31

Windermere, FL Houses for Rent with Garage

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  • /32

    $5,500 Per Month

    • 6 Beds
    • 4.5 Baths
    • 4,522 Sq Ft
    • House for Rent

    17538 Black Rail St, Windermere, FL 34786

    Welcome to this beautiful 6-bedroom, 5-bathroom home in the desirable Windermere area. Designed with high ceilings and an open, spacious layout, this home is filled with natural light and offers plenty of room for both relaxing and entertaining. Whether you're gathering with family or enjoying a quiet evening, you'll love the comfort, elegance, and generous living spaces this exceptional home has

    Agent Photo

    Elaine Garcia

    GARCIA REALTY GROUP

    17538 Black Rail St, Windermere, FL 34786
  • /45

    $4,980 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,136 Sq Ft
    • House for Rent

    7023 Kiwano Way, Windermere, FL 34786

    Welcome to this beautiful, spacious two-story home located in the highly sought-after Sanctuary at Lakes of Windermere. This nearly new residence offers 5 bedrooms, 4.5 bathrooms, a private home office, an upstairs bonus room, and a thoughtfully designed floor plan that perfectly blends luxury, comfort, and functionality. Elegant French doors open to a dedicated home office, providing the ideal

    Agent Photo

    Wendy Fischer

    PREMIER SOTHEBYS INT'L REALTY

    7023 Kiwano Way, 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
  • /58

    $3,900 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,696 Sq Ft
    • House for Rent

    13544 Riggs Way, Windermere, FL 34786

    Welcome to this beautifully updated home in the highly desirable Enclave at Berkshire Park in Windermere. Situated on an oversized corner lot of approximately .25 acres, this spacious residence offers the perfect combination of comfort, functionality, and curb appeal. Recently refreshed with brand-new interior paint and new carpet throughout, the home also features a newer roof and a spacious

    Evan Caulfield STOCKWORTH REALTY GROUP

    13544 Riggs Way, Windermere, FL 34786
  • /47

    $4,000 Per Month

    • 5 Beds
    • 3.5 Baths
    • 3,472 Sq Ft
    • House for Rent

    13272 Penshurst Ln, Windermere, FL 34786

    5 bedroom, 3 bath home nestled in the community of Windermere Sound. Located near schools, parks, shopping and more, this home is waiting for you! A Large house like this, is sure not to last long.

    Donny Hang Fung BLUEHOUSE REALTY GROUP LLC

    13272 Penshurst Ln, Windermere, FL 34786
  • /20

    $3,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,139 Sq Ft
    • House for Rent

    6526 Golden Dewdrop Trail, Windermere, FL 34786

    Beautiful rental home in the desirable **Windermere Landing** community! This freshly painted 2-story home offers approximately **2,139 sq. ft.**, featuring **3 bedrooms, 2.5 bathrooms, and a 2-car garage**. The home has a bright **open-concept layout**, spacious living and dining areas, and a functional kitchen with **granite countertops** and plenty of cabinet space. Bathrooms also feature

    Sergio Duarte FLORIDA LEGACY REALTY LLC

    6526 Golden Dewdrop Trail, Windermere, FL 34786
  • /44

    $3,200 Per Month

    • 4 Beds
    • 2 Baths
    • 2,300 Sq Ft
    • House for Rent

    12947 Runswick Ave, Windermere, FL 34786

    MOVE-IN READY! Beautiful and spacious 4-bedroom, 2-bath home located in the highly desirable Lakes of Windermere community. Surrounded by mature landscaping, scenic lakes, walking trails, and top-rated schools, this home even offers the opportunity to enjoy Disney fireworks just steps from your front door. This well-designed single-story home features luxury vinyl plank and tile flooring

    Cui Li RATIO REAL ESTATE, LLC

    12947 Runswick Ave, Windermere, FL 34786
  • /24

    $3,080 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,970 Sq Ft
    • House for Rent

    12784 Garridan Ave, Windermere, FL 34786

    Stunning Beautiful Upgraded home in the desirable Wickham Park community in heart of Windermere. NO carpet. Perfect location. Top rated schools. Rent includes hoa fee and lawncare. Well-maintained 4 bedroom & 2.5 bath & 1 loft/retreat upstairs & 2 car garage on front. Newer painting. Sizable back yard with extended pave. Open floor plan with lots of upgrades. Great natural light in the whole

    Jacky Liu YORK MILLS REALTY LLC

    12784 Garridan Ave, 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
  • /90

    $5,500 Per Month

    • 6 Beds
    • 4 Baths
    • 4,176 Sq Ft
    • House for Rent

    8278 Procida Isle Ln, Windermere, FL 34786

    Stunning upgraded house in Windermere Isle in Gas community, Fully Fenced, NO Carpet in the house. Rent includes full lawn services and spectrum cable and internet service, save a lot bill. Two downstairs bedrooms are perfect for a guest bedroom and a home office. Tankless water heater. Beautiful engineer wood flooring and Ceiling fan with remote control in all rooms. Popular Designer paint,

