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Apartments under $2,000 for Rent in Winter Haven, FL

1,003 Rentals
.
  23. Building Photo - 383 Winter Ridge Blvd
    2 BEDS, 2 BATHS
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    383 Winter Ridge Blvd Unit 383

    383 Winter Ridge Blvd, Winter Haven, FL 33881
  24. Building Photo - 7903 Waterview Way
    2 BEDS, 2 BATHS
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650

    7903 Waterview Way

    7903 Waterview Way, Winter Haven, FL 33884
  33. Building Photo - 336 Kayden Cv
    3 BEDS, 2 BATHS
    $1,950
    Total Monthly Price Total Monthly Price New
    Base Rent$1,950
    Required Monthly FeesNone
    Total Monthly Price$1,950

    336 Kayden Cv

    336 Kayden Cv, Winter Haven, FL 33884
    Apply
  34. Building Photo - 5626 Struthers Ct
    2 BEDS, 1 BATH
    $1,600
    Total Monthly Price Total Monthly Price New
    Base Rent$1,600
    Required Monthly FeesNone
    Total Monthly Price$1,600

    5626 Struthers Ct

    5626 Struthers Ct, Winter Haven, FL 33884
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  35. 2 BEDS, 1 BATH
    $1,575
    Total Monthly Price Total Monthly Price New
    Base Rent$1,575
    Required Monthly FeesNone
    Total Monthly Price$1,575

    650 Ave B SW Unit 650 Avenue B SW

    650 Ave B SW, Winter Haven, FL 33880
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  36. 2 BEDS, 1 BATH
    $1,525
    Total Monthly Price Total Monthly Price New
    Base Rent$1,525
    Required Monthly FeesNone
    Total Monthly Price$1,525

    1407 N Lake Shipp Dr SW

    1407 N Lake Shipp Dr SW, Winter Haven, FL 33880
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  37. 2 BEDS, 1 BATH
    $1,400
    Total Monthly Price Total Monthly Price New
    Base Rent$1,400
    Required Monthly FeesNone
    Total Monthly Price$1,400

    913 S Char Mil Ave

    913 S Char Mil Ave, Lake Alfred, FL 33850
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  38. Building Photo - 731 Avenue A SW
    4 BEDS, 2 BATHS
    $1,850
    Total Monthly Price Total Monthly Price New
    Base Rent$1,850
    Required Monthly FeesNone
    Total Monthly Price$1,850

    731 Avenue A SW Unit B

    731 Avenue A SW, Winter Haven, FL 33880
  39. Building Photo - 448 Avenue A NE
    1 BED, 1 BATH
    $1,375
    Total Monthly Price Total Monthly Price New
    Base Rent$1,375
    Required Monthly FeesNone
    Total Monthly Price$1,375

    448 Avenue A NE Unit Cozy Cottage

    448 Avenue A NE, Winter Haven, FL 33881
  41. Building Photo - 1341 Ave S NW
    4 BEDS, 2 BATHS
    $1,895

    1341 Ave S NW

    1341 Ave S NW, Winter Haven, FL 33881
Showing 42 of 188 results, Page 2 of 5

Winter Haven at a Glance

Average Rent

$1,339
(All bedrooms and property types)
Learn more about
Average Rent in Winter Haven
5

School Rating

out of 10 Rating
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Schools in Winter Haven

Renting in Winter Haven

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Winter Haven

(For 1 bedroom apartments)

Education

GreatSchools Rating
Chain of Lakes Collegiate High

Public High School

Public
Grades 9-12
Students
GreatSchools Rating
Winter Haven Senior High School

Public High School

Public
Grades 9-12
Students
GreatSchools Rating
Jewett Middle Academy Magnet

Public Middle School

Public
Grades 6-8
Students
GreatSchools Rating
Westwood Middle School

Public Middle School

Public
Grades 6-8
Students
GreatSchools Rating
Denison Middle School

Public Middle School

Public
Grades 6-8
Students
GreatSchools Rating
Hartridge Academy

Public Elementary School

Public
Grades K-5
Students

Data provided by GreatSchools.org 2025 © 2025. All rights reserved.

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