28

5-Bedroom Houses 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
  • /19

    $3,095 per month

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

    6452 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 $3192.90. That covers your base rent, $3095.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Community

    6452 Breeze Filled Ln, Winter Garden, FL 34787
  • /48

    $5,000 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
  • /20

    $3,295 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 $3439.90. That covers your base rent, $3295.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1137 Burland Cir, Winter Garden, FL 34787
  • /40

    $11,495 per month

    • 7 Beds
    • 8 Baths
    • 6,514 Sq Ft
    • House for Rent

    15711 Panther Lake Dr, Winter Garden, FL 34787

    Welcome to an unparalleled offering of luxury lakefront living in the prestigious Lakeshore community of Winter Garden. This exceptional estate spans over 6,500 square feet of thoughtfully curated living space, blending timeless sophistication with modern functionality. Privately nestled along the shimmering shoreline of a serene, non-motorized lake, this residence boasts its own private dock and

    Karen Ledet EXP REALTY LLC

    15711 Panther Lake Dr, Winter Garden, FL 34787
  • /39

    $3,700 per month

    • 5 Beds
    • 3 Baths
    • 3,382 Sq Ft
    • House for Rent

    944 Lost Grove Cir, Winter Garden, FL 34787

    Welcome to this move-in ready 5-bedroom, 3-bathroom two-story home located at 944 Lost Grove Circle in Winter Garden, FL. Offering 2,856 sq ft of living space, this spacious home includes a 2-car garage and a versatile loft with built-in speakers, perfect for a movie room or family entertainment area with a true cinematic feel.As you enter, you’re greeted by an open-concept living and

    Sabrina Freeman CHARLES RUTENBERG REALTY ORLANDO

    944 Lost Grove Cir, 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
  • /29

    $3,498 per month

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

    6526 Tabebuia Pkwy, Winter Garden, FL 34787

    BRAND NEW! 5-Bedroom, 3-Bathroom Single-Family Home in the Desirable Silverleaf Oaks CommunityNow is your chance to rent a brand-new home! This stunning 5-bedroom, 3-bathroom property, built by Pulte, offers modern comfort and thoughtful design in the sought-after Silverleaf Oaks neighborhood.The home features one bedroom and a full bathroom conveniently located on the first

    Ron Biegelaar WINDERMERE INTERNATIONAL REALTY

    6526 Tabebuia Pkwy, Winter Garden, FL 34787
  • /32

    $3,700 per month

    • 5 Beds
    • 3 Baths
    • 2,600 Sq Ft
    • House for Rent

    7254 Desert Mandarin St, Winter Garden, FL 34787

    Spectacular and well maintained 5/3 house with one bedroom and complete bathroom downstairs, an office/den space, small closet/storage, open kitchen with double wall oven, big pantry, wine cooler, many cabinets and drawers. All tile and laminated floors, 4 good size bedrooms upstairs and the laundry room with its own sink. The patio is partially covered, ideal space to relax after a day of work

    Roberto Castillo 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
  • /45

    $5,800 per month

    • 5 Beds
    • 4.5 Baths
    • 3,860 Sq Ft
    • House for Rent

    16477 Silver Brook Way, Winter Garden, FL 34787

    Imagine waking up every morning in a home that feels like it was designed just for you! This gorgeous 2025-built house in Winter Garden is waiting to become the backdrop for your family's most cherished memories. You'll absolutely adore the spacious 3,896 square feet of living space that gives everyone room to breathe, play, and grow. With 5 generously-sized bedrooms and 4.5 stylish bathrooms,

    Paulo Victor Ferreira CHARLES RUTENBERG REALTY ORLANDO

    16477 Silver Brook Way, Winter Garden, FL 34787
  • /86

    $6,500 per month

    • 5 Beds
    • 4 Baths
    • 3,856 Sq Ft
    • House for Rent

    14807 Winter Stay Dr, Winter Garden, FL 34787

    Lovers of Horizon West, Winter Garden, Disney World, Golf, Sunsets, Swimming Pools, Heated Spas, and Relaxation... Prepare to be captivated by this stunning luxury rental home at 14807 Winter Stay Drive, Winter Garden, FL. Boasting 3,856 square feet of meticulously designed living space, this modern oasis offers an unparalleled blend of elegance, comfort, and convenience. Step outside and

    Daniel Betancourt EXP REALTY LLC

    14807 Winter Stay Dr, Winter Garden, FL 34787
  • /20

    $4,500 per month

    • 5 Beds
    • 4.5 Baths
    • 3,136 Sq Ft
    • House for Rent

    15095 Mayberry Dr, Winter Garden, FL 34787

    Stunning Lakeview Home for Rent – Spacious, Elegant, and Move-In Ready!Welcome to your future home – a truly impressive rental property offering luxury, space, and breathtaking views. This beautiful 5-bedroom, 4.5-bathroom residence is perfectly designed for those who value comfort, style, and functionality.With 3,243 square feet of living space, every room in this home feels open and

    Moniele Coelho WRA BUSINESS & REAL ESTATE

    15095 Mayberry Dr, Winter Garden, FL 34787
  • /55

    $6,000 per month

    • 5 Beds
    • 3.5 Baths
    • 4,305 Sq Ft
    • House for Rent

    1734 Amsel Falls Park Terrace, Winter Garden, FL 34787

    Welcome to this stunning 5-bedroom, 4 full bath, and 2 half bath modern masterpiece with high ceilings and exquisite iron rod railing. The heart of the home is the modern kitchen, a chef's dream with sleek countertops, top-of-the-line appliances, and ample storage space. Step outside to discover the ultimate entertainment oasis - a pool house with a large game room and large theater style loft,

