Cheap Apartments for Rent in the Downtown Winter Haven Neighborhood of Winter Haven, FL from $600 (35 Rentals)

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

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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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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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

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

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property at 67 Deena Way

67 Deena Way

Winter HavenFL33880
Showing Results 1-35, Page 1 of 1

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 1 Bed unit found at The Landings Apartment Homes priced from $899. Central Haven Apartments has the second lowest priced unit, which is a Studio apartment currently listed from $1,000. Here are the most affordable Downtown Winter Haven apartments for rent in Winter Haven, FL:

Apartment ListingModel NameBed/BathPriced From
The Landings Apartment Homes1 Bedroom - BRANDYWYNE1BR,1BA$899
Central Haven ApartmentsStudio, 1 bathStudio,1BA$1,000
Haven at Lake DeerStudioStudio,1BA$1,099
The JadeCozy One1BR,1BA$1,200
Lakeview Tower-62+ CommunityStudioStudio,1BA$1,208
Briarcrest at Winter HavenThe Hamilton II2BR,2BA$1,220
The BreezeA1Studio,1BA$1,330
RainDanceB-21BR,1BA$1,450
Lakeshore Club1 Bedroom, 1.5 Bathroom1BR,1BA$1,575

Best Value Apartments for Rent in Downtown Winter Haven, FL

As of December 01, 2025 the best value apartment in the Downtown Winter Haven area is the $1.26 price per square foot 2x2.5 Lake Front Model at The Townhomes of Evergreen on Lake Idylwild in the in the Inwood neighborhood starting from $1,795. The second greatest value Downtown Winter Haven apartment is the The Hamilton II Model at Briarcrest at Winter Haven starting at $1,220 with a $0.99 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 Idylwild2x2.5 Lake Front2BR,2.5BA$1.26
Briarcrest at Winter HavenThe Hamilton II2BR,2BA$0.99
Lakeshore Club2 Bedroom, 2 Bathroom2BR,2BA$1.71
Central Haven Apartments2 Beds, 1 bath2BR,1BA$1.50
RainDanceA-51BR,1BA$2.29
669 Avenue B NW, Unit 2669 Avenue B NW1BR,1BA$2.08
The Landings Apartment Homes1 Bedroom - BRANDYWYNE1BR,1BA$1.56
The JadeLarge Sunny One1BR,1BA$2.83
Haven at Lake DeerStudioStudio ,1BA$2.44
Lakeview Tower-62+ CommunityStudioStudio ,1BA$3.02

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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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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Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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Pet Friendly Lifestyle
Downtown Winter Haven, Winter Haven, FL

Ranked #13

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 $899 at The Landings Apartment Homes.

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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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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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.