21

Homes for Rent in Winter Garden, FL with 5-Bedrooms

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  • /17

    $2,835 Per Month

    • 5 Beds
    • 2.5 Baths
    • 2,220 Sq Ft
    • House for Rent

    1848 Sherbourne St, Winter Garden, FL 34787

    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 $2979.90. That covers your base rent, $2835.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1848 Sherbourne St, Winter Garden, FL 34787
  • /57

    $5,995 Per Month

    • 5 Beds
    • 4.5 Baths
    • 4,199 Sq Ft
    • House for Rent

    8222 Topsail Place, Winter Garden, FL 34787

    STUNNING, well-maintained Executive estate home with everything you've been looking for! This gorgeous GARDENIA model by TOLL BROTHERS features 4200 square feet of living space with AMAZING VIEWS of a tranquil pond in the front, retention space in back in the desirable LAKESHORE community in HORIZON WEST, providing the perfect ONE OF A KIND idyllic space you've been looking for! You will enjoy

    Jonathan Jankowski CHASTAIN REAL ESTATE COMPANY LLC

    8222 Topsail Place, Winter Garden, FL 34787
  • /10

    $5,000 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,724 Sq Ft
    • House for Rent

    16324 Silver Grv Blvd, Winter Garden, FL 34787

    Welcome to this stunning, nearly new residence in the highly desirable community of Silverleaf Reserve at Hamlin in Winter Garden. Built in 2023, this modern two-story home offers approximately 3,743 sq. ft. of thoughtfully designed living space filled with natural light and seamless indoor–outdoor flow. The flexible layout provides multiple options for a home office, game room, or media

    16324 Silver Grv Blvd, Winter Garden, FL 34787
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    $6,500 Per Month

    • 5 Beds
    • 7 Baths
    • 4,019 Sq Ft
    • House for Rent

    706 Canopy Estates Dr, Winter Garden, FL 34787

    Luxury lease opportunity in the gated community of Canopy Oaks, offering an exceptional combination of space, privacy, and convenience in one of Winter Garden's most desirable locations. Ideally situated near major healthcare facilities, business centers, Downtown Winter Garden, Winter Garden Village, and Orlando's attractions and entertainment destinations, this A.R. Bailey Homes Delray model is

    Lisa Rutkowski PREMIER SOTHEBY'S INTL. REALTY

    706 Canopy Estates Dr, Winter Garden, FL 34787
  • /49

    $4,799 Per Month

    • 5 Beds
    • 4 Baths
    • 3,760 Sq Ft
    • Spectacular 5/4 with 3 car garage home in Winter Garden

    9240 Wood Crane Dr, Winter Garden, FL 34787

    Spectacular 5/4 with 3 car garage home. This home has all the bells and whistles for your enjoyment, Modern kitchen with open floor plan to family/living room and access to large screened in patio. Fenced backyard. Upstairs has a large Loft and 4 bedrooms including the spacious master bedroom/master bathroom. This home is a must see located in Watermark Sub-division with to many features to

    9240 Wood Crane Dr, Winter Garden, FL 34787
  • /100

    $12,950 Per Month

    • 5 Beds
    • 5 Baths
    • 4,038 Sq Ft
    • House for Rent

    16870 Sanctuary Dr, Winter Garden, FL 34787

    Experience elevated lakefront living in one of Winter Garden’s most desirable communities. This fully furnished luxury residence offers a rare combination of design, comfort, and lifestyle, perfectly positioned on a premium lakefront lot with one of the most breathtaking views in the area. Featuring 5 spacious bedrooms and 5 bathrooms, this home was thoughtfully designed with high-end custom

    Lino Cervino FORTUNE GLOBAL REALTY

    16870 Sanctuary Dr, Winter Garden, FL 34787
  • /37

    $5,500 Per Month

    • 6 Beds
    • 3.5 Baths
    • 4,056 Sq Ft
    • Orchard Hills 6 bed / 3.5 Bath - Partially Furniushed

    4207 Oak Lodge Way, Winter Garden, FL 34787

    Take a look at this beautiful 6 bedroom 3.5 bath, partially furnished. A total split level home with a crystal clear pool, barbecue grilling, bar area, fire place and the pool has a waterfall that can be controlled via wifi. Two car garage mature landscaping. This home has tons of space, a loft upstairs that can be used for play, movie, or just an area to relax. Spacious master suite, master

    4207 Oak Lodge Way, Winter Garden, FL 34787
  • /44

    $5,900 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,643 Sq Ft
    • House for Rent

