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Displaying: For Rent

Location: Winter Haven

Property Type(s): Single Family

Price: $2,000 to $2,499

Winter Haven - 59 properties found

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  • 368 KAYDEN CV, WINTER HAVEN, FL 33884

    $2,29056 Days on yellowkey   MLS ID: O6402509

    For RENT O6402509 - 368 KAYDEN CV, WINTER HAVEN, FL 33884 36 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2112
       Built: 2026
    Community: Peace Creek Reserve 40'S
    Single Family


    Estimated Monthly Payment: $13 (change assumption)
    Mortgage ($13)


    Taxes:

    Elementary School: Wahneta Elem

    High School: Lake Region High

    Tax Year:

    Middle School: Westwood Middle


  • 1498 AUSTIN ST, WINTER HAVEN, FL 33884

    $2,00091 Days on yellowkey   MLS ID: P4938243

    0 Days Off yellowkey (back on 6/16/2026)

    For RENT P4938243 - 1498 AUSTIN ST, WINTER HAVEN, FL 33884 24 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1935
       Built: 2023
    Community: Peace Crk Reserve
    Single Family


    Estimated Monthly Payment: $11 (change assumption)
    Mortgage ($11)


    Taxes:

    Elementary School: South Pointe Elementary

    High School: Lake Region High

    Tax Year:

    Middle School: Westwood Middle


  • 1127 SEEDORF DR, WINTER HAVEN, FL 33881

    $2,4009 Days on yellowkey   MLS ID: O6415155

    For RENT O6415155 - 1127 SEEDORF DR, WINTER HAVEN, FL 33881 27 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2004
       Built: 2022
    Community: Lake Lucerne Ph 6
    Single Family


    Estimated Monthly Payment: $13 (change assumption)
    Mortgage ($13)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 3905 GIORGIO DR, WINTER HAVEN, FL 33884

    $2,05047 Days on yellowkey   MLS ID: O6406247

    REDUCED by $50 (2.4%) on 06/15/2026

    For RENT O6406247 - 3905 GIORGIO DR, WINTER HAVEN, FL 33884 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1707
       Built: 2026

    Single Family


    Estimated Monthly Payment: $11 (change assumption)
    Mortgage ($11)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1662 TEAGAN LN, WINTER HAVEN, FL 33884

    $2,20035 Days on yellowkey   MLS ID: O6409324

    REDUCED by $200 (8.3%) on 06/15/2026

    For RENT O6409324 - 1662 TEAGAN LN, WINTER HAVEN, FL 33884 21 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1432
       Built: 2024
    Community: Peace Crk Reserve
    Single Family


    Estimated Monthly Payment: $12 (change assumption)
    Mortgage ($12)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1042 MICHELANGELO LN, WINTER HAVEN, FL 33884

    $2,27548 Days on yellowkey   MLS ID: S5149443

    REDUCED by $200 (8.1%) on 06/15/2026

    For RENT S5149443 - 1042 MICHELANGELO LN, WINTER HAVEN, FL 33884 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2386
       Built: 2022
    Community: Estates/Lk Florence
    Single Family


    Estimated Monthly Payment: $12 (change assumption)
    Mortgage ($12)


    Taxes:

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year:

    Middle School: Denison Middle


  • 172 INMAN BLVD, WINTER HAVEN, FL 33881

    $2,09910 Days on yellowkey   MLS ID: O6416831

    For RENT O6416831 - 172 INMAN BLVD, WINTER HAVEN, FL 33881 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1560
       Built: 2023
    Community: Inman Grvs Ph 1
    Single Family


    Estimated Monthly Payment: $12 (change assumption)
    Mortgage ($12)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 295 LAKE SMART CIR, WINTER HAVEN, FL 33881

    $2,10033 Days on yellowkey   MLS ID: L4962064

    0 Days Off yellowkey (back on 6/13/2026)

    For RENT L4962064 - 295 LAKE SMART CIR, WINTER HAVEN, FL 33881 15 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1725
       Built: 2021
    Community: Lake Smart Pointe
    Single Family


    Estimated Monthly Payment: $12 (change assumption)
    Mortgage ($12)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 866 SUMMER GLEN DR, WINTER HAVEN, FL 33880

    $2,00013 Days on yellowkey   MLS ID: P4938960

    0 Days Off yellowkey (back on 6/13/2026)

    For RENT P4938960 - 866 SUMMER GLEN DR, WINTER HAVEN, FL 33880 12 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1739
       Built: 2006
    Community: Coventry Cove
    Single Family


    Estimated Monthly Payment: $11 (change assumption)
    Mortgage ($11)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • WINTER HAVEN, FL 33881

    $2,40025 Days on yellowkey   MLS ID: S5150920

    For RENT S5150920 - WINTER HAVEN, FL 33881 12 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1717
       Built: 2018
    Community: Lake Lucerne Ph 1
    Single Family


