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5-Bedroom Homes for Rent in Winter Garden, FL

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  • /38

    $6,500 per month

    • 5 Beds
    • 6 Baths
    • 4,025 Sq Ft
    • House for Rent

    10472 Petrillo Way, Winter Garden, FL 34787

    Now available for RENT, FOR SALE OR with a LEASE-PURCHASE OPTION. With nightly views of the Disney fireworks and access to top-rated schools, this is more than just a home — it’s a lifestyle you’ll love coming home to. Welcome to 10472 Petrillo Way, located in the serene Winding Bay Preserve community of Winter Garden. This stunning K. Hovnanian Grayson Model home, built in 2022, and offers the

    Agent Photo

    Alexis Bress

    EXP REALTY LLC

    (321) 405-1259

    10472 Petrillo Way, Winter Garden, FL 34787
  • /15

    $2,875 - $3,295 per month

    Silverleaf Oaks

    4 - 5 Beds

    6496 Tabebuia Pkwy, Winter Garden, FL 34787

    Brand-new homes in a prime Winter Garden location near trails, shopping and public lagoons.Silverleaf Oaks features brand-new 3 to 5-bedroom, 2.5 to 3-bathroom homes. Located just outside Orlando, each home offers Smart Home technology, granite countertops and 2-car garages. Residents enjoy easy access to nearby retailers, scenic trails and public lagoons in Winter Garden. Silverleaf Oaks

    6496 Tabebuia Pkwy, Winter Garden, FL 34787
  • /24

    $3,600 per month

    • 5 Beds
    • 3 Baths
    • 3,152 Sq Ft
    • Property for Rent

    15168 Evergreen Oak Loop, Winter Garden, FL 34787

    .... Move in ready ..... Fully Fence ....Rent includes Basic Cable & Internet, Tesla Car Charger, Washer, and Dryer.... No Carpet..... Brand new Luxury Vinyl Flooring in all bedrooms.... This house is located in the desirable Independence community. The Community features amazing amenities including 2 Community Pools, Play Grounds, Boat Ramp, Fishing Docks, Tennis courts, Basketball courts, 2

    Jennie Ho MAY HO REALTY

    15168 Evergreen Oak Loop, Winter Garden, FL 34787
  • /18

    $3,500 per month

    • 5 Beds
    • 3.5 Baths
    • 3,559 Sq Ft
    • House for Rent

    6024 Sunset Isle Dr, Winter Garden, FL 34787

    This property has the best location in Winter Garden. If you want a High School, Elementary School, and Middle School that is top rated this is your home. The Independence Community in Winter Garden boasts a club house, arcade room, gym, boat ramps, and swimming pool. The monthly rent includes all outside yard work. You will not have to go out in the Florida heat.

    6024 Sunset Isle Dr, Winter Garden, FL 34787
  • /27

    $3,700 per month

    • 5 Beds
    • 3 Baths
    • 3,420 Sq Ft
    • House for Rent

    902 Lost Grove Cir, Winter Garden, FL 34787

    This spacious 5-bedroom, 3-bath home has everything you need for comfortable living. The first floor features a private bedroom with a full bath — perfect for guests or family. Upstairs, the oversized master suite boasts dual sinks, a relaxing garden tub, and plenty of space to unwind, along with three additional guest bedrooms.A large loft adds flexibility — ideal for a playroom, home

    Jackie Yuan JHY REALTY INVESTMENTS, LLC

    902 Lost Grove Cir, Winter Garden, FL 34787
  • /17

    $3,415 per month

    • 5 Beds
    • 4 Baths
    • 3,414 Sq Ft
    • House for Rent

    1239 Juniper Hammock St, Winter Garden, FL 34787

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

    1239 Juniper Hammock St, Winter Garden, FL 34787
  • /43

    $6,800 per month

    • 5 Beds
    • 3.5 Baths
    • 4,497 Sq Ft
    • House for Rent

    4940 Palmetto Park Dr, Winter Garden, FL 34787

    Welcome to 4940 Palmetto Park Dr, located in the highly sought-after Orchard Hills community in Winter Garden! This beautifully designed 5-bedroom, 4-bathroom home with a loft, Media Room and dedicated office/den is move-in ready and offers the perfect balance of luxury, comfort, and convenience.From the moment you arrive, you’ll notice the spacious open floor plan, soaring ceilings, and

