Windermere, FL Homes for Rent

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  $3,700 per month

  • 4 Beds
  • 3.5 Baths
  • 2,931 Sq Ft
  • House for Rent

  8752 Powder Ridge Trail, Windermere, FL 34786

  Beautiful corner lot, Barret model, including 4 bedrooms, 3.5 bathrooms, huge extra room, living room, summer kitchen, and 2-car garage.The functional open floor plan allows for great entertaining.Stainless steel appliances.A-rated schools and the best area to live.Close to restaurants, markets, and major highways.This beautiful home will be available for rent starting January

  Tatiana Felice MS LAND & BUILDING LLC

  8752 Powder Ridge Trail, Windermere, FL 34786
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  $4,332 per month

  • 4 Beds
  • 3 Baths
  • 2,738 Sq Ft
  • House for Rent

  2533 Ridgewind Way, Windermere, FL 34786

  4 Bedroom Home For Rent In Windermere3-Car Garage, Pool View, Screened-in Pool, Screened-in Patio, Master Bedrm Downstairs, Huge Master Suite, Huge Family Room, Hardwood Flooring, Tile in Wet Areas, Additional $150 charge for Pool Maintenance. The deposit amount is based upon the application results. Pets: OK - Medium 50lbs (Dangerous Pets are not permitted, Pit Bulls, etc.) Priced $3,999.00

  Jay Myers ORLANDO REALTY & PROPERTY MGNT

  2533 Ridgewind Way, 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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  $3,500 per month

  • 4 Beds
  • 3.5 Baths
  • 2,770 Sq Ft
  • House for Rent

  13638 Ancilla Blvd, Windermere, FL 34786

  Discover this beautifully maintained two-story single-family home in the heart of Windermere, offering 4 spacious bedrooms, 2 full bathrooms, primary bedroom is downstairs. It has a 2-car garage. With 2,770 sq/ft of living space and a total of 3,513 sq/ft, this property provides comfort, space, and functionality for today’s lifestyle. Enjoy Florida living at its best with your own private

  Jose Solano FUSION FLORIDA REALTY LLC

  13638 Ancilla Blvd, Windermere, FL 34786
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  $6,500 per month

  • 5 Beds
  • 4 Baths
  • 3,805 Sq Ft
  • House for Rent

  311 E 8th Ave, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Luxury Lakefront Executive Rental | Downtown Windermere | Lake Bessie. Now offered at an exceptional value, this rare luxury lakefront rental in Downtown Windermere delivers the ultimate Florida lifestyle for relocating executives and discerning families. Set on the shores of Lake Bessie, this beautifully renovated residence blends refined comfort,

  Karen O'Neil COLDWELL BANKER REALTY

  311 E 8th Ave, Windermere, FL 34786
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  $2,450 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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  $10,999 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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  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Condo for Rent

  11564 Mizzon Dr Unit 907, Windermere, FL 34786

  Spacious condominium in the heart of Windermere. This first floor 3 bedroom, 2 bath features a walk in kitchen, large dining-living combo area, dual entrance second bathroom, and screened in porch leading to the garden area. With a split floor plan, the primary bedroom features a private bath and large walk-in closet. Enjoy exceptional community amenities, including a fitness center, a clubhouse

  Katie Drewry WATSON REALTY CORP

  11564 Mizzon Dr Unit 907, Windermere, FL 34786
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  $3,990 per month

  • 4 Beds
  • 3.5 Baths
  • 3,091 Sq Ft
  • House for Rent

  7211 Still Pond Ln, Windermere, FL 34786

  This property will be ready to be your home next January.Welcome to this former model home in one of Windermere's coveted communities. This custom-designed model is situated on a premium corner lot and offers a combination of luxury, convenience and comfort. As you drive down beautifully manicured streets and past serene lakes, you will arrive at this charming home with its quaint covered porch.