    Krushna Patel COMPASS FLORIDA LLC

    1734 Amsel Falls Park Terrace, Winter Garden, FL 34787
  • /63

    $4,600 per month

    • 5 Beds
    • 5 Baths
    • 4,305 Sq Ft
    • House for Rent

    9567 Meadow Hunt Way, Winter Garden, FL 34787

    Welcome to this beautifully upgraded 5-bedroom, 5-bathroom floorplan, where comfort meets style in the highly sought-after Watermark community. One of the bedrooms has been thoughtfully converted into a spacious media room by the original owners in 2019, but it can easily function as a fifth bedroom if needed. From the charming front porch to the shining luxury tile floors, this home is filled

    Jing Yue INTEREALTY SERVICE

    9567 Meadow Hunt Way, Winter Garden, FL 34787
  • /43

    $7,750 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
  • /85

    $9,950 per month

    • 7 Beds
    • 6.5 Baths
    • 5,976 Sq Ft
    • House for Rent

    15469 Shorebird Ln, Winter Garden, FL 34787

    Luxury Lakefront Living at Its Finest Breathtaking Views & Prime Location Discover the pinnacle of elegance and comfort in this stunning lakefront model home, perfectly positioned on an oversized corner lot (0.54 Acres) with unparalleled views of the Lake and the Orange County National Golf Course in the front of the property. Seamless Indoor-Outdoor Living Step through the grand two-story foyer

    Christine Kim SOGO REAL ESTATE SERVICES LLC

    15469 Shorebird Ln, 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
  • /46

    $3,900 per month

    • 5 Beds
    • 3 Baths
    • 2,945 Sq Ft
    • House for Rent

    13909 Eylewood Dr, Winter Garden, FL 34787

    Stunning 5-Bedroom Home for Rent in Stoneybrook West – Winter GardenSOLAR PANELS INCLUDED! Your power bill will be very low. Located in one of Winter Garden’s most sought-after gated communities, this beautifully furnished two-story home offers 5 bedrooms, 3.5 bathrooms, and an unbeatable blend of comfort and luxury.Step into a bright, open floor plan with soaring

    Umberto Da Cunha Neto WRA BUSINESS & REAL ESTATE

    13909 Eylewood Dr, 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

    Well appointed Executive home in coveted Deerfield Place Subdivision with Lawn Care Included! A rare, spacious, 5 bedroom, 4 bath home with over 3400 square feet. Downstairs features 1 bedroom and full bath, Formal Dining Room, Formal Sitting Room and a generous Family Area. This home also features beautiful wood laminate flooring, oversize kitchen, huge upstairs bonus room. a private, expansive,

    Barry Stephens MAINFRAME REAL ESTATE

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

    $4,040 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
  • /30

    $3,300 per month

    • 5 Beds
    • 3 Baths
    • 3,380 Sq Ft
    • House for Rent

    718 Willett Dr, Winter Garden, FL 34787

    Welcome to the charming Winter Garden neighborhood of Regency Oaks ! I'm thrilled to present to you this spacious 5-bedroom, 3-bathroom gem that perfectly embodies the comfort and convenience you've been searching for. Located in the sought-after Winter Garden area, this home is just minutes away from the bustling Fowler Grove shopping district and the vibrant downtown Winter Garden scene, where

    Doreen Landi ENGEL & VOLKERS CLERMONT

    718 Willett Dr, Winter Garden, FL 34787
  • /30

    $6,500 per month

    • 5 Beds
    • 4.5 Baths
    • 3,816 Sq Ft
    • House for Rent

    15161 Canoe Place, Winter Garden, FL 34787

    AVAILABLE 06/26/2025 – FULLY FURNISHEDDiscover this stunning furnished corner-lot home in Winter Garden, located in the highly sought-after Lake Shore community, one of Central Florida’s most desirable neighborhoods.With 3,816 sq ft of living space, this elegant two-story home offers the perfect blend of comfort and functionality. The first floor features a private guest suite, a bright formal

    Maqueli Gewehr WRA BUSINESS & REAL ESTATE

    15161 Canoe Place, Winter Garden, FL 34787
  • /29

    $4,500 per month

    • 5 Beds
    • 4 Baths
    • 3,175 Sq Ft
    • House for Rent

    14582 Old Thicket Trace, Winter Garden, FL 34787

    One or more photo(s) has been virtually staged. INDEPENDENCE POOL home with Carriage House / In law suite above garage (1 bedroom, 1 bath and kitchen area ) is what you have been waiting for. Situated on a large corner lot with lots of curb appeal. As you walk up to your future home you are greeted by your large front porch. Exquisite flooring and granite through out. Stainless steel applianced

    Sabah Rab APEX INTERNATIONAL BROKERAGE

    14582 Old Thicket Trace, Winter Garden, FL 34787
  • /44

    $5,400 per month

    • 5 Beds
    • 3.5 Baths
    • 4,384 Sq Ft
    • House for Rent

    14572 Black Quill Dr, Winter Garden, FL 34787

    Prime Location in Horizon West – A rare opportunity to own a stunning property in one of the most sought-after communities in Central Florida. Situated within walking distance to the vibrant Hamlin area, this home is ideally located near a wide array of amenities including upscale restaurants, luxury cinemas, top-rated schools, and major banking institutions.This meticulously maintained,

    Marcelo Moura DOUBLE M GROUP COMPANY

    14572 Black Quill Dr, Winter Garden, FL 34787
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