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

951 Rentals
.
  12. Building Photo - 1756 2nd St NE
    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

    1756 2nd St NE

    1756 2nd St NE, Winter Haven, FL 33881
  13. Building Photo - 1445 Wallace Manor Pass
    3 BEDS, 2 BATHS
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    1445 Wallace Manor Pass

    1445 Wallace Manor Pass, Winter Haven, FL 33880
  14. Building Photo - 407 Ave A SE
    3 BEDS, 2 BATHS
    $1,700

    407 Ave A SE

    407 Ave A SE, Winter Haven, FL 33880
  15. Building Photo - 715 Magnolia Pl
    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

    715 Magnolia Pl Unit 715

    715 Magnolia Pl, Winter Haven, FL 33884
  16. 2 BEDS, 2 BATHS
    $1,400
    Total Monthly Price Total Monthly Price New
    Base Rent$1,400
    Required Monthly FeesNone
    Total Monthly Price$1,400

    711 Lake Jessie Dr

    711 Lake Jessie Dr, Winter Haven, FL 33881
  17. 2 BEDS, 2 BATHS
    $1,400
    Total Monthly Price Total Monthly Price New
    Base Rent$1,400
    Required Monthly FeesNone
    Total Monthly Price$1,400

    8302 Waterview Way

    8302 Waterview Way, Winter Haven, FL 33884
  21. Building Photo - 5667 Struthers Ct
    2 BEDS, 1 BATH
    $1,350
    Total Monthly Price Total Monthly Price New
    Base Rent$1,350
    Required Monthly FeesNone
    Total Monthly Price$1,350

    5667 Struthers Ct

    5667 Struthers Ct, Winter Haven, FL 33884
  25. Building Photo - 54 Sunset Cir
    3 BEDS, 3 BATHS
    $1,600

    54 Sunset Cir

    54 Sunset Cir, Lake Alfred, FL 33850
  28. Building Photo - 103 11th St SE
    Rent Special
    Rent Special
    2 BEDS, 3 BATHS
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650

    103 11th St SE

    103 11th St SE, Winter Haven, FL 33880
    Apply
  29. Building Photo - 711 Avenue B NE
    3 BEDS, 2 BATHS
    $1,825
    Total Monthly Price Total Monthly Price New
    Base Rent$1,825
    Required Monthly FeesNone
    Total Monthly Price$1,825

    711 Avenue B NE

    711 Avenue B NE, Winter Haven, FL 33881
    Apply
  30. Building Photo - 926 30th St NW
    Rent Special
    Rent Special
    3 BEDS, 2 BATHS
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000

    926 30th St NW

    926 30th St NW, Winter Haven, FL 33881
    Apply
  31. 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
    Apply
  32. 1 BED, 1 BATH
    $1,199
    Total Monthly Price Total Monthly Price New
    Base Rent$1,199
    Required Monthly FeesNone
    Total Monthly Price$1,199

    399 Ave B Ave SE Unit 399. Ave B

    399 Ave B Ave SE, Winter Haven, FL 33880
    Apply
  33. 3 BEDS, 2 BATHS
    $1,750
    Total Monthly Price Total Monthly Price New
    Base Rent$1,750
    Required Monthly FeesNone
    Total Monthly Price$1,750

    690 Avenue C SE Unit 690

    690 Avenue C SE, Winter Haven, FL 33880
  41. 2 BEDS, 1 BATH
    $1,299

    513 Ave J SE

    513 Ave J SE, Winter Haven, FL 33880
Showing 42 of 184 results, Page 2 of 5

Winter Haven at a Glance

Average Rent

$1,329
(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
328 Students
GreatSchools Rating
Winter Haven Senior High School

Public High School

Public
Grades 9-12
2,635 Students
GreatSchools Rating
Jewett Middle Academy Magnet

Public Middle School

Public
Grades 6-8
569 Students
GreatSchools Rating
Westwood Middle School

Public Middle School

Public
Grades 6-8
669 Students
GreatSchools Rating
Denison Middle School

Public Middle School

Public
Grades 6-8
775 Students
GreatSchools Rating
Hartridge Academy

Public Elementary School

Public
Grades K-5
190 Students

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

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