9

Windermere, FL Homes for Rent in a Gated Community

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  • /26

    $5,490 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,596 Sq Ft
    • House for Rent

    10914 Ledgement Ln, Windermere, FL 34786

    Stunning 4BR/3 full + 2 half bath rental in a gated Windermere community! Enjoy all-tile flooring throughout and your own private in-ground pool. Spacious, low-maintenance, and move-in ready — close to top schools, shopping, and dining. Schedule a showing today!

    Agent Photo

    Rohini Bandaru

    LA ROSA REALTY KISSIMMEE

    10914 Ledgement Ln, Windermere, FL 34786
  • /23

    $9,500 Per Month

    • 5 Beds
    • 7 Baths
    • 5,205 Sq Ft
    • House for Rent

    11406 Waterstone Loop Dr, Windermere, FL 34786

    Welcome to Waterstone Windermere, with tranquil living and charm, this area boasts connecting lakes, ideal for boating and walking. this property consist of 5 bedrooms, 5 full bathrooms and 2 half baths. it’s 10-15 mins drive from Disney many restaurants and bars, Reputable schools and many other features.

    Kimroy Mussington WEICHERT REALTORS HALLMARK PRO

    11406 Waterstone Loop Dr, Windermere, FL 34786
  • /22

    $15,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,836 Sq Ft
    • House for Rent

    6119 Payne Stewart Dr, Windermere, FL 34786

    Among the shores of beautiful Lake Chase within the gates of Isleworth Golf & Country Club, this modern golf villa offers a prime lakefront location in proximity to the Clubhouse. The interior boasts 2,836 square feet of living space, with an open floor plan set against a backdrop of picturesque water views. This completely renovated single-story floor plan, includes built-in bar and dining area,

    Michelle Corbin ISLEWORTH REALTY LLC

    6119 Payne Stewart Dr, Windermere, FL 34786
  • /100

    $5,500 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,549 Sq Ft
    • House for Rent

    9247 Legado Dr, Windermere, FL 34786

    FULLY FURNISHED HOME FOR RENT IN WINDERMERE!Experience comfort, convenience, and the best of the Florida lifestyle in this beautiful 4-bedroom home, offered for rent 100% fully furnished and move-in ready.Ideally located in one of Windermere’s most desirable areas, just minutes from Walt Disney World, this home combines an exceptional location with privacy, space, and beautiful

    Silvia Cervi ONLI REALTY GROUP LLC

    9247 Legado Dr, Windermere, FL 34786
  • /30

    $7,500 Per Month

    • 4 Beds
    • 3 Baths
    • 2,562 Sq Ft
    • House for Rent

    8411 Woburn Ct, Windermere, FL 34786

    Welcome to this 4-bedroom, 3-bathroom home located on a quiet cul-de-sac in the guard-gated community of Keene's Pointe. Backing to the Tibet-Butler Preserve, this property offers peaceful conservation views and added privacy.Inside, you'll find a bright, open floor plan with plenty of natural light and tasteful updates throughout. The remodeled kitchen features modern cabinetry, granite

    Jessica Dessire Cueva PA CHARLES RUTENBERG REALTY ORLANDO

    8411 Woburn Ct, Windermere, FL 34786
  • /64

    $29,000 Per Month

    • 7 Beds
    • 7 Baths
    • 8,000 Sq Ft
    • House for Rent

    9725 Chestnut Ridge Dr, Windermere, FL 34786

    A rare opportunity to lease a beautifully renovated residence within Isleworth, offering exceptional space, privacy, comfort, and an elevated Central Florida lifestyle.Newly renovated and exceptionally private, this sophisticated Isleworth residence offers approximately 8,000 square feet of beautifully designed living space, combining refined luxury with the comfort and functionality of

    Dianna Desboyaux DOUGLAS ELLIMAN

    9725 Chestnut Ridge Dr, Windermere, FL 34786
  • /29

    $7,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,578 Sq Ft
    • House for Rent

    8351 Bowden Way, Windermere, FL 34786

    Virtually Staged. Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled 4-bedroom, 3-bathroom Windermere residence offers an exceptional blend of timeless architecture, sophisticated finishes, and effortless Florida living. From the moment you enter, the light-filled interior welcomes you with soaring coffered ceilings, custom-laid wood-look tile

    John Goggin STOCKWORTH REALTY GROUP

    8351 Bowden Way, Windermere, FL 34786
  • /25

    $3,500 Per Month

    • 5 Beds
    • 4.5 Baths
    • 2,874 Sq Ft
    • House for Rent

    1125 Lascala Dr, Windermere, FL 34786

    Mediterranean style property with five bedrooms, four and a half bathrooms on two floors in gated community. New flooring. One of the bedrooms is on the first floor next to a full bathroom, making it ideal to function as an office or guest suite. The remaining bedrooms are on the second floor with the master bedroom has crown molding and a huge walk-in closet. Fully equipped kitchen with granite

    Charles Woolley BHHS FLORIDA REALTY

    1125 Lascala Dr, Windermere, FL 34786

Rental Home Trends

Number of Homes for Rent
9
Median Rent
$5,995
Median Single Family Home Rent
$5,000
Median Townhouse Rent
$2,575
Median Condo Rent
$2,100
How to Rent a Home