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Windermere, FL Houses for Rent with Pool

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  • /31

    $2,950 per month

    • 4 Beds
    • 2.5 Baths
    • 2,092 Sq Ft
    • House for Rent

    11804 Silverlake Park Dr, Windermere, FL 34786

    Welcome to this beautiful 4-bedroom, 2.5-bathroom home in the highly desirable Windermere Trails community. Ideally located just minutes from Walt Disney World and within walking distance to A-rated Bay Lake Elementary, this home offers exceptional convenience for families and professionals alike.Inside, you'll find a spacious open-concept layout with brand-new vinyl flooring throughout

    Xiaoyu Su RATIO REAL ESTATE, LLC

    11804 Silverlake Park Dr, Windermere, FL 34786
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    $5,300 per month

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

    11445 Vicolo Loop, Windermere, FL 34786

    Gorgeous pool home ready for tenant in desirable gated Belmere community with private pool and spa. Solid flooring throughout. Primary bedroom and additional bedrooms on first floor. Bonus room/bedroom and bath on second floor. 3 car garage; tile roof; paver driveway. Community has tennis, playground amenities and very walkable. Pool and lawncare included in rent. Bike ride to downtown

    Dawn Briggs BLUE MAGNOLIA REALTY LLC

    11445 Vicolo Loop, Windermere, FL 34786
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    $7,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,851 Sq Ft
    • House for Rent

    8399 Bowden Way, Windermere, FL 34786

    This stunning waterfront home with a pool in the desirable 24-guard gated neighborhood of Keene’s Pointe is available for immediate occupancy! Welcome home to your exquisite single-story remodeled home spanning 2,851 sq ft with an open-concept design, featuring wood floors with contemporary style throughout. Highlights include spacious bedrooms, a separate study, living room, dining room, and a

    Simon Simaan THE SIMON SIMAAN GROUP

    8399 Bowden Way, Windermere, FL 34786
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    $4,200 per month

    • 4 Beds
    • 3 Baths
    • 2,453 Sq Ft
    • House for Rent

    1461 Glenheather Dr, Windermere, FL 34786

    WINDERMERE GEM RENTAL | Welcome to the luxurious 24 hr guard gated community of Reserve at Belmere. This enchanting 4 bedroom/3 bathroom home has to be seen with your own eyes. Enjoy an open/split floor plan suited perfectly for any family. Enjoy the grand outdoor living space which features a very large pool and oversized jacuzzi with child safety fence and fully screened enclosed plus a full

    Keith Conklin FOLIO REALTY LLC

    1461 Glenheather Dr, Windermere, FL 34786
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    $2,990 per month

    • 3 Beds
    • 2.5 Baths
    • 2,211 Sq Ft
    • House for Rent

    11235 Rapallo Ln, Windermere, FL 34786

    Perfect beautiful 3 bed 2.5 bath home for rent. This beautiful home is located in the gated community of Belmere Village. Featuring laminate flooring in the bedrooms,otherwise tiled,formal dining/living and a large family room, large screened patio and nicely landscaped. The master bedroom features a bonus room off to the side which has a closet and could be a small childs room, separated by

    D'Anne KinCannon IN TOUCH REAL ESTATE LLC

    11235 Rapallo Ln, 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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    $1,500 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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    $3,600 per month

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft
    • House for Rent

    953 Lascala Dr, Windermere, FL 34786

    Absolutely beautiful rental home located in the highly sought-after gated community of Belmere Village in Windermere. This spacious home features a stunning screened in pool area with a large backyard, perfect for relaxing evenings or entertaining guests.The updated gourmet kitchen offers granite countertops, a breakfast bar, and overlooks the recently renovated family room. Double doors

    Amine Berrada ATLAS BLUE REALTY INC

    953 Lascala Dr, Windermere, FL 34786
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    $2,880 per month

    • 3 Beds
    • 2 Baths
    • 1,948 Sq Ft
    • House for Rent

    13535 Darchance Rd, Windermere, FL 34786

    Perfect location in Windermere! Ready to move in! Beautiful and spacious Single Story Home. Oversize lot without rear neighbors! Great school zone. Tons of upgrade in the house, including graded wood flooring and light fixture, gourmet kitchen package, siltstone countertop, elegant backsplash, 42"maple cabinets with crown molding, reverse osmosis for drinking water. Also, a whole house water

