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 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.	$769,900	Airbnb cash on cash: 5.13% Traditional cash on cash: 4.56% Airbnb Rental Income: $5841 Traditional Rental Income: $4270 Airbnb ROI: 5.13% Traditional ROI: 4.56%
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.	$1,950,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 0.59% Airbnb Rental Income: $5841 Traditional Rental Income: $4548 Airbnb ROI: 0.67% Traditional ROI: 0.59%
12936 DROXFORD ROAD Windermere, FL The seller will install a brand-new roof prior to closing, ensuring the property is fully ...	5 beds \| 4 baths \| 2,960 sq.ft.	$659,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 3.11% Airbnb Rental Income: $5841 Traditional Rental Income: $3631 Airbnb ROI: 4.82% Traditional ROI: 3.11%
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: 2.79% Airbnb Rental Income: $5841 Traditional Rental Income: $3870 Airbnb ROI: 3.92% Traditional ROI: 2.79%
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.	$680,000	Airbnb cash on cash: 5.49% Traditional cash on cash: 4.8% Airbnb Rental Income: $5841 Traditional Rental Income: $4237 Airbnb ROI: 5.49% Traditional ROI: 4.8%
6846 HELMSLEY CIRCLE Windermere, FL Under contract-accepting backup offers. NEW ROOF! Welcome to 6846 Helmsley Circle in beaut...	5 beds \| 3 baths \| 2,555 sq.ft.	$609,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 3.47% Airbnb Rental Income: $5841 Traditional Rental Income: $3513 Airbnb ROI: 5.52% Traditional ROI: 3.47%
13232 LONGACRE DRIVE Windermere, FL Wonderful home in desired Windermere. This two-story home features five large bedrooms a...	5 beds \| 3 baths \| 2,511 sq.ft.	$689,000	Airbnb cash on cash: 4.73% Traditional cash on cash: 2.98% Airbnb Rental Income: $5841 Traditional Rental Income: $3556 Airbnb ROI: 4.73% Traditional ROI: 2.98%
11208 Ledgement Ln Windermere, FL 11208 Ledgement Ln, Windermere, FL 34786 \| Single Family Residential	5 beds \| 3 baths \| 2,988 sq.ft.	$1,000,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 2.26% Airbnb Rental Income: $5841 Traditional Rental Income: $4105 Airbnb ROI: 2.88% Traditional ROI: 2.26%
13124 Filly Ct Windermere, FL 13124 Filly Ct, Windermere, FL 34786 \| Single Family Residential	5 beds \| 3 baths \| 3,300 sq.ft.	$1,575,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 0.97% Airbnb Rental Income: $5841 Traditional Rental Income: $4316 Airbnb ROI: 1.22% Traditional ROI: 0.97%
1134 KELSO BOULEVARD Windermere, FL Experience refined, low-maintenance lakefront living in this 2-bedroom, 2-bathroom custom ...	2 beds \| 2 baths \| 2,044 sq.ft.	$1,590,000	Airbnb cash on cash: 0.39% Traditional cash on cash: -0.15% Airbnb Rental Income: $4898 Traditional Rental Income: $3098 Airbnb ROI: 0.39% Traditional ROI: -0.15%
11866 Camden Park Dr Windermere, FL 11866 Camden Park Dr, Windermere, FL 34786 \| Single Family Residential	5 beds \| 4 baths \| 3,337 sq.ft.	$984,900	Airbnb cash on cash: 2.76% Traditional cash on cash: 1.41% Airbnb Rental Income: $5841 Traditional Rental Income: $3439 Airbnb ROI: 2.76% Traditional ROI: 1.41%
11339 Camden Park Dr Windermere, FL 11339 Camden Park Dr, Windermere, FL 34786 \| Single Family Residential	5 beds \| 4 baths \| 3,492 sq.ft.	$1,490,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 0.42% Airbnb Rental Income: $5841 Traditional Rental Income: $3594 Airbnb ROI: 1.2% Traditional ROI: 0.42%
11952 Camden Park Dr Windermere, FL 11952 Camden Park Dr, Windermere, FL 34786 \| Single Family Residential	5 beds \| 4 baths \| 3,337 sq.ft.	$1,649,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 0.15% Airbnb Rental Income: $5841 Traditional Rental Income: $3527 Airbnb ROI: 0.9% Traditional ROI: 0.15%
11419 Camden Park Dr Windermere, FL 11419 Camden Park Dr, Windermere, FL 34786 \| Single Family Residential	5 beds \| 4 baths \| 3,686 sq.ft.	$1,375,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 0.56% Airbnb Rental Income: $5841 Traditional Rental Income: $3530 Airbnb ROI: 1.46% Traditional ROI: 0.56%
13145 ZORI LANE Windermere, FL One or more photo(s) has been virtually staged. Priced right and move-in ready! Situated i...	5 beds \| 4 baths \| 3,597 sq.ft.	$775,000	Airbnb cash on cash: 3.85% Traditional cash on cash: 3.79% Airbnb Rental Income: $5841 Traditional Rental Income: $4637 Airbnb ROI: 3.85% Traditional ROI: 3.79%
12405 CRUXBURY DRIVE Windermere, FL Discover this spotless corner-unit townhome in Windermere Lakes, offering some privacy wit...	2 beds \| 3 baths \| 1,429 sq.ft.	$415,000	Airbnb cash on cash: 6.9% Traditional cash on cash: 2.78% Airbnb Rental Income: $4898 Traditional Rental Income: $2293 Airbnb ROI: 6.9% Traditional ROI: 2.78%
5106 Tildens Grove Blvd Windermere, FL 5106 Tildens Grove Blvd, Windermere, FL 34786 \| Single Family Residential	6 beds \| 4 baths \| 4,572 sq.ft.	$1,700,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 0.07% Airbnb Rental Income: $5841 Traditional Rental Income: $3526 Airbnb ROI: 0.8% Traditional ROI: 0.07%
715 Magnolia St Windermere, FL 715 Magnolia St, Windermere, FL 34786 \| Single Family Residential	5 beds \| 4 baths \| 3,390 sq.ft.	$1,250,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 1.36% Airbnb Rental Income: $5841 Traditional Rental Income: $3865 Airbnb ROI: 2.06% Traditional ROI: 1.36%
6152 Golden Dewdrop Trl Windermere, FL 6152 Golden Dewdrop Trl, Windermere, FL 34786 \| Single Family Residential	8 beds \| 5 baths \| 4,830 sq.ft.	$1,130,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 2.29% Airbnb Rental Income: $5841 Traditional Rental Income: $4628 Airbnb ROI: 2.34% Traditional ROI: 2.29%
11564 Mizzon Dr #903/110 Windermere, FL 11564 Mizzon Dr #903/110, Windermere, FL 34786 \| Condo/Coop	3 beds \| 2 baths \| 1,442 sq.ft.	$339,000	Airbnb cash on cash: 2.32% Traditional cash on cash: 1.73% Airbnb Rental Income: $2597 Traditional Rental Income: $1788 Airbnb ROI: 2.32% Traditional ROI: 1.73%
11564 Mizzon Dr #202 (919) Windermere, FL 11564 Mizzon Dr #202 (919), Windermere, FL 34786 \| Condo/Coop	2 beds \| 2 baths \| 1,161 sq.ft.	$295,000	Airbnb cash on cash: 9.84% Traditional cash on cash: 1.58% Airbnb Rental Income: $4898 Traditional Rental Income: $1598 Airbnb ROI: 9.84% Traditional ROI: 1.58%
1925 BREEZY HILL DRIVE WINDERMERE FLORIDA 34786 Windermere, FL Modern luxury meets resort-style living in this stunning 5-bedroom estate located in the h...	5 beds \| 3 baths \| 3,063 sq.ft.	$880,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 1.48% Airbnb Rental Income: $5841 Traditional Rental Income: $2865 Airbnb ROI: 3.69% Traditional ROI: 1.48%
2068 Roberts Point Dr Windermere, FL 2068 Roberts Point Dr, Windermere, FL 34786 \| Single Family Residential	5 beds \| 4 baths \| 4,876 sq.ft.	$2,350,000	Airbnb cash on cash: 0.05% Traditional cash on cash: -0.32% Airbnb Rental Income: $5841 Traditional Rental Income: $3862 Airbnb ROI: 0.05% Traditional ROI: -0.32%
8179 Maritime Flag St #101 Windermere, FL 8179 Maritime Flag St #101, Windermere, FL 34786 \| Condo/Coop	3 beds \| 2 baths \| 1,442 sq.ft.	$330,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 1.83% Airbnb Rental Income: $2597 Traditional Rental Income: $1788 Airbnb ROI: 2.43% Traditional ROI: 1.83%

