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 47 Airbnb properties available for sale in Winter-springs

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

In July 2026, the average Airbnb occupancy rate in Winter-springs is 39%.

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 .

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
451 HARBOR WINDS COURT Winter Springs, FL Under contract-accepting backup offers. Virtually Staged. Welcome to 451 Harbor Winds Cour...	3 beds \| 3 baths \| 1,914 sq.ft.	$357,500	Airbnb cash on cash: 5.01% Traditional cash on cash: 4.53% Airbnb Rental Income: $3583 Traditional Rental Income: $2637 Airbnb ROI: 5.01% Traditional ROI: 4.53%
471 HARBOR WINDS COURT Winter Springs, FL Welcome to your own slice of Winter Springs paradise at 417 Harbor Winds Court! Tucked awa...	3 beds \| 3 baths \| 1,680 sq.ft.	$330,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 4.74% Airbnb Rental Income: $3583 Traditional Rental Income: $2627 Airbnb ROI: 5.28% Traditional ROI: 4.74%
1024 DINERO DRIVE Winter Springs, FL Beautiful 3-bedroom, 2-bath pool/spa home located in the highly desirable Sunrise Estates ...	3 beds \| 2 baths \| 1,463 sq.ft.	$419,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 3.49% Airbnb Rental Income: $3583 Traditional Rental Income: $2341 Airbnb ROI: 4.65% Traditional ROI: 3.49%
299 WOODGREEN LANE Winter Springs, FL Welcome to this BEAUTIFULLY UPDATED 3-bedroom, 2.5-bath townhome in the PEACEFUL Mount Gre...	3 beds \| 3 baths \| 1,326 sq.ft.	$285,000	Airbnb cash on cash: 7.56% Traditional cash on cash: 4.13% Airbnb Rental Income: $3583 Traditional Rental Income: $1876 Airbnb ROI: 7.56% Traditional ROI: 4.13%
622 ANHINGA ROAD Winter Springs, FL $374,900 NEW TILE ROOF INSTALLED APRIL 2026 + TRANSFERABLE 4-POINT INSPECTION + APPROXIMAT...	3 beds \| 3 baths \| 1,721 sq.ft.	$374,900	Airbnb cash on cash: 5.27% Traditional cash on cash: 5.02% Airbnb Rental Income: $3583 Traditional Rental Income: $2709 Airbnb ROI: 5.27% Traditional ROI: 5.02%
1314 Augusta National Blvd Winter Springs, FL Pay in Bitcoin for this modern, yet cozy family home in Tuscawilla, for sale by owner! Sp...	3 beds \| 3 baths \| 2,004 sq.ft.	$600,000	Airbnb cash on cash: 2.75% Traditional cash on cash: 2.23% Airbnb Rental Income: $3583 Traditional Rental Income: $2508 Airbnb ROI: 2.75% Traditional ROI: 2.23%
600 NORTHERN WAY #302 Winter Springs, FL Under contract-accepting backup offers. Virtually Staged. Seller may consider buyer conces...	3 beds \| 2 baths \| 1,425 sq.ft.	$269,900	Airbnb cash on cash: 5.41% Traditional cash on cash: 3.17% Airbnb Rental Income: $3583 Traditional Rental Income: $2226 Airbnb ROI: 5.41% Traditional ROI: 3.17%
276 SAN GABRIEL STREET Winter Springs, FL Price Improvements. This 3-bedroom, 2-bathroom home in Deersong-2 is a fantastic opportuni...	3 beds \| 2 baths \| 1,089 sq.ft.	$285,000	Airbnb cash on cash: 7.25% Traditional cash on cash: 4.28% Airbnb Rental Income: $3583 Traditional Rental Income: $1998 Airbnb ROI: 7.25% Traditional ROI: 4.28%
444 BLUE BAYOU LANE Winter Springs, FL Welcome to 444 Blue Bayou Lane, a fully renovated 3-story end-unit townhome in a prime loc...	3 beds \| 4 baths \| 1,854 sq.ft.	$385,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 2.78% Airbnb Rental Income: $3583 Traditional Rental Income: $2431 Airbnb ROI: 3.79% Traditional ROI: 2.78%
