Windermere, FL Houses for Rent

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  $2,800 per month

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft
  • House for Rent

  805 Oakdale St, Windermere, FL 34786

  Live amongst the oaks in this 3BD/2BA large corner lot home in the heart of Olde Windermere. Just a short walk to the historic downtown of Windermere.Stainless steel appliances, granite countertops with wine racks! Area boasts parks, tennis courts, public library, full time police security! Come home to "Olde Windermere"! Lawn care included. Application Fee: $50 each adult (18+) due at end of

  Kenneth Warren PREMIER MANAGEMENT GROUP INC

  805 Oakdale St, Windermere, FL 34786
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  $3,800 per month

  • 5 Beds
  • 3.5 Baths
  • 3,689 Sq Ft
  • House for Rent

  12821 Westside Village Loop, Windermere, FL 34786

  This stunning home sits on a corner 5 bedrooms plus an office and huge bonus room. once you into the large foyer where you will find the office with a double door entry and a guest bath. The formal dining room has a contemporary tray ceiling and leads into the butlers pantry with built in cabinetry and a large walk in pantry. The open concept kitchen features stainless steel appliances, granite

  Marcos Del Nero LA ROSA REALTY KISSIMMEE

  12821 Westside Village Loop, Windermere, FL 34786
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  $4,150 per month

  • 4 Beds
  • 2.5 Baths
  • 2,145 Sq Ft
  • House for Rent

  2943 Marquesas Ct, Windermere, FL 34786

  Come tour this incredible New England-style pool home in the Town of Windermere that sits on a meticulously manicured one-acre corner lot on a serene, tree-lined street, in the gated community of Lake Crescent Reserve. Lake Crescent is an exclusive community of 21 custom homes with mostly waterfront homes on Lake Crescent. All residents have full use of a private boat ramp to the Butler Chain of

  Jessica Alicea INTEGRITY REAL ESTATE GROUP, LLC

  2943 Marquesas Ct, Windermere, FL 34786
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  $3,200 per month

  • 4 Beds
  • 3.5 Baths
  • 2,420 Sq Ft
  • House for Rent

  7224 Halton Ct, Windermere, FL 34786

  Welcome to this beautifully refreshed two-story home offering over 2,400 sq ft of living space in the desirable Enclave community in Windermere. The first floor features a functional layout with living and dining areas, a comfortable family room, and a kitchen equipped with stainless-steel appliances, a breakfast bar, big pantry and plenty of space for everyday living and entertaining. Step

  Tatyana Clark COLDWELL BANKER RESIDENTIAL RE

  7224 Halton Ct, Windermere, FL 34786
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  $6,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,309 Sq Ft
  • House for Rent

  8418 Bowden Way, Windermere, FL 34786

  Welcome to this beautifully updated 3-bedroom, 2.5-bathroom home located in the highly sought-after, guard-gated community of Keene’s Pointe in Windermere. Situated on a desirable corner lot, this stunning residence offers both privacy and charm in one of Central Florida’s most exclusive neighborhoods.The home has undergone a full renovation, featuring modern finishes throughout, including

  Jessica Dessire Cueva PA CHARLES RUTENBERG REALTY ORLANDO

  8418 Bowden Way, Windermere, FL 34786
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  $6,800 per month

  • 5 Beds
  • 4.5 Baths
  • 3,835 Sq Ft
  • House for Rent

  7231 Sangalla Dr, Windermere, FL 34786

  Exclusive Gated Community of Casa Del Lago • Updated Interior • Low Maintenance Resort-Style Backyard with Artificial Turf • 5 Bedrooms + Office + Huge Loft • Live in one of Windermere’s most prestigious gated communities, surrounded by breathtaking lakefront estates and just minutes from everything Central Florida has to offer. This luxury 5-bedroom, 5-bath executive home delivers a rare

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  7231 Sangalla Dr, Windermere, FL 34786
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  $4,000 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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  $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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  $15,000 per month

  • 5 Beds
  • 5.5 Baths
  • 5,339 Sq Ft
  • House for Rent

  6844 Valhalla Way, Windermere, FL 34786

  Beautiful and fully furnished home in Keene's Pointe golf community. Guard gated community. A Tuscan style luxury home with a large covered back patio with fireplace and large pool overlooking the 14th green Bear Club. Master and extra suite on first floor and three more suites upstairs. This house has a very big loft, perfect for entertaining.