  Victor Barroeta MBT REALTY LLC

  7211 Still Pond Ln, Windermere, FL 34786
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  $2,050 per month

  • 3 Beds
  • 2.5 Baths
  • 1,644 Sq Ft
  • Townhouse for Rent

  8265 Maritime Flag St Unit 101, Windermere, FL 34786

  Move right in! This beautiful 3-bedroom, 2.5-bath corner-unit townhouse is available for immediate move-in and offers the perfect combination of space, comfort, and community living. Step inside to a bright, open-concept layout where the spacious kitchen flows seamlessly into the dining and living areas—ideal for entertaining guests or unwinding at the end of the day. As a corner unit, the home

  Carissa Lawhun FLORIDA REALTY INVESTMENTS

  8265 Maritime Flag St Unit 101, Windermere, FL 34786
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  $3,900 per month

  • 4 Beds
  • 2.5 Baths
  • 2,648 Sq Ft
  • House for Rent

  5426 Gemgold Ct, Windermere, FL 34786

  Discover the best current value for a lakefront property in Windermere with this stunning WATERFRONT HOUSE featuring a private DOCK in the highly sought-after Summerport community! Recently remodeled on the first floor, this home now features a captivating open layout complemented by newer luxury vinyl floors throughout. With 4 bedrooms, 21⁄2 baths, and a 2-car garage, this lovely property is an

  Hector Leon LPT REALTY, LLC

  5426 Gemgold Ct, Windermere, FL 34786
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  $4,700 per month

  • 5 Beds
  • 4.5 Baths
  • 2,628 Sq Ft
  • House for Rent

  13225 Charfield St, Windermere, FL 34786

  Welcome to this beautifully RENOVATED home, located in the friendly Lake Sawyer community and offers the perfect blend of comfort, style, and efficiency. The home has been tastefully updated with contemporary finishes, new flooring, fresh interior paint, and modern hardware throughout. The fully remodeled kitchen features granite countertops, modern stainless steel appliances, updated cabinetry,

  Eduardo Pavone CELEBRITY GLOBAL REALTY LLC

  13225 Charfield St, 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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  $17,900 per month

  • 7 Beds
  • 6 Baths
  • 4,609 Sq Ft
  • House for Rent

  4303 Isabella Cir, Windermere, FL 34786

  Luxury Windermere House for Lease Discover an exceptional opportunity to lease a stunning, fully furnished luxury house in the highly sought-after community of Windermere. Recently renovated and meticulously maintained, this rental property offers the perfect blend of elegance, comfort, and modern convenience. This two-story residence features five spacious bedrooms, including a grand primary

  Jennifer Olmeda WRA BUSINESS & REAL ESTATE

  4303 Isabella Cir, Windermere, FL 34786
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  $5,000 per month

  • 4 Beds
  • 4.5 Baths
  • 3,483 Sq Ft
  • House for Rent

  11905 Camden Park Dr, Windermere, FL 34786

  This rare opportunity for a lovely two-story rental home in Keene's Pointe is now available and move in ready for immediate occupancy. Located in the highly sought after guard gated community of Keene's Pointe, this terrific floor plan boasts 4BR/4.5 Baths + office + bonus room and a 3 Car Garage. Primary Suite is located on the man floor with all other bedrooms on the second floor along with a

  Angela Durruthy KEENE'S POINTE REALTY

  11905 Camden Park Dr, Windermere, FL 34786
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  $3,900 per month

  • 5 Beds
  • 4.5 Baths
  • 3,312 Sq Ft
  • House for Rent

  13106 Orange Isle Dr, Windermere, FL 34786

  Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a corner unit, this 5- bedroom, 4.5 bathroom in Windermere combines the modern elegance, and a touch of magic with its a DISNEY Fireworks view, offering a lifestyle of unparalleled comfort. Upon entering, you are greeted by those who appreciate a dedicated workspace, the home includes a spacious office and a