Vacation Rentals in Windermere

There are 24 vacation rental properties available for sale in the city of Windermere . The median list price of Airbnb properties available for sale in Windermere is $1,255,000 and the average price per square foot is $310. The cash on cash return on vacation rentals in Windermere is N/A%. 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 24 Airbnb properties available for sale in Windermere.

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

In April 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 CIRCLE

Windermere, FL

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

$769,900

Airbnb cash on cash: 5.13%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $5841

Traditional Rental Income: $4270

Airbnb ROI: 5.13%

Traditional ROI: 4.56%

13048 Lake Roper Ct

Windermere, FL

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

$1,950,000

Airbnb cash on cash: 0.67%

Traditional cash on cash: 0.59%

Airbnb Rental Income: $5841

Traditional Rental Income: $4548

Airbnb ROI: 0.67%

Traditional ROI: 0.59%

12936 DROXFORD ROAD

Windermere, FL

5 beds | 4 baths | 2,960 sq.ft.

$659,000

Airbnb cash on cash: 4.82%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $5841

Traditional Rental Income: $3631

Airbnb ROI: 4.82%

Traditional ROI: 3.11%

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: 2.79%

Airbnb Rental Income: $5841

Traditional Rental Income: $3870

Airbnb ROI: 3.92%

Traditional ROI: 2.79%

6712 THORNHILL CIRCLE

Windermere, FL

5 beds | 4 baths | 2,976 sq.ft.

$680,000

Airbnb cash on cash: 5.49%

Traditional cash on cash: 4.8%

Airbnb Rental Income: $5841

Traditional Rental Income: $4237

Airbnb ROI: 5.49%

Traditional ROI: 4.8%

6846 HELMSLEY CIRCLE

Windermere, FL

5 beds | 3 baths | 2,555 sq.ft.

$609,000

Airbnb cash on cash: 5.52%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $5841

Traditional Rental Income: $3513

Airbnb ROI: 5.52%

Traditional ROI: 3.47%

13232 LONGACRE DRIVE

Windermere, FL

5 beds | 3 baths | 2,511 sq.ft.

$689,000

Airbnb cash on cash: 4.73%

Traditional cash on cash: 2.98%

Airbnb Rental Income: $5841

Traditional Rental Income: $3556

Airbnb ROI: 4.73%

Traditional ROI: 2.98%

11208 Ledgement Ln

Windermere, FL

5 beds | 3 baths | 2,988 sq.ft.

$1,000,000

Airbnb cash on cash: 2.88%

Traditional cash on cash: 2.26%

Airbnb Rental Income: $5841

Traditional Rental Income: $4105

Airbnb ROI: 2.88%