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
8168 Boat Hook Loop #724 Windermere, FL Virtually Staged. Imagine coming home to a resort-style community just minutes from Walt D...	3 beds \| 2 baths \| 1,455 sq.ft.	$325,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 1.41% Airbnb Rental Income: $3361 Traditional Rental Income: $1797 Airbnb ROI: 4.08% Traditional ROI: 1.41%
7712 Fordson Ln Windermere, FL This Berkshire Place townhome offers a thoughtfully arranged two-story layout with three b...	3 beds \| 2 baths \| 1,644 sq.ft.	$350,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 2.92% Airbnb Rental Income: $3361 Traditional Rental Income: $2384 Airbnb ROI: 3.61% Traditional ROI: 2.92%
14077 ANCILLA Boulevard Windermere, FL There is something truly special about coming home to Summerport, and this move-in-ready t...	3 beds \| 3 baths \| 1,651 sq.ft.	$399,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 2.94% Airbnb Rental Income: $3361 Traditional Rental Income: $2338 Airbnb ROI: 3.67% Traditional ROI: 2.94%
12718 Windermere Isles Pl Windermere, FL Spectacular residence tucked away on a quiet cul-de-sac in the heart of Windermere. Situat...	5 beds \| 4 baths \| 3,487 sq.ft.	$1,375,000	Airbnb cash on cash: 9.28% Traditional cash on cash: 2.37% Airbnb Rental Income: $17742 Traditional Rental Income: $5349 Airbnb ROI: 9.28% Traditional ROI: 2.37%
7327 Millstone St Windermere, FL Virtually Staged. This former model corner unit townhome (3 bed, 2.5 bath) offers maintena...	3 beds \| 2 baths \| 1,531 sq.ft.	$449,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 2.4% Airbnb Rental Income: $3361 Traditional Rental Income: $2377 Airbnb ROI: 2.96% Traditional ROI: 2.4%
12988 Borland St Windermere, FL Welcome to 12988 Borland Street in sought-after Wickham Park, where comfort, convenience, ...	3 beds \| 2 baths \| 1,460 sq.ft.	$435,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 2.93% Airbnb Rental Income: $3361 Traditional Rental Income: $2427 Airbnb ROI: 3.39% Traditional ROI: 2.93%
14442 Desert Haven St #4305 Windermere, FL Beautiful Two-Story Condo in Gated Windermere Community - Minutes from Disney World Welcom...	3 beds \| 2 baths \| 1,534 sq.ft.	$359,900	Airbnb cash on cash: 3.54% Traditional cash on cash: 3.38% Airbnb Rental Income: $3361 Traditional Rental Income: $2558 Airbnb ROI: 3.54% Traditional ROI: 3.38%
13161 LAKE BUTLER Boulevard Windermere, FL Extraordinary lake front opportunity in Windermere on 1.75 acres! PRIVATE GATES! NO HOA! S...	5 beds \| 5 baths \| 4,500 sq.ft.	$3,200,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 1.52% Airbnb Rental Income: $17742 Traditional Rental Income: $9064 Airbnb ROI: 3.39% Traditional ROI: 1.52%
13420 BONICA Way Windermere, FL Experience the Florida lifestyle in this stunning fully furnished 5-Bed/4-Bath pool home o...	5 beds \| 4 baths \| 4,489 sq.ft.	$1,875,000	Airbnb cash on cash: 6.12% Traditional cash on cash: 1.72% Airbnb Rental Income: $17742 Traditional Rental Income: $6932 Airbnb ROI: 6.12% Traditional ROI: 1.72%
4301 Down Point Ln Windermere, FL Lakefront estate on Lake Down in the Butler Chain of Lakes with over 150 feet of frontage ...	5 beds \| 4 baths \| 7,153 sq.ft.	$2,950,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 0.83% Airbnb Rental Income: $17742 Traditional Rental Income: $6855 Airbnb ROI: 3.66% Traditional ROI: 0.83%
6606 SAWYER SHORES Lane Windermere, FL One or more photo(s) has been virtually staged. Pre-Construction. To be built. One or more...	5 beds \| 4 baths \| 5,516 sq.ft.	$2,500,000	Airbnb cash on cash: 5.11% Traditional cash on cash: 1.74% Airbnb Rental Income: $17742 Traditional Rental Income: $6784 Airbnb ROI: 5.11% Traditional ROI: 1.74%
1316 ESTANCIA WOODS Loop Windermere, FL Elegant and spacious home in the highly sought after Estancia at Windermere community, off...	5 beds \| 7 baths \| 5,448 sq.ft.	$2,170,000	Airbnb cash on cash: 5.98% Traditional cash on cash: 4.33% Airbnb Rental Income: $17742 Traditional Rental Income: $11272 Airbnb ROI: 5.98% Traditional ROI: 4.33%
6857 VALHALLA Way Windermere, FL Under contract-accepting backup offers. Perfection has an address along with comfortable F...	5 beds \| 7 baths \| 7,153 sq.ft.	$3,700,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 0.71% Airbnb Rental Income: $17742 Traditional Rental Income: $9582 Airbnb ROI: 2.18% Traditional ROI: 0.71%
8866 Herencia Aly Windermere, FL Welcome to this beautifully maintained 3-bedroom, 2-bathroom home featuring a spacious lof...	3 beds \| 2 baths \| 1,577 sq.ft.	$415,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 2.94% Airbnb Rental Income: $3361 Traditional Rental Income: $2407 Airbnb ROI: 3.47% Traditional ROI: 2.94%