    Li Xue AGENT GROUP REALTY

    8278 Procida Isle Ln, Windermere, FL 34786
  • /33

    $3,100 Per Month

    • 4 Beds
    • 3 Baths
    • 2,190 Sq Ft
    • House for Rent

    8625 Greenbank Blvd, Windermere, FL 34786

    Single family home with 4 bedrooms and 3 full bathrooms in desirable Lakes of Windermere Peachtree subdivision. This is quaint community convenient to Disney attractions for work or play and is gated and zoned for Windermere High School. Available just in time for the new school year. Located on a scenic pond w conservation area view, with no rear neighbors and uninhibited views of the

    Charles Woolley BHHS FLORIDA REALTY

    8625 Greenbank Blvd, Windermere, FL 34786
  • /43

    $4,750 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,144 Sq Ft
    • House for Rent

    8764 Powder Ridge Trail, Windermere, FL 34786

    LOCATION!! LOCATION!!! This stunning house has a large kitchen with a large central island, with quartz and also has a back splash, and a large pantry room, and a casual dining room. The first floor is entirely super charming and elegant porcelain title. The outside has a balcony and also space to have your party outdoors. There are two more rooms with a large space. The master suite on the

    Gilson Rodrigues KARDOSH REALTY

    8764 Powder Ridge Trail, Windermere, FL 34786
  • /16

    $3,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,903 Sq Ft
    • House for Rent

    5007 River Gem Ave, Windermere, FL 34786

    Welcome to the perfect rental home in the desirable community of Summerport! This home has it all as it sits on a corner lot, has both a front porch and screened-in back porch, fully fenced in lush backyard (lawn care included!) with paver patio and much more! Inside you're greeted by what could be a formal living room or dining room space and from there enter the fully loaded kitchen with LG

    Lukasz Sokolowski, PA HOST MANAGEMENT GROUP LLC

    5007 River Gem Ave, 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
  • /42

    $14,000 Per Month

    • 7 Beds
    • 5.5 Baths
    • 5,221 Sq Ft
    • House for Rent

    6219 Tiroco Way, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Welcome to luxury living in the guarded, gated community of Waterstone in Windermere, Florida. This exceptional residence at 6219 Tiroco Way blends elegance, comfort, and modern efficiency, featuring solar power and an impressive floor plan designed for both everyday living and entertaining.The home offers 7 bedrooms, 51⁄2 bathrooms, a media

    Ryan Solberg MAXLIFE REALTY LLC

    6219 Tiroco Way, Windermere, FL 34786
  • /17

    $3,850 Per Month

    • 5 Beds
    • 3 Baths
    • 2,983 Sq Ft
    • House for Rent

    6728 Bridgewater Village Rd, Windermere, FL 34786

    Beautiful 5 bedroom 3 bath home located in the desirable Vineyards community. This spacious home features an open floor plan, gourmet kitchen, walk in closets, ceramic tile, laminate, and carpet throughout. The home is nestled on a conservation lot with a screen enclosed patio, which is great for entertaining. The community amenities include pool, and playground. Conveniently located near

    Angela Magac THE PROPERTY STOP LLC

    6728 Bridgewater Village Rd, 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
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    $3,950 Per Month

    • 5 Beds
    • 4 Baths
    • 2,800 Sq Ft
    • House for Rent

    9088 Outlook Rock Trail, Windermere, FL 34786

    Welcome home to this beautifully updated 5-bedroom, 4-bath residence in the highly sought-after Windermere Trails community. Featuring newly installed flooring, this spacious home offers the perfect blend of comfort, style, and functionality. With two private en-suite bedrooms, an open-concept living area, and a large paved patio, there's plenty of space for everyday living, entertaining, or

    Maria Serrano Whitehead EPIQUE REALTY INC.

    9088 Outlook Rock Trail, Windermere, FL 34786
  • /16

    $2,850 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,306 Sq Ft
    • House for Rent

    13231 Overstreet Rd, Windermere, FL 34786

    Vacant! Great Location! Great House!! Must See!!! Move into this home inside the lovely Berkshire Park community in the very desirable town of Windermere. This house is full of upgrades and is an Energy Star certified home. Downstairs has tiled floors, and a private study room. It oversees the front porch. Kitchen has all appliances and granite countertop. It opens to the Great Room and provides

    Daniel Zheng CINO INTERNATIONAL INC

    13231 Overstreet Rd, Windermere, FL 34786
  • /100

    $15,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 5,273 Sq Ft
    • House for Rent

