33

Windermere, FL Houses for Rent with Community Pool

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    $2,950 per month

    • 3 Beds
    • 2.5 Baths
    • 2,234 Sq Ft
    • House for Rent

    6758 Duncaster St, Windermere, FL 34786

    Additional Photography coming soon- Call with any Questions!Explore a roomy residence located at 6758 Duncaster Street. This property boasts 3 bedrooms and 2.5 bathrooms, providing 2,234 square feet of living area. Relish in outdoor leisure on the porch, private patio, and extra patio space. The home includes covered parking and an attached garage that accommodates two vehicles for your

    6758 Duncaster St, Windermere, FL 34786
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    $2,995 per month

    • 4 Beds
    • 2.5 Baths
    • 2,460 Sq Ft
    • House for Rent

    12563 Cragside Ln, Windermere, FL 34786

    Magnificent 4 bedroom 2.5 bathroom home! Move in ready with new lush carpet and fresh 2-tone paint. Beautiful tiled flooring leads you into the spacious kitchen with a long breakfast bar and a spacious island. The kitchen also showcases a custom backsplash, stainless steel appliances, large cabinets, and plenty of counter space. The open floor plan gives this home the perfect space for

    Ya-Lan Chien CINO INTERNATIONAL INC

    12563 Cragside Ln, Windermere, FL 34786
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    $4,688 total monthly price

    • 4 Beds
    • 3 Baths
    • 2,775 Sq Ft
    • House for Rent

    11745 Via Lucerna Cir, Windermere, FL 34786

    Experience luxury living in this beautifully updated 4-bedroom, 2.5-bathroom single-story home located in the prestigious 24/7 gated camera surveillance Belmere community in Windermere.This home has been completely and tastefully remodeled with luxury finishes throughout, transforming it into a modern sanctuary of comfort and elegance. Every detail has been upgraded with intention,

    11745 Via Lucerna Cir, Windermere, FL 34786
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    $7,000 per month

    • 2 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • House for Rent

    812 East Blvd, Windermere, FL 34786

    Ready for immediate occupancy. No HOA. Welcome to Sunrise on The Lake, an exceptional, fully remodeled one-story retreat in the heart of downtown Windermere with stunning views over Lake Bessie. Wake up to breathtaking sunrises and, on clear evenings, enjoy the rare treat of watching rocket launches from Cape Canaveral right your home. Inside, every detail feels elevated, solid wood floors, level

    Simon Simaan THE SIMON SIMAAN GROUP

    812 East Blvd, Windermere, FL 34786
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    $3,200 per month

    • 4 Beds
    • 2.5 Baths
    • 2,781 Sq Ft
    • House for Rent

    6876 Merrick Landing Blvd, Windermere, FL 34786

    Beautiful home located in the highly desirable Vineyards community in Windermere, offering a perfect blend of comfort, convenience, and lifestyle. This well-maintained property features an open and bright floor plan, spacious living areas, and modern finishes throughout. The kitchen is designed for both functionality and entertaining, with ample cabinetry, quality countertops, and a welcoming

    Delia Lugo INTERNATIONAL REAL ESTATE LLC

    6876 Merrick Landing Blvd, Windermere, FL 34786
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    $2,850 per month

    • 3 Beds
    • 2 Baths
    • 2,148 Sq Ft
    • House for Rent

    12863 Holdenbury Ln, Windermere, FL 34786

    Beautiful house for rent in Windermere!! location, location and location. 3 bedrooms, 2 baths, 2 car garages. Beautiful large backyard and screen porch. Great school system. House is in highly desirable Lakes of Windermere! NO CARPETS!! The interior is FRESHLY Painted in alabaster tones, 3 Bedrooms, 2-baths, property is loaded with upgrades and has purposeful utility and functionality. Enter into

