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Apartments for Rent in Winter Haven, FL under $2000

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  • Rent specials Rewards
    1 bd $1,269+
    2 bd $1,439+
    Base rent
    Verified Listing

    The Waverly At Winter Haven

    1015 Lake Forest Blvd, Winter Haven, FL 33884
    Apply online • Pet friendly • Fitness center
  • Rent specials 20 units available
    1 bd $1,258
    2 bd $1,499+
    3 bd $1,708
    Base rent
    Verified Listing

    Magnolia At Lake Hamilton

    2850 W Lake Hamilton Dr, Winter Haven, FL 33881
    Apply online • Pet friendly • Fitness center
  • Rent specials
    Studio $1,099
    1 bd $1,175+
    2 bd $1,345+
    Base rent
    Verified Listing

    Haven At Lake Deer

    4.5 (9)
    350 24Th St. NW, Winter Haven, FL 33880
    Apply online • Pet friendly • Fitness center
  • Rent specials
    1 bd $749+
    2 bd $999+
    3 bd $1,275
    Base rent
    Verified Listing

    The Landings Apartment Homes

    102 Landings Way, Winter Haven, FL 33880
    Apply online • Pet friendly • Air conditioner
  • Only 1 unit left
    3 bd $1,685
    Base rent
    Verified Listing

    536 Haines Trl Winter Haven, FL 33881

    4.0 (3)
    536 Haines Trl, Winter Haven, FL 33881
    Apply online • Pet friendly • Dishwasher
  • Rent specials Rewards
    1 bd $1,269+
    2 bd $1,439+
    Base rent
    Verified Listing

    The Waverly At Winter Haven

    1015 Lake Forest Blvd, Winter Haven, FL 33884
    Apply online • Pet friendly • Fitness center
  • Only 1 unit left
    3 bd $1,955
    Base rent
    Verified Listing

    444 LANHAM DRIVE WINTER HAVEN, FL 33881

    444 LANHAM DRIVE, WINTER HAVEN, FL 33881
    Apply online • Pet friendly • Dishwasher
  • Only 1 unit left
    3 bd $1,945
    Base rent
    Verified Listing

    4693 OSPREY WAY WINTER HAVEN, FL 33881

    4693 OSPREY WAY, WINTER HAVEN, FL 33881
    Apply online • Pet friendly • Dishwasher
  • 3950 Country Place 2-3 Beds Apartment for Rent
    Rent specials
    2 bd $999+
    3 bd $1,275
    Base rent
    Verified Listing

    Country Place Apartment Homes

    3.5 (4)
    3950 Country Place, Winter Haven, FL 33880
    Apply online • Pet friendly
  • 418 19Th Street 1-2 Beds Apartment for Rent
    Rent specials
    1 bd $749+
    2 bd $1,285
    Base rent
    Verified Listing

    Brandywyne Apartment Homes

    4.0 (6)
    418 19Th Street, Winter Haven, FL 33884
    Apply online • Pet friendly • Patio/Balcony
  • 102 Landings Way 1-2 Beds Apartment for Rent
    1 bd $1,100+
    2 bd $1,360
    Base rent
    Verified Listing

    The Landings Apartment Homes

    3.0 (5)
    102 Landings Way, Winter Haven, FL 33880
    Apply online • Pet friendly • Washer/Dryer
  • 3301 Avenue G NW Studio Apartment for Rent
    Only 2 units left
    Studio $575
    Base rent
    Verified Listing

    Lake Deer Owner LLC

    3301 Avenue G NW, Winter Haven, FL 33880
    Apply online • Pet friendly • Pool
  • Ask for pricing
    Verified Listing

    1473 Lucerne Loop Road NE

    1473 Lucerne Loop Road NE, Winter Haven, FL 33881
    Pet friendly • Dishwasher • Air conditioner
  • 2 bd $1,300
    Base rent
    Verified Listing

    400 El Camino Drive, Unit 203

    400 El Camino Drive, Winter Haven, FL 33884
    Pet friendly • Dishwasher • Patio/Balcony
  • 1 bd $1,100
    Base rent
    Verified Listing

    233 21st St SW, Unit 1

    233 21St St SW, Winter Haven, FL 33880
    Air conditioner
  • 26-0-city

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 11 Sep 2026.

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

In Winter Haven, 36% of the residents are renting compared to 64% owning a home, according to data from the U.S. Census Bureau. Large-scale apartment buildings with more than 50 units represent 10% of Winter Haven's rentals, 51% are small-scale complexes with under 50 units, and 37% are single-family rentals.

Search for apartments in Winter Haven, FL under $2,000

There’s more than one way to spend $2,000 on rent in Winter Haven, FL, so the first step is to start thinking about what you really want from your new home. Be mindful of what makes you tick. Look for 2 bedroom apartments for rent for less than $2,000 if you want to share your living space and don’t mind being further away from the city center. Search for 3 bedroom apartments if you’re moving in with family or planning to share part of your life and living expenses with more friends. If city bustle is what you live for, you might want to search for a studio or 1 bedroom apartment closer to the city center.

The perfect $2,000 rental near you

Don’t dismiss the idea of a studio just because it sounds small and featureless: studios come in many shapes and sizes, and it only takes a few strikes of creativity to go from drab to lively. If an all-in-one-room apartment spells total lack of privacy for you, have a look at the 1 bedroom apartments for rent in Winter Haven, FL. Customize your search by using more RentCafe filters. Decide what amenities you can’t live without and focus your search on the apartments that offer them. Are you bringing in a pet? Narrow your options to pet-friendly apartments for rent. Want more windows so that natural light floods your home? Hardwood floors or plush carpet in the living area? There are 26 apartments for rent below $2,000 in Winter Haven, FL for every taste. Decide what you need, stay focused, and you’re bound to find your perfect apartment in no time.