Cheap Apartments for Rent in the Downtown Winter Haven Neighborhood of Winter Haven, FL from $600 (25 Rentals)

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Search the lowest-cost Apartments available for rent right now in the Downtown Winter Haven area of Winter Haven.

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

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Tzadik Brandywyne
1 to 2 Bedroom Apartments

Tzadik Brandywyne

411 18th St SEWinter Haven, FL 33884
  • Utilities Included
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Lakeside Terrace
1 to 2 Bedroom Apartments

Lakeside Terrace

391 Avenue O NEWinter Haven, FL 33881
Senior Living
  • Utilities Included

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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property at 117 Ave B NE

117 Ave B NE

Winter HavenFL33881
property at 115 8th St SE

115 8th St SE

Winter HavenFL33880
property at 631 Ave H NW

631 Ave H NW

Winter HavenFL33881

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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Downtown Winter Haven, Winter Haven, FL Local Guide

Cheapest Available Downtown Winter Haven Apartments for Rent

 

The cheapest available apartment rental in the Downtown Winter Haven area of Winter Haven, FL is a Studio unit found at Central Haven Apartments priced from $1,000. Briarcrest at Winter Haven has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,080. Here are the most affordable Downtown Winter Haven apartments for rent in Winter Haven, FL:

Apartment ListingModel NameBed/BathPriced From
Central Haven ApartmentsStudio, 1 bathStudio,1BA$1,000
Briarcrest at Winter HavenAriana II1BR,1BA$1,080
Haven at Lake DeerStudio1BR,1BA$1,099
The Landings Apartment Homes1 Bedroom - LANDINGS1BR,1BA$1,100
Barrington Place At Winter HavenB12BR,1BA$1,285

Best Value Apartments for Rent in Downtown Winter Haven, FL

As of October 14, 2025 the best value apartment in the Downtown Winter Haven area is the $1.16 price per square foot 2x2.5 Model at The Townhomes of Evergreen on Lake Idylwild in the in the Inwood neighborhood starting from $1,650. The second greatest value Downtown Winter Haven apartment is the 2 Bedroom, 2 Bathroom Model at Lakeshore Club starting at $1,699 with a $1.71 price per square foot in the Graydon Hills neighborhood. Here is today’s list of the best values for Downtown Winter Haven apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
The Townhomes of Evergreen on Lake Idylwild2x2.52BR,2.5BA$1.16
Lakeshore Club2 Bedroom, 2 Bathroom2BR,2BA$1.71
Barrington Place At Winter HavenB12BR,1.5BA$1.30
Briarcrest at Winter HavenAriana II1BR,1BA$1.22
Central Haven Apartments2 Beds, 1 bath2BR,1BA$1.50
RainDanceB-41BR,1BA$2.51
318 Palmetto Ave NW, Unit 318318 Palmetto Ave NW2BR,1BA$2.17
The Landings Apartment Homes1 Bedroom - LANDINGS1BR,1BA$1.91
Haven at Lake DeerStudioStudio ,1BA$2.44
1862 4th St SE, Unit A1862 4th St SEStudio ,1BA$2.79

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Pet Friendly Lifestyle
Downtown Winter Haven, Winter Haven, FL

Ranked #10

Among cities in Florida for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

3.0
Pet Friendly

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Best Local Schools in
Downtown Winter Haven, Winter Haven, FL

School data provided by Great Schools

Lifestyle Ratings

ApartmentHomeLiving brings you Lifestyle Ratings of neighborhoods, cities, and rental properties across Florida and customized analysis for Central Winter Haven. Lifestyle Ratings show you the best fit for your needs and interests. This takes in many factors including searching for the best amenities, and easy access to the parks, kid and pet-friendly communities, availability of transit options, and other valuable search options. These search options are in the site filters at the top of this page.

Getting Around the Downtown Winter Haven Neighborhood in Winter Haven, FL

Walk Score®

69 / 100

Somewhat Walkable

Some errands can be accomplished on foot

Bike Score®

62 / 100

Bikeable

Some bike infrastructure

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about Cheap Downtown Winter Haven Apartments

What is the Cheapest Studio apartment in Downtown Winter Haven?

Currently the most affordable Cheap Studio Apartment in Downtown Winter Haven is at Central Haven Apartments listed at $1,000.

How much is rent for a Cheap One Bedroom Downtown Winter Haven Apartment?

The lowest price for a Cheap One Bedroom Downtown Winter Haven Apartment is $1,080 at Briarcrest at Winter Haven.

What is the lowest price for a Cheap Two Bedroom Downtown Winter Haven Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Downtown Winter Haven is starting from $1,220 at Briarcrest at Winter Haven.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.

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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Written by: Christine Leonard, Esq.

Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.