    10577 Down Lakeview Cir, Windermere, FL 34786

    Lease or Lease Purchase available! Experience true lakefront living on the famed Butler Chain of Lakes in this exceptional custom home offering 137 feet of pristine shoreline on nearly one acre of high, dry land. Enjoy sweeping panoramic water views, refreshing lake breezes, and even nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and enter through an impressive

    Simon Simaan THE SIMON SIMAAN GROUP

    10577 Down Lakeview Cir, Windermere, FL 34786
  • /19

    $3,195 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,925 Sq Ft
    • House for Rent

    11316 Rapallo Ln, Windermere, FL 34786

    Beautiful 3-bedroom, 2-bathroom home with a bonus office/flex room in a highly desirable Windermere community. This spacious home features separate living, dining, and family rooms, along with a large primary suite and a luxurious bathroom with a Jacuzzi tub. Enjoy relaxing on the screened patio, perfect for outdoor living year-round. Conveniently located near shopping, restaurants, grocery

    Wade Darius CITY CAPITAL GROUP INC

    11316 Rapallo Ln, Windermere, FL 34786
  • /18

    $2,795 Per Month

    • 3 Beds
    • 2 Baths
    • 1,868 Sq Ft
    • House for Rent

    7730 Brofield Ave, Windermere, FL 34786

    GREAT HOUSE!! GREAT LOCATION !! MUST SEE !!! NEW CARPET! With 3 bed plus Bonus Room, 2 full Bath Windermere Home Awaits You! High Ceilings, 42' wood Kitchen Cabinets, Granite Countertops with Stainless Appliances, Double Paneled Windows will make you want to live there! Spacious Master Retreat looking on Wooded View, Large Walk in Closet, Master bath with Dual Sink, Garden Tub, separated shower,

    Daniel Zheng CINO INTERNATIONAL INC

    7730 Brofield Ave, 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
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    $12,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,737 Sq Ft
    • House for Rent

    10355 Trout Rd, Orlando, FL 32836

    Exceptional single-story lakefront residence on 1.57 acres of beautifully landscaped, mature grounds offering privacy, exclusivity, and breathtaking water views. This home features custom finishes throughout, including wood beam ceilings, personalized flooring, and seamless indoor-outdoor living with expansive glass doors connecting the living, dining, and kitchen areas. The chef’s kitchen

    Any Alves WRA BUSINESS & REAL ESTATE

    10355 Trout Rd, Orlando, FL 32836
  • /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
  • /14

    $2,975 Per Month

    • 3 Beds
    • 2 Baths
    • 2,190 Sq Ft
    • House for Rent

    8526 Greenbank Blvd, Windermere, FL 34786

    Prepare to fall in love with this home that perfectly blends elegance, comfort, and convenience. Featuring 3 spacious bedrooms, 2 beautifully designed bathrooms, and a bonus room, this property is ideal for families, professionals, or anyone seeking a serene retreat. The formal living and dining rooms provide an inviting space for entertaining, while the great room offers a cozy yet open area for

    Johany Utrera AVID REALTY LLC

    8526 Greenbank Blvd, 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
  • /13

    $2,850 Per Month

    • 3 Beds
    • 2 Baths
    • 1,492 Sq Ft
    • House for Rent

    9142 Sabal Palm Cir, Windermere, FL 34786

    Beautiful 3-bedroom, 2-bath pool home featuring an open floor plan, updated kitchen with stainless steel appliances, tile flooring throughout, a split-bedroom layout, 2-car garage, and a fully fenced backyard with a screened-in pool. Ideally located just minutes from Walt Disney World, Winter Garden Village, Restaurant Row, major highways including SR-429 and Florida’s Turnpike, and an easy drive

    Justin V LaManna HOMEVEST REALTY

    9142 Sabal Palm Cir, Windermere, FL 34786
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    $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
  • /46

    $5,750 Per Month

    • 5 Beds
    • 4 Baths
    • 3,648 Sq Ft
    • House for Rent

    8414 Vivaro Isle Way, Windermere, FL 34786

    Welcome home to your Windermere Isle Mediterranean estate. From the minute you arrive at this move in ready, model like home, you are greeted by a cozy hand cut stone façade & barrel tile roof reminiscent of rich Tuscan architecture. The brick paver driveway leads you to the inviting front porch & through the leaded glass front door to an open floor plan featuring your formal living & dining

    T.J. ODonnell CHARLES RUTENBERG REALTY ORLANDO

    8414 Vivaro Isle Way, Windermere, FL 34786

Rental Home Trends

Number of Houses for Rent
31
Median Single Family Home Rent
$5,000
Median 3 Bedroom Single Family Home Rent
$3,200
Median 4 Bedroom Single Family Home Rent
$5,500
Median 5 Bedroom Single Family Home Rent
$5,800
How to Rent a Home