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
8180 Boat Hook Loop #109 Windermere, FL Invest in your future, TODAY! Have you been looking for that perfect Florida condo to pur...	2 beds \| 2 baths \| 1,161 sq.ft.	$299,500	Airbnb cash on cash: 9.71% Traditional cash on cash: 1.8% Airbnb Rental Income: $4898 Traditional Rental Income: $1663 Airbnb ROI: 9.71% Traditional ROI: 1.8%
13019 LANGSTAFF DRIVE Windermere, FL Under contract-accepting backup offers. Tucked away in the peaceful Lake Reams Townhome co...	2 beds \| 3 baths \| 1,375 sq.ft.	$360,000	Airbnb cash on cash: 8.13% Traditional cash on cash: 3.02% Airbnb Rental Income: $4898 Traditional Rental Income: $2167 Airbnb ROI: 8.13% Traditional ROI: 3.02%
811 Main St Windermere, FL Exclusive Rare Opportunity to own this expansivev100'x160' double lot in downtown Winderme...	2 beds \| 1 baths \| 1,398 sq.ft.	$649,999	Airbnb cash on cash: 3.83% Traditional cash on cash: 0.75% Airbnb Rental Income: $4898 Traditional Rental Income: $2026 Airbnb ROI: 3.83% Traditional ROI: 0.75%
6390 SOUTHBRIDGE STREET Windermere, FL One or more photo(s) has been virtually staged. Seller may consider buyer concessions if m...	4 beds \| 3 baths \| 1,632 sq.ft.	$395,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 2.61% Airbnb Rental Income: $3311 Traditional Rental Income: $2269 Airbnb ROI: 3.42% Traditional ROI: 2.61%
12633 HADDON DRIVE Windermere, FL Under contract-accepting backup offers. Sitting on a premium corner lot with mature landsc...	5 beds \| 4 baths \| 3,000 sq.ft.	$650,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 4.18% Airbnb Rental Income: $5841 Traditional Rental Income: $4012 Airbnb ROI: 5.28% Traditional ROI: 4.18%
12533 CRAGSIDE LANE Windermere, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	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%
8355 TORCELLO ISLE DRIVE Windermere, FL Virtually Staged. *Seller offers $20,000 credit to buyer at closing towards closing costs ...	5 beds \| 4 baths \| 4,202 sq.ft.	$950,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 1.68% Airbnb Rental Income: $5841 Traditional Rental Income: $3632 Airbnb ROI: 2.86% Traditional ROI: 1.68%
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.	$650,000	Airbnb cash on cash: 5.07% Traditional cash on cash: 3.22% Airbnb Rental Income: $5841 Traditional Rental Income: $3556 Airbnb ROI: 5.07% Traditional ROI: 3.22%
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%
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%
13145 ZORI LANE Windermere, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Mo...	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%
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%
1925 BREEZY HILL DRIVE WINDERMERE FLORIDA 34786 Windermere, FL Under contract-accepting backup offers. Now offered at an improved price, this stunning 5-...	5 beds \| 3 baths \| 3,063 sq.ft.	$862,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 1.53% Airbnb Rental Income: $5841 Traditional Rental Income: $2865 Airbnb ROI: 3.79% Traditional ROI: 1.53%
2068 Roberts Point Dr Windermere, FL 2068 Roberts Point Dr, Windermere, FL 34786 \| Single Family Residential	5 beds \| 4 baths \| 4,876 sq.ft.	$2,250,000	Airbnb cash on cash: 0.14% Traditional cash on cash: -0.25% Airbnb Rental Income: $5841 Traditional Rental Income: $3862 Airbnb ROI: 0.14% Traditional ROI: -0.25%
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%
4474 Begonia Ct Windermere, FL 4474 Begonia Ct, Windermere, FL 34786 \| Single Family Residential	5 beds \| 4 baths \| 4,380 sq.ft.	$1,170,000	Airbnb cash on cash: 2.19% Traditional cash on cash: 1.45% Airbnb Rental Income: $5841 Traditional Rental Income: $3872 Airbnb ROI: 2.19% Traditional ROI: 1.45%
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.	$714,999	Airbnb cash on cash: 4.36% Traditional cash on cash: 2.41% Airbnb Rental Income: $5841 Traditional Rental Income: $3383 Airbnb ROI: 4.36% Traditional ROI: 2.41%
7174 BEEK STREET Windermere, FL Welcome to this solid built 1-story 5 bedroom split plan, 3 full baths home with 2464 squa...	5 beds \| 3 baths \| 2,464 sq.ft.	$725,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 2.41% Airbnb Rental Income: $5841 Traditional Rental Income: $3044 Airbnb ROI: 4.82% Traditional ROI: 2.41%
9663 Gotha Rd Windermere, FL 9663 Gotha Rd, Windermere, FL 34786 \| Single Family Residential	5 beds \| 3 baths \| 3,731 sq.ft.	$1,299,900	Airbnb cash on cash: 1.91% Traditional cash on cash: 0.44% Airbnb Rental Income: $5841 Traditional Rental Income: $2905 Airbnb ROI: 1.91% Traditional ROI: 0.44%
11617 Camden Park Dr Windermere, FL 11617 Camden Park Dr, Windermere, FL 34786 \| Single Family Residential	6 beds \| 4 baths \| 3,463 sq.ft.	$1,375,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 0.47% Airbnb Rental Income: $5841 Traditional Rental Income: $3421 Airbnb ROI: 1.46% Traditional ROI: 0.47%
