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

769 Rentals
.
  31. Building Photo - 54 Sunset Cir
    3 BEDS, 3 BATHS
    $1,600

    54 Sunset Cir

    54 Sunset Cir, Lake Alfred, FL 33850
  32. Building Photo - 357 Winter Ridge Blvd
    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

    357 Winter Ridge Blvd Unit 357

    357 Winter Ridge Blvd, Winter Haven, FL 33881
    Apply
  33. Building Photo - 1131 5th St SW
    Rent Special
    Rent Special
    1 BED, 1 BATH
    $850
    Total Monthly Price Total Monthly Price New
    Base Rent$850
    Required Monthly FeesNone
    Total Monthly Price$850

    1131 5th St SW Unit 4 downstairs

    1131 5th St SW, Winter Haven, FL 33880
    Apply
  34. Building Photo - 711 Avenue B NE
    Rent Special
    Rent Special
    3 BEDS, 2 BATHS
    $1,685
    Total Monthly Price Total Monthly Price New
    Base Rent$1,685
    Required Monthly FeesNone
    Total Monthly Price$1,685

    711 Avenue B NE

    711 Avenue B NE, Winter Haven, FL 33881
    Apply
  35. Building Photo - 1536 Axel Cir
    4 BEDS, 2 BATHS
    $1,875
    Total Monthly Price Total Monthly Price New
    Base Rent$1,875
    Required Monthly FeesNone
    Total Monthly Price$1,875

    1536 Axel Cir

    1536 Axel Cir, Winter Haven, FL 33880
    Apply
  38. 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

    5850 Cypress Gardens Blvd Unit #607

    5850 Cypress Gardens Blvd, Winter Haven, FL 33884
    Apply
  39. Building Photo - 448 Avenue A NE
    1 BED, 1 BATH
    $1,475
    Total Monthly Price Total Monthly Price New
    Base Rent$1,475
    Required Monthly FeesNone
    Total Monthly Price$1,475

    448 Avenue A NE Unit Cozy Cottage

    448 Avenue A NE, Winter Haven, FL 33881
    Apply
  40. Building Photo - 709 Mosley Rd
    2 BEDS, 1 BATH
    $1,250
    Total Monthly Price Total Monthly Price New
    Base Rent$1,250
    Required Monthly FeesNone
    Total Monthly Price$1,250

    709 Mosley Rd Unit 709

    709 Mosley Rd, Lake Alfred, FL 33850
    Apply
  41. 1 BED, 1 BATH
    $1,000
    Total Monthly Price Total Monthly Price New
    Base Rent$1,000
    Required Monthly FeesNone
    Total Monthly Price$1,000

    101 Lake Sears Dr

    101 Lake Sears Dr, Winter Haven, FL 33880
  42. 3 BEDS, 2 BATHS
    $1,600
    Total Monthly Price Total Monthly Price New
    Base Rent$1,600
    Required Monthly FeesNone
    Total Monthly Price$1,600

    690 Avenue C SE Unit 690

    690 Avenue C SE, Winter Haven, FL 33880
Showing 42 of 194 results, Page 2 of 5

Winter Haven at a Glance

Average Rent

$1,323
(All bedrooms and property types)
Learn more about
Average Rent in Winter Haven
5

School Rating

out of 10 Rating
Learn more about
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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