Windermere, FL Homes for Rent with Community Pool

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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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  $2,750 per month

  • 3 Beds
  • 2.5 Baths
  • 1,748 Sq Ft
  • Townhouse for Rent

  12813 Gracehill Ln, Windermere, FL 34786

  This beautifully maintained townhouse offers 3 bedrooms and 2.5 bathrooms with a peaceful pond view. The kitchen features granite countertops, 42-inch wood cabinets, stainless steel appliances, and a pantry, providing both functionality and style. The first floor includes spacious living, dining, and family areas, along with a convenient laundry room. The entire second floor features brand new

  Melquisedec Martins NOVA REAL ESTATE SERVICES INC

  12813 Gracehill Ln, Windermere, FL 34786
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  $3,400 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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  $2,700 per month

  • 3 Beds
  • 2.5 Baths
  • 1,570 Sq Ft
  • Townhouse for Rent

  11619 Water Run Aly, Windermere, FL 34786

  Located in the desirable Ashlin Park neighborhood of Windermere, this well-maintained 3-bedroom, 2.5-bath townhome features a bright, open floor plan with an abundance of natural light. The kitchen features quartz countertops, stainless steel appliances, and espresso cabinetry. The primary suite includes a walk-in closet and a private bath. Enjoy a private interior courtyard connecting the home

  Cristiane Carneiro Spfndola Rocha L WRA BUSINESS & REAL ESTATE

  11619 Water Run Aly, 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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  $2,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,540 Sq Ft
  • Townhouse for Rent

  7843 Hardenton St, Windermere, FL 34786

  Townhome Windermere area 3 Bedroom and 2.5 Bathroom, 2 car garage, 2 story unit. The kitchen cabinets 42", with quartz counters, island/breakfast bar, and stainless steel appliances, open private patio. Wickham Park has a community pool, clubhouse and parks. Great location, close to street mall and supermarket, Close to Disney, Winter Garden Village and major highways (529, turnpike, I4). Close

  Franca Troisi MY REALTY GROUP, LLC.

  7843 Hardenton St, Windermere, FL 34786
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  $2,650 per month

  • 2 Beds
  • 2.5 Baths
  • 1,239 Sq Ft
  • Townhouse for Rent

  12623 Langstaff Dr, Windermere, FL 34786

  ONE OF A KIND, EXECUTIVE WINDERMERE 2 BEDROOM 2.5 BATHROOMS TOWNHOME FURNISHED & DECORATED! This recently renovated home is in the sought-after Lake Reams Community only a minute drive to the backside of Disney! As you open the front door you are drawn to Upscale Interior, filled with Upgrades & a Warm Family Décor. The eating area overlooks an Enclosed Custom-Made Courtyard leading to a Detached

  Ernesto Cisneros ELITE REALTY ENTERPRISES LLC

  12623 Langstaff Dr, 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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  $2,475 per month

  • 3 Beds
  • 2.5 Baths
  • 1,485 Sq Ft
  • Townhouse for Rent

  7613 Sutherton Ln, Windermere, FL 34786

  Stunning End-Unit Townhome in the Heart of Windermere!Welcome to this beautifully maintained 3-bedroom, 2.5-bath unit freshly painted unit, offering excellent natural light and a functional open floor plan in one of Windermere’s most desirable communities.Enjoy outdoor living with a private patio, ideal for relaxing or entertaining. The home features a detached 2-car garage plus a

  Laura Lerma 2 GOOD REALTY

  7613 Sutherton Ln, 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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  $2,650 per month

  • 3 Beds
  • 2.5 Baths
  • 1,624 Sq Ft
  • Property for Rent

  11642 Water Run Aly, Windermere, FL 34786

  3 bedroom 2 bathroom townhouse.Ashlin Park is a peaceful community located in the beautiful town of Windermere. This neighborhood offers a community pool and clubhouse for your comfort and convenience. Ashlin Park is an ideal location due to its proximity to the Lakeside Shopping Center, many highly rated K-12 schools and Walt Disney World.1 Year Lease HOA Approval might be required.

  Rafael Izquierdo Lasaracina VS INTERNATIONAL PROPERTIES

  11642 Water Run Aly, Windermere, FL 34786
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  $2,095 per month

  • 2 Beds
  • 2 Baths
  • 1,161 Sq Ft
  • Condo for Rent

  8264 Maritime Flag St Unit 1419, Windermere, FL 34786

  Beautiful Lakeside at Lakes of Windermere 2nd floor 2 bedroom condo with an open floor open, 42" cabinets, under cabinet lighting, breakfast bar and crown molding. Master bedroom has a large walk in closet and the master bath comes with a large vanity and walk in shower. All appliances including washer and dryer are included, along with water, sewer and valet trash. World class amenities include

  Amanda Beckman RED DOOR INVESTMENT GRP LLC

  8264 Maritime Flag St Unit 1419, 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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  $2,400 per month

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft
  • Townhouse for Rent

  8145 Serenity Spring Dr Unit GE, Windermere, FL 34786

  Beautiful townhome 3 BED, 2.5 BATH, 1 CAR GARAGE in resort style gated community. Stainless steel kitchen appliances, washer & dryer, upgraded wood cabinets, granite kitchen counter tops. All three bedrooms are upstairs, where there is carpet in the bedrooms and tile in the bathrooms & laundry. The community offers a community resort pool, fitness center, large pond with walking trails around the

  Isabel Sirizzotti SUNNY 365 REALTY GROUP

  8145 Serenity Spring Dr Unit GE, 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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  $2,750 per month

  • 3 Beds
  • 2.5 Baths
  • 1,912 Sq Ft
  • Townhouse for Rent

  13718 Beckman Dr, Windermere, FL 34786

  Beautiful TOWHOME AT WINDERMERE AREA. kitchen with upgraded 42`` cabinets, stainless steel appliances. Upstairs vinyl floor, Master suite with walk in closet ,bathroom with dual sinks. Club house with pool.

  Monica Duran MD3 HOMES LLC

  13718 Beckman Dr, 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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