    Corey Cannon BHHS FLORIDA REALTY

    4940 Palmetto Park Dr, Winter Garden, FL 34787
  • /20

    $2,845 per month

    • 5 Beds
    • 4 Baths
    • 3,406 Sq Ft
    • House for Rent

    1137 Burland Cir, 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 $2989.90. That covers your base rent, $2845.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1137 Burland Cir, Winter Garden, FL 34787
  • /74

    $6,500 per month

    • 6 Beds
    • 4 Baths
    • 4,209 Sq Ft
    • House for Rent

    694 Brooks Field Dr, Winter Garden, FL 34787

    Discover an extraordinary corner-lot estate in Winter Garden’s coveted 34787 zip code—where every detail delivers luxury and comfort. Professionally decorated and fully furnished, this contemporary home offers six spacious bedrooms (including a first-floor primary suite), four full baths, and 4,209 sqft of flawlessly designed living. You’re only a 27-minute, 17-mile drive from Disney Springs, a

    Daniel Pavel WRA BUSINESS & REAL ESTATE

    694 Brooks Field Dr, Winter Garden, FL 34787
  • /20

    $3,495 per month

    • 5 Beds
    • 4 Baths
    • 3,414 Sq Ft
    • House for Rent

    932 Mcpherson Place, 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 $3639.90. That covers your base rent, $3495.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    932 Mcpherson Place, Winter Garden, FL 34787
  • /39

    $5,000 per month

    • 5 Beds
    • 4 Baths
    • 3,897 Sq Ft
    • House for Rent

    9225 Holliston Creek Place, Winter Garden, FL 34787

    Welcome to Your Dream Home in the Heart of Winter Garden!Built by Meritage Homes, this stunning single-family residence perfectly blends elegance, functionality, and resort-style living. Situated on a spacious corner lot, the home boasts upgraded landscaping, custom holiday lighting, and a 2-car side-entry garage for enhanced curb appeal and convenience.Step inside and prepare to

    Matt McKee COMPASS FLORIDA LLC

    9225 Holliston Creek Place, Winter Garden, FL 34787
  • /18

    $3,295 per month

    • 5 Beds
    • 3 Baths
    • 2,231 Sq Ft
    • House for Rent

    6446 Breeze Filled Ln, 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 $3392.90. That covers your base rent, $3295.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Community

    6446 Breeze Filled Ln, Winter Garden, FL 34787
  • /33

    $9,980 per month

    • 7 Beds
    • 6.5 Baths
    • 5,283 Sq Ft
    • House for Rent

    16689 Broadwater Ave, Winter Garden, FL 34787

    Here’s your opportunity to reside in this stunning lake house, which is currently for sale but also seeking tenants. Featuring two bedrooms downstairs and five upstairs, it's perfect for family and guests. Enjoy a home theater and a large screened back patio with breathtaking lake views. Currently on the market for sale, if rented this home will remove it from the for sale market. Don’t miss this

    Krushna Patel COMPASS FLORIDA LLC

    16689 Broadwater Ave, Winter Garden, FL 34787
  • /29

    $4,300 per month

    • 5 Beds
    • 4 Baths
    • 3,626 Sq Ft
    • House for Rent

    12535 Dallington Terrace, Winter Garden, FL 34787

    This gorgeous 5BD/4BA M/I “Brookshire II” home in Foxcrest at Stonecrest offers spacious, flexible living with a solar-heated, saltwater screened pool and a built-in summer kitchen—perfect for year-round enjoyment. The open-concept floor plan features a gourmet kitchen with granite counters, 42" cabinetry, double ovens, and stainless appliances, flowing into a large great room with direct access

    Dean D Nikolic PMI PROPERTY ALLIANCE

    12535 Dallington Terrace, Winter Garden, FL 34787
  • /62

    $7,500 per month

    • 5 Beds
    • 4 Baths
    • 3,993 Sq Ft
    • House for Rent

    12151 Walker Pond Rd, Winter Garden, FL 34787

    Welcome to “Home Again Ranch,” your extraordinary 12+ acre farm that is around the corner from Windermere and tucked away on a quiet cul-de-sac road. You don’t need to drive hours to experience country living at its finest. Rent a large parcel of land zoned agricultural with NO HOA in the heart of one of Central Florida’s most desirable residential areas. The charming main residence has close to

