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 Welcome to a truly rare opportunity in Windermereâwhere TOP-RATED SCHOOLS, access to the...	5 beds \| 4 baths \| 3,072 sq.ft.	$699,900	Airbnb cash on cash: 4.52% Traditional cash on cash: 3.19% Airbnb Rental Income: $5841 Traditional Rental Income: $3812 Airbnb ROI: 4.52% Traditional ROI: 3.19%
14466 BRIDGEWATER CROSSINGS BOULEVARD Windermere, FL Under contract-accepting backup offers. Video Tour Available Welcome to Summerport whe...	4 beds \| 3 baths \| 1,642 sq.ft.	$410,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 2.84% Airbnb Rental Income: $3311 Traditional Rental Income: $2136 Airbnb ROI: 3.97% Traditional ROI: 2.84%
2128 LAKE CRESCENT COURT Windermere, FL Short Sale. Come see it today! Finally Bank above price to close. This property sounds li...	5 beds \| 3 baths \| 2,987 sq.ft.	$856,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 1.35% Airbnb Rental Income: $5841 Traditional Rental Income: $3132 Airbnb ROI: 3.29% Traditional ROI: 1.35%
2540 HEMPEL COVE CT Windermere, FL Stunning Renovation on 1 Acre in Lake Down Cove. Located at the end of a quiet cul-de-sac,...	5 beds \| 3 baths \| 3,356 sq.ft.	$1,299,900	Airbnb cash on cash: 1.42% Traditional cash on cash: 0.9% Airbnb Rental Income: $5841 Traditional Rental Income: $4045 Airbnb ROI: 1.42% Traditional ROI: 0.9%
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%
14365 CREST PALM AVENUE Windermere, FL One or more photo(s) has been virtually staged. Under Construction. Sample Images The Elli...	5 beds \| 4 baths \| 3,628 sq.ft.	$1,050,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 2.91% Airbnb Rental Income: $5841 Traditional Rental Income: $4341 Airbnb ROI: 3.26% Traditional ROI: 2.91%
1638 WHITNEY ISLES DRIVE Windermere, FL Welcome to luxury living in the highly desirable gated community of Belmere, located in Wi...	5 beds \| 4 baths \| 3,151 sq.ft.	$895,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.71% Airbnb Rental Income: $5841 Traditional Rental Income: $4219 Airbnb ROI: 3.27% Traditional ROI: 2.71%
9319 WOODBREEZE BOULEVARD Windermere, FL WONDERFUL WINDERMERE 4 BED/ 2 BATH HOME LOCATED IN THE CHARMING COMMUNITY OF SILVER WOODS....	4 beds \| 2 baths \| 1,798 sq.ft.	$589,900	Airbnb cash on cash: 2.87% Traditional cash on cash: 2.86% Airbnb Rental Income: $3311 Traditional Rental Income: $2565 Airbnb ROI: 2.87% Traditional ROI: 2.86%
12335 CRUXBURY DRIVE Windermere, FL Discover this spacious 2-bedroom, 2.5-bath end-unit townhome nestled in a charming Winderm...	2 beds \| 3 baths \| 1,510 sq.ft.	$397,499	Airbnb cash on cash: 7.83% Traditional cash on cash: 3.36% Airbnb Rental Income: $4898 Traditional Rental Income: $2227 Airbnb ROI: 7.83% Traditional ROI: 3.36%
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%
6948 DUNCASTER STREET Windermere, FL PRICED TO SELL! Lowest price in Windermere per SqFt. Stunning Home â 3,946 Sq Ft! Welcom...	5 beds \| 4 baths \| 3,946 sq.ft.	$798,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.8% Airbnb Rental Income: $5841 Traditional Rental Income: $4315 Airbnb ROI: 4.28% Traditional ROI: 3.8%
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 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%

Vacation Rentals in Windermere

There are 13 vacation rental properties available for sale in the city of Windermere . The median list price of Airbnb properties available for sale in Windermere is $995,000 and the average price per square foot is $292. 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 13 Airbnb properties available for sale in Windermere.

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

In October 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.

$699,900

Airbnb cash on cash: 4.52%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $5841

Traditional Rental Income: $3812

Airbnb ROI: 4.52%

Traditional ROI: 3.19%

14466 BRIDGEWATER CROSSINGS BOULEVARD

Windermere, FL

4 beds | 3 baths | 1,642 sq.ft.

$410,000

Airbnb cash on cash: 3.97%

Traditional cash on cash: 2.84%

Airbnb Rental Income: $3311

Traditional Rental Income: $2136

Airbnb ROI: 3.97%

Traditional ROI: 2.84%

2128 LAKE CRESCENT COURT

Windermere, FL

5 beds | 3 baths | 2,987 sq.ft.

$856,000

Airbnb cash on cash: 3.29%

Traditional cash on cash: 1.35%

Airbnb Rental Income: $5841

Traditional Rental Income: $3132

Airbnb ROI: 3.29%

Traditional ROI: 1.35%

2540 HEMPEL COVE CT

Windermere, FL

5 beds | 3 baths | 3,356 sq.ft.

$1,299,900

Airbnb cash on cash: 1.42%

Traditional cash on cash: 0.9%

Airbnb Rental Income: $5841

Traditional Rental Income: $4045

Airbnb ROI: 1.42%

Traditional ROI: 0.9%

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%

14365 CREST PALM AVENUE

Windermere, FL

5 beds | 4 baths | 3,628 sq.ft.

$1,050,000

Airbnb cash on cash: 3.26%

Traditional cash on cash: 2.91%

Airbnb Rental Income: $5841

Traditional Rental Income: $4341

Airbnb ROI: 3.26%

Traditional ROI: 2.91%

1638 WHITNEY ISLES DRIVE

Windermere, FL

5 beds | 4 baths | 3,151 sq.ft.

$895,000

Airbnb cash on cash: 3.27%

Traditional cash on cash: 2.71%

Airbnb Rental Income: $5841

Traditional Rental Income: $4219

Airbnb ROI: 3.27%

Traditional ROI: 2.71%

9319 WOODBREEZE BOULEVARD

Windermere, FL

4 beds | 2 baths | 1,798 sq.ft.

$589,900

Airbnb cash on cash: 2.87%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $3311

Traditional Rental Income: $2565

Airbnb ROI: 2.87%