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Apartments for Rent in Winter Haven, FL

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Listings

3 bed 2 bath home Gallery 1
1 of 24

3 bed 2 bath home

$2,000
1768 Carnostie Road, Winter Haven, FL 33884
(863) 656-3642
1 unit available
3 bed
Amenities
On-site laundry, Dishwasher, Pet friendly, Garage, Stainless steel, Pool + more
Recently updated units
2753 Whispering Trails Drive Gallery 1
1 of 17

2753 Whispering Trails Drive

$2,000
2753 Whispering Trails Drive, Winter Haven, FL 33884
(813) 676-3252
1 unit available
4 bed
Amenities
Patio / balcony, Pet friendly, Pool, Ceiling fan, Extra storage, and Microwave
Pet Paradise
Charming pet-friendly home near thrilling attractions.
This delightful home welcomes pets, offering a warm and inviting space with modern updates for comfortable living. Residents enjoy its ideal location near Legoland and Disney, providing easy access to thrilling attractions. The community is described as quiet and family-friendly, with a peaceful environment and added security from being gated.
Recently updated units
308 Kayden Cv Gallery 1
1 of 12

308 Kayden Cv

$2,000
308 Kayden Cv, Winter Haven, FL 33859
(787) 529-7141
1 unit available
3 bed
Amenities
In unit laundry, Dishwasher, Garage, Air conditioning, and Furnished
Recently updated units
1925 Ave O, Sw Gallery 1
1 of 9

1925 Ave O, Sw

$1,275
1925 Avenue O Southwest, Winter Haven, FL 33880
(863) 294-7420
1 unit available
2 bed
Amenities
In unit laundry, Granite counters, Dishwasher, Pet friendly, Parking, Stainless steel + more
Recently updated units
554 Reddicks Circle Gallery 1
1 of 8

554 Reddicks Circle

$2,100
554 Reddicks Circle, Winter Haven, FL 33884
(386) 320-1531
1 unit available
3 bed
Amenities
In unit laundry, Hardwood floors, Dishwasher, Pet friendly, Garage, and Air conditioning
Recently updated units
2265 3rd St NE Gallery 1
1 of 17

2265 3rd St NE

$1,525
2265 3rd Street Northeast, Winter Haven, FL 33881
(863) 213-6353
1 unit available
3 bed
Amenities
In unit laundry, Recently renovated, Stainless steel, Gym, Extra storage, and Refrigerator
Recently updated units
2227 9th St. SE Gallery 1
1 of 18

2227 9th St. SE

$999
2227 9th Street Southeast, Winter Haven, FL 33880
(863) 250-4166
1 unit available
1 bed
Amenities
24hr maintenance, Carport, and Air conditioning
Recently updated units
3237 COUNTRY WALK CLUB CIRCLE Gallery 1
1 of 18

3237 COUNTRY WALK CLUB CIRCLE

$1,800
3237 Country Walk Club Circle, Winter Haven, FL 33881
(813) 689-3115
1 unit available
4 bed
Amenities
Granite counters, Dishwasher, Garage, Recently renovated, Stainless steel, Walk in closets + more
Recently updated units
503 AVENUE B NW Gallery 1
1 of 13

503 AVENUE B NW

$1,995
503 Avenue B Northwest, Winter Haven, FL 33881
(888) 883-8509
1 unit available
2 bed
Amenities
In unit laundry, Dishwasher, Pool, Tennis court, Fireplace, and Ice maker
Recently updated units
2500 21ST STREET NW Gallery 1
1 of 41

2500 21ST STREET NW

$1,700
2500 21st Street Northwest, Winter Haven, FL 33881
(863) 967-0096
1 unit available
2 bed
Amenities
In unit laundry, Patio / balcony, Dishwasher, Garage, Pool, Ceiling fan + more
Recently updated units
2040 SAN MARCOS DRIVE SE Gallery 1
1 of 18

2040 SAN MARCOS DRIVE SE

$1,400
2040 San Marcos Drive Southeast, Winter Haven, FL 33880
(863) 259-4600
1 unit available
2 bed
Amenities
Dishwasher, Pool, Ceiling fan, Fireplace, Range, and Refrigerator
Recently updated units
1192 NORMANDY HEIGHTS CIRCLE Gallery 1
1 of 29