140 SEVILLE CHASE DRIVE Winter Springs, FL Welcome to a residence that truly embodies the phrase "NEIGHBOR'S ENVY, OWNER'S PRIDE" - a...	5 beds \| 4 baths \| 3,129 sq.ft.	$769,900	Airbnb cash on cash: 3.4% Traditional cash on cash: 3.28% Airbnb Rental Income: $5023 Traditional Rental Income: $3908 Airbnb ROI: 3.4% Traditional ROI: 3.28%
30 MOREE LOOP #39 Winter Springs, FL Welcome to your move-in ready 3-bedroom, 2.5-bath townhome-style condo located in the desi...	3 beds \| 3 baths \| 1,400 sq.ft.	$210,000	Airbnb cash on cash: 8.67% Traditional cash on cash: 5.37% Airbnb Rental Income: $3583 Traditional Rental Income: $2141 Airbnb ROI: 8.67% Traditional ROI: 5.37%
934 TORREY PINE DRIVE Winter Springs, FL Virtually Staged. Beautifully remodeled golf course home in the highly desirable Tuscawill...	3 beds \| 2 baths \| 1,678 sq.ft.	$499,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 3.89% Airbnb Rental Income: $3583 Traditional Rental Income: $2726 Airbnb ROI: 4.04% Traditional ROI: 3.89%
314 SAN GABRIEL STREET Winter Springs, FL **BUYER INCENTIVE AVAILABLE!! Preferred Lender is offering a COMPLIMENTARY TEMPORARY RATE ...	3 beds \| 2 baths \| 1,091 sq.ft.	$279,990	Airbnb cash on cash: 7.93% Traditional cash on cash: 5.5% Airbnb Rental Income: $3583 Traditional Rental Income: $2157 Airbnb ROI: 7.93% Traditional ROI: 5.5%
270 SAN GABRIEL STREET Winter Springs, FL Quick Closing Available. Welcome to 270 San Gabriel Street in Winter Springsânow offered...	3 beds \| 2 baths \| 1,089 sq.ft.	$249,900	Airbnb cash on cash: 9.75% Traditional cash on cash: 7.55% Airbnb Rental Income: $3583 Traditional Rental Income: $2278 Airbnb ROI: 9.75% Traditional ROI: 7.55%
116 PHILADELPHIA WAY Winter Springs, FL Well-appointed 3-bedroom, 2.5-bath townhome for sale in a gated community, offering a grea...	3 beds \| 3 baths \| 1,468 sq.ft.	$310,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 4.53% Airbnb Rental Income: $3583 Traditional Rental Income: $2430 Airbnb ROI: 5.79% Traditional ROI: 4.53%
421 HORIZON DRIVE Winter Springs, FL Welcome to 421 Horizon Drive in Winter Springs, located in The Seasons community. This mov...	3 beds \| 2 baths \| 1,069 sq.ft.	$294,900	Airbnb cash on cash: 6.93% Traditional cash on cash: 4.8% Airbnb Rental Income: $3583 Traditional Rental Income: $2205 Airbnb ROI: 6.93% Traditional ROI: 4.8%
476 CLUB DRIVE Winter Springs, FL Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-a...	3 beds \| 2 baths \| 1,460 sq.ft.	$275,000	Airbnb cash on cash: 6.56% Traditional cash on cash: 4.84% Airbnb Rental Income: $3583 Traditional Rental Income: $2352 Airbnb ROI: 6.56% Traditional ROI: 4.84%
130 DEER SONG DRIVE Winter Springs, FL Welcome to 130 Deer Song Dr in the heart of Winter Springs an exceptional opportunity to o...	3 beds \| 2 baths \| 1,105 sq.ft.	$310,000	Airbnb cash on cash: 6.79% Traditional cash on cash: 5.17% Airbnb Rental Income: $3583 Traditional Rental Income: $2323 Airbnb ROI: 6.79% Traditional ROI: 5.17%
171 CONSTITUTION WAY Winter Springs, FL Welcome to this beautifully maintained townhome located in the desirable gated community o...	3 beds \| 3 baths \| 1,468 sq.ft.	$315,000	Airbnb cash on cash: 6.26% Traditional cash on cash: 3.52% Airbnb Rental Income: $3583 Traditional Rental Income: $1984 Airbnb ROI: 6.26% Traditional ROI: 3.52%