    Jacky Liu KYLIN REALTY LLC

    13535 Darchance Rd, Windermere, FL 34786
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    $13,000 per month

    • 5 Beds
    • 6.5 Baths
    • 6,248 Sq Ft
    • House for Rent

    8402 Lake Burden Cir Unit 2, Windermere, FL 34786

    Experience luxury waterfront living in the prestigious gated community of Keene's Pointe. This custom estate offers over 6,000 sq ft of elegant living space with 5 bedroom ensuites and a full pool bath with shower and powder room off of the Theater. A chef's kitchen with stainless-steel appliances, gas range open to the breakfast nook and family room. Perfect for entertaining, the formal dining

    Toni Marie Cafferty COMPASS FLORIDA LLC

    8402 Lake Burden Cir Unit 2, Windermere, FL 34786
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    $4,000 per month

    • 4 Beds
    • 3 Baths
    • 2,892 Sq Ft
    • House for Rent

    9332 Windy Ridge Rd, Windermere, FL 34786

    Rare Windermere farmhouse retreat on 1.2 acres with no HOA, surrounded by multimillion-dollar estates. This beautifully updated 4-bedroom, 3.5-bath home blends timeless charm with everyday comfort. Inside, you'll find wood and tile flooring throughout, a cozy wood-burning fireplace in the family room, and a functional mudroom with laundry to keep things organized. The wrap-around porch invites

    Ahmad Hassan COMPASS FLORIDA LLC

    9332 Windy Ridge Rd, Windermere, FL 34786
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    $19,900 per month

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

    3999 Isabella Cir, Windermere, FL 34786

    AVAILABLE IN OCTOBER - 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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    $3,900 per month

    • 4 Beds
    • 3 Baths
    • 3,057 Sq Ft
    • House for Rent

    9014 Outlook Rock Trail, Windermere, FL 34786

    Windermere 4/Bed × 3/Bath – FurnishedDiscover your next home in a premier Windermere neighborhood—just minutes from top-rated schools and Disney!Furnished: $3,900/month; - Included in Rent:Free high-speed internet, Access to security system, Lawn care included.Zoned to stellar public and private schools, including Bay Lake Elementary, Horizon West Middle, Windermere High, and

    Maria Serrano Whitehead EPIQUE REALTY, INC.

    9014 Outlook Rock Trail, Windermere, FL 34786
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    $4,300 per month

    • 3 Beds
    • 2.5 Baths
    • 2,301 Sq Ft
    • House for Rent

    13318 Longacre Dr, Windermere, FL 34786

    Located in the heart of Central Florida, this executive home offers the ideal combination of modern elegance, functionality, and a prime Windermere location. This spacious 2-story home features 3 bedrooms, 2.5 bathrooms, and 2,301 square feet of living space—plus a flexible bonus room perfect for a home office, den, or playroom. Nestled on a 6,098 sq ft lot with a private fenced-in backyard and

    Leo Pacheco ODYSSEY REAL ESTATE SERVICES LLC

    13318 Longacre Dr, Windermere, FL 34786
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    $3,700 per month

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

    7282 Backwoods Trail, Windermere, FL 34786

    Welcome to the perfect home waiting for you in Windermere, FL! This FULLY furnished house features 4 bedrooms and 4 bathrooms, providing ample space for all your needs. Enjoy the convenience of an association pool, gym, and playground right at your fingertips. Whether you're looking to relax by the pool, stay active in the gym, or have fun at the playground, this home has everything you need for

    Julien Silva JOHN SILVA REALTY & ASSOCIATES

    7282 Backwoods Trail, Windermere, FL 34786
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    $3,400 per month

    • 4 Beds
    • 3 Baths
    • 2,551 Sq Ft
    • House for Rent

    11032 Belmere Isles Ct, Windermere, FL 34786

    Beautiful 4 bedroom, 3 bath home located within guard gated community of the Reserves of Belmere. Screened in pool overlooking pond. Eat in kitchen. Two car garage. Located on cud-a-sac. Come see!