    Maria Castro-Aversano LPT REALTY, LLC

    12863 Holdenbury Ln, Windermere, FL 34786
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    $4,500 per month

    • 4 Beds
    • 3 Baths
    • 2,813 Sq Ft
    • House for Rent

    13466 Zori Ln, Windermere, FL 34786

    Location, location!!! Beautifully maintained home in highly desirable community of Providence! A rated schools, shops and restaurants are minutes away for your convenience. 4 bedroom 3 full bath home offers, additional office, formal dining area, private pool with spa and 3 car garage. Home has a NEW roof and AC installed in 2020, new water filter system and a pool heater. Open floor plan with

    Sevara Botirova Patel CHARLES RUTENBERG REALTY ORLANDO

    13466 Zori Ln, Windermere, FL 34786
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    $3,200 per month

    • 4 Beds
    • 2.5 Baths
    • 2,439 Sq Ft
    • House for Rent

    12803 Holdenbury Ln, Windermere, FL 34786

    AVAILABLE MAY 2026! Spacious 4-bedroom, 2.5-bath home in the desirable Lakes of Windermere community. This well-designed floor plan features all bedrooms upstairs, with the main floor offering a large living room, formal dining room, office/reading room, and a convenient half bath for guests. The primary suite includes dual vanities, a garden tub, and two large walk-in closets. The kitchen is

    Silvia Odebrecht ICON REALTY ASSOCIATES INC

    12803 Holdenbury Ln, Windermere, FL 34786
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    $4,850 per month

    • 4 Beds
    • 6 Baths
    • 3,425 Sq Ft
    • House for Rent

    7545 Lake Albert Dr, Windermere, FL 34786

    Coming soon, April 15 Welcome to this beautiful 3,400 sq. ft. lakefront home on Lake Albert! This spacious residence features 4 bedrooms and 3.5 bathrooms, offering plenty of room for comfortable living and entertaining. Enjoy Florida living at its finest with a private pool and serene water views-perfect for relaxing or hosting guests. The home offers generous living spaces, ideal for families

    Allyssa Rodriguez La Rosa Realty Llc

    7545 Lake Albert Dr, Windermere, FL 34786
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    $3,100 per month

    • 4 Beds
    • 2.5 Baths
    • 2,618 Sq Ft
    • House for Rent

    4542 Blue Major Dr, Windermere, FL 34786

    VACANT! Great location! Great Home! Move into this Great home inside the lovely SUMMERPORT/WINDERMERE community. This house is full of upgrades and is an Energy Star certified home. Downstairs it has all tiled floors and new laminate. Kitchen has all full appliances and granite countertops. You can also enjoy Disney fireworks at night. Upstairs there is a large master bedroom, and three bedrooms.

    Daniel Zheng CINO INTERNATIONAL INC

    4542 Blue Major Dr, Windermere, FL 34786
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    $13,500 per month

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

    11051 Coniston Way, Windermere, FL 34786

    This exquisite custom residence in the Reserve at Lake Butler Sound community offers unparalleled luxury and sophistication. Striking wrought-iron arched double entry doors open to a seamless, airy floor plan featuring elegant travertine flooring and captivating views of the pool and lanai area.Elegant wrought-iron chandeliers grace the welcoming foyer and generous dining space. This home is

    Juan Delgado LA ROSA REALTY LLC

    11051 Coniston Way, Windermere, FL 34786
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    $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
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    $4,500 per month

    • 4 Beds
    • 3.5 Baths
    • 3,390 Sq Ft
    • House for Rent

    6615 Helmsley Cir, Windermere, FL 34786

    Beautifully remodeled and impeccably maintained, this spacious 3,390 sq. ft. two-story home offers 5 bedrooms, 3.5 bathrooms, an office, and an attached 2-car garage in the highly desirable community of Preston Square in Windermere. Perfectly situated on a premium lot with no rear neighbors, the home features a charming front porch and covered balcony overlooking the serene, tree-lined

