REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search


Displaying: For Rent

Location: Winter Haven

Property Type(s): Single Family

Price: $1,500 to $1,999

Winter Haven - 38 properties found

Sort:
  • 603 TERRANOVA DR, WINTER HAVEN, FL 33884

    $1,9858 Days on yellowkey   MLS ID: B4902246

    0 Days Off yellowkey (back on 5/1/2026)

    For RENT B4902246 - 603 TERRANOVA DR, WINTER HAVEN, FL 33884 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1699
       Built: 2004
    Community: Terranova Ph 01A
    Single Family


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


    Taxes:

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year:

    Middle School: Denison Middle


  • 4819 SUMMERFIELD CIR, WINTER HAVEN, FL 33881

    $1,800138 Days on yellowkey   MLS ID: O6366521

    0 Days Off yellowkey (back on 5/1/2026)

    For RENT O6366521 - 4819 SUMMERFIELD CIR, WINTER HAVEN, FL 33881 17 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1688
       Built: 2016
    Community: Country Club Estates
    Single Family


    Estimated Monthly Payment: $10 (change assumption)
    Mortgage ($10)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 2007 9TH ST NE, WINTER HAVEN, FL 33881

    $1,8004 Days on yellowkey   MLS ID: S5148784

    For RENT S5148784 - 2007 9TH ST NE, WINTER HAVEN, FL 33881 13 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1242
       Built: 1967
    Community: Lake Idyll Estates
    Single Family


    Estimated Monthly Payment: $10 (change assumption)
    Mortgage ($10)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1744 TEAGAN LN, WINTER HAVEN, FL 33884

    $1,8004 Days on yellowkey   MLS ID: S5148933

    For RENT S5148933 - 1744 TEAGAN LN, WINTER HAVEN, FL 33884 16 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1444
       Built: 2024
    Community: Peace Crk Reserve
    Single Family


    Estimated Monthly Payment: $10 (change assumption)
    Mortgage ($10)


    Taxes:

    Elementary School: South Pointe Elementary

    High School: Lake Region High

    Tax Year:

    Middle School: Westwood Middle


  • 2893 WHISPERING TRAILS DR, WINTER HAVEN, FL 33884

    $1,75040 Days on yellowkey   MLS ID: S5146531

    REDUCED by $150 (7.9%) on 04/30/2026

    For RENT S5146531 - 2893 WHISPERING TRAILS DR, WINTER HAVEN, FL 33884 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1268
       Built: 2017
    Community: Whispering Trails Ph 02
    Single Family


    Estimated Monthly Payment: $10 (change assumption)
    Mortgage ($10)


    Taxes:

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year:

    Middle School: Denison Middle


  • 1228 HAINES DR, WINTER HAVEN, FL 33881

    $1,9956 Days on yellowkey   MLS ID: S5148202

    For RENT S5148202 - 1228 HAINES DR, WINTER HAVEN, FL 33881 11 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1431
       Built: 2019

    Single Family


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


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 3992 WARBLER DR, WINTER HAVEN, FL 33880

    $1,8005 Days on yellowkey   MLS ID: S5148815

    For RENT S5148815 - 3992 WARBLER DR, WINTER HAVEN, FL 33880 15 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1632
       Built: 2004
    Community: Queens Cove Ph 04
    Single Family


    Estimated Monthly Payment: $10 (change assumption)
    Mortgage ($10)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1776 CARNOSTIE RD, WINTER HAVEN, FL 33884

    $1,8007 Days on yellowkey   MLS ID: O6402709

    0 Days Off yellowkey (back on 4/29/2026)

    For RENT O6402709 - 1776 CARNOSTIE RD, WINTER HAVEN, FL 33884 14 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1269
       Built: 2022

    Single Family


    Estimated Monthly Payment: $10 (change assumption)
    Mortgage ($10)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • WINTER HAVEN, FL 33880

    $1,81920 Days on yellowkey   MLS ID: TB8497765

    REDUCED by $30 (1.6%) on 04/29/2026

    For RENT TB8497765 - WINTER HAVEN, FL 33880 15 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1300
       Built: 2010
    Community: Central Pointe
    Single Family


    Estimated Monthly Payment: $10 (change assumption)
    Mortgage ($10)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • WINTER HAVEN, FL 33884

    $1,97920 Days on yellowkey   MLS ID: TB8497756

    REDUCED by $20 (1.0%) on 04/29/2026

    For RENT TB8497756 - WINTER HAVEN, FL 33884 18 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2150
       Built: 2006
    Community: Whispering Trls Ph 01
    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 33884