9527 Queensbury Ct Windermere, FL PRICE IMPROVEMENT!!!! UPDATED PHOTOS! Rare opportunity to purchase in the Windermere's Win...	5 beds \| 4 baths \| 5,378 sq.ft.	$1,375,000	Airbnb cash on cash: 8.47% Traditional cash on cash: 0.37% Airbnb Rental Income: $17742 Traditional Rental Income: $3876 Airbnb ROI: 8.47% Traditional ROI: 0.37%
1118 Estancia Woods Loop Windermere, FL A Masterpiece of Luxury Living in Windermere Welcome to an extraordinary custom estate in ...	5 beds \| 5 baths \| 4,228 sq.ft.	$1,985,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 0.28% Airbnb Rental Income: $17742 Traditional Rental Income: $4937 Airbnb ROI: 5.52% Traditional ROI: 0.28%
1700 Lake Roberts Ct Windermere, FL Welcome to this exceptional luxury residence offering 5 spacious bedrooms, 4 beautifully a...	5 beds \| 4 baths \| 3,929 sq.ft.	$1,350,000	Airbnb cash on cash: 9.59% Traditional cash on cash: 2.09% Airbnb Rental Income: $17742 Traditional Rental Income: $5193 Airbnb ROI: 9.59% Traditional ROI: 2.09%
11027 Hawkshead Ct Windermere, FL Back on market due to buyer non-performance. Exceptional value in Lake Butler Sound! Welco...	5 beds \| 3 baths \| 3,486 sq.ft.	$1,549,000	Airbnb cash on cash: 7.39% Traditional cash on cash: -0.9% Airbnb Rental Income: $17742 Traditional Rental Income: $2520 Airbnb ROI: 7.39% Traditional ROI: -0.9%
7723 Fairgrove Ave Windermere, FL Well maintained, move-in ready 3 bedrooms, 2.5 bathrooms townhouse in the Lake Sawyer Sout...	3 beds \| 2 baths \| 1,680 sq.ft.	$380,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 2.7% Airbnb Rental Income: $3361 Traditional Rental Income: $2386 Airbnb ROI: 3.33% Traditional ROI: 2.7%
9316 Gladys Garden Ct Windermere, FL Virtually Staged. An exceptional new construction offering within The Gardens of Isleworth...	5 beds \| 6 baths \| 5,471 sq.ft.	$6,500,000	Airbnb cash on cash: 0.83% Traditional cash on cash: -0.46% Airbnb Rental Income: $17742 Traditional Rental Income: $6831 Airbnb ROI: 0.83% Traditional ROI: -0.46%
13137 Penshurst Ln Windermere, FL This charming 3/2 home in the heart of Windermere is sure to make you fall in love! The co...	3 beds \| 2 baths \| 1,948 sq.ft.	$550,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 2.51% Airbnb Rental Income: $3361 Traditional Rental Income: $2338 Airbnb ROI: 3.03% Traditional ROI: 2.51%
5579 Somersby Rd Windermere, FL Virtually Staged. This one has it all! Welcome home to this beautifully updated townhome i...	3 beds \| 2 baths \| 1,579 sq.ft.	$375,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 2.53% Airbnb Rental Income: $3361 Traditional Rental Income: $2296 Airbnb ROI: 3.43% Traditional ROI: 2.53%
13160 SUNKISS Loop Windermere, FL Welcome to this beautifully maintained one-story home in the highly desirable Summerport c...	3 beds \| 2 baths \| 1,790 sq.ft.	$675,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 1.96% Airbnb Rental Income: $3361 Traditional Rental Income: $2504 Airbnb ROI: 2.14% Traditional ROI: 1.96%
13231 Roxboro Rd Windermere, FL Virtually Staged. Discover this beautifully maintained 3-bedroom, 2-bath corner-lot home i...	3 beds \| 2 baths \| 1,706 sq.ft.	$579,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 2.24% Airbnb Rental Income: $3361 Traditional Rental Income: $2277 Airbnb ROI: 2.86% Traditional ROI: 2.24%
9904 Brentford Ct Windermere, FL Exceptional Keene's Pointe Pool Home with Rare Multi-Generational Layout with a Pond View!...	5 beds \| 4 baths \| 4,504 sq.ft.	$2,250,000	Airbnb cash on cash: 4.53% Traditional cash on cash: 1.67% Airbnb Rental Income: $17742 Traditional Rental Income: $8483 Airbnb ROI: 4.53% Traditional ROI: 1.67%
9921 Lake Louise Dr Windermere, FL Positioned along the back nine of Isleworth's renowned championship golf course, this exce...	5 beds \| 5 baths \| 6,970 sq.ft.	$6,650,000	Airbnb cash on cash: 0.1% Traditional cash on cash: -0.77% Airbnb Rental Income: $17742 Traditional Rental Income: $9245 Airbnb ROI: 0.1% Traditional ROI: -0.77%
6055 Louise Cove Dr Windermere, FL Stately and elegant lakefront estate showcasing the best of Isleworth West. This grand hom...	5 beds \| 5 baths \| 7,158 sq.ft.	$6,900,000	Airbnb cash on cash: 0.23% Traditional cash on cash: -0.44% Airbnb Rental Income: $17742 Traditional Rental Income: $10315 Airbnb ROI: 0.23% Traditional ROI: -0.44%
3986 Isabella Cir Windermere, FL EXCEPTIONAL LAKEFRONT LUXURY ESTATE IN CASABELLA AT WINDERMERE Discover an extraordinary l...	5 beds \| 5 baths \| 5,342 sq.ft.	$3,599,000	Airbnb cash on cash: 2.62% Traditional cash on cash: 0.81% Airbnb Rental Income: $17742 Traditional Rental Income: $8567 Airbnb ROI: 2.62% Traditional ROI: 0.81%
8641 Brookvale Dr Windermere, FL Beautiful end-unit townhome in Windermere featuring the larger floor plan in the Lake Ream...	3 beds \| 2 baths \| 1,526 sq.ft.	$410,000	Airbnb cash on cash: 4.96% Traditional cash on cash: 4.37% Airbnb Rental Income: $3361 Traditional Rental Income: $2384 Airbnb ROI: 4.96% Traditional ROI: 4.37%