1328 ANDES DRIVE Winter Springs, FL Welcome to 1328 Andes Dr! Tile floors run throughout this well-maintained 4-bed, 2-bath in...	4 beds \| 2 baths \| 1,582 sq.ft.	$373,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 4.5% Airbnb Rental Income: $3298 Traditional Rental Income: $2340 Airbnb ROI: 5.12% Traditional ROI: 4.5%
560 PLEASANT GROVE DRIVE Winter Springs, FL Welcome to Tuska Oaksâa well-established community in the heart of Winter Springs known ...	3 beds \| 2 baths \| 1,654 sq.ft.	$425,000	Airbnb cash on cash: 4.25% Traditional cash on cash: 3.02% Airbnb Rental Income: $3583 Traditional Rental Income: $2305 Airbnb ROI: 4.25% Traditional ROI: 3.02%
600 NORTHERN WAY #205 Winter Springs, FL Come see 600 Northern Way, a residence significantly improved with fresh interior paint an...	3 beds \| 2 baths \| 1,425 sq.ft.	$233,000	Airbnb cash on cash: 9.01% Traditional cash on cash: 5.31% Airbnb Rental Income: $3583 Traditional Rental Income: $1983 Airbnb ROI: 9.01% Traditional ROI: 5.31%
807 BUCKIE DRIVE Winter Springs, FL Move Right In this Updated Highlands Home! Desirable Gas Stove in Kitchen along with newer...	3 beds \| 2 baths \| 1,574 sq.ft.	$375,000	Airbnb cash on cash: 5.39% Traditional cash on cash: 3.77% Airbnb Rental Income: $3583 Traditional Rental Income: $2228 Airbnb ROI: 5.39% Traditional ROI: 3.77%
335 KIRKCALDY DRIVE Winter Springs, FL Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like...	3 beds \| 2 baths \| 1,178 sq.ft.	$329,900	Airbnb cash on cash: 6.48% Traditional cash on cash: 3.88% Airbnb Rental Income: $3583 Traditional Rental Income: $1991 Airbnb ROI: 6.48% Traditional ROI: 3.88%
820 WAKULLA LANE Winter Springs, FL Move-in ready and thoughtfully updated, this 3-bedroom, 2-bath home offers bright, comfort...	3 beds \| 3 baths \| 1,658 sq.ft.	$419,900	Airbnb cash on cash: 4.07% Traditional cash on cash: 2.65% Airbnb Rental Income: $3583 Traditional Rental Income: $2241 Airbnb ROI: 4.07% Traditional ROI: 2.65%
629 RYAN COURT Winter Springs, FL Beautifully maintained 3-bedroom, 2-bathroom home located in the highly sought-after Highl...	3 beds \| 2 baths \| 1,857 sq.ft.	$475,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 3.88% Airbnb Rental Income: $3583 Traditional Rental Income: $2479 Airbnb ROI: 4.6% Traditional ROI: 3.88%
65 S DEVON AVENUE Winter Springs, FL Discover the charm and convenience of life in Winter Springs at 65 S Devon Avenue â a mo...	3 beds \| 2 baths \| 1,075 sq.ft.	$314,900	Airbnb cash on cash: 7.43% Traditional cash on cash: 4.41% Airbnb Rental Income: $3583 Traditional Rental Income: $1903 Airbnb ROI: 7.43% Traditional ROI: 4.41%
214 PERTH COURT #A Winter Springs, FL Under contract-accepting backup offers. Exceptional investment opportunity in the highly s...	6 beds \| N/A baths \| 2,247 sq.ft.	$589,900	Airbnb cash on cash: 3.03% Traditional cash on cash: 2.09% Airbnb Rental Income: $3583 Traditional Rental Income: $2276 Airbnb ROI: 3.03% Traditional ROI: 2.09%
600 NORTHERN WAY #1804 Winter Springs, FL Welcome to Tuscany Place in the heart of sought after Tuscawilla! This well-maintained tow...	4 beds \| 3 baths \| 1,726 sq.ft.	$299,900	Airbnb cash on cash: 6.38% Traditional cash on cash: 5.21% Airbnb Rental Income: $3298 Traditional Rental Income: $2229 Airbnb ROI: 6.38% Traditional ROI: 5.21%
143 HAYES ROAD Winter Springs, FL Welcome to 143 Hayes Rd, Winter Springs a rare opportunity to own a beautifully renovated...	3 beds \| 2 baths \| 1,649 sq.ft.	$479,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 3.92% Airbnb Rental Income: $3583 Traditional Rental Income: $2463 Airbnb ROI: 4.66% Traditional ROI: 3.92%
