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Winter Garden Single Family Homes For Rent - 99 homes

Winter Garden Single Family Home Rentals are located in Orange County, Florida. Find Single Family Homes in Winter Garden for rent with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Winter Garden single family houses.

Location: Winter Garden

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  • 10649 ATWATER BAY DR, WINTER GARDEN, FL 34787

    $3,500Listed 07/06/2026 10:16AM   MLS ID: O6422504

    For RENT O6422504 - 10649 ATWATER BAY DR, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2476
       Built: 2019
    Community: Waterleigh Ph 2D
    Single Family


    Estimated Monthly Payment: $19 (change assumption)
    Mortgage ($19)


    Taxes:

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Water Spring Middle


  • 17131 BEACHGRASS ALY, WINTER GARDEN, FL 34787

    $3,2006 Days on yellowkey   MLS ID: O6421324

    REDUCED by $200 (5.9%) on 07/06/2026

    For RENT O6421324 - 17131 BEACHGRASS ALY, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2195
       Built: 2026

    Single Family


    Estimated Monthly Payment: $18 (change assumption)
    Mortgage ($18)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1944 PORTCASTLE CIR, WINTER GARDEN, FL 34787

    $2,700Listed 07/06/2026 12:08PM   MLS ID: O6421978

    For RENT O6421978 - 1944 PORTCASTLE CIR, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1857
       Built: 2006
    Community: Stone Crk A-1 & A-2
    Single Family


    Estimated Monthly Payment: $15 (change assumption)
    Mortgage ($15)


    Taxes:

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year:

    Middle School: SunRidge Middle


  • 15006 SUMMER HARVEST ST, WINTER GARDEN, FL 34787

    $3,35012 Days on yellowkey   MLS ID: O6419493

    0 Days Off yellowkey (back on 7/6/2026)

    For RENT O6419493 - 15006 SUMMER HARVEST ST, WINTER GARDEN, FL 34787 24 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2450
       Built: 2024
    Community: Harvest/Ovation
    Single Family


    Estimated Monthly Payment: $18 (change assumption)
    Mortgage ($18)


    Taxes:

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Water Spring Middle


  • 13891 TITLE WAY, WINTER GARDEN, FL 34787

    $2,85025 Days on yellowkey   MLS ID: S5151841

    0 Days Off yellowkey (back on 7/6/2026)

    REDUCED by $150 (5.0%) on 06/24/2026

    For RENT S5151841 - 13891 TITLE WAY, WINTER GARDEN, FL 34787 25 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2492
       Built: 2022
    Community: Storey Grove
    Single Family


    Estimated Monthly Payment: $16 (change assumption)
    Mortgage ($16)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 17051 QUICKSILVER AVE, WINTER GARDEN, FL 34787

    $3,0007 Days on yellowkey   MLS ID: O6420878

    0 Days Off yellowkey (back on 7/6/2026)

    For RENT O6420878 - 17051 QUICKSILVER AVE, WINTER GARDEN, FL 34787 12 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2508
       Built: 2021
    Community: Waterside On Johns Lake
    Single Family


    Estimated Monthly Payment: $16 (change assumption)
    Mortgage ($16)


    Taxes:

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year:

    Middle School: Hamlin Middle


  • 17119 QUICKSILVER AVE, WINTER GARDEN, FL 34787

    $3,0001 Day on yellowkey   MLS ID: O6422443

    For RENT O6422443 - 17119 QUICKSILVER AVE, WINTER GARDEN, FL 34787 15 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2030
       Built: 2021
    Community: Waterside On Johns Lake - Phase 2C
    Single Family


    Estimated Monthly Payment: $16 (change assumption)
    Mortgage ($16)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 17398 CHANNEL WAY, WINTER GARDEN, FL 34787

    $3,2751 Day on yellowkey   MLS ID: O6422420

    For RENT O6422420 - 17398 CHANNEL WAY, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2782
       Built: 2019
    Community: Waterside/Johns Lk-Ph 2B
    Single Family


    Estimated Monthly Payment: $18 (change assumption)
    Mortgage ($18)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 9240 WOODCRANE DR, WINTER GARDEN, FL 34787

    $4,79992 Days on yellowkey   MLS ID: O6396748

    REDUCED by $700 (12.7%) on 06/09/2026

    For RENT O6396748 - 9240 WOODCRANE DR, WINTER GARDEN, FL 34787 46 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3760
       Built: 2015
    Community: Watermark Ph 1B
    Single Family


    Estimated Monthly Payment: $26 (change assumption)
    Mortgage ($26)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 2031 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $3,45033 Days on yellowkey   MLS ID: O6413931

    For RENT O6413931 - 2031 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 28 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2048
       Built: 2000
    Community: Wintermere Pointe
    Single Family


    Estimated Monthly Payment: $19 (change assumption)
    Mortgage ($19)


