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Apartments under $1,400 for Rent in Winter Haven, FL

330 Rentals
.
  3. $326 Off
    Price Drop. $326 Off
    |
    1 BED
    $1,441
    Total Monthly Price Total Monthly Price New
    Base Rent$1,299
    Required Monthly Fees$142
    Total Monthly Price$1,441

    Prose Cypress Pointe

    3110 Gowan Dr, Winter Haven, FL 33884
    (689) 219-8438
  21. Building Photo - Oakcrest Apartments
    Rent Special
    Rent Special
    1 BED
    $975

    Oakcrest Apartments

    101-123 Oak Crest Dr NW, Winter Haven, FL 33881
  22. $197 Off
    Price Drop. $197 Off
    1 BED
    $950

    Lakeview Tower

    745 Avenue A SW, Winter Haven, FL 33880
  26. Building Photo - 411 Ave E SE
    1 BED, 1 BATH
    $950
    Total Monthly Price Total Monthly Price New
    Base Rent$950
    Required Monthly FeesNone
    Total Monthly Price$950

    411 Ave E SE Unit B

    411 Ave E SE, Winter Haven, FL 33880
  27. Building Photo - 123 E Main St
    1 BED, 1 BATH
    $1,200
    Total Monthly Price Total Monthly Price New
    Base Rent$1,200
    Required Monthly FeesNone
    Total Monthly Price$1,200

    123 E Main St

    123 E Main St, Dundee, FL 33838
    Apply
  28. Building Photo - 7708 Waterview Way
    1 BED, 1.5 BATHS
    $1,350
    Total Monthly Price Total Monthly Price New
    Base Rent$1,350
    Required Monthly FeesNone
    Total Monthly Price$1,350

    7708 Waterview Way Unit 7708 Waterview Way

    7708 Waterview Way, Winter Haven, FL 33884
  29. 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
  30. 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
Showing 42 of 82 results, Page 1 of 2

Winter Haven at a Glance

Average Rent

$1,343
(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

Winter Haven, FL Apartments for Rent

Winter Haven earns its nickname "The Chain of Lakes City" from 50 connected lakes and canals flowing through the community. Anyone searching for apartments for rent in Winter Haven can choose from lakefront spots to downtown homes, with studios going for about $1,020 and two-bedroom apartment communities running around $1,516 monthly. The historic Interlaken neighborhood shows off colonial revival buildings, while newer developments bring modern living spaces that fit different budgets and tastes.

Renting in Winter Haven means year-round fun on the water—boating, fishing, and water sports across the city's lakes. Downtown's Central Avenue puts local shops and restaurants within walking distance of several residential areas. The city hosts Legoland Florida, a major regional draw built where Cypress Gardens once stood. Winter Haven sits in Polk County, right between Tampa and Orlando, with easy Interstate 4 access for anyone commuting to either city. The warm weather and waterfront views make it a smart choice for renters wanting affordable Central Florida living.

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
2,467 Students
GreatSchools Rating
Jewett Middle Academy Magnet

Public Middle School

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

Public Middle School

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

Public Middle School

Public
Grades 6-8
738 Students
GreatSchools Rating
Hartridge Academy

Public Elementary School

Public
Grades K-5
201 Students

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

Apartments for Rent Near Winter Haven

Winter Haven Apartments for Rent in Your Budget

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