2230 Ridgewind Way Windermere, FL 2230 Ridgewind Way, Windermere, FL 34786 \| Single Family Residential	5 beds \| 4 baths \| 3,064 sq.ft.	$1,259,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 0.86% Airbnb Rental Income: $5841 Traditional Rental Income: $3544 Airbnb ROI: 1.83% Traditional ROI: 0.86%
11326 Ledgement Ln Windermere, FL 11326 Ledgement Ln, Windermere, FL 34786 \| Single Family Residential	5 beds \| 3 baths \| 3,182 sq.ft.	$899,999	Airbnb cash on cash: 3.36% Traditional cash on cash: 1.07% Airbnb Rental Income: $5841 Traditional Rental Income: $2754 Airbnb ROI: 3.36% Traditional ROI: 1.07%
9527 Queensbury Ct Windermere, FL 9527 Queensbury Ct, Windermere, FL 34786 \| Single Family Residential	5 beds \| 4 baths \| 5,378 sq.ft.	$1,499,900	Airbnb cash on cash: 1.33% Traditional cash on cash: 0.75% Airbnb Rental Income: $5841 Traditional Rental Income: $3876 Airbnb ROI: 1.33% Traditional ROI: 0.75%
12555 CRUXBURY DRIVE Windermere, FL Under contract-accepting backup offers. **This house comes with a REDUCED RATE through the...	2 beds \| 3 baths \| 1,211 sq.ft.	$350,000	Airbnb cash on cash: 8.63% Traditional cash on cash: 3.15% Airbnb Rental Income: $4898 Traditional Rental Income: $2093 Airbnb ROI: 8.63% Traditional ROI: 3.15%
13450 Sunkiss Loop Windermere, FL 13450 Sunkiss Loop, Windermere, FL 34786 \| Single Family Residential	5 beds \| 2 baths \| 2,272 sq.ft.	$574,900	Airbnb cash on cash: 6.39% Traditional cash on cash: 1.73% Airbnb Rental Income: $5841 Traditional Rental Income: $2175 Airbnb ROI: 6.39% Traditional ROI: 1.73%
11768 Hampstead St Windermere, FL 11768 Hampstead St, Windermere, FL 34786 \| Single Family Residential	6 beds \| 4 baths \| 3,900 sq.ft.	$1,318,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 0.68% Airbnb Rental Income: $5841 Traditional Rental Income: $3419 Airbnb ROI: 1.71% Traditional ROI: 0.68%
Ravenstone Plan Windermere, FL Ravenstone Plan, Windermere, FL 34786 \| Single Family Residential	5 beds \| 2 baths \| 3,450 sq.ft.	$1,248,225	Airbnb cash on cash: 2.07% Traditional cash on cash: -0.15% Airbnb Rental Income: $5841 Traditional Rental Income: $2105 Airbnb ROI: 2.07% Traditional ROI: -0.15%
Ashland Plan Windermere, FL Ashland Plan, Windermere, FL 34786 \| Single Family Residential	4 beds \| 2 baths \| 2,448 sq.ft.	$1,139,225	Airbnb cash on cash: 0.45% Traditional cash on cash: 0.09% Airbnb Rental Income: $3311 Traditional Rental Income: $2189 Airbnb ROI: 0.45% Traditional ROI: 0.09%
Edgeworth Plan Windermere, FL Edgeworth Plan, Windermere, FL 34786 \| Single Family Residential	4 beds \| 2 baths \| 2,848 sq.ft.	$1,131,225	Airbnb cash on cash: 0.47% Traditional cash on cash: 0.22% Airbnb Rental Income: $3311 Traditional Rental Income: $2305 Airbnb ROI: 0.47% Traditional ROI: 0.22%
Duval Plan Windermere, FL Duval Plan, Windermere, FL 34786 \| Single Family Residential	5 beds \| 4 baths \| 3,542 sq.ft.	$1,146,990	Airbnb cash on cash: 2.41% Traditional cash on cash: 1.42% Airbnb Rental Income: $5841 Traditional Rental Income: $3618 Airbnb ROI: 2.41% Traditional ROI: 1.42%
Clearpoint Plan Windermere, FL Clearpoint Plan, Windermere, FL 34786 \| Single Family Residential	4 beds \| 2 baths \| 2,466 sq.ft.	$1,129,225	Airbnb cash on cash: 0.47% Traditional cash on cash: 0.11% Airbnb Rental Income: $3311 Traditional Rental Income: $2189 Airbnb ROI: 0.47% Traditional ROI: 0.11%
Kensington Plan Windermere, FL Kensington Plan, Windermere, FL 34786 \| Single Family Residential	2 beds \| 2 baths \| 2,306 sq.ft.	$1,110,225	Airbnb cash on cash: 1.8% Traditional cash on cash: -0.07% Airbnb Rental Income: $4898 Traditional Rental Income: $1970 Airbnb ROI: 1.8% Traditional ROI: -0.07%
Hallwood Plan Windermere, FL Hallwood Plan, Windermere, FL 34786 \| Single Family Residential	2 beds \| 2 baths \| 1,594 sq.ft.	$1,040,225	Airbnb cash on cash: 2.04% Traditional cash on cash: -0.1% Airbnb Rental Income: $4898 Traditional Rental Income: $1823 Airbnb ROI: 2.04% Traditional ROI: -0.1%
Norfolk Plan Windermere, FL Norfolk Plan, Windermere, FL 34786 \| Single Family Residential	4 beds \| 2 baths \| 1,806 sq.ft.	$1,041,225	Airbnb cash on cash: 0.67% Traditional cash on cash: 0.04% Airbnb Rental Income: $3311 Traditional Rental Income: $1960 Airbnb ROI: 0.67% Traditional ROI: 0.04%
Foxhill Plan Windermere, FL Foxhill Plan, Windermere, FL 34786 \| Single Family Residential	4 beds \| 3 baths \| 2,256 sq.ft.	$1,136,225	Airbnb cash on cash: 0.46% Traditional cash on cash: 0.33% Airbnb Rental Income: $3311 Traditional Rental Income: $2436 Airbnb ROI: 0.46% Traditional ROI: 0.33%
Cambria Plan Windermere, FL Cambria Plan, Windermere, FL 34786 \| Single Family Residential	3 beds \| 2 baths \| 1,506 sq.ft.	$979,225	Airbnb cash on cash: 0.18% Traditional cash on cash: 0.04% Airbnb Rental Income: $2597 Traditional Rental Income: $1844 Airbnb ROI: 0.18% Traditional ROI: 0.04%