  Marilene Auge CHARLES RUTENBERG REALTY ORLANDO

  6844 Valhalla Way, 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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  $4,300 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

  Gladys Bezerra FLORIDA CONNEXION PROPERTIES

  13106 Orange Isle Dr, Windermere, FL 34786
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  $13,500 per month

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

  6219 Tiroco Way, Windermere, FL 34786

  Luxurious furnished house for RENT with 7 bedrooms and 5/1 bathrooms, huge Resort like pool and patio located in the elegant gated community of Waterstone. Two story ceilings, an enormous crystal chandelier, wood floors and an open wood staircase defines the foyer and living room. With a private study and formal dining room, gourmet kitchen features a large island, breakfast bar, granite tops

  Claudia D'Aquino CENTURY 21 CARIOTI

  6219 Tiroco Way, Windermere, FL 34786
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  $2,575 per month

  • 3 Beds
  • 2.5 Baths
  • 1,852 Sq Ft
  • House for Rent

  1047 Lascala Dr, Windermere, FL 34786

  Beautiful 3-Bedroom, 2.5-Bath Home in Gated Belmere Village – Windermere Welcome to this stunning single-story home in the highly sought-after gated community of Belmere Village. Offering spacious living and thoughtful design, this residence includes 3 bedrooms, 2.5 baths, and a versatile office/den plus a built-in hallway desk area—perfect for homework, crafts, or a home workspace. The master

  Lisa Ingram INGRAM REALTY SERVICES LLC

  1047 Lascala Dr, Windermere, FL 34786
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  $4,200 per month

  • 4 Beds
  • 3.5 Baths
  • 3,059 Sq Ft
  • House for Rent

  7508 Lake Albert Dr, Windermere, FL 34786

  Don't miss this custom-built 4-bedroom, 3.5-bath Windermere Pool Home – beautifully updated and move-in ready! Conveniently located near theme parks, shopping, and top-rated schools, this stunning property offers a perfect blend of style, comfort, and practicality. Volume ceilings tower above the foyer and home office, while the gourmet kitchen features granite countertops, stainless steel

  Marcio Silva MS LAND & BUILDING LLC

  7508 Lake Albert Dr, Windermere, FL 34786
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  $3,200 per month

  • 3 Beds
  • 2.5 Baths
  • 2,043 Sq Ft
  • House for Rent

  7241 Sunny Meadow Aly, Windermere, FL 34786

  This beautiful single-family residence FOR RENT offers the perfect combination of modern comfort and resort-style living. Great floorpan featuring 3 Bedrooms, 2-1/2 Bathroons and a great office. From the moment you arrive, you'll be captivated by the inviting atmosphere and community amenities, including a sparkling, resort-style pool—ideal for relaxing weekends. The heart of the home is the

  Daniela de Rodriguez B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE

  7241 Sunny Meadow Aly, Windermere, FL 34786
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  $4,500 per month

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

  14409 Crest Palm Ave, Windermere, FL 34786

  Be the First to Live In This Brand-New 2025 Windermere Home! Move-In Ready | Smart Home | Pet Friendly | 2-Car Garage | Loft & Bonus Room | Internet & WiFi Included! Experience sophisticated, luxurious living in this expansive 6-bedroom, 3.5-bath, two-story home, featuring a bright, open-concept layout that seamlessly connects the gourmet kitchen, inviting family room, and elegant dining

  Katrina Anarumo RENT A FLORIDA HOME

  14409 Crest Palm 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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  $4,600 per month