    16628 Silver Brook Way, Winter Garden, FL 34787

    Welcome to this stunning nearly new home located in the desirable Silverleaf Oaks community in Winter Garden. Built by Pulte Homes, this Scarlett floor plan offers 5 bedrooms, 4.5 bathrooms, 3,643 sq. ft. of living space, and a 2-car garage.This modern open-concept home features high-end upgrades throughout, including a gourmet kitchen with built-in Whirlpool appliances, 42” cabinets,

    Drielen Ferreira MANAGER PROP

    16628 Silver Brook Way, Winter Garden, FL 34787
  • /46

    $4,799 Per Month

    • 5 Beds
    • 4 Baths
    • 3,760 Sq Ft
    • House for Rent

    9240 Woodcrane Dr, Winter Garden, FL 34787

    Spectacular 5/4 with 3 car garage home. This home has all the bells and whistles for your enjoyment, Modern kitchen with open floor plan to family/living room and access to large screened in patio. Fenced backyard. Upstairs has a large Loft and 4 bedrooms including the spacious master bedroom/master bathroom. This home is a must see located in Watermark Sub-division with to many features to list.

    Jessica Martinez Cestero HAMPTON & HAMPTON MGMT LEASING

    9240 Woodcrane Dr, Winter Garden, FL 34787
  • /11

    $3,800 Per Month

    • 5 Beds
    • 3 Baths
    • 3,150 Sq Ft
    • House for Rent

    15061 Evergreen Oak Loop, Winter Garden, FL 34787

    SIGNATURE LAKES. BEAUTIFUL 5 BEDROOM, 3 BATH, TWO STORY, ELEGANT HOME IN RESIDENTIAL WINTER GARDEN NEIGHBORHOOD. Rent inlcudes basic cable and internet. Two club houses, two pools, gym, walking trails,community acitivities.This home offers a bright and airy atmosphere with abundant natural light throughout.The open-concept floor plan creates a seamless flow between the living,dining and kitchen

    Victoria Ralicki, PA FLORIDA REALTY INVESTMENTS

    15061 Evergreen Oak Loop, Winter Garden, FL 34787
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    $5,900 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,892 Sq Ft
    • House for Rent

    14612 Glade Hill Park Way, Winter Garden, FL 34787

    Pet Friendly! MOVE-IN READY TODAY! Luxury unfurnished home for rent in Winter Garden/Horizon West! It features 3 MASTER SUITES—one conveniently located on the first floor and two on the second— a rare and versatile layout ideal for multigenerational living. Designer upgrades are found throughout, and recessed lighting in every room creates a warm, bright, and inviting atmosphere from the moment

    Ashley Jimenez LA ROSA REALTY INTERNACIONAL L

    14612 Glade Hill Park Way, Winter Garden, FL 34787
  • /24

    $5,600 Per Month

    • 6 Beds
    • 4 Baths
    • 3,210 Sq Ft
    • House for Rent

    3425 Turningwind Ln, Winter Garden, FL 34787

    Set on a manicured corner lot in the desirable gated community of Windward Cay, the Southern plantation-style exterior — warm yellow stucco, black shutters, full-width upper balcony with black iron railings, and a charming front porch with columns — makes a statement most homes simply can't match. A paver driveway leads to a 3-car garage, and the beautifully maintained grounds set the tone for

    Robert Sullivan COLDWELL BANKER REALTY

    3425 Turningwind Ln, Winter Garden, FL 34787
  • /51

    $5,000 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,743 Sq Ft
    • House for Rent

    16324 Silver Grove Blvd, Winter Garden, FL 34787

    Welcome to this stunning, nearly new residence in the highly desirable community of Silverleaf Reserve at Hamlin in Winter Garden. Built in 2023, this modern two-story home offers approximately 3,743 sq. ft. of thoughtfully designed living space filled with natural light and seamless indoor–outdoor flow. The flexible layout provides multiple options for a home office, game room, or media

    Ron Biegelaar WINDERMERE INTERNATIONAL REALTY

    16324 Silver Grove Blvd, Winter Garden, FL 34787
  • /47

    $5,000 Per Month

    • 5 Beds
    • 3.5 Baths
    • 2,631 Sq Ft
    • House for Rent

    455 Winter Grove Blvd, Winter Garden, FL 34787

    Welcome to this stunning new construction home (2026) located in the desirable city of Winter Garden. This beautifully designed residence offers 5 bedrooms, 3 full bathrooms, and 1 half bath, providing ample space for comfortable living and entertaining. The home features a spacious open floor plan, modern finishes, and abundant natural light throughout. The kitchen flows seamlessly into the

    Paloma Eduar Andrade Froldi WRA BUSINESS & REAL ESTATE

    455 Winter Grove Blvd, Winter Garden, FL 34787
  • /39

    $5,500 Per Month

    • 6 Beds
    • 4 Baths
    • 4,704 Sq Ft
    • House for Rent

    17987 Gourd Neck Loop, Winter Garden, FL 34787

    Prepare to be amazed by this expansive, newly renovated rental in a charming sub-division of Winter Garden, Florida! Offering a rare SIX bedrooms and FOUR bathrooms, this is the perfect solution for a large family or corporate housing. Best of all, the home is fully furnished and ready for immediate move-in, with a preferred lease start of August 1st. The entire home has been spectacularly

    Joel Parrott EXPERT REALTY SOLUTIONS INC.