Vacation Rentals in Windermere

There are 77 vacation rental properties available for sale in the city of Windermere . The median list price of Airbnb properties available for sale in Windermere is $1,049,372 and the average price per square foot is $335. The cash on cash return on vacation rentals in Windermere is 2.00%. The average monthly short term rental income in Windermere is $3,361.

Windermere, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 77 Airbnb properties available for sale in Windermere.

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

In September 2026, the average Airbnb occupancy rate in Windermere is 33%.

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

8168 Boat Hook Loop #724

Windermere, FL

3 beds | 2 baths | 1,455 sq.ft.

$325,000

Airbnb cash on cash: 4.08%

Traditional cash on cash: 1.41%

Airbnb Rental Income: $3361

Traditional Rental Income: $1797

Airbnb ROI: 4.08%

Traditional ROI: 1.41%

7712 Fordson Ln

Windermere, FL

3 beds | 2 baths | 1,644 sq.ft.

$350,000

Airbnb cash on cash: 3.61%

Traditional cash on cash: 2.92%

Airbnb Rental Income: $3361

Traditional Rental Income: $2384

Airbnb ROI: 3.61%

Traditional ROI: 2.92%

14077 ANCILLA Boulevard

Windermere, FL

3 beds | 3 baths | 1,651 sq.ft.

$399,000

Airbnb cash on cash: 3.67%

Traditional cash on cash: 2.94%

Airbnb Rental Income: $3361

Traditional Rental Income: $2338

Airbnb ROI: 3.67%

Traditional ROI: 2.94%

12718 Windermere Isles Pl

Windermere, FL

5 beds | 4 baths | 3,487 sq.ft.

$1,375,000

Airbnb cash on cash: 9.28%

Traditional cash on cash: 2.37%

Airbnb Rental Income: $17742

Traditional Rental Income: $5349

Airbnb ROI: 9.28%

Traditional ROI: 2.37%

7327 Millstone St

Windermere, FL

3 beds | 2 baths | 1,531 sq.ft.

$449,000

Airbnb cash on cash: 2.96%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $3361

Traditional Rental Income: $2377

Airbnb ROI: 2.96%

Traditional ROI: 2.4%

12988 Borland St

Windermere, FL

3 beds | 2 baths | 1,460 sq.ft.

$435,000

Airbnb cash on cash: 3.39%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $3361

Traditional Rental Income: $2427

Airbnb ROI: 3.39%

Traditional ROI: 2.93%

14442 Desert Haven St #4305

Windermere, FL

3 beds | 2 baths | 1,534 sq.ft.

$359,900

Airbnb cash on cash: 3.54%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $3361

Traditional Rental Income: $2558

Airbnb ROI: 3.54%

Traditional ROI: 3.38%

13161 LAKE BUTLER Boulevard

Windermere, FL

5 beds | 5 baths | 4,500 sq.ft.

$3,200,000

Airbnb cash on cash: 3.39%

Traditional cash on cash: 1.52%

Airbnb Rental Income: $17742

Traditional Rental Income: $9064

Airbnb ROI: 3.39%