    Barbara Schafer Holland CLASSIC INTERNATIONAL REALTY LLC

    11032 Belmere Isles Ct, Windermere, FL 34786
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    $12,000 per month

    • 5 Beds
    • 4.5 Baths
    • 4,417 Sq Ft
    • House for Rent

    5001 Latrobe Dr, Windermere, FL 34786

    Available for immediate occupancy. This beautiful, traditional five-bedroom pool home is on a quiet cul-de-sac in Isleworth, Windermere. The traditional brick exterior, grand French doors, and warm mahogany wood floors invite friends and family home. Enjoy views of majestic oaks, the 7th fairway, and Lake Bessie on this half-acre lot. This two-story home is perfect for entertaining and easy to

    Laura Diss Q BOUTIQUE SPECIALTY REALTY INC

    5001 Latrobe Dr, Windermere, FL 34786
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    $19,000 per month

    • 6 Beds
    • 5.5 Baths
    • 7,971 Sq Ft
    • House for Rent

    4260 Isabella Cir, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Welcome to 4260 Isabella Circle, nestled in the heart of scenic Windermere, FL. This exceptional residence blends luxury, comfort, and convenience. Located in a tranquil and upscale community, you’ll enjoy close proximity to top-rated schools, shopping centers, fine dining, parks, and more.Step inside to experience an expansive open layout

    Julimar Barreiro Pastrana SERHANT

    4260 Isabella Cir, Windermere, FL 34786
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    $5,700 per month

    • 4 Beds
    • 3 Baths
    • 2,830 Sq Ft
    • House for Rent

    2113 Grove Point Ln, Windermere, FL 34786

    Discover this stunning rental home located in the Waterford Pointe community on Lake Roberts. Enjoy exclusive access to a private community boat ramp in a serene, gated neighborhood.This beautifully furnished residence features new bamboo flooring, high-end appliances, and elegant decor throughout. Designed for year-round Florida living, the home includes a private in-ground pool, spa,

    Alexandra Costa Thomas THE FLORIDA LOUNGE REALTY LLC

    2113 Grove Point Ln, Windermere, FL 34786
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    $39,500 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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    $3,299 per month

    • 4 Beds
    • 3.5 Baths
    • 2,619 Sq Ft
    • House for Rent

    8674 Abbotsbury Dr, Windermere, FL 34786

    Welcome to 8674 Abbotsbury Dr, a stunning 4-bedroom, 3.5-bathroom residence offering 2,619 sq ft of thoughtfully designed living space in the heart of Windermere. This home blends luxury and comfort in one of Central Florida’s most desirable and safe communities—just minutes from Disney’s employee parking lot and the vibrant Horizon West area.Step inside to find a spacious open-concept

    Elsy Camacho EC REAL ESTATE INVEST.& RENTAL

    8674 Abbotsbury Dr, Windermere, FL 34786
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    $15,000 per month

    • 5 Beds
    • 4.5 Baths
    • 4,345 Sq Ft
    • House for Rent

    4279 Isabella Cir, Windermere, FL 34786

    Welcome to 4279 Isabella Cir, Windermere, FL 34786. Offered as a lease with an option to purchase. This 5-bedroom, 4/2-bathroom home has been completely remodeled and upgraded, perfectly marrying luxury with comfort. As you enter, you are greeted by an impressive formal living room with 30’ ceilings and two stories of windows that offer a stunning view of the sparkling swimming pool. Within the

    John Silva JOHN SILVA REALTY & ASSOCIATES

    4279 Isabella Cir, Windermere, FL 34786
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    $12,700 per month

    • 6 Beds
    • 6 Baths
    • 5,667 Sq Ft
    • House for Rent

    13515 Bellaria Cir, Windermere, FL 34786

    Must see, luxury home! Very rare property of its size available for rent in prestigious Windermere. This 2-story, 6 bedroom, 6 bath triple car garage home features a great room with marble fireplace, over-sized windows facing the rear deck & resort style pool, has a heated spa and pool. The pool is the dramatic focal point of the main level, accompanied by a formal dining room. Chef's kitchen,