    Estimated Monthly Payment: $13 (change assumption)
    Mortgage ($13)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 265 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881

    $2,20012 Days on yellowkey   MLS ID: O6414019

    For RENT O6414019 - 265 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1426
       Built: 2020
    Community: Lucerne Park Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $12 (change assumption)
    Mortgage ($12)


    Taxes:

    Elementary School: Lake Alfred Elem

    High School: Haines City Senior High

    Tax Year:

    Middle School: Daniel Jenkins Academy of Technology Middle


  • 241 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881

    $2,00048 Days on yellowkey   MLS ID: S5149482

    0 Days Off yellowkey (back on 6/10/2026)

    For RENT S5149482 - 241 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1725
       Built: 2020
    Community: Lucerne Park Reserve
    Single Family


    Estimated Monthly Payment: $11 (change assumption)
    Mortgage ($11)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1050 MICHELANGELO LN, WINTER HAVEN, FL 33884

    $2,10023 Days on yellowkey   MLS ID: P4938891

    For RENT P4938891 - 1050 MICHELANGELO LN, WINTER HAVEN, FL 33884 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1659
       Built: 2022
    Community: Estates/Lk Florence
    Single Family


    Estimated Monthly Payment: $12 (change assumption)
    Mortgage ($12)


    Taxes:

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year:

    Middle School: Denison Middle


  • 521 REGGIE RD, WINTER HAVEN, FL 33884

    $2,45092 Days on yellowkey   MLS ID: L4960535

    REDUCED by $150 (5.8%) on 06/09/2026

    For RENT L4960535 - 521 REGGIE RD, WINTER HAVEN, FL 33884 24 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2093
       Built: 2024
    Community: Peace Crk Reserve
    Single Family


    Estimated Monthly Payment: $13 (change assumption)
    Mortgage ($13)


    Taxes:

    Elementary School: Chain O Lakes Elem

    High School: Winter Haven Senior

    Tax Year:

    Middle School: McLaughlin Academy Of Excellence


  • 624 HONEY BELL RD, WINTER HAVEN, FL 33880

    $2,00016 Days on yellowkey   MLS ID: S5151468

    For RENT S5151468 - 624 HONEY BELL RD, WINTER HAVEN, FL 33880 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1690
       Built: 2022
    Community: Squires Grove Ph 2
    Single Family


    Estimated Monthly Payment: $11 (change assumption)
    Mortgage ($11)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 252 SANTA ROSA DR, WINTER HAVEN, FL 33884

    $2,495144 Days on yellowkey   MLS ID: TB8470100

    For RENT TB8470100 - 252 SANTA ROSA DR, WINTER HAVEN, FL 33884 22 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2116
       Built: 1988
    Community: Overlook Estates
    Spa: Yes

    Single Family


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


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 504 TWIN BOWFISH WAY, WINTER HAVEN, FL 33881

    $2,15037 Days on yellowkey   MLS ID: O6408732

    For RENT O6408732 - 504 TWIN BOWFISH WAY, WINTER HAVEN, FL 33881 23 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1989
       Built: 2022
    Community: Lake Lucerne Ph 5
    Single Family


    Estimated Monthly Payment: $12 (change assumption)
    Mortgage ($12)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 2371 BRASSIE CT, WINTER HAVEN, FL 33884

    $2,350105 Days on yellowkey   MLS ID: O6389720

    INCREASED by $100 (4.4%) on 06/05/2026

    For RENT O6389720 - 2371 BRASSIE CT, WINTER HAVEN, FL 33884 23 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2522
       Built: 2022
    Community: Villamar Ph 3
    Single Family


    Estimated Monthly Payment: $13 (change assumption)
    Mortgage ($13)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 693 REGGIE RD, WINTER HAVEN, FL 33884

    $2,30044 Days on yellowkey   MLS ID: S5149706

    For RENT S5149706 - 693 REGGIE RD, WINTER HAVEN, FL 33884 20 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1933
       Built: 2024
    Community: Peace Crk Reserve
    Single Family


    Estimated Monthly Payment: $13 (change assumption)
    Mortgage ($13)


    Taxes:

    Elementary School: Wahneta Elem

    High School: Lake Region High

    Tax Year:

    Middle School: Westwood Middle


  • 1343 BENEVENTO DR, WINTER HAVEN, FL 33884

    $2,00021 Days on yellowkey   MLS ID: O6413294

    For RENT O6413294 - 1343 BENEVENTO DR, WINTER HAVEN, FL 33884 12 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1849
       Built: 2020
    Community: Villamar Ph 2
    Single Family


    Estimated Monthly Payment: $11 (change assumption)
    Mortgage ($11)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


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