  Victor De Oliveira FLORIDA CONNEXION PROPERTIES

  13106 Orange Isle Dr, Windermere, FL 34786
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  $2,550 per month

  • 3 Beds
  • 2.5 Baths
  • 1,534 Sq Ft
  • Condo for Rent

  14242 Desert Haven St Unit GE, Windermere, FL 34786

  Located in the gated community of Oasis Cove, this 3-bedroom, 2.5-bathroom condo offers a comfortable, low-maintenance lifestyle just minutes from Disney—with clear views of the nightly fireworks from your own home. The interior features a functional two-story layout with all bedrooms located upstairs, providing separation between living and private spaces. The main floor includes an open-concept

  James Goodyear REAL BROKER, LLC

  14242 Desert Haven St Unit GE, Windermere, FL 34786
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  $2,800 per month

  • 4 Beds
  • 2.5 Baths
  • 1,997 Sq Ft
  • Townhouse for Rent

  7681 Fordson Ln, Windermere, FL 34786

  Experience modern, energy-efficient living with SOLAR PANELS that provide sustainable power and an exceptionally low electric bill! This beautiful townhome for rent is located in the highly desirable community of Windermere Sound. Offering 4 bedrooms and 2.5 bathrooms, this spacious property features ceramic tile flooring in the main areas and carpet in the bedrooms for added comfort. The open

  Reina Mendez REILE REALTY CORP

  7681 Fordson Ln, Windermere, FL 34786
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  $2,475 per month

  • 3 Beds
  • 2.5 Baths
  • 1,545 Sq Ft
  • Townhouse for Rent

  12910 Calderdale Ave, Windermere, FL 34786

  Townhome located in Wickham Park a desirable Windermere Community. Freshly painted and brand new carpet in all bedrooms and pergo laminate flooring in the living/dining area. End unit with Three Bedrooms, Two and one half baths. Kitchen has 42" wood cabinets, all Appliances, Granite Counter Tops and opens to the Living/Dinning area. All bedrooms are on the second floor, Master suite has a walk in

  Jane Sims SIMS REALTY LLC

  12910 Calderdale Ave, Windermere, FL 34786
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  $4,500 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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  $1,275 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  2156 Merrybells Dr, Kissimmee, FL 34746

  Welcome to this beautifully appointed mother-in-law suite featuring a spacious bedroom with ample natural light, a full bathroom, and a separate living area ideal for relaxing or entertaining. The suite also includes a kitchenette with modern cabinetry, a dedicated entrance for added privacy, and direct access to the main home when desired. Thoughtfully designed with neutral finishes and tile

  Mayling Marrero KELLER WILLIAMS ADVANTAGE III

  2156 Merrybells Dr, Kissimmee, FL 34746
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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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  $5,800 per month

  • 3 Beds
  • 2 Baths
  • 1,725 Sq Ft
  • House for Rent

  12860 Lake Sawyer Ln, Windermere, FL 34786

  Private LAKEFRONT estate home on that sits on almost 2 acres of land, gated for extreme privacy! Fully furnished with an open floorplan great for families and entertaining. This home features 3 cozy bedrooms with a king, queen, and full bed to accommodate all guests comfortably. Enjoy the convenience of 2 bathrooms, one with a relaxing jetted bathtub. Kitchen features butcher block countertops,

  Aleem Kanji CROWN REALTY COMPANY

  12860 Lake Sawyer Ln, Windermere, FL 34786
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  $2,949 per month

  • 3 Beds
  • 2 Baths
  • 2,160 Sq Ft
  • House for Rent

  5239 Beach River Rd, Windermere, FL 34786

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3093.90. That covers your base rent, $2949.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  5239 Beach River Rd, 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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  $3,400 per month

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • House for Rent

  11602 Ashlin Park Blvd, Windermere, FL 34786

  Property Id: 904398Welcome to this charming three-bedroom, two-and-a-half-bathroom rental property in the desirable Windermere area. Set on a spacious corner lot, this home features a generous three-car garage and ample outdoor space. Inside, you'll find brand-new carpet(not pictured) and fresh paint throughout, complemented by upgraded kitchen and bathrooms for a modern touch.The

  11602 Ashlin Park Blvd, Windermere, FL 34786

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