    Taxes:

    Elementary School: Lake Whitney Elem

    High School: Windermere High School

    Tax Year:

    Middle School: SunRidge Middle


  • 450 WINTER GROVE BLVD, WINTER GARDEN, FL 34787

    $6,0005 Days on yellowkey   MLS ID: O6418449

    For RENT O6418449 - 450 WINTER GROVE BLVD, WINTER GARDEN, FL 34787 100 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4272
       Built: 2026
    Community: Winter Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $33 (change assumption)
    Mortgage ($33)


    Taxes:

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year:

    Middle School: SunRidge Middle


  • 1631 SHERBOURNE ST, WINTER GARDEN, FL 34787

    $2,6803 Days on yellowkey   MLS ID: O6422395

    For RENT O6422395 - 1631 SHERBOURNE ST, WINTER GARDEN, FL 34787 21 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1709
       Built: 2001
    Community: Stone Creek 44/131
    Single Family


    Estimated Monthly Payment: $15 (change assumption)
    Mortgage ($15)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 7171 SUMMERLAKE GROVES ST, WINTER GARDEN, FL 34787

    $3,2507 Days on yellowkey   MLS ID: O6421017

    For RENT O6421017 - 7171 SUMMERLAKE GROVES ST, WINTER GARDEN, FL 34787 22 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2598
       Built: 2017
    Community: Highlands/Summerlake Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $18 (change assumption)
    Mortgage ($18)


    Taxes:

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Hamlin Middle


  • 16453 HAMLIN VIEW ST, WINTER GARDEN, FL 34787

    $3,1004 Days on yellowkey   MLS ID: O6422141

    For RENT O6422141 - 16453 HAMLIN VIEW ST, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2088
       Built: 2025
    Community: Hamlin Pointe
    Single Family


    Estimated Monthly Payment: $17 (change assumption)
    Mortgage ($17)


    Taxes:

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Hamlin Middle


  • 14180 TITLE WAY, WINTER GARDEN, FL 34787

    $3,2005 Days on yellowkey   MLS ID: O6421850

    For RENT O6421850 - 14180 TITLE WAY, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2481
       Built: 2020
    Community: Storey Grove Ph 2
    Single Family


    Estimated Monthly Payment: $18 (change assumption)
    Mortgage ($18)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • WINTER GARDEN, FL 34787

    $2,7495 Days on yellowkey   MLS ID: O6421793

    For RENT O6421793 - WINTER GARDEN, FL 34787 15 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1606
       Built: 2006
    Community: Stone Crk A-1 & A-2
    Single Family


    Estimated Monthly Payment: $15 (change assumption)
    Mortgage ($15)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 15010 SUMMER HARVEST ST, WINTER GARDEN, FL 34787

    $3,200151 Days on yellowkey   MLS ID: O6371081

    REDUCED by $200 (5.9%) on 06/17/2026

    For RENT O6371081 - 15010 SUMMER HARVEST ST, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2322
       Built: 2024
    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $18 (change assumption)
    Mortgage ($18)


    Taxes:

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Water Spring Middle


  • 8222 TOPSAIL PL, WINTER GARDEN, FL 34787

    $5,99524 Days on yellowkey   MLS ID: O6416728

    REDUCED by $255 (4.1%) on 06/27/2026

    For RENT O6416728 - 8222 TOPSAIL PL, WINTER GARDEN, FL 34787 57 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4199
       Built: 2021
    Community: Lakeshore Preserve Ph 5
    Single Family


    Estimated Monthly Payment: $33 (change assumption)
    Mortgage ($33)


    Taxes:

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year:

    Middle School: Water Spring Middle


  • 545 FIRST CAPE CORAL DR, WINTER GARDEN, FL 34787

    $3,2007 Days on yellowkey   MLS ID: O6420237

    For RENT O6420237 - 545 FIRST CAPE CORAL DR, WINTER GARDEN, FL 34787 28 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2563
       Built: 2006
    Community: Black Lake Park Ph 01
    Single Family


    Estimated Monthly Payment: $18 (change assumption)
    Mortgage ($18)


    Taxes:

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year:

    Middle School: SunRidge Middle


  • WINTER GARDEN, FL 34787

    $2,5895 Days on yellowkey   MLS ID: O6421784

    For RENT O6421784 - WINTER GARDEN, FL 34787 16 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1651
       Built: 2002
    Community: Stone Creek 48 140
    Single Family


    Estimated Monthly Payment: $14 (change assumption)
    Mortgage ($14)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None




Why Bother Searching Elsewhere for Winter Garden Single Family Homes for Rent?

Winter Garden home, townhome, and condo, villa, and other listing sale data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on single family homes for rent in Winter Garden. You can use our website to view Multiple Listing Service (MLS) data on Winter Garden single family homes. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Winter Garden single family home listings.



Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.