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
13118 Sunkiss Loop Windermere, FL Price reduced by $20K, seller's lost is your gain. Come visit this lovely home located in ...	4 beds \| 2 baths \| 2,547 sq.ft.	$579,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 2.14% Airbnb Rental Income: $3311 Traditional Rental Income: $2371 Airbnb ROI: 2.51% Traditional ROI: 2.14%
9639 WESTOVER CLUB CIRCLE Windermere, FL Under contract-accepting backup offers. There's room for everyone here.Â Nearly 3,300 squa...	5 beds \| 3 baths \| 3,248 sq.ft.	$847,500	Airbnb cash on cash: 3.36% Traditional cash on cash: 2.73% Airbnb Rental Income: $5841 Traditional Rental Income: $4187 Airbnb ROI: 3.36% Traditional ROI: 2.73%
12533 CRAGSIDE LANE Windermere, FL Welcome to Lakes of Windermere, where comfort, thoughtful upgrades, and an unbeatable Cent...	4 beds \| 2 baths \| 2,151 sq.ft.	$575,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 1.45% Airbnb Rental Income: $3311 Traditional Rental Income: $2287 Airbnb ROI: 1.98% Traditional ROI: 1.45%
12936 DROXFORD ROAD Windermere, FL Lakes of Windermere STUNNER! This Ashton Woods Kensington model comes with an amazing bonu...	5 beds \| 4 baths \| 2,960 sq.ft.	$629,000	Airbnb cash on cash: 5.09% Traditional cash on cash: 3.31% Airbnb Rental Income: $5841 Traditional Rental Income: $3631 Airbnb ROI: 5.09% Traditional ROI: 3.31%
14348 CREST PALM AVENUE Windermere, FL One or more photo(s) has been virtually staged. Baldwin Floorplan â 3,724 Sq. Ft. \| 4 Be...	4 beds \| 4 baths \| 3,721 sq.ft.	$1,109,990	Airbnb cash on cash: 1.09% Traditional cash on cash: -0.57% Airbnb Rental Income: $3311 Traditional Rental Income: $857 Airbnb ROI: 1.09% Traditional ROI: -0.57%
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%
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 \| 2,788 sq.ft.	$999,950	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%
12941 Westside Village Loop Windermere, FL 12941 Westside Village Loop, Windermere, FL 34786 \| Single Family Residential	5 beds \| 3 baths \| 3,717 sq.ft.	$929,900	Airbnb cash on cash: 3.26% Traditional cash on cash: 2.69% Airbnb Rental Income: $5841 Traditional Rental Income: $4188 Airbnb ROI: 3.26% Traditional ROI: 2.69%
6965 Tettenhall Ln Windermere, FL 6965 Tettenhall Ln, Windermere, FL 34786 \| Single Family Residential	5 beds \| 3 baths \| 2,972 sq.ft.	$679,000	Airbnb cash on cash: 5.22% Traditional cash on cash: 4.6% Airbnb Rental Income: $5841 Traditional Rental Income: $4285 Airbnb ROI: 5.22% Traditional ROI: 4.6%
4415 Blue Major Dr Windermere, FL 4415 Blue Major Dr, Windermere, FL 34786 \| Single Family Residential	5 beds \| 3 baths \| 3,211 sq.ft.	$815,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 3.22% Airbnb Rental Income: $5841 Traditional Rental Income: $4110 Airbnb ROI: 3.97% Traditional ROI: 3.22%
6752 Trellis Vine Loop Windermere, FL 6752 Trellis Vine Loop, Windermere, FL 34786 \| Single Family Residential	5 beds \| 3 baths \| 3,820 sq.ft.	$930,000	Airbnb cash on cash: 3.16% Traditional cash on cash: 2.71% Airbnb Rental Income: $5841 Traditional Rental Income: $4289 Airbnb ROI: 3.16% Traditional ROI: 2.71%
8767 Iron Mountain Trl Windermere, FL 8767 Iron Mountain Trl, Windermere, FL 34786 \| Single Family Residential	5 beds \| 3 baths \| 3,724 sq.ft.	$870,000	Airbnb cash on cash: 3.65% Traditional cash on cash: 1.26% Airbnb Rental Income: $5841 Traditional Rental Income: $2738 Airbnb ROI: 3.65% Traditional ROI: 1.26%
9257 Outlook Rock Trl Windermere, FL 9257 Outlook Rock Trl, Windermere, FL 34786 \| Single Family Residential	5 beds \| 4 baths \| 3,619 sq.ft.	$899,990	Airbnb cash on cash: 3.59% Traditional cash on cash: 2.1% Airbnb Rental Income: $5841 Traditional Rental Income: $3431 Airbnb ROI: 3.59% Traditional ROI: 2.1%
8236 Procida Isle Ln Windermere, FL 8236 Procida Isle Ln, Windermere, FL 34786 \| Single Family Residential	6 beds \| 4 baths \| 4,176 sq.ft.	$1,100,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 1.06% Airbnb Rental Income: $5841 Traditional Rental Income: $3438 Airbnb ROI: 2.27% Traditional ROI: 1.06%