417 CRUZ BAY CIRCLE Winter Springs, FL If you are looking for a turnkey property, this home is it! A rare find end unit has been...	3 beds \| 3 baths \| 2,176 sq.ft.	$435,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.81% Airbnb Rental Income: $3583 Traditional Rental Income: $2668 Airbnb ROI: 4.13% Traditional ROI: 3.81%
618 LOCUST COURT Winter Springs, FL The seller is currently in a multiple offer scenario related to the Buyer/Property Address...	3 beds \| 2 baths \| 1,326 sq.ft.	$228,800	Airbnb cash on cash: 9.58% Traditional cash on cash: 6.79% Airbnb Rental Income: $3583 Traditional Rental Income: $2193 Airbnb ROI: 9.58% Traditional ROI: 6.79%
1018 WEATHERED WOOD CIRCLE Winter Springs, FL Welcome to refined, low-maintenance living in the highly sought-after Wedgewood Golf Villa...	3 beds \| 2 baths \| 1,718 sq.ft.	$369,000	Airbnb cash on cash: 6.11% Traditional cash on cash: 4.81% Airbnb Rental Income: $3583 Traditional Rental Income: $2348 Airbnb ROI: 6.11% Traditional ROI: 4.81%
1020 TAPROOT DRIVE Winter Springs, FL Under contract-accepting backup offers. Welcome to highly sought-after Oak Forest in Winte...	3 beds \| 3 baths \| 1,905 sq.ft.	$509,900	Airbnb cash on cash: 3.71% Traditional cash on cash: 3.29% Airbnb Rental Income: $3583 Traditional Rental Income: $2599 Airbnb ROI: 3.71% Traditional ROI: 3.29%
538 CRIMSON LANE Winter Springs, FL PRICED to Sell! Motivated Seller. Welcome to 538 Crimson Lane, a beautifully designed town...	3 beds \| 4 baths \| 1,854 sq.ft.	$369,900	Airbnb cash on cash: 4.39% Traditional cash on cash: 4.26% Airbnb Rental Income: $3583 Traditional Rental Income: $2751 Airbnb ROI: 4.39% Traditional ROI: 4.26%
984 TURKEY HOLLOW CIRCLE Winter Springs, FL Under contract-accepting backup offers. Virtually Staged. A spacious 3-bedroom, 2-bathroom...	3 beds \| 2 baths \| 1,821 sq.ft.	$410,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 4.29% Airbnb Rental Income: $3583 Traditional Rental Income: $2419 Airbnb ROI: 5.28% Traditional ROI: 4.29%
877 BENCHWOOD DRIVE Winter Springs, FL Inviting curb appeal welcomes you into this beautifully maintained Winter Springs pool hom...	3 beds \| 2 baths \| 1,612 sq.ft.	$450,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 3.89% Airbnb Rental Income: $3583 Traditional Rental Income: $2447 Airbnb ROI: 4.72% Traditional ROI: 3.89%
907 GLEN ABBEY CIRCLE Winter Springs, FL Welcome home to this beautiful, move-in-ready residence nestled in the highly sought-after...	3 beds \| 2 baths \| 1,791 sq.ft.	$410,000	Airbnb cash on cash: 5.17% Traditional cash on cash: 4.13% Airbnb Rental Income: $3583 Traditional Rental Income: $2400 Airbnb ROI: 5.17% Traditional ROI: 4.13%
576 PINEBRANCH CIRCLE Winter Springs, FL Under contract-accepting backup offers. Welcome to this beautifully maintained townhome in...	3 beds \| 3 baths \| 1,602 sq.ft.	$340,000	Airbnb cash on cash: 5.29% Traditional cash on cash: 3.24% Airbnb Rental Income: $3583 Traditional Rental Income: $2140 Airbnb ROI: 5.29% Traditional ROI: 3.24%
324 DORNOCH COURT Winter Springs, FL Welcome Home to Dornoch Ct in The Highlands of Winter Springs. Situated among tree lined s...	3 beds \| 2 baths \| 1,579 sq.ft.	$399,000	Airbnb cash on cash: 5.64% Traditional cash on cash: 4.19% Airbnb Rental Income: $3583 Traditional Rental Income: $2257 Airbnb ROI: 5.64% Traditional ROI: 4.19%

