Springs, FL

5 beds | 3 baths | 2,852 sq.ft.

$515,000

Airbnb cash on cash: 5.59%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $4737

Traditional Rental Income: $3013

Airbnb ROI: 5.59%