    $1,7496 Days on yellowkey   MLS ID: TB8502889

    For RENT TB8502889 - WINTER HAVEN, FL 33884 13 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1540
       Built: 2023
    Community: Peace Crk Reserve
    Single Family


    Estimated Monthly Payment: $10 (change assumption)
    Mortgage ($10)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 165 OSPREY HEIGHTS DR, WINTER HAVEN, FL 33880

    $1,67548 Days on yellowkey   MLS ID: P4938155

    0 Days Off yellowkey (back on 4/29/2026)

    For RENT P4938155 - 165 OSPREY HEIGHTS DR, WINTER HAVEN, FL 33880 9 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1393
       Built: 2003
    Community: Osprey Landings Ph 02
    Single Family


    Estimated Monthly Payment: $9 (change assumption)
    Mortgage ($9)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 4981 KAIA AVE, WINTER HAVEN, FL 33884

    $1,9006 Days on yellowkey   MLS ID: O6400860

    For RENT O6400860 - 4981 KAIA AVE, WINTER HAVEN, FL 33884 16 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1269
       Built: 2025
    Community: Villamar Ph 6 & 6D
    Single Family


    Estimated Monthly Payment: $10 (change assumption)
    Mortgage ($10)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 400 RED HAWK LOOP, WINTER HAVEN, FL 33880

    $1,6007 Days on yellowkey   MLS ID: L4961436

    For RENT L4961436 - 400 RED HAWK LOOP, WINTER HAVEN, FL 33880 18 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1056
       Built: 1995
    Community: Spirit Lake Village Ph 01
    Single Family


    Estimated Monthly Payment: $9 (change assumption)
    Mortgage ($9)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 1341 AVENUE S NW, WINTER HAVEN, FL 33881

    $1,79540 Days on yellowkey   MLS ID: L4960493

    REDUCED by $100 (5.3%) on 04/27/2026

    For RENT L4960493 - 1341 AVENUE S NW, WINTER HAVEN, FL 33881 15 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1566
       Built: 1959
    Community: Stately Oaks
    Single Family


    Estimated Monthly Payment: $10 (change assumption)
    Mortgage ($10)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 235 HAYLEY ST, WINTER HAVEN, FL 33884

    $1,80045 Days on yellowkey   MLS ID: S5146226

    0 Days Off yellowkey (back on 4/27/2026)

    REDUCED by $100 (5.3%) on 04/20/2026

    For RENT S5146226 - 235 HAYLEY ST, WINTER HAVEN, FL 33884 9 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1432
       Built: 2024
    Community: Peace Crk Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $10 (change assumption)
    Mortgage ($10)


    Taxes:

    Elementary School: Chain O Lakes Elem

    High School: Bartow High

    Tax Year:

    Middle School: Bartow Middle


  • 227 VOLUSIA DR, WINTER HAVEN, FL 33884

    $1,90027 Days on yellowkey   MLS ID: P4938372

    For RENT P4938372 - 227 VOLUSIA DR, WINTER HAVEN, FL 33884 15 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1250
       Built: 1974
    Community: Eloise Woods Lake Mariam Unit
    Single Family


    Estimated Monthly Payment: $10 (change assumption)
    Mortgage ($10)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 3022 HICKORY ST NW, WINTER HAVEN, FL 33881

    $1,90040 Days on yellowkey   MLS ID: A4687467

    REDUCED by $100 (5.0%) on 04/26/2026

    For RENT A4687467 - 3022 HICKORY ST NW, WINTER HAVEN, FL 33881 41 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1602
       Built: 1955
    Community: Biltmore Shores
    Single Family


    Estimated Monthly Payment: $10 (change assumption)
    Mortgage ($10)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 3063 LAUREL OAK LN, WINTER HAVEN, FL 33884

    $1,69575 Days on yellowkey   MLS ID: O6369521

    REDUCED by $100 (5.6%) on 04/21/2026

    For RENT O6369521 - 3063 LAUREL OAK LN, WINTER HAVEN, FL 33884 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1269
       Built: 2023
    Community: Villamar
    Spa: No

    Single Family


    Estimated Monthly Payment: $9 (change assumption)
    Mortgage ($9)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 729 CRESTWOOD DR, WINTER HAVEN, FL 33881

    $1,55012 Days on yellowkey   MLS ID: R4911103

    For RENT R4911103 - 729 CRESTWOOD DR, WINTER HAVEN, FL 33881 14 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1156
       Built: 1960
    Community: Crestwood
    Single Family


    Estimated Monthly Payment: $8 (change assumption)
    Mortgage ($8)


    Taxes:

    Elementary School: Inwood Elem

    High School: Winter Haven Senior

    Tax Year:

    Middle School: Westwood Middle


12




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.