Apartments for Rent in Winter Haven, FL under $2000
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1 bd $1,499+2 bd $1,650+Base rent1015 Lake Forest Blvd, Winter Haven, FL 33884Apply online • Pet friendly • Fitness center
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Studio $1,0991 bd $1,099+2 bd $1,399+Base rent4.5 (9)350 24Th St. NW, Winter Haven, FL 33880Apply online • Pet friendly • Fitness center
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1 bd $899+2 bd $1,099+3 bd $1,275Base rent102 Landings Way, Winter Haven, FL 33880Apply online • Pet friendly • Air conditioner
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1 bd $1,2592 bd $1,5423 bd $1,709+Base rent2850 W Lake Hamilton Dr, Winter Haven, FL 33881Apply online • Pet friendly • Fitness center
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3 bd $1,580Base rent4.5 (1)1715 Lake Shipp Dr N, Winter Haven, FL 33880Apply online • Pet friendly • Air conditioner
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1 bd $1,499+2 bd $1,650+Base rent1015 Lake Forest Blvd, Winter Haven, FL 33884Apply online • Pet friendly • Fitness center
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4 bd $1,795Base rent220 Southern Breeze Loop, Winter Haven, FL 33880Apply online • Pet friendly • Dishwasher
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4 bd $1,835Base rent850 TERRANOVA ROAD, WINTER HAVEN, FL 33884Apply online • Pet friendly • Dishwasher
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3 bd $1,695Base rent3414 Cove Ct W, Winter Haven, FL 33880Apply online • Pet friendly • Dishwasher
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3 bd $1,685Base rent163 Southern Breeze Loop, Winter Haven, FL 33880Apply online • Pet friendly • Dishwasher
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3 bd $1,880Base rent175 Kings Pond Ave, Winter Haven, FL 33880Apply online • Pet friendly • Dishwasher
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3 bd $1,995Base rent835 SUMMER GLEN DRIVE, WINTER HAVEN, FL 33880Apply online • Pet friendly • Dishwasher
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4 bd $1,820Base rent175 Southern Breeze Loop, Winter Haven, FL 33880Apply online • Pet friendly • Dishwasher
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3 bd $1,815Base rent40 Saint Kitts Circle, Winter Haven, FL 33884Apply online • Pet friendly • Dishwasher
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4 bd $1,905Base rent192 Southern Breeze Loop, Winter Haven, FL 33880Apply online • Pet friendly • Dishwasher
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4 bd $1,965Base rent112 Southern Breeze Loop, Winter Haven, FL 33880Apply online • Pet friendly • Dishwasher
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Rent specials2 bd $1,1503 bd $1,275Base rent3.5 (4)3950 Country Place, Winter Haven, FL 33880Apply online • Pet friendly -
Rent specials1 bd $899+2 bd $1,285Base rent4.0 (6)418 19Th Street, Winter Haven, FL 33884Apply online • Pet friendly • Patio/Balcony
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Rent specials1 bd $1,100+2 bd $1,285+Base rent3.0 (5)102 Landings Way, Winter Haven, FL 33880Apply online • Pet friendly • Washer/Dryer
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Studio $575Base rent3301 Avenue G NW, Winter Haven, FL 33880Pet friendly • Pool
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1 bd $1,100Base rent233 21St St SW, Winter Haven, FL 33880Air conditioner
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1 bd $1,100Base rent233 21St St SW, Winter Haven, FL 33880Air conditioner
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3 bd $1,950Base rent554 Reddicks Circle, Winter Haven, FL 33884Dishwasher • Air conditioner • Washer/Dryer
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2 bd $1,500Base rent400 El Camino Drive, Winter Haven, FL 33884Pet friendly • Dishwasher • Washer/Dryer
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3 bd $1,800Base rent7421 Florida 544, Winter Haven, FL 33881Pet friendly • Air conditioner • Washer/Dryer
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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 30 Jul 2026.
What are the best apartments in Winter Haven, FL?
The best apartments in Winter Haven, FL are: The Waverly at Winter Haven, Haven at Lake Deer, The Landings Apartment Homes, Magnolia at Lake Hamilton and Episcopal Catholic Apartments.
What type of rental buildings are in Winter Haven, FL?
In Winter Haven 36% of the housing is rented out compared to 64% of homes are owned, according to the most recent Census Bureau estimates. 10% of Winter Haven's apartments are found in large buildings of 50 units or more, 51% are located in smaller apartment complexes with less than 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.