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Apartments for Rent in Winter Haven, FL with a Swimming Pool

577 Rentals
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  2. Building Photo - Prose Cypress Pointe
    $411 Off
    Price Drop. $411 Off
    |
    1 BED
    $1,441+
    2 BEDS
    $1,691+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,299 - $1,625
    Required Monthly Fees$142
    Total Monthly Price$1,441 - $1,767

    Prose Cypress Pointe

    3110 Gowan Dr, Winter Haven, FL 33884
    (689) 219-8438
  3. 1 Month Free
    1 Month Free
    STUDIO
    $1,350+
    1 BED
    $1,428+
    2 BEDS
    $1,995+

    The Breeze

    265 Ave E SW, Winter Haven, FL 33880
    (863) 356-8805
  19. Building Photo - 748 Reggie Rd
    4 BEDS, 2 BATHS
    $2,600
    Total Monthly Price Total Monthly Price New
    Base Rent$2,600
    Required Monthly FeesNone
    Total Monthly Price$2,600

    748 Reggie Rd

    748 Reggie Rd, Winter Haven, FL 33884
  21. 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
  22. 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 - 2454 Taloncrest Ct
    5 BEDS, 3 BATHS
    $2,750
    Total Monthly Price Total Monthly Price New
    Base Rent$2,750
    Required Monthly FeesNone
    Total Monthly Price$2,750

    2454 Taloncrest Ct

    2454 Taloncrest Ct, Eagle Lake, FL 33839
  25. 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
  30. Building Photo - 112 Lagoon Rd
    3 BEDS, 2 BATHS
    $2,500

    112 Lagoon Rd

    112 Lagoon Rd, Winter Haven, FL 33884

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Winter Haven at a Glance

Average Rent

$1,333
(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
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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