Cheap Apartments for Rent in the Downtown Winter Haven Neighborhood of Winter Haven, FL from $500 (36 Rentals)

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

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

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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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Lakeside Terrace
1 to 2 Bedroom Apartments

Lakeside Terrace

391 Avenue O NEWinter Haven, FL 33881
Senior Living
  • Utilities Included
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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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710 Avenue C SW
1 to 2 Bedroom Apartments

710 Avenue C SW

710 Avenue C SWWinter Haven, FL 33880

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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property at 117 5th St NE

$1,250 - $1,600

1 To 2 Bedroom Rentals

Available Now

117 5th St NE

Winter HavenFL33881
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669 Avenue B NW
1 Bedroom Apartments

669 Avenue B NW

669 Avenue B NWWinter Haven, FL 33881
property at 1550 11th St NE

$1,300

Total Monthly Price

Total Monthly Price

Base Rent
$1,300
Total Monthly Price
$1,300

2 Bedroom, 2 Bath Condo for Rent

Available Now

1550 11th St NE, Unit D7

1550 11th St NE
Winter HavenFL33881

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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Showing Results 1-36, 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. Lakeview Tower has the second lowest priced unit, which is a 1 Bed apartment currently listed from $950. 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
Lakeview TowerOne Bedroom1BR,1BA$950
Central Haven ApartmentsStudio, 1 bathStudio,1BA$1,000
Briarcrest at Winter HavenAriana II1BR,1BA$1,090
710 Avenue C SW1/11BR,1BA$1,150
Barrington Place At Winter HavenA11BR,1BA$1,165
Haven at Lake Deer1 Bedroom1BR,1BA$1,199
The JadeSunny One1BR,1BA$1,200

Best Value Apartments for Rent in Downtown Winter Haven, FL

As of July 08, 2026 the best value apartment in the Downtown Winter Haven area is the $1.63 price per square foot Raingarden Model at Raingarden Apartments in the in the Graydon Hills neighborhood starting from $3,250. The second greatest value Downtown Winter Haven apartment is the 690 Avenue C SE Model at 690 Avenue C SE, Unit 690 starting at $1,750 with a $1.24 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.
Raingarden ApartmentsRaingarden2BR,2.5BA$1.63
690 Avenue C SE, Unit 690690 Avenue C SE3BR,2BA$1.24
Lakeshore Club2 Bedroom, 2 Bathroom2BR,2BA$1.61
Briarcrest at Winter HavenAriana II1BR,1BA$1.23
Central Haven Apartments2 Beds, 1 bath2BR,1BA$1.50
Barrington Place At Winter HavenA11BR,1BA$1.47
399 Ave B Ave SE, Unit 399. Ave B399 Ave B Ave SE1BR,1BA$1.78
710 Avenue C SW1/11BR,1BA$1.84
The Landings Apartment Homes1 Bedroom - BRANDYWYNE1BR,1BA$1.56
Lakeview TowerOne Bedroom1BR,1BA$1.65

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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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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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 #16

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.

Frequently Asked Questions about Cheap Downtown Winter Haven Apartments

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 $1,185 at Briarcrest at Winter Haven.

What is the most affordable Downtown Winter Haven Three Bedroom Apartment?

The best deal on a cheap Downtown Winter Haven Three Bedroom Apartment rental is at Briarcrest at Winter Haven and starts from $1,470.

Expert Rental Resources

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.

Articles, How-To's, and Tips

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.