Vacation Rentals in Windermere

There are 52 vacation rental properties available for sale in the city of Windermere . The median list price of Airbnb properties available for sale in Windermere is $1,611,668 and the average price per square foot is $407. 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 52 Airbnb properties available for sale in Windermere.

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

In June 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

8180 Boat Hook Loop #109

Windermere, FL

2 beds | 2 baths | 1,161 sq.ft.

$299,500

Airbnb cash on cash: 9.71%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $4898

Traditional Rental Income: $1663

Airbnb ROI: 9.71%

Traditional ROI: 1.8%

13019 LANGSTAFF DRIVE

Windermere, FL

2 beds | 3 baths | 1,375 sq.ft.

$360,000

Airbnb cash on cash: 8.13%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $4898

Traditional Rental Income: $2167

Airbnb ROI: 8.13%

Traditional ROI: 3.02%

811 Main St

Windermere, FL

2 beds | 1 baths | 1,398 sq.ft.

$649,999

Airbnb cash on cash: 3.83%

Traditional cash on cash: 0.75%

Airbnb Rental Income: $4898

Traditional Rental Income: $2026

Airbnb ROI: 3.83%

Traditional ROI: 0.75%

6390 SOUTHBRIDGE STREET

Windermere, FL

4 beds | 3 baths | 1,632 sq.ft.

$395,000

Airbnb cash on cash: 3.42%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $3311

Traditional Rental Income: $2269

Airbnb ROI: 3.42%

Traditional ROI: 2.61%

12633 HADDON DRIVE

Windermere, FL

5 beds | 4 baths | 3,000 sq.ft.

$650,000

Airbnb cash on cash: 5.28%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $5841

Traditional Rental Income: $4012

Airbnb ROI: 5.28%

Traditional ROI: 4.18%

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%

8355 TORCELLO ISLE DRIVE

Windermere, FL

5 beds | 4 baths | 4,202 sq.ft.

$950,000

Airbnb cash on cash: 2.86%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $5841

Traditional Rental Income: $3632

Airbnb ROI: 2.86%

Traditional ROI: 1.68%

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%