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
6615 Helmsley Cir Windermere, FL Beautifully remodeled and impeccably maintained, this spacious 3,390 sq. ft. two-story hom...	5 beds \| 3 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%
13048 Lake Roper Ct Windermere, FL Auction Property. Waterfront home featuring 4 bedrooms, 3.5 baths, and a gracious amount ...	5 beds \| 3 baths \| 4,130 sq.ft.	$1,999,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 0.41% Airbnb Rental Income: $5841 Traditional Rental Income: $4282 Airbnb ROI: 0.63% Traditional ROI: 0.41%
3443 Wild Myrtle Ct 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%
12936 Droxford Rd Windermere, FL Lakes of Windermere STUNNER! This Ashton Woods Kensington model comes with an amazing bonu...	5 beds \| 3 baths \| 2,960 sq.ft.	$699,000	Airbnb cash on cash: 4.49% Traditional cash on cash: 3.2% Airbnb Rental Income: $5841 Traditional Rental Income: $3839 Airbnb ROI: 4.49% Traditional ROI: 3.2%
9106 Panzani Pl Windermere, FL Discover this beautiful 5-bedroom, 4-bathroom residence nestled inside the exclusive gated...	5 beds \| 4 baths \| 3,610 sq.ft.	$890,000	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%
12335 Cruxbury Dr Windermere, FL PRICE REDUCED! Discover this spacious 2-bedroom, 2.5-bath end-unit townhome nestled in a ...	2 beds \| 2 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 Ave 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%
6891 NORTHWICH DRIVE Windermere, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Ne...	5 beds \| 3 baths \| 2,759 sq.ft.	$625,000	Airbnb cash on cash: 6.18% Traditional cash on cash: 3.66% Airbnb Rental Income: $5841 Traditional Rental Income: $3213 Airbnb ROI: 6.18% Traditional ROI: 3.66%
6712 Thornhill Cir Windermere, FL With timeless curb appeal and a front porch built for slow mornings, this Windermere home ...	5 beds \| 3 baths \| 2,976 sq.ft.	$680,000	Airbnb cash on cash: 5.49% Traditional cash on cash: 4.46% Airbnb Rental Income: $5841 Traditional Rental Income: $4025 Airbnb ROI: 5.49% Traditional ROI: 4.46%
6846 Helmsley Cir Windermere, FL NEW ROOF! Welcome to 6846 Helmsley Circle in beautiful Windermere, FL! This stunning 5-bed...	5 beds \| 3 baths \| 2,555 sq.ft.	$625,000	Airbnb cash on cash: 5.23% Traditional cash on cash: 2.4% Airbnb Rental Income: $5841 Traditional Rental Income: $2998 Airbnb ROI: 5.23% Traditional ROI: 2.4%
12716 LANGSTAFF DRIVE Windermere, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. BA...	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%
416 Magnolia St Windermere, FL Back on the Market. Buyer unable to secure financing. Step into a storybook cottage tuck...	2 beds \| 1 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%
8225 Bryce Canyon Ave Windermere, FL Beautiful 4-Bedroom Home in Windermere, FL â Prime Location and Comfort for the Whole Fa...	4 beds \| 2 baths \| 1,840 sq.ft.	$560,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 2.37% Airbnb Rental Income: $3311 Traditional Rental Income: $2545 Airbnb ROI: 2.42% Traditional ROI: 2.37%
13232 Longacre Dr Windermere, FL Wonderful home in desired Windermere. This two-story home features five large bedrooms a...	5 beds \| 3 baths \| 2,511 sq.ft.	$710,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 1.94% Airbnb Rental Income: $5841 Traditional Rental Income: $2942 Airbnb ROI: 4.56% Traditional ROI: 1.94%
2512 Park Royal Dr Windermere, FL This impeccably updated residence showcases a comprehensive renovation completed in 2025, ...	5 beds \| 3 baths \| 3,259 sq.ft.	$1,200,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 2.18% Airbnb Rental Income: $5841 Traditional Rental Income: $3831 Airbnb ROI: 2.94% Traditional ROI: 2.18%

Vacation Rentals in Windermere

There are 60 vacation rental properties available for sale in the city of Windermere . The median list price of Airbnb properties available for sale in Windermere is $912,000 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 60 Airbnb properties available for sale in Windermere.

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

In February 2026, 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

6615 Helmsley Cir

Windermere, FL

5 beds | 3 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%

13048 Lake Roper Ct

Windermere, FL

5 beds | 3 baths | 4,130 sq.ft.

$1,999,000

Airbnb cash on cash: 0.63%

Traditional cash on cash: 0.41%

Airbnb Rental Income: $5841

Traditional Rental Income: $4282

Airbnb ROI: 0.63%

Traditional ROI: 0.41%

3443 Wild Myrtle Ct

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%

12936 Droxford Rd

Windermere, FL

5 beds | 3 baths | 2,960 sq.ft.

$699,000

Airbnb cash on cash: 4.49%

Traditional cash on cash: 3.2%

Airbnb Rental Income: $5841

Traditional Rental Income: $3839

Airbnb ROI: 4.49%

Traditional ROI: 3.2%

9106 Panzani Pl

Windermere, FL

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

$890,000

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%

12335 Cruxbury Dr

Windermere, FL

2 beds | 2 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 Ave

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%

Traditional ROI: 2.04%

6891 NORTHWICH DRIVE

Windermere, FL

5 beds | 3 baths | 2,759 sq.ft.

$625,000

Airbnb cash on cash: 6.18%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $5841

Traditional Rental Income: $3213

Airbnb ROI: 6.18%