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%
7418 BENTONSHIRE AVENUE Windermere, FL Experience the ideal blend of comfort, style, and convenience in the highly sought-after W...	2 beds \| 3 baths \| 1,228 sq.ft.	$330,000	Airbnb cash on cash: 9.2% Traditional cash on cash: 3.68% Airbnb Rental Income: $4898 Traditional Rental Income: $2183 Airbnb ROI: 9.2% Traditional ROI: 3.68%
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.	$975,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 2.5% Airbnb Rental Income: $5841 Traditional Rental Income: $4475 Airbnb ROI: 2.72% Traditional ROI: 2.5%
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%
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 CIRCLE 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.	$637,500	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 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%
8225 BRYCE CANYON AVENUE Windermere, FL Beautiful 4-Bedroom Home in Windermere, FL â Prime Location and Comfort for the Whole Fa...	4 beds \| 3 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 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.	$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%
6146 Golden Dewdrop Trl Windermere, FL 6146 Golden Dewdrop Trl, Windermere, FL 34786 \| Single Family Residential	7 beds \| 5 baths \| 4,751 sq.ft.	$1,200,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 2.07% Airbnb Rental Income: $5841 Traditional Rental Income: $4652 Airbnb ROI: 2.1% Traditional ROI: 2.07%
1369 Glenwick Dr Windermere, FL 1369 Glenwick Dr, Windermere, FL 34786 \| Single Family Residential	4 beds \| 3 baths \| 2,400 sq.ft.	$657,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 1.61% Airbnb Rental Income: $3311 Traditional Rental Income: $2428 Airbnb ROI: 1.84% Traditional ROI: 1.61%
17538 Black Rail St Windermere, FL 17538 Black Rail St, Windermere, FL 34786 \| Single Family Residential	6 beds \| 4 baths \| 4,522 sq.ft.	$1,480,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 0.39% Airbnb Rental Income: $5841 Traditional Rental Income: $3408 Airbnb ROI: 1.32% Traditional ROI: 0.39%
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: -0.03% Airbnb Rental Income: $5841 Traditional Rental Income: $2854 Airbnb ROI: 1.22% Traditional ROI: -0.03%
9426 Palm Tree Dr Windermere, FL 9426 Palm Tree Dr, Windermere, FL 34786 \| Single Family Residential	4 beds \| 2 baths \| 2,063 sq.ft.	$650,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 1.48% Airbnb Rental Income: $3311 Traditional Rental Income: $2165 Airbnb ROI: 2.14% Traditional ROI: 1.48%

Vacation Rentals in Windermere

There are 29 vacation rental properties available for sale in the city of Windermere . The median list price of Airbnb properties available for sale in Windermere is $1,037,000 and the average price per square foot is $306. 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 29 Airbnb properties available for sale in Windermere.

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

In January 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%

7418 BENTONSHIRE AVENUE

Windermere, FL

2 beds | 3 baths | 1,228 sq.ft.

$330,000

Airbnb cash on cash: 9.2%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $4898

Traditional Rental Income: $2183

Airbnb ROI: 9.2%

Traditional ROI: 3.68%

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.

$975,000

Airbnb cash on cash: 2.72%

Traditional cash on cash: 2.5%

Airbnb Rental Income: $5841

Traditional Rental Income: $4475

Airbnb ROI: 2.72%

Traditional ROI: 2.5%

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%

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%