  • 6 Beds
  • 5.5 Baths
  • 3,746 Sq Ft
  • House for Rent

  4345 Saltmarsh Sparrow Dr, Windermere, FL 34786

  WELCOME HOME to Summerport! This stunning 6-bedroom, 5.5-bathroom residence is now available for rent in the highly desirable Summerport neighborhood—zoned for top-rated A+ schools!Step inside and enjoy a thoughtfully designed split two-story floor plan with plenty of room for family and entertaining. The first floor features a versatile office/den with French doors, a bright family room, and

  Silvia Odebrecht ICON REALTY ASSOCIATES INC

  4345 Saltmarsh Sparrow Dr, 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

  AVAILABLE IN December - 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

  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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  $35,900 per month

  • 7 Beds
  • 10 Baths
  • 8,362 Sq Ft
  • House for Rent

  9343 Tibet Pointe Cir, Windermere, FL 34786

  Perfectly sited on pristine Lake Tibet in Keene's Pointe Country Club, this stunning lakefront Stonebridge custom home has been completely updated. The modern exterior color brightens the façade and creates a unique transitional style. The wrought iron and glass doors add a refined entry. Opening to the two-story formal areas featuring timeless elements of stone flooring, elegant ceiling details,

  Juan Delgado LA ROSA REALTY LLC

  9343 Tibet Pointe Cir, Windermere, FL 34786
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  $3,150 per month

  • 4 Beds
  • 3.5 Baths
  • 2,600 Sq Ft
  • House for Rent

  13426 Chariho Ln, Windermere, FL 34786

  Welcome to this beautifully maintained 4-bedroom, 3-bath home with a loft and office located in a highly sought-after gated community in Windermere. This spacious residence offers a fresh, move-in-ready feel with fairly new carpeting throughout the stairs and second floor. The thoughtfully designed floor plan features a first-floor master suite, providing privacy and convenience, along with a

  Courtney James LA ROSA REALTY ORLANDO LLC

  13426 Chariho Ln, Windermere, FL 34786
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  $4,500 per month

  • 4 Beds
  • 2.5 Baths
  • 2,588 Sq Ft
  • House for Rent

  12025 Lake Butler Blvd, Windermere, FL 34786

  Welcome to your 4-bedroom, 3-bathroom, three car garage sanctuary! As you open your beautiful door, expect to be wowed at your perfect masterpiece. You are greeted by your huge family room leading into the living room with a wood burning fireplace. Your living room boasts lighting through your rear doors leading to your gorgeous, screen enclosed patio. This home has a layout picture-perfect for

  Camille Simon MCO REALTY

  12025 Lake Butler Blvd, Windermere, FL 34786
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  $5,900 per month

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

  307 W 4th Ave, Windermere, FL 34786

  Executive rental pool home located in the charming town of Windermere! The location is just two block from Main st and all that downtown Windermere has to offer! This single-story, 4-bedroom (2 primary bedrooms), 3-bathroom home, sits on an oversized corner lot in the shade of majestic oak trees. Enjoy a gourmet kitchen featuring stainless steel appliances, two brand new refrigerators, a

  Katie Bray MAINFRAME REAL ESTATE

  307 W 4th Ave, Windermere, FL 34786
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  $7,500 per month

  • 4 Beds
  • 3.5 Baths
  • 3,328 Sq Ft
  • House for Rent

  2844 Midsummer Dr, Windermere, FL 34786

  Fabulous gated one acre Windermere Chain of Lakes Estate with Private tennis court is currently available for lease, This 5 bedroom 3 1/2 bath includes in-law suite with private entrance. New boat dock for the avid boater along with sandy beach for ultimate waterfront entertainment. Enjoy the beautiful west facing sunsets from your large covered patio or dine beside your double sided wood burning

  Dennis Conklin WINDERMERE COCOA BEACH CENTER

  2844 Midsummer Dr, Windermere, FL 34786

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