8552 Powder Ridge Trl Windermere, FL 8552 Powder Ridge Trl, Windermere, FL 34786 \| Single Family Residential	5 beds \| 3 baths \| 2,612 sq.ft.	$680,000	Airbnb cash on cash: 5.2% Traditional cash on cash: 1.98% Airbnb Rental Income: $5841 Traditional Rental Income: $2637 Airbnb ROI: 5.2% Traditional ROI: 1.98%
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%
12640 Salomon Cove Dr Windermere, FL 12640 Salomon Cove Dr, Windermere, FL 34786 \| Single Family Residential	5 beds \| 3 baths \| 3,694 sq.ft.	$1,295,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 0.2% Airbnb Rental Income: $5841 Traditional Rental Income: $2752 Airbnb ROI: 1.8% Traditional ROI: 0.2%
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%
9225 Mcdavid Ct Windermere, FL 9225 Mcdavid Ct, Windermere, FL 34786 \| Single Family Residential	4 beds \| 2 baths \| 2,713 sq.ft.	$815,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 1.07% Airbnb Rental Income: $3311 Traditional Rental Income: $2363 Airbnb ROI: 1.34% Traditional ROI: 1.07%
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.	$750,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 3.95% Airbnb Rental Income: $5841 Traditional Rental Income: $4637 Airbnb ROI: 4.01% Traditional ROI: 3.95%
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.	$1,175,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 1.57% Airbnb Rental Income: $5841 Traditional Rental Income: $3865 Airbnb ROI: 2.31% Traditional ROI: 1.57%
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 #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.	$325,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 1.89% Airbnb Rental Income: $2597 Traditional Rental Income: $1788 Airbnb ROI: 2.5% Traditional ROI: 1.89%
2219 Ridgewind Way Windermere, FL 2219 Ridgewind Way, Windermere, FL 34786 \| Single Family Residential	6 beds \| 3 baths \| 3,364 sq.ft.	$1,299,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 0.25% Airbnb Rental Income: $5841 Traditional Rental Income: $2911 Airbnb ROI: 1.71% Traditional ROI: 0.25%
5427 NAGAMI DRIVE Windermere, FL Under contract-accepting backup offers. **HIGHEST AND BEST DUE TOMORROW APRIL 27th, 2026 (...	5 beds \| 4 baths \| 3,493 sq.ft.	$799,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 3.24% Airbnb Rental Income: $5841 Traditional Rental Income: $4491 Airbnb ROI: 3.49% Traditional ROI: 3.24%
6379 SWANSON STREET Windermere, FL From the moment you arrive, this Mediterranean home in the highly sought after Enclave mak...	5 beds \| 4 baths \| 3,804 sq.ft.	$1,119,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 1.11% Airbnb Rental Income: $5841 Traditional Rental Income: $3464 Airbnb ROI: 2.27% Traditional ROI: 1.11%
5421 Tildens Grove Blvd Windermere, FL 5421 Tildens Grove Blvd, Windermere, FL 34786 \| Single Family Residential	5 beds \| 4 baths \| 5,922 sq.ft.	$1,999,900	Airbnb cash on cash: 0.4% Traditional cash on cash: -0.22% Airbnb Rental Income: $5841 Traditional Rental Income: $3535 Airbnb ROI: 0.4% Traditional ROI: -0.22%
1430 Glenwick Dr Windermere, FL 1430 Glenwick Dr, Windermere, FL 34786 \| Single Family Residential	4 beds \| 3 baths \| 2,606 sq.ft.	$779,900	Airbnb cash on cash: 1.29% Traditional cash on cash: 1.28% Airbnb Rental Income: $3311 Traditional Rental Income: $2564 Airbnb ROI: 1.29% Traditional ROI: 1.28%
4474 Begonia Ct Windermere, FL 4474 Begonia Ct, Windermere, FL 34786 \| Single Family Residential	5 beds \| 4 baths \| 4,380 sq.ft.	$1,270,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 1.19% Airbnb Rental Income: $5841 Traditional Rental Income: $3872 Airbnb ROI: 1.87% Traditional ROI: 1.19%
13842 ORANGE CREST DRIVE Windermere, FL PRICED UNDER APPRAISED VALUE! Nestled behind the gated enclave of Eden Isle in Summerport,...	5 beds \| 3 baths \| 2,620 sq.ft.	$749,888	Airbnb cash on cash: 4.11% Traditional cash on cash: 2.26% Airbnb Rental Income: $5841 Traditional Rental Income: $3383 Airbnb ROI: 4.11% Traditional ROI: 2.26%
13633 ANCILLA BOULEVARD Windermere, FL Under contract-accepting backup offers. Wake up to serene pond views in this beautifully u...	5 beds \| 4 baths \| 3,588 sq.ft.	$849,000	Airbnb cash on cash: 3.92% Traditional cash on cash: 3.45% Airbnb Rental Income: $5841 Traditional Rental Income: $4304 Airbnb ROI: 3.92% Traditional ROI: 3.45%