    Simon Simaan THE SIMON SIMAAN GROUP

    12151 Walker Pond Rd, Winter Garden, FL 34787
  • /59

    $3,995 per month

    • 5 Beds
    • 3 Baths
    • 3,747 Sq Ft
    • House for Rent

    2205 Wintermere Pointe Dr, Winter Garden, FL 34787

    Now available for rent in beautiful Winter Garden! Fall in love with this stunning and spacious 5-bedroom, 3-bathroom home located in a gated community with a warm, welcoming neighborhood feel. This home is designed to impress, offering four bedrooms upstairs and a versatile downstairs bedroom perfect for guests or a home office. The master suite is a true retreat, featuring a soaking tub,

    Johany Utrera AVID REALTY LLC

    2205 Wintermere Pointe Dr, Winter Garden, FL 34787
  • /48

    $4,900 per month

    • 5 Beds
    • 4.5 Baths
    • 4,222 Sq Ft
    • House for Rent

    7699 Bowery Dr, Winter Garden, FL 34787

    Welcome to elevated Florida living in the exclusive Ravenna community of Horizon West in Winter Garden, FL. This expansive Winston model by Park Square Homes offers over 4,000 square feet of thoughtfully designed space, blending timeless finishes, modern convenience, and stunning views of Sawgrass Lake along with nightly Disney fireworks. Step through grand 8’ double doors into a soaring

    Brigida Lopez LA ROSA REALTY ORLANDO LLC

    7699 Bowery Dr, Winter Garden, FL 34787
  • /42

    $7,500 per month

    • 5 Beds
    • 4.5 Baths
    • 3,767 Sq Ft
    • House for Rent

    17546 Lake Star Rd, Winter Garden, FL 34787

    Welcome to this stunning 5-bedroom, 4-bathroom residence located in the highly desirable community of Waterleigh in Winter Garden. With over 3,700 sqft of heated living space and situated on an expansive 1.45-acre lot, this home offers an exceptional blend of luxury, comfort, and functionality.Step inside to find soaring cathedral ceilings, elegant crown molding, and a thoughtfully

    Elizabeth Chipre MY REALTY GROUP, LLC.

    17546 Lake Star Rd, Winter Garden, FL 34787
  • /35

    $4,800 per month

    • 5 Beds
    • 3.5 Baths
    • 3,793 Sq Ft
    • House for Rent

    14005 Peach Orchard Way, Winter Garden, FL 34787

    Beautiful 5 bedroom single family home in Horizon West of Winter Garden. This home has 5 bedrooms, 3 1⁄2 bathrooms, an Office and a Loft. The first floor is an open floor plan with Formal Livingroom, Dining Room, Huge Family Room and massive Kitchen. The kitchen features granite countertops, 42" cabinets, walk in Pantry and large Island. The first level also offers a Bedroom with attached

    Thomas Belsky CENTURY 21 CARIOTI

    14005 Peach Orchard Way, Winter Garden, FL 34787
  • /24

    $4,500 per month

    • 5 Beds
    • 4 Baths
    • 2,840 Sq Ft
    • House for Rent

    16124 Azure Key St, Winter Garden, FL 34787

    ** PREMIUM LOT – WATER VIEW-MAINTENANCE FREE COMMUNITY with SMART HOME TECHNOLOGY. Welcome to this beautiful spacious home located in Winter Garden’s highly coveted Waterleigh community which features beautiful homes, incredible amenities and lake views at every turn. A beautiful porch welcomes you to this home, as you enter the foyer, to the left is a bedroom and full bath that can be

    Heather O'Neill FLORIDA HOMES REALTY & MTG

    16124 Azure Key St, Winter Garden, FL 34787
  • /26

    $3,700 per month

    • 5 Beds
    • 3 Baths
    • House for Rent

    7254 Desert Mandarin St, Winter Garden, FL 34787

    This stunning 5/3 home located in one of Winter Garden most sought-after communities. With a full bedroom and bathroom on the first floor, perfect four your guests and another area that you can use as a formal living room or private office. Step into an open concept living area, and a modern kitchen featuring stainless steel appliances, high quality cabinetry and a large center island, ideal for

    Ana Maria Relayze Century 21 World Connection

    7254 Desert Mandarin St, Winter Garden, FL 34787
  • /30

    $7,350 per month

    • 5 Beds
    • 4 Baths
    • 2,617 Sq Ft
    • House for Rent

    Unlisted Address

    Luxury Home in Gated Tilden Place – Winter Garden, FLDiscover exceptional luxury and lifestyle in this 5-bedroom, 4-bathroom executive residence, located in the exclusive gated community of Tilden Place, one of Winter Garden’s most desirable neighborhoods.Property Highlights:5 Bedrooms | 4 Bathrooms | 2-Car GarageFlexible Loft/Bonus Room (can be used as 5th bedroom or