    Angela Gann KELLER WILLIAMS ELITE PARTNERS III REALTY

    6615 Helmsley Cir, Windermere, FL 34786
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    $2,495 per month

    • 3 Beds
    • 2 Baths
    • 1,601 Sq Ft
    • House for Rent

    935 Lascala Dr, Windermere, FL 34786

    Beautiful 3/2 home with two car garage, in a gated community, good schools, tile roof, Wood and tile flooring, high ceiling, ceiling fans, wood cabinetry, build-in desk, gas stove, stainless appliances, ample closet space, Master bedroom with dual vanity, tub, and a very large glass-enclosed walk-in show, walk-in closet, it has privet access to the beautiful back yard. This gated community has

    Ya-Lan Chien CINO INTERNATIONAL INC

    935 Lascala Dr, Windermere, FL 34786
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    $12,800 per month

    • 8 Beds
    • 7.5 Baths
    • 8,203 Sq Ft
    • House for Rent

    13643 Lake Cawood Dr, Windermere, FL 34786

    Text listing agent for appointment

    Wenwen Wang JWJ REALTY LLC

    13643 Lake Cawood Dr, Windermere, FL 34786
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    $3,500 per month

    • 4 Beds
    • 2.5 Baths
    • 3,011 Sq Ft
    • House for Rent

    12761 Bideford Ave, Windermere, FL 34786

    Beautiful 4-bedroom 2.5 bath home located in the desirable Lakes of Windermere community. This two-story corner lot home has everything you can ask for, formal living and dining rooms, kitchen with granite countertops, stainless steel appliances, and a breakfast bar that opens to a large family room, on the first floor you also have a massive master bedroom suite, with a large closet and the

    Paul Moscoso Donoso SHINING OAK REALTY

    12761 Bideford Ave, Windermere, FL 34786
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    $6,995 per month

    • 5 Beds
    • 4 Baths
    • 3,694 Sq Ft
    • House for Rent

    3265 Hidden Lake Dr, Winter Garden, FL 34787

    Rarely Available Lakefront Boater's Dream in Winter Garden/Windermere area at an amazing price! This home sits on a massive 1.5+ acre lot on the waterfront of Lake Roper. The home is a sprawling 3700 SF one story home with extremely high ceilings. The main room is an enormous Great room plan combining the Kitchen, Living Great room, Formal Dining Room and Office flex room ALL overlooking the

    Billy Cannon, Jr BHHS FLORIDA REALTY

    3265 Hidden Lake Dr, Winter Garden, FL 34787
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    $3,500 per month

    • 4 Beds
    • 2.5 Baths
    • 2,981 Sq Ft
    • House for Rent

    12925 Holdenbury Ln, Windermere, FL 34786

    Located in a highly sought-after top-rated school zone, this beautifully designed two-story home offers the perfect blend of space, privacy, and functionality. Featuring four spacious bedrooms and 2.5 bathrooms, the home is thoughtfully laid out to accommodate modern living. The showpiece of the home is the oversized gourmet kitchen, complete with abundant cabinet and counter space and two large

    Jing Yue INTEREALTY SERVICE

    12925 Holdenbury Ln, Windermere, FL 34786
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    $3,000 per month

    • 4 Beds
    • 3 Baths
    • 2,345 Sq Ft
    • House for Rent

    5019 Blue Major Dr, Windermere, FL 34786

    Welcome home to this beautifully maintained property in Windermere’s sought-after Summerport community. Enjoy a chef-inspired kitchen complete with solid countertops, updated stainless steel appliances, and a gas range—perfect for everyday living and entertaining. New interior paint, stylish flooring throughout, and upgraded lighting and bathroom fixtures make this home the perfect rental!

    Alex Sadowski KELLER WILLIAMS REALTY AT THE PARKS

    5019 Blue Major Dr, Windermere, FL 34786
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    $17,500 per month

    • 5 Beds
    • 6.5 Baths
    • 5,639 Sq Ft
    • House for Rent

    801 W 2nd Ave, Windermere, FL 34786

    With an option to purchase, this extraordinary Windermere estate presents a rare opportunity to enjoy refined lakefront living on the Butler Chain of Lakes. Set along one of the area’s most desirable streets, the residence has undergone more than $350,000 in recent luxurious upgrades, including a reimagined kitchen and fireplace, new windows and doors, upgraded landscape lighting, refreshed

    Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

    801 W 2nd Ave, Windermere, FL 34786
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    $5,500 per month

    • 4 Beds
    • 4.5 Baths
    • 3,512 Sq Ft
    • House for Rent

    11560 Claymont Cir, Windermere, FL 34786

    Welcome to this spacious, fully furnished, 4-bedroom, 4.5-bathroom home nestled within a desirable gated golf community of Keene's Pointe. Thoughtfully designed for comfort and functionality, this impressive residence features a first-floor primary suite offering privacy and convenience, complete with a well-appointed ensuite bath. The home boasts generous living areas filled with natural light,

    Rose Sepulveda-Morales WATSON REALTY CORP.

    11560 Claymont Cir, Windermere, FL 34786
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    $9,850 per month

    • 4 Beds
    • 4.5 Baths
    • 4,239 Sq Ft
    • House for Rent

    1115 Estancia Woods Loop, Windermere, FL 34786

    Rare Newer Construction (2017) Windermere Pool Home located in close proximity to Downtown Windermere. This is a 2 Story home with tiled roof and so many upgrades and amenities. Beautiful Open floorplan with all of the upgrades. Through the large Sliding Glass doors, you flow into a fully covered Lanai and into the stunning brick paved pool area w/ Jacuzzi and the Scenic Landscaped Lot. This is

    Corey Cannon BHHS FLORIDA REALTY

    1115 Estancia Woods Loop, Windermere, FL 34786
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    $3,049 per month

    • 4 Beds
    • 2.5 Baths
    • 2,214 Sq Ft
    • House for Rent

    11507 Charnock Dr, Windermere, FL 34786

    Brand New Windermere 4 Bedroom Home For RentPriced Low, Call Now!, 2 Car Garage, BRAND NEW HOME, Upstairs Bonus Area Too!, Corner Lot, Granite Countertops, 42” Cabinets, Tile Flooring, Carpeted Bedrooms, COMMUNITY Pool, COMMUNITY Clubhouse, COMMUNITY Playground, JUST 30 MINUTES To: Downtown Orlando, CONVENIENT To: 429, JUST MINUTES To: Walt Disney World, CONVENIENT To: Major Roads, Shopping,

    Jay Myers ORLANDO REALTY & PROPERTY MGNT

    11507 Charnock Dr, Windermere, FL 34786
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    $12,000 per month

    • 3 Beds
    • 3 Baths
    • 2,646 Sq Ft
    • House for Rent

    6131 Payne Stewart Dr, Windermere, FL 34786

    Looking for Luxurious home in a prime location? Look no further! Located in the Isleworth Country Club, this stunning single-family home at 6131 Payne Stewart Drive is now available for rent. Situated in a fantastic waterfront location on Lake Chase, which is part of the Butler Chain of Lakes, this home is a short walk away from the world-renowned Isleworth Golf and Country Club. With breath

    Jill Irwin IRWIN REALTY GROUP LLC

    6131 Payne Stewart Dr, Windermere, FL 34786
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    $4,500 per month

    • 5 Beds
    • 4 Baths
    • 3,300 Sq Ft
    • House for Rent

    1351 Glenwick Dr, Windermere, FL 34786

    POOL HOME!!! WITH MOTHER IN LAW SUIT!!! 5 BEDROOMS 4 FULL BATHS!!! MAN-GATED COMMUNITY IN WINDERMERE!!! Stunning Windermere home at 1351 Glenwick Dr! Spacious open floor plan, modern kitchen, and elegant finishes throughout. Perfect for entertaining or relaxing in the private backyard. Close to top schools, shopping, and dining. A must-see blend of luxury, comfort, and location!

    Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

    1351 Glenwick Dr, Windermere, FL 34786
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    $5,500 per month

    • 3 Beds
    • 2 Baths
    • 2,056 Sq Ft
    • House for Rent

    8447 Bowden Way, Windermere, FL 34786

    Welcome to Keenes Point - Windermere, a stunning 3-bedroom, 2-bathroom home located in the desirable Windermere, FL. This property is nestled within a secure gated community, offering an added layer of peace and security. The home boasts a private pool, perfect for cooling off during those hot Florida summers. The private backyard provides ample space for outdoor activities or simply enjoying the

    Julien Silva JOHN SILVA REALTY & ASSOCIATES

    8447 Bowden Way, 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

    One or more photo(s) has been virtually staged. The moment you step inside this 5-bedroom, 4-bath luxury home in the heart of Windermere—a rare opportunity for anyone relocating to the Orlando - is the moment you may change your mind about living anywhere else in Central Florida. This residence offers top-rated schools, tree-lined walking trails with sparkling lake views, a resort-style community

    Maria Serrano Whitehead EPIQUE REALTY, INC.

    9088 Outlook Rock Trail, Windermere, FL 34786
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    $9,999 per month

    • 3 Beds
    • 3 Baths
    • 3,255 Sq Ft
    • House for Rent

    5243 W Lake Butler Rd, Windermere, FL 34786

    Experience Lakefront Luxury Living - where every day feels like a vacation. Prepare to be captivated by this fully renovated three-bedroom, three-bath lakefront home on the highly sought-after Lake Butler. Part of the Butler Chain of Lakes, featuring 13 connected lakes. A true retreat that blends resort-style amenities with refined design. Nestled on pristine waterfront, this property offers

    Steve Simpson 407 PROPERTIES

    5243 W Lake Butler Rd, Windermere, FL 34786
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    $4,475 per month

    • 6 Beds
    • 3.5 Baths
    • 3,764 Sq Ft
    • House for Rent

    14415 Crest Palm Ave, Windermere, FL 34786

    Be the First to Call This Home Yours! Brand New Luxurious 2025! Move-In Ready! Pet Friendly! 2-Car Garage! Smart Home! Stunning 6 Bedrooms, Loft, Bonus Room, Stylish Upgrades! Internet & WiFi Included! Step into luxurious, modern living in this expansive 6-bedroom, 3.5-bath, two-story smart home featuring a bright, open-concept layout that seamlessly connects the gourmet kitchen, family room, and

    Katrina Anarumo RENT A FLORIDA HOME

    14415 Crest Palm Ave, Windermere, FL 34786
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    $17,950 per month

    • 6 Beds
    • 8 Baths
    • 6,881 Sq Ft
    • House for Rent

    3999 Isabella Cir, Windermere, FL 34786

    Exquisite Luxury Retreat in Prime Windermere Location Welcome to 3999 Isabella Cir, an architectural masterpiece nestled within the prestigious community of Casabella at Windermere, FL. This opulent estate is a true embodiment of refined living, offering a harmonious blend of elegant design, impeccable craftsmanship, and unparalleled comfort. Situated on an expansive half acre lot, this

    Lucas DeSouza DELUCA REAL ESTATE SERVICES CORP

    3999 Isabella Cir, Windermere, FL 34786
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    $5,475 per month

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

    307 W 4th Ave, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Available for lease, this refined single-story pool residence is located in the Town of Windermere, just moments from Main Street and the downtown district’s dining, shopping, and community amenities. Positioned on an oversized corner lot beneath mature oak trees, the property offers a private and well-composed setting with thoughtful indoor and

    Rob Gaudreau MAINFRAME REAL ESTATE

    307 W 4th Ave, Windermere, FL 34786
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    $3,200 per month

    • 3 Beds
    • 2 Baths
    • 1,723 Sq Ft
    • House for Rent

    9322 Palm Tree Dr, Windermere, FL 34786

    Live in one of the most sought after locations of Windermere! Welcome to 9322 Palm Tree Drive, located just minutes from Disney, Dr. Phillips, and Restaurant Row without the traffic and chaos. Located in the Silver Woods community off Apopka Vineland Rd, this 3 bedroom, 2 bath pool home is the perfect spot as your new home. This home features an open layout with comfortable living spaces and a

    Jeff Inman FHG REALTY, LLC

    9322 Palm Tree Dr, Windermere, FL 34786
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