11

Windermere, FL Homes for Rent in a Gated Community

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  • /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
  • /37

    $12,500 Per Month

    • 3 Beds
    • 3 Baths
    • 3,535 Sq Ft
    • House for Rent

    9701 Lake Isleworth Ct, Windermere, FL 34786

    RECENTLY RENOVATED within the gates of Isleworth Golf and Country Club on a lovely cul-de-sac, you will discover this Golf Villa, boasting over 3,500 square feet of space. With 3 bedrooms plus an office, which could easily be used as a 4th bedroom, this charming villa has a spacious master suite with a garden view step-down shower, a notable kitchen with breakfast nook, formal dining room, and

    Michelle Corbin ISLEWORTH REALTY LLC

    9701 Lake Isleworth Ct, Windermere, FL 34786
  • /32

    $6,990 Per Month

    • 4 Beds
    • 3 Baths
    • 2,817 Sq Ft
    • House for Rent

    11820 Waterstone Loop Dr, Windermere, FL 34786

    Welcome to this beautifully maintained single-story home located in the highly sought-after Waterstone community in Windermere. Offering 4 bedrooms and 3 full bathrooms, this residence combines comfort, functionality, and elegant living in a prime Central Florida location.The spacious floor plan features a large living room with a cozy fireplace, a centrally located dining area, and an

    Charles Kohlinger BHHS FLORIDA REALTY

    11820 Waterstone Loop Dr, Windermere, FL 34786
  • /58

    $13,000 Per Month

    • 5 Beds
    • 5.5 Baths
    • 5,498 Sq Ft
    • House for Rent

    11051 Coniston Way, Windermere, FL 34786

    A rare opportunity to lease a furnished executive estate in the prestigious guard-gated community of Lake Butler Sound. Perfect for corporate relocations, executive families, or those building, renovating, or transitioning between homes, this turnkey residence offers flexible lease terms in one of Windermere's most sought-after communities. Thoughtfully designed for comfortable everyday living

    Julian Correa THE SIMON SIMAAN GROUP

    11051 Coniston Way, 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
  • /55

    $7,000 Per Month

    • 4 Beds
    • 6 Baths
    • 3,786 Sq Ft
    • House for Rent

    8463 Tibet Butler Dr, Windermere, FL 34786

    Keene's Pointe gated/24-hour attended home featuring 4 bedrooms, 4 full/2 half baths, formal living and dining rooms, loft, and bonus/game room. This spacious home has low maintenance laminate flooring throughout. The master suite is on the first floor with access to the lanai, walk-in closet with customized shelving and bath with tub, shower and two vanities. The kitchen and family room are

    Teresa Stewart SOUTHERN REALTY GROUP LLC

    8463 Tibet Butler Dr, Windermere, FL 34786
  • /33

    $6,150 Per Month

    • 6 Beds
    • 4.5 Baths
    • 4,028 Sq Ft
    • House for Rent

    11538 Delwick Dr, Windermere, FL 34786

    Available on AUGUST 1, 2026. Move in and enjoy from day one. Inside exclusive 24-hour guard-gated Reserve at Belmere — one of Windermere's most desirable communities. Thr Estate offers over 4,000 square feet of living space. 6 bedrooms, 4.5 bathrooms, a dedicated home office with French doors, and a generous bonus room that's perfect as a playroom, home theater, or game room, there's space here

    Yana Ogor CHARLES RUTENBERG REALTY ORLANDO

    11538 Delwick Dr, Windermere, FL 34786
  • /44

    $4,000 Per Month

    • 3 Beds
    • 2 Baths
    • 2,077 Sq Ft
    • House for Rent

    1363 Glenwick Dr, Windermere, FL 34786

    A $35 Resident Benefit Package charge will be added to rent. - Gorgeous 3-bedroom, 2-bath home in Windermere located inside the gated and guarded Reserve at Belmere. This residence features a two-car garage, paved driveway and entry, and a manicured lawn. Enjoy a screen-enclosed private pool and easy access to on-site recreational amenities including a community fitness center, volleyball court,

    Francisco Nieves-Taranto CT HOMES REALTY CORPORATION

    1363 Glenwick Dr, Windermere, FL 34786
  • /30

    $7,850 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
  • /30

    $2,600 Per Month

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • House for Rent

    8838 Abbotsbury Dr, Windermere, FL 34786

    Sited in the Preserve at Lakes of Windermere, a gated community, this three-bedroom, two-bathroom home sits in a highly desirable location. This single-story home offers a bright, open-concept floor plan with a formal living room, dinning room, family room, kitchen and breakfast nook. The private master bathroom offers a garden tub, separate glassed shower, dual sinks and large walk-in closet.

    Maria Quintero STOCKWORTH REALTY GROUP

    8838 Abbotsbury Dr, Windermere, FL 34786
  • /29

    $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
11
Median Rent
$2,900
Median Single Family Home Rent
$3,500
Median Townhouse Rent
$2,550
Median Condo Rent
$2,125
How to Rent a Home