Vacation Rentals in Windermere

There are 54 vacation rental properties available for sale in the city of Windermere . The median list price of Airbnb properties available for sale in Windermere is $1,125,000 and the average price per square foot is $287. 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 54 Airbnb properties available for sale in Windermere.

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

In May 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

13118 Sunkiss Loop

Windermere, FL

4 beds | 2 baths | 2,547 sq.ft.

$579,000

Airbnb cash on cash: 2.51%

Traditional cash on cash: 2.14%

Airbnb Rental Income: $3311

Traditional Rental Income: $2371

Airbnb ROI: 2.51%

Traditional ROI: 2.14%

9639 WESTOVER CLUB CIRCLE

Windermere, FL

5 beds | 3 baths | 3,248 sq.ft.

$847,500

Airbnb cash on cash: 3.36%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $5841

Traditional Rental Income: $4187

Airbnb ROI: 3.36%

Traditional ROI: 2.73%

12533 CRAGSIDE LANE

Windermere, FL

4 beds | 2 baths | 2,151 sq.ft.

$575,000

Airbnb cash on cash: 1.98%

Traditional cash on cash: 1.45%

Airbnb Rental Income: $3311

Traditional Rental Income: $2287

Airbnb ROI: 1.98%

Traditional ROI: 1.45%

12936 DROXFORD ROAD

Windermere, FL

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

$629,000

Airbnb cash on cash: 5.09%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $5841

Traditional Rental Income: $3631

Airbnb ROI: 5.09%

Traditional ROI: 3.31%

14348 CREST PALM AVENUE

Windermere, FL

4 beds | 4 baths | 3,721 sq.ft.

$1,109,990

Airbnb cash on cash: 1.09%

Traditional cash on cash: -0.57%

Airbnb Rental Income: $3311

Traditional Rental Income: $857

Airbnb ROI: 1.09%

Traditional ROI: -0.57%

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%

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%