    17987 Gourd Neck Loop, Winter Garden, FL 34787
  • /45

    $3,800 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,619 Sq Ft
    • House for Rent

    14768 Field Daisy Dr, Winter Garden, FL 34787

    Brand-new home available for rent in Winter Garden. The layout includes a first-floor guest suite and a bonus room above the garage that serves as the fifth bedroom, offering flexibility for a home office, playroom, media room, or guest space. Unlike many new construction rentals, this home was thoughtfully upgraded beyond the builder's standard finishes. Features include upgraded cabinetry and

    Paula Maestrini EMPIRE NETWORK REALTY

    14768 Field Daisy Dr, Winter Garden, FL 34787
  • /32

    $4,000 Per Month

    • 5 Beds
    • 3.5 Baths
    • 2,934 Sq Ft
    • House for Rent

    15143 Kirsty Aly, Winter Garden, FL 34787

    Welcome to this beautifully maintained 5-bedroom, 3.5-bathroom move in ready home, ideally situated on a desirable corner lot in the heart of Hamlin, Winter Garden. With a thoughtfully designed layout, this home features one bedroom on the main floor—perfect for guests or multi generational living—and three additional bedrooms upstairs, offering plenty of space and privacy for the whole

    Jin Cheng ARION REALTY

    15143 Kirsty Aly, Winter Garden, FL 34787
  • /42

    $4,200 Per Month

    • 6 Beds
    • 4 Baths
    • 4,194 Sq Ft
    • House for Rent

    1450 Juniper Hammock St, Winter Garden, FL 34787

    Welcome to this exceptional opportunity to reside in a meticulously maintained 6-bedroom, 4-bathroom, 3-car garage home in the McAllister Landing community, just minutes from the historic charm of Downtown Winter Garden. Situated at the corner of a serene and well-established neighborhood, this residence is surrounded by the captivating allure of majestic oak trees. Upon entry, discover a

    Cui Li RATIO REAL ESTATE, LLC

    1450 Juniper Hammock St, Winter Garden, FL 34787
  • /17

    $3,695 Per Month

    • 5 Beds
    • 3 Baths
    • 3,462 Sq Ft
    • House for Rent

    806 Lost Grove Cir, Winter Garden, FL 34787

    Spacious and beautifully designed 5-bedroom, 3-bathroom home with a 3-car garage located in the heart of Winter Garden. Offering approximately 3,462 square feet of living space, this home features a versatile floor plan perfect for families of all sizes. The first floor includes a formal dining room, a spacious family room, a separate sitting room, and a well-appointed kitchen with granite

    Amanda Yuan MULTI CHOICE REALTY LLC

    806 Lost Grove Cir, Winter Garden, FL 34787
  • /43

    $7,500 Per Month

    • 6 Beds
    • 6.5 Baths
    • 5,174 Sq Ft
    • House for Rent

    7759 Green Mountain Way, Winter Garden, FL 34787

    Welcome to your dream home in Winter Garden, where elegance meets comfort in this stunning single-family executive home with a picturesque view of Lake Hancock. With 6 bedrooms, 6.5 bathrooms, and a host of impressive features, this residence offers a lifestyle of unparalleled grandeur and convenience. As you step inside, you'll be greeted by high ceilings and an open, modern floor plan that

    Esther Griller FLORIDA REALTY INVESTMENTS

    7759 Green Mountain Way, Winter Garden, FL 34787
  • /69

    $10,500 Per Month

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

    15704 Marina Bay Dr, Winter Garden, FL 34787

    Experience elevated Florida living in this exquisite, fully furnished luxury residence at 15704 Marina Bay Drive in the highly desirable Winter Garden area. Beautifully designed with sophisticated finishes, elegant furnishings, and a thoughtfully curated interior, this exceptional home offers a seamless blend of comfort, style, and convenience. From the moment you enter, you'll be welcomed by an

    Corey Cannon BHHS FLORIDA REALTY

    15704 Marina Bay Dr, Winter Garden, FL 34787

Rental Home Trends

Number of 5 Bedroom Homes for Rent
21
Median 5 Bedroom Single Family Home Rent
$4,365
How to Rent a Home