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Apartments for Rent in Winter Haven, FL under $2000

110 Rentals Available
Apartments for Rent in Winter Haven, FL under $2000. 110 Rentals Available
  • Rent Specials
    A modern kitchen with a stainless steel refrigerator and a white countertop at The Waverly at Winter Haven Apartments, Florida, 33884 A well-lit bedroom with a large bed, a chair, and a coffee table at The Waverly at Winter Haven Apartments, Florida
    Today

    1015 Lake Forest Blvd, Winter Haven, FL 33884
    Available
    1 BED $1,480+
    2 BEDS $1,565+
    A modern kitchen with a stainless steel refrigerator and a white countertop at The Waverly at Winter Haven Apartments, Florida, 33884 A well-lit bedroom with a large bed, a chair, and a coffee table at The Waverly at Winter Haven Apartments, Florida A modern dining area with a stone wall and a television at The Waverly at Winter Haven Apartments, Winter Haven, Florida A large outdoor swimming pool with a tiled edge and a shaded area with lounge chairs at The Waverly at Winter Haven Apartments, Winter Haven, 33884
    Amenities
    • Washer/Dryer
    • Patio/Balcony
    • Fitness Center
    • Pets Allowed
  • a kitchen with white appliances and wooden cabinets
    Today

    2684 Whispering Trails Dr, Winter Haven, FL 33884
    3 BEDS $1,835
  • A kitchen with wooden cabinets and a white countertop.
    Today

    5658 Forest Ridge Dr, Winter Haven, FL 33881
    3 BEDS $1,560
  • A spacious kitchen and living room with a ceiling fan.
    Today

    107 Southern Breeze Loop, Winter Haven, FL 33880
    3 BEDS $1,730
  • 1349 Lucerne Loop Road NE 4 Beds Apartment for Rent
    Today

    1349 Lucerne Loop Road NE, Winter Haven, FL 33881
    4 BEDS $1,900
  • A kitchen with white cabinets and a black fridge.
    44
    Today

    102 Landings Way, Winter Haven, FL 33880
    1 BED $899+
    2 BEDS $1,150+
    3 BEDS $1,275
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  • A modern living room with a large painting of a woman on the wall.
    7
    Today

    350 24Th St. NW, Winter Haven, FL 33880
    STUDIO $1,099
    1 BED $1,299
    2 BEDS $1,385+
  • A bedroom with a bed and a ceiling fan.
    1 day ago

    1545 Foxridge Run Southwest, Winter Haven, FL 33880
    3 BEDS $1,599
  • A kitchen with black and white cabinets and a granite countertop.
    1 day ago

    208 E Lake Howard Dr NW, Winter Haven, FL 33881
    2 BEDS $1,875
  • A kitchen with white cabinets and a granite countertop.
    1 day ago

    1925 Ave O SW, Winter Haven, FL 33880
    2 BEDS $1,400
  • A kitchen with wooden floors and stainless steel appliances.
    1 day ago

    1935 Ave O SW, Winter Haven, FL 33880
    2 BEDS $1,400

  • More Rentals Near Winter Haven, FL

  • a living room with a stone fireplace and a wooden table
    29
    Today

    4315 Talon Loop, Lakeland, FL 33812
    1 BED Ask for Pricing
    2 BEDS $1,703+
    3 BEDS $1,860+
  • Interactive banner bedroom
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  • a large kitchen with granite counter tops and stainless steel appliances
    Today

    190 Windsor Reserve Drive, Eagle Lake, FL 33839
    4 BEDS $1,965
  • a white kitchen with granite counter tops and stainless steel appliances
    Today

    142 Windsor Reserve Drive, Eagle Lake, FL 33839
    3 BEDS $1,725
  • A living room with a white couch and a black and white rug.
    1 day ago

    410 Oak Street, Auburndale, FL 33823
    1 BED $1,000
  • A kitchen with a dining table set up with a chair and a painting on the wall.
    1 day ago