    MARCELLA REGINATO SELECTA REALTY LLC

    Unlisted Address
  • /95

    $7,500 per month

    • 5 Beds
    • 4.5 Baths
    • 3,965 Sq Ft
    • House for Rent

    13271 Tollcross Way, Winter Garden, FL 34787

    Discover modern elegance and timeless luxury in this exceptional new construction home by Toll Brothers. This residence boasts sophisticated upgrades throughout, a well-distributed formal floor plan with a separate formal dining room, and a well-appointed kitchen featuring a walk-in pantry and open views of breakfast area and great room. Designed for comfort and entertaining, the great room

    Carolina Mariano Da Silva PREMIER SOTHEBYS INT'L REALTY

    13271 Tollcross Way, Winter Garden, FL 34787
  • /43

    $4,295 per month

    • 5 Beds
    • 4 Baths
    • 3,610 Sq Ft
    • House for Rent

    13773 Werrington Dr, Winter Garden, FL 34787

    Ready for this beautiful house in one of highly desirable community in Winter Garden - Encore at Ovation ready to rent! Available on beginning of July. This spacious two story house is builded on a corner lot, it has 5 bedrooms and full 4 bathrooms with a formal dining room and gourmet kitchen, quartz countertop. This dynamic lifestyles community, you will enjoy Fitness CenterResort-style

    Yan Zuo EAST PEARL REALTY

    13773 Werrington Dr, Winter Garden, FL 34787
  • /43

    $4,500 per month

    • 5 Beds
    • 3.5 Baths
    • 2,960 Sq Ft
    • House for Rent

    10520 Petrillo Way, Winter Garden, FL 34787

    Welcome to 10520 Petrillo Way, an exceptional fully furnished one-story rental home located in an exclusive Winter Garden, Florida community, offering unparalleled comfort, space, and a prime location just minutes from Disney World! This bright and airy 4-bedroom residence boasts high ceilings, abundant natural light, and a versatile layout including a private annex with its own bedroom,

    Elkin Marcillo MARCILLO REAL ESTATE LLC

    10520 Petrillo Way, Winter Garden, FL 34787
  • /25

    $3,895 per month

    • 5 Beds
    • 4 Baths
    • 3,439 Sq Ft
    • House for Rent

    173 Donner Dr, Winter Garden, FL 34787

    ***LEASE SPECIAL*** OFFERING A DISCOUNT OF $1800 OFF THE FIRST MONTH'S RENT FOR AN 18 MONTH LEASE*** I wanted to share details about an executive home available in the desirable Deerfield Place Subdivision. This spacious home boasts 5 bedrooms and 4 bathrooms across more than 3400 square feet. The downstairs features a convenient bedroom and full bath, a formal dining room, a formal sitting

    Barry Stephens MAINFRAME REAL ESTATE

    173 Donner Dr, Winter Garden, FL 34787
  • /46

    $3,840 per month

    • 5 Beds
    • 4 Baths
    • 3,649 Sq Ft
    • House for Rent

    15313 Hayworth Dr, Winter Garden, FL 34787

    This home features a BRAND NEW roof, NEW garage door opener & NEW vinyl fencing in the back yard for privacy and security add a TON more value. Welcome to the magnificent Belle Meade gated neighborhood in Winter Garden, where you'll find this incredible 5-bedroom home that is sure to leave you in awe. With over 3645 square feet of living space and 4 bathrooms, this Cambridge-built home is sure to

    David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

    15313 Hayworth Dr, Winter Garden, FL 34787
  • /74

    $11,000 per month

    • 5 Beds
    • 5.5 Baths
    • 5,054 Sq Ft
    • House for Rent

    7514 John Hancock Dr, Winter Garden, FL 34787

    Step into luxury living in the heart of Winter Garden, where lakeside charm meets refined elegance.Situated along the stunning shores of Lake Hancock, this impressive two-story home offers 5 spacious bedrooms, 5.5 bathrooms, and a 3-car garage, all crafted for comfort, style, and convenience.Professional photos coming soon!From the moment you enter, you’re welcomed by soaring

    Patricia Mascarenhas Bonina Zimath CHARLES RUTENBERG REALTY ORLANDO

    7514 John Hancock Dr, Winter Garden, FL 34787
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