1192 NORMANDY HEIGHTS CIRCLE

$2,300
1192 Normandy Heights Circle, Winter Haven, FL 33880
(407) 207-2220
1 unit available
4 bed
Amenities
Patio / balcony, Dishwasher, Garage, Recently renovated, Bbq/grill, and Microwave
Recently updated units
281 ARBUTHNOT STREET Gallery 1
1 of 31

281 ARBUTHNOT STREET

$1,900
281 Arbuthnot Street, Winter Haven, FL 33881
(866) 473-3476
1 unit available
3 bed
Amenities
In unit laundry, Patio / balcony, Dishwasher, Dogs allowed, Garage, Stainless steel + more
Recently updated units
403 AVENUE J SE Gallery 1
1 of 7

403 AVENUE J SE

$1,550
403 Avenue J Southeast, Winter Haven, FL 33880
(407) 447-7253
1 unit available
2 bed
Amenities
Dishwasher, Recently renovated, Ceiling fan, Microwave, Range, and Refrigerator
Recently updated units
1103 CYPRESS GARDENS BOULEVARD Gallery 1
1 of 12

1103 CYPRESS GARDENS BOULEVARD

$1,000
1103 Cypress Gardens Boulevard, Winter Haven, FL 33884
(863) 293-1234
1 unit available
1 bed
Amenities
Ceiling fan, Range, and Refrigerator
Recently updated units
5150 MICHELLE STREET Gallery 1
1 of 36

5150 MICHELLE STREET

$1,800
5150 Michelle Street, Winter Haven, FL 33881
(863) 802-5262
1 unit available
4 bed
Amenities
Dishwasher, Garage, Stainless steel, Walk in closets, Ceiling fan, Extra storage + more
Recently updated units

Average rent in Winter Haven, Florida

The average rent for a 1 bedroom apartment in Winter Haven is $1,242+, while the average rent for a 2 bedroom apartment is $1,518+. Rent rates updated 3 days ago
Studio
$1,099+
Prices trending down
1 Bed
$1,242+
Prices trending down
2 Beds
$1,518+
Prices trending down
3+ Beds
$1,580+
Prices trending down
* Averages are based on the rental prices of properties listed on Apartment List that don’t include fees

Top neighborhoods

Top neighborhoods in Winter Haven, FL

  • Map of Cypresswood Country Club

    Cypresswood Country Club

    What's it like to live in Cypresswood Country Club?

    Golf course views attract residents to Cypresswood Country Club, where homes surrounding fairways offer scenic vistas and peaceful evenings. Residents enjoy community tennis courts and the neighborhood's proximity to Legoland Florida. Though summer afternoon thunderstorms regularly interrupt outdoor activities, the designated lightning shelters throughout common areas provide safe options during storms. The area's relative affordability compared to Orlando or Tampa neighborhoods creates opportunities for retirees seeking golf course living without premium resort pricing.

    Great for

    • Families
    • Retirees
    • Professionals
    • Young Renters
    • Commuters

    Neighborhood vibe

    • Mixed-Use
    • Peaceful
    • Mixed-Use & Commercial
    View 4 listings

Find more rentals by

Amenities
  • Winter Haven Apartments with Garages (55)
  • Winter Haven Apartments with Washer-Dryers (50)
  • Winter Haven Furnished Apartments (4)
  • Winter Haven Luxury Apartments (97)
  • Winter Haven Pet Friendly Apartments (82)
Bedrooms
  • 1 Bedroom Apartments in Winter Haven (13)
Price
  • Winter Haven Apartments with Move-in Specials (6)
  • Winter Haven Cheap Apartments (6)
Neighborhoods
  • Cypresswood Country Club (4)

Frequently Asked Questions (FAQs)

Winter Haven Rent Report: March 2026

Welcome to the Apartment List March 2026 Rent Report for Winter Haven, FL. Currently, the overall median rent in the city stands at $1,109, after falling 1.7% last month. Prices are now down 2.5% year-over-year. Read on to learn more about what’s been happening in the Winter Haven rental market and how it compares to trends throughout the nation as a whole.