Airbnb Properties for Sale in Windermere, FL

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

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

Airbnb For Sale in Windermere, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
12654 CRAGSIDE LANE Windermere, FL Under contract-accepting backup offers. Welcome to a truly rare opportunity in Windermere ...	5 beds \| 4 baths \| 3,072 sq.ft.	$679,900	Airbnb cash on cash: 4.68% Traditional cash on cash: 3.32% Airbnb Rental Income: $5841 Traditional Rental Income: $3812 Airbnb ROI: 4.68% Traditional ROI: 3.32%
6615 HELMSLEY CIRCLE Windermere, FL Beautifully remodeled and impeccably maintained, this spacious 3,390 sq. ft. two-story hom...	5 beds \| 4 baths \| 3,390 sq.ft.	$799,900	Airbnb cash on cash: 4.9% Traditional cash on cash: 4.43% Airbnb Rental Income: $5841 Traditional Rental Income: $4329 Airbnb ROI: 4.9% Traditional ROI: 4.43%
13833 ANCILLA BOULEVARD Windermere, FL Under contract-accepting backup offers. Welcome to this ONE STORY TOWNHOME on a CORNER LOT...	2 beds \| 2 baths \| 1,155 sq.ft.	$355,000	Airbnb cash on cash: 8.78% Traditional cash on cash: 2.84% Airbnb Rental Income: $4898 Traditional Rental Income: $1913 Airbnb ROI: 8.78% Traditional ROI: 2.84%
3443 WILD MYRTLE COURT Windermere, FL Welcome to 3443 Wild Myrtle Court, a beautifully renovated executive home nestled on a ser...	5 beds \| 3 baths \| 2,918 sq.ft.	$1,200,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 2.11% Airbnb Rental Income: $5841 Traditional Rental Income: $3693 Airbnb ROI: 2.99% Traditional ROI: 2.11%
9106 PANZANI PLACE Windermere, FL Discover this beautiful 5-bedroom, 4-bathroom residence nestled inside the exclusive gated...	5 beds \| 4 baths \| 3,610 sq.ft.	$915,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 1.6% Airbnb Rental Income: $5841 Traditional Rental Income: $3632 Airbnb ROI: 2.82% Traditional ROI: 1.6%
12530 CLIMBING VINE COURT Windermere, FL Tucked at the end of a quiet cul-de-sac in the sought after community of Windstone, this b...	5 beds \| 4 baths \| 3,407 sq.ft.	$999,000	Airbnb cash on cash: 2.64% Traditional cash on cash: 2.42% Airbnb Rental Income: $5841 Traditional Rental Income: $4475 Airbnb ROI: 2.64% Traditional ROI: 2.42%
12335 CRUXBURY DRIVE Windermere, FL PRICE REDUCED! Discover this spacious 2-bedroom, 2.5-bath end-unit townhome nestled in a ...	2 beds \| 3 baths \| 1,510 sq.ft.	$369,999	Airbnb cash on cash: 8.48% Traditional cash on cash: 3.68% Airbnb Rental Income: $4898 Traditional Rental Income: $2227 Airbnb ROI: 8.48% Traditional ROI: 3.68%
7409 FAIRGROVE AVENUE Windermere, FL Enjoy resort-style living in the heart of Windermere! Located just minutes from major attr...	5 beds \| 3 baths \| 3,357 sq.ft.	$769,000	Airbnb cash on cash: 3.92% Traditional cash on cash: 2.04% Airbnb Rental Income: $5841 Traditional Rental Income: $3332 Airbnb ROI: 3.92% Traditional ROI: 2.04%
9107 Dollanger Ct Windermere, FL 9107 Dollanger Ct, Windermere, FL 32819 \| Single Family Residential	4 beds \| 2 baths \| 2,872 sq.ft.	$785,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 1.38% Airbnb Rental Income: $3311 Traditional Rental Income: $2539 Airbnb ROI: 1.43% Traditional ROI: 1.38%
6891 NORTHWICH DRIVE Windermere, FL One or more photo(s) has been virtually staged. Nestled within Lakes of Windermere sits a ...	5 beds \| 3 baths \| 2,759 sq.ft.	$624,500	Airbnb cash on cash: 6.18% Traditional cash on cash: 3.67% Airbnb Rental Income: $5841 Traditional Rental Income: $3213 Airbnb ROI: 6.18% Traditional ROI: 3.67%
6712 THORNHILL CIRCLE Windermere, FL With timeless curb appeal and a front porch built for slow mornings, this Windermere home ...	5 beds \| 4 baths \| 2,976 sq.ft.	$695,000	Airbnb cash on cash: 5.35% Traditional cash on cash: 4.34% Airbnb Rental Income: $5841 Traditional Rental Income: $4025 Airbnb ROI: 5.35% Traditional ROI: 4.34%
6846 HELMSLEY CIRCLE Windermere, FL Welcome to 6846 Helmsley Circle in beautiful Windermere, FL! This stunning 5-bedroom, 3-ba...	5 beds \| 3 baths \| 2,555 sq.ft.	$656,625	Airbnb cash on cash: 5.05% Traditional cash on cash: 2.31% Airbnb Rental Income: $5841 Traditional Rental Income: $2998 Airbnb ROI: 5.05% Traditional ROI: 2.31%
12716 LANGSTAFF DRIVE Windermere, FL One or more photo(s) has been virtually staged. BACK ON THE MARKET!( due to Financial issu...	2 beds \| 3 baths \| 1,181 sq.ft.	$345,000	Airbnb cash on cash: 8.74% Traditional cash on cash: 3.38% Airbnb Rental Income: $4898 Traditional Rental Income: $2154 Airbnb ROI: 8.74% Traditional ROI: 3.38%
8521 Sandberry Blvd Windermere, FL 8521 Sandberry Blvd, Windermere, FL 32819 \| Single Family Residential	4 beds \| 2 baths \| 2,440 sq.ft.	$635,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 2.02% Airbnb Rental Income: $3311 Traditional Rental Income: $2415 Airbnb ROI: 2.28% Traditional ROI: 2.02%
12748 LANGSTAFF DRIVE Windermere, FL Discover comfort and convenience in this beautifully maintained 2 bedrooms, 2.5 bathrooms ...	2 beds \| 3 baths \| 1,380 sq.ft.	$330,000	Airbnb cash on cash: 9.08% Traditional cash on cash: 3.47% Airbnb Rental Income: $4898 Traditional Rental Income: $2153 Airbnb ROI: 9.08% Traditional ROI: 3.47%
14342 CREST PALM AVENUE Windermere, FL SAMPLE IMAGE The Deerfield floorplan is a spacious two-story home designed for growing fam...	5 beds \| 4 baths \| 3,764 sq.ft.	$1,082,976	Airbnb cash on cash: 3.21% Traditional cash on cash: 2.9% Airbnb Rental Income: $5841 Traditional Rental Income: $4365 Airbnb ROI: 3.21% Traditional ROI: 2.9%
416 MAGNOLIA STREET Windermere, FL Under contract-accepting backup offers. Step into a storybook cottage tucked in the heart ...	2 beds \| 2 baths \| 2,115 sq.ft.	$885,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 1.56% Airbnb Rental Income: $4898 Traditional Rental Income: $2617 Airbnb ROI: 3.11% Traditional ROI: 1.56%
8632 Spindletop Dr Windermere, FL 8632 Spindletop Dr, Windermere, FL 32819 \| Single Family Residential	6 beds \| 4 baths \| 3,645 sq.ft.	$980,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 1.84% Airbnb Rental Income: $5841 Traditional Rental Income: $3660 Airbnb ROI: 2.96% Traditional ROI: 1.84%
13907 ANCILLA BOULEVARD Windermere, FL Under contract-accepting backup offers. Video Tour Available Welcome to Summerport! Thi...	2 beds \| 2 baths \| 1,155 sq.ft.	$360,000	Airbnb cash on cash: 8.14% Traditional cash on cash: 2.28% Airbnb Rental Income: $4898 Traditional Rental Income: $1914 Airbnb ROI: 8.14% Traditional ROI: 2.28%

