Note: Properties with the Total Monthly Price badge include all required fees. Tap the badge for more details.
-

Bedrooms

Bathrooms

Deals & Discount Filters
All Filters

Deals & Discounts

Price Range

–

Beds & Baths

Beds

Baths

Home Type

Pet Policy

Interior & Community Amenities

Speciality Housing

Keyword Search

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

429 Rentals
.
  2. Building Photo - Prose Cypress Pointe
    $346 Off
    Price Drop. $346 Off
    |
    1 BED
    $1,441+
    2 BEDS
    $1,741+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,299 - $1,860
    Required Monthly Fees$142
    Total Monthly Price$1,441 - $2,002

    Prose Cypress Pointe

    3110 Gowan Dr, Winter Haven, FL 33884
    (689) 219-8438
  3. 2 Months Free
    2 Months Free
    |
    STUDIO
    $1,250+
    1 BED
    $1,395+
    2 BEDS
    $1,850+

    The Breeze

    265 Ave E SW, Winter Haven, FL 33880
    (863) 356-8805
  25. Building Photo - 1938 Sarah St
    4 BEDS, 3 BATHS
    $2,150
    Total Monthly Price Total Monthly Price New
    Base Rent$2,150
    Required Monthly FeesNone
    Total Monthly Price$2,150

    1938 Sarah St

    1938 Sarah St, Winter Haven, FL 33884
  26. Building Photo - 5850 Cypress Gardens Blvd
    3 BEDS, 3 BATHS
    $1,450
    Total Monthly Price Total Monthly Price New
    Base Rent$1,450
    Required Monthly FeesNone
    Total Monthly Price$1,450

    5850 Cypress Gardens Blvd Unit 806

    5850 Cypress Gardens Blvd, Winter Haven, FL 33884
  27. 2 BEDS, 3 BATHS
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    504 Orange Blossom Dr

    504 Orange Blossom Dr, Winter Haven, FL 33880
  28. 2 BEDS, 2 BATHS
    $1,200
    Total Monthly Price Total Monthly Price New
    Base Rent$1,200
    Required Monthly FeesNone
    Total Monthly Price$1,200

    8402 Waterview Way Unit 8402

    8402 Waterview Way, Winter Haven, FL 33884
  29. 3 BEDS, 2 BATHS
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650

    333 N Lake Howard Dr Unit 211B

    333 N Lake Howard Dr, Winter Haven, FL 33880
  30. Building Photo - 715 Magnolia Pl
    2 BEDS, 2 BATHS
    $1,700
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700
    Required Monthly FeesNone
    Total Monthly Price$1,700

    715 Magnolia Pl Unit 715

    715 Magnolia Pl, Winter Haven, FL 33884
  31. Building Photo - 8302 Waterview Way
    2 BEDS, 2 BATHS
    $1,300
    Total Monthly Price Total Monthly Price New
    Base Rent$1,300
    Required Monthly FeesNone
    Total Monthly Price$1,300

    8302 Waterview Way

    8302 Waterview Way, Winter Haven, FL 33884
  32. 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

    407 Eagle Pond Dr Unit 4F

    407 Eagle Pond Dr, Winter Haven, FL 33884
  33. 4 BEDS, 2 BATHS
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000

    3683 Julius Estates Blvd

    3683 Julius Estates Blvd, Winter Haven, FL 33881
  34. 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

    1026 Medinah Dr

    1026 Medinah Dr, Winter Haven, FL 33884
  36. Building Photo - 700 Mirror Ter NW
    1 BED, 2 BATHS
    $1,400
    Total Monthly Price Total Monthly Price New
    Base Rent$1,400
    Required Monthly FeesNone
    Total Monthly Price$1,400

    700 Mirror Ter NW Unit 705

    700 Mirror Ter NW, Winter Haven, FL 33881
Showing 42 of 48 results, Page 1 of 2

Winter Haven at a Glance

Average Rent

$1,325
(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
2,635 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.

Apartments for Rent Near Winter Haven

Specialty Housing

Choose by Amenities

tooltips


I would like to...
0 out of 400 characters
By clicking above, you agree we may pass along your info so this property or the property’s affiliates can email, call, text, or autodial you to follow up and for any purpose. You also agree to... By clicking above, you agree we may pass along your info so this property or the property’s affiliates can email, call, text, or autodial you to follow up and for any purpose. You also agree to Apartmentfinder.com’s Privacy Statement and Terms of Service. Consent is not a condition for services. Message and data rates may apply. Read More Read Less

Submitting Request

Thank You

Your email has been sent.

Learn about our ratings.