    Jessica Martinez Cestero HAMPTON & HAMPTON MGMT LEASING

    13515 Bellaria Cir, Windermere, FL 34786
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    $7,250 per month

    • 4 Beds
    • 4 Baths
    • 3,531 Sq Ft
    • House for Rent

    6425 Cartmel Ln, Windermere, FL 34786

    Nestled behind the 24-hour guard gates of Reserve at Lake Butler Sound, this exceptional residence offers a rare opportunity to live in one of Windermere’s most sought-after luxury communities. Perfectly positioned on a sprawling 0.49-acre lot, this beautifully maintained home features a light-filled open-concept layout with refined designer finishes throughout.With five bedrooms (or four

    Robert Larkan EXECUTIVE PROPERTIES

    6425 Cartmel Ln, Windermere, FL 34786
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    $8,000 per month

    • 5 Beds
    • 4.5 Baths
    • 4,028 Sq Ft
    • House for Rent

    6020 Marleon Dr, Windermere, FL 34786

    Welcome to 6020 Marleon Drive, a beautifully appointed 5-bedroom, 4.5-bathroom home located in the highly sought-after, family-friendly community of Lake Cypress Cove in Windermere, FL. With over 4,000 square feet of thoughtfully designed living space on more than half an acre, this home offers the perfect blend of luxury and comfort for your growing family. The open floor plan creates a warm and

    Charles Newman UNITED REALTY GROUP INC

    6020 Marleon Dr, Windermere, FL 34786
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    $8,995 per month

    • 4 Beds
    • 3.5 Baths
    • 3,751 Sq Ft
    • House for Rent

    6533 Cartmel Ln, Windermere, FL 34786

    One or more photo(s) has been virtually staged. AUTHENTIC MEDITERRANEAN ELEGANCE IN WINDERMERE! This beautiful 4 bedroom/3.5 bath single story pool home has everything a discerning tenant is looking for in a rental residence. Drive through the fountained 24-hour guard gated front entrance of Reserve at Lake Butler Sound and take notice of the winding tree lined street that leads you to the

    Mary Currie BHHS FLORIDA REALTY

    6533 Cartmel Ln, Windermere, FL 34786
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    $12,500 per month

    • 4 Beds
    • 4.5 Baths
    • 4,013 Sq Ft
    • House for Rent

    6036 Greatwater Dr, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Welcome to Keene’s Pointe! Discover the charm of this custom-built home located on the 17th Fairway of the renown Jack Nicklaus Signature Golf Course and across from the lakefront mansions that line this quiet cul-de- sac on Greatwater Drive. This 4BR/4Full Bath/1 Half Bath golf course home exudes warmth from the gorgeous hardwood floors and

    Angela Durruthy KEENE'S POINTE REALTY

    6036 Greatwater Dr, Windermere, FL 34786
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    $3,999 per month

    • 4 Beds
    • 3 Baths
    • 3,114 Sq Ft
    • House for Rent

    13461 Zori Ln, Windermere, FL 34786

    THIS HOME JUST GOT A NEW FACE LIFT INSIDE. NEW PAINT,COUNTERTOP, LIGHTER FLOORING, CARPET IN THE THEATER ROOM AND MORE.This stunning 4-bedroom, 3-bathroom home for rent is located in the desirable Windermere community, just minutes away from the newly built Windermere High School. With a spacious and elegant floor plan, this home offers a luxurious living experience. The downstairs features a

    Courtney James LA ROSA REALTY ORLANDO LLC

    13461 Zori Ln, Windermere, FL 34786
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    $6,450 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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    $13,500 per month

    • 3 Beds
    • 3 Baths
    • 3,247 Sq Ft
    • House for Rent

    9742 Green Island Cove, Windermere, FL 34786

    Nestled along the shores of beautiful Lake Louise within the gates of Isleworth Golf & Country Club, this charming golf villa offers a prime lakefront location in proximity to the Clubhouse. The interior boasts more than 3,000 square feet of living space, with an open floor plan set against a backdrop of picturesque water views. Elegant hardwood floors travel throughout the single-story floor

    Monica Lochmandy ISLEWORTH REALTY LLC

    9742 Green Island Cove, Windermere, FL 34786
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