Vacation Rentals in Windermere

There are 19 vacation rental properties available for sale in the city of Windermere . The median list price of Airbnb properties available for sale in Windermere is $949,500 and the average price per square foot is $277. The cash on cash return on vacation rentals in Windermere is 1.00%. The average monthly short term rental income in Windermere is $3,311.

Windermere, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 19 Airbnb properties available for sale in Windermere.

In 2025, the best neighborhood to buy short term rental property is Windermere.

In December 2025, the average Airbnb occupancy rate in Windermere is 69%.

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

Your search for investment property begins and ends here

Airbnb For Sale in Windermere, FL

12654 CRAGSIDE LANE

Windermere, FL

5 beds | 4 baths | 3,072 sq.ft.

$679,900

Airbnb cash on cash: 4.68%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $5841

Traditional Rental Income: $3812

Airbnb ROI: 4.68%

Traditional ROI: 3.32%

6615 HELMSLEY CIRCLE

Windermere, FL

5 beds | 4 baths | 3,390 sq.ft.

$799,900

Airbnb cash on cash: 4.9%

Traditional cash on cash: 4.43%

Airbnb Rental Income: $5841

Traditional Rental Income: $4329

Airbnb ROI: 4.9%

Traditional ROI: 4.43%

13833 ANCILLA BOULEVARD

Windermere, FL

2 beds | 2 baths | 1,155 sq.ft.

$355,000

Airbnb cash on cash: 8.78%

Traditional cash on cash: 2.84%

Airbnb Rental Income: $4898

Traditional Rental Income: $1913

Airbnb ROI: 8.78%

Traditional ROI: 2.84%

3443 WILD MYRTLE COURT

Windermere, FL

5 beds | 3 baths | 2,918 sq.ft.

$1,200,000

Airbnb cash on cash: 2.99%

Traditional cash on cash: 2.11%

Airbnb Rental Income: $5841

Traditional Rental Income: $3693

Airbnb ROI: 2.99%

Traditional ROI: 2.11%

9106 PANZANI PLACE

Windermere, FL

5 beds | 4 baths | 3,610 sq.ft.

$915,000

Airbnb cash on cash: 2.82%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $5841

Traditional Rental Income: $3632

Airbnb ROI: 2.82%

Traditional ROI: 1.6%

12530 CLIMBING VINE COURT

Windermere, FL

5 beds | 4 baths | 3,407 sq.ft.

$999,000

Airbnb cash on cash: 2.64%

Traditional cash on cash: 2.42%

Airbnb Rental Income: $5841

Traditional Rental Income: $4475

Airbnb ROI: 2.64%

Traditional ROI: 2.42%

12335 CRUXBURY DRIVE

Windermere, FL

2 beds | 3 baths | 1,510 sq.ft.

$369,999

Airbnb cash on cash: 8.48%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $4898

Traditional Rental Income: $2227

Airbnb ROI: 8.48%

Traditional ROI: 3.68%

7409 FAIRGROVE AVENUE

Windermere, FL

5 beds | 3 baths | 3,357 sq.ft.

$769,000

Airbnb cash on cash: 3.92%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $5841

Traditional Rental Income: $3332

Airbnb ROI: 3.92%