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Winter Garden, FL Homes for Rent with Private Pool

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    $7,000 per month

    • 4 Beds
    • 3 Baths
    • 3,364 Sq Ft
    • House for Rent

    7849 Freestyle Ln, Winter Garden, FL 34787

    Rare opportunity to rent in an exclusive private gated and coveted water-skiing community of Isles of Lake Hancock. Amidst gorgeous views and private streets of beautiful estate homes you will find this stunning and spacious 4 bedroom, 3 bath pool home. Resting entirely on one story, this completely upgraded home is open, light and bright. Brilliantly laid out, the large rooms avail privacy, with

    Kelly Zannini HOMEVEST REALTY

    7849 Freestyle Ln, Winter Garden, FL 34787
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    $6,000 per month

    • 5 Beds
    • 4.5 Baths
    • 4,045 Sq Ft
    • House for Rent

    15155 Canoe Place, Winter Garden, FL 34787

    Location, location, location. This luxury FULLY FURNISHED HOME is located in one of the most sought-after subdivisions of Winter Garden, Lakeshore Preserve. It has a relaxing pool and spa/jacuzzi, over 4,000 sqft, 5 bedrooms, 4.5 bathrooms, bonus room upstairs, and 2 car garage. Rare double master bedrooms one on the first level and another on the second floor. The kitchen is a chef's delight

    Neyla Fernandes ALL CENTRAL FLORIDA REALTY LLC

    15155 Canoe Place, Winter Garden, FL 34787
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    $3,900 per month

    • 4 Beds
    • 3.5 Baths
    • 3,341 Sq Ft
    • House for Rent

    Unlisted Address

    This beautifully maintained home offers the perfect blend of comfort, space, and resort-style living. Freshly painted and thoughtfully designed, it welcomes you with a bright, open layout ideal for both everyday living and entertaining. Conveniently located minutes from Winter Garden Village shopping and Entertainment, major hwys, and hospital. Step outside to your private backyard oasis,

    Lauraine Quintana BHM PROPERTIES II, LLC

    Unlisted Address
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    $6,000 per month

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

    15372 Gilligan Ct, Winter Garden, FL 34787

    Stunning One-Story Home for Rent in the Heart of Horizon West – Fully Upgraded with Heated Pool This beautifully renovated one-story home offers an open-concept layout with thoughtfully designed living spaces and high-end upgrades throughout. Featuring 4 bedrooms and 3.5 bathrooms, the home includes a convenient Jack-and-Jill suite with a shared full bathroom, providing comfort and privacy for

    Caroline Nijenhuis De Santis WRA BUSINESS & REAL ESTATE

    15372 Gilligan Ct, Winter Garden, FL 34787
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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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    $11,500 per month

    • 5 Beds
    • 5.5 Baths
    • 5,005 Sq Ft
    • House for Rent

    15704 Marina Bay Dr, Winter Garden, FL 34787

    Location, Location, Location!?This spectacular lakefront estate truly has it all. Thoughtfully upgraded throughout, the home features a gourmet kitchen with 42" cabinetry, an oversized island, and an expansive walk-in pantry—ideal for both everyday living and entertaining. A modern wine room adds a distinctive touch, while breathtaking lake views welcome you the moment you enter the home.The

    Marcelo Moura DOUBLE M GROUP COMPANY

    15704 Marina Bay Dr, Winter Garden, FL 34787
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    $5,400 per month

    • 4 Beds
    • 3.5 Baths
    • 2,832 Sq Ft
    • House for Rent

    14931 Lebeau Loop, Winter Garden, FL 34787

    Welcome to this beautifully designed 4-bedroom home offering modern comfort, thoughtful upgrades, and versatile living spaces in one of Winter Garden’s most desirable areas. Designed by an interior architect, the home blends style and functionality with a flexible layout that adapts easily to different lifestyles. The interior features 4 bedrooms, including 2 spacious suites, along with a

    Juliana Mucher FLORIDA REALTY INVESTMENTS

    14931 Lebeau Loop, Winter Garden, FL 34787
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    $6,400 per month

    • 4 Beds
    • 3.5 Baths
    • 2,943 Sq Ft
    • House for Rent

    5133 Citrus Leaf Blvd, Winter Garden, FL 34787

    Beautifully maintained 4-bedroom, 3.5-bath lakefront home for rent in the highly desirable Silverleaf community of Winter Garden. This craftsman-style residence offers excellent curb appeal with manicured landscaping and an inviting front porch. Conveniently located near A-rated schools, and just minutes from shopping, dining, entertainment, the Winter Garden Farmers Market, and major attractions

    Carolina Mariano Da Silva PREMIER SOTHEBYS INT'L REALTY

    5133 Citrus Leaf Blvd, Winter Garden, FL 34787
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    $9,995 per month

    • 5 Beds
    • 4.5 Baths
    • 4,671 Sq Ft
    • House for Rent

    12927 Canopy Woods Way, Winter Garden, FL 34787

    Beautiful Fully Furnished, French Country model Home. This gorgeous pool home features 5 Bedrooms (2 Master Suites 1st and 2nd floor) plus an office/study with 4.5 baths, Cinema (with top of the line equipment and sound system, over $30K) with 3 car garage on a prime location in Winter Garden, nearby shopping, highway, hospital and Disney Parks. Canopy Oaks is a gated community, home of 49

    Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

    12927 Canopy Woods Way, Winter Garden, FL 34787
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