Vacation Rentals in Winter Springs

There are 47 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 $441,736 and the average price per square foot is $225. The cash on cash return on vacation rentals in Winter Springs is 4.00%. The average monthly short term rental income in Winter Springs is $3,583.

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

There are 47 Airbnb properties available for sale in Winter Springs.

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

In July 2026, the average Airbnb occupancy rate in Winter Springs is 39%.

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

451 HARBOR WINDS COURT

Winter Springs, FL

3 beds | 3 baths | 1,914 sq.ft.

$357,500

Airbnb cash on cash: 5.01%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $3583

Traditional Rental Income: $2637

Airbnb ROI: 5.01%

Traditional ROI: 4.53%

471 HARBOR WINDS COURT

Winter Springs, FL

3 beds | 3 baths | 1,680 sq.ft.

$330,000

Airbnb cash on cash: 5.28%

Traditional cash on cash: 4.74%

Airbnb Rental Income: $3583

Traditional Rental Income: $2627

Airbnb ROI: 5.28%

Traditional ROI: 4.74%

1024 DINERO DRIVE

Winter Springs, FL

3 beds | 2 baths | 1,463 sq.ft.

$419,000

Airbnb cash on cash: 4.65%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $3583

Traditional Rental Income: $2341

Airbnb ROI: 4.65%

Traditional ROI: 3.49%

299 WOODGREEN LANE

Winter Springs, FL

3 beds | 3 baths | 1,326 sq.ft.

$285,000

Airbnb cash on cash: 7.56%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $3583

Traditional Rental Income: $1876

Airbnb ROI: 7.56%

Traditional ROI: 4.13%

622 ANHINGA ROAD

Winter Springs, FL

3 beds | 3 baths | 1,721 sq.ft.

$374,900

Airbnb cash on cash: 5.27%

Traditional cash on cash: 5.02%

Airbnb Rental Income: $3583

Traditional Rental Income: $2709

Airbnb ROI: 5.27%

Traditional ROI: 5.02%

1314 Augusta National Blvd

Winter Springs, FL

3 beds | 3 baths | 2,004 sq.ft.

$600,000

Airbnb cash on cash: 2.75%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $3583

Traditional Rental Income: $2508

Airbnb ROI: 2.75%

Traditional ROI: 2.23%

600 NORTHERN WAY #302

Winter Springs, FL

3 beds | 2 baths | 1,425 sq.ft.

$269,900

Airbnb cash on cash: 5.41%

Traditional cash on cash: 3.17%

Airbnb Rental Income: $3583

Traditional Rental Income: $2226

Airbnb ROI: 5.41%

Traditional ROI: 3.17%

276 SAN GABRIEL STREET

Winter Springs, FL

3 beds | 2 baths | 1,089 sq.ft.

$285,000

Airbnb cash on cash: 7.25%

Traditional cash on cash: 4.28%

Airbnb Rental Income: $3583

Traditional Rental Income: $1998

Airbnb ROI: 7.25%