    117 Noxon St, Auburndale, FL 33823
    2 BEDS $1,950
  • A kitchen with a FirstKey Homes logo.
    Today

    505 ORSOTA COURT, AUBURNDALE, FL 33823
    4 BEDS $1,970
  • A kitchen with a white door and a white countertop.
    1 day ago

    165 Sofia Lane, Lake Alfred, FL 33850
    4 BEDS $1,999
  • A living room with a brown couch and a painting on the wall.
    1 day ago

    216 Smith Ave, Lake Hamilton, FL 33851
    3 BEDS $1,800
  • A modern house with a grey exterior and a white garage door.
    Today

    219 Ash Way, Auburndale, FL 33823
    4 BEDS $1,900
  • a living room with furniture and a fireplace
    138
    Today

    980 East Church Street, Bartow, FL 33830
    Income Restricted
    2 BEDS Ask for Pricing
    3 BEDS Ask for Pricing
    4 BEDS Ask for Pricing
  • A white kitchen with a table in the middle.
    1 day ago

    3645 Majestic Dr, Polk County, FL 33803
    3 BEDS $1,900
  • A living room with a black couch and a chandelier.
    Today

    5190 Ariva Blvd., Lakeland, FL 33812
    1 BED $1,434+
    2 BEDS $1,664+
    3 BEDS $1,699+
  • A living room with a white couch and a ceiling fan.
    1 day ago

    1305 Fairview Ave, Bartow, FL 33830
    3 BEDS $1,650
  • A kitchen with white cabinets and a black stove top oven.
    106
    Today

    1969 Crystal Grove Drive (Unit#2) - Office, Lakeland, FL 33801
    STUDIO Ask for Pricing
    1 BED Ask for Pricing
    2 BEDS Ask for Pricing
11-14-city
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Getting around in Winter Haven, FL

26 /100
Car-Dependent
35 /100
Somewhat Bikeable
Walk Score®: 26, Bike Score®: 35

Frequently asked questions

When were prices and availability in Winter Haven, FL last updated?

Prices and availability in Winter Haven, FL were last updated on 25 Nov 2025.

What are the best apartments in Winter Haven, FL?

The best apartments in Winter Haven, FL are: The Waverly at Winter Haven, Episcopal Catholic Apartments, 2684 Whispering Trails Dr Winter Haven, FL 33884, 5658 Forest Ridge Dr Winter Haven, FL 33881 and 3134 WHISPERING TRAILS STREET WINTER HAVEN, FL 33884.

What type of rental buildings are in Winter Haven, FL?

In Winter Haven 38% of the housing is rented out compared to 62% of homes are owned, according to the most recent Census Bureau estimates. 11% of Winter Haven’s apartments are found in large buildings of 50 units or more, 49% are located in smaller apartment complexes with less than 50 units, and 38% are single-family rentals.

Renting apartments in Winter Haven, FL under $2,000

Are you looking for a smart space where you can easily combine comfort with convenience? You will surely find the property that perfectly fits your needs with this variety of options. RentCafe offers you 110 apartments for rent in Winter Haven, FL from 25 modern buildings, so you’ll certainly find something suitable for you. If you want to live alone or with your partner, you might want to look for a studio or browse through our selection of 1 bedroom apartments. If you need more space but you don’t want to spend more than necessary on a monthly rent, check out our 2 bedroom or 3 bedroom apartments for less than $2,000, and make the most out of your budget.

Finding the best rental near you

Winter Haven, FL is an amazing place to call home, with several rentals under $2,000 for you to choose from. There are many options and filters you can apply to your search to make the process easier and to find your next apartment faster and more efficiently. Asking yourself ‘are there any cheap apartments near me’? With our helpful filters, you can easily find the home of your dreams that also fits within your budget. With rent prices as low as $899 in Winter Haven, FL, you can find affordable and appealing apartments that match your requirements. Sort your search by ‘Rent’ ascending to see the cheapest ones at the top of the list. As soon as you find your perfect apartment, make sure to contact the property to check for availability or apply online directly on RentCafe.

Finding a home nearby is easier than you think. Check out our Apartments Near Me page and take your pick!