Cheap Apartments for Rent in Winter Haven, FL from $500 (58 Rentals)

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Search the lowest-cost Apartments available for rent right now in 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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property at 140 Ave W NW

$1,100

2 Bedroom Rentals

Available Now

140 Ave W NW

Winter HavenFL33881

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

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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Wahneta Palms
2 to 3 Bedroom Apartments

Wahneta Palms

225 Wahneta Palms DrWinter Haven, FL 33880
  • Utilities Included
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Auburn Village
1 to 2 Bedroom Apartments

Auburn Village

3020 Maple DrWinter Haven, FL 33881
Senior Living
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1 Lamplight Ln
1 Bedroom Apartments

1 Lamplight Ln

1 Lamplight LnWinter Haven, FL 33884
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710 Avenue C SW
1 to 2 Bedroom Apartments

710 Avenue C SW

710 Avenue C SWWinter Haven, FL 33880

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 932 Hart St

$850

Total Monthly Price

Total Monthly Price

Base Rent
$850
Total Monthly Price
$850

Studio, 1 Bath Home for Rent

Available Jun 1

932 Hart St

Lake WalesFL33859
property at 123 E Main St

$1,000

Total Monthly Price

Total Monthly Price

Base Rent
$1,000
Total Monthly Price
$1,000

1 Bedroom, 1 Bath Home for Rent

Available Now

123 E Main St

DundeeFL33838
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Fountainview Apartments
Studio to 2 Bedroom Apartments

Fountainview Apartments

527 W Florida AveHaines City, FL 33844
  • Utilities Included

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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Showing Results 1-50, Page 1 of 2

Winter Haven, FL Local Guide

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Staff Writer
Local Guide Expert

Cheapest Neighborhoods for Apartments in Winter Haven, FL

Pricing Updated: 05/31/2026

Current apartment rentals in the Winter Haven, FL area range in price from to with an overall median price of . Here is today’s list neighborhoods with the lowest median pricing for Winter Haven Apartments for rent:

NeighborhoodMedian PriceMin PriceAvailable Units
Downtown Winter Haven$2,495$60041

Cheapest Available Winter Haven Apartments for Rent

 

The cheapest available apartment rental in Winter Haven, FL is a 1 Bed unit found at The Landings Apartment Homes in the Westwood Villas neighborhood priced from $899. Lakeview Tower in the Graydon Hills neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $950. Here is today’s list of the most affordable Winter Haven apartments for rent:

Apartment ListingModel NameBed/BathPriced From
The Landings Apartment Homes1 Bedroom - LANDINGS1BR,1BA$899
Lakeview TowerOne Bedroom1BR,1BA$950
Oakcrest Apartments123 Oakcrest1BR,1BA$975
Villas at Lake Smart Apartments2BR 2BA2BR,2BA$993
306 Lake Millsite Rd E1/11BR,1BA$1,000
Central Haven ApartmentsStudio, 1 bathStudio,1BA$1,000
Briarcrest at Winter HavenAriana II1BR,1BA$1,080
Barrington Place At Winter HavenA11BR,1BA$1,130
Haven at Lake Deer1 Bedroom1BR,1BA$1,135
Della Vita Apartments1 Bed 1 Bath1BR,1BA$1,160

Best Value Apartments for Rent in Winter Haven, FL

As of May 31, 2026 the best value apartment in the Winter Haven area is the $1.42 price per square foot Two Bedrooms/Two Baths Model at The Arbours at Garden Grove in the in the Cypress Grove neighborhood starting from $1,572. The second greatest value Winter Haven apartment is the 501 Avenue L NE Model at 501 Avenue L NE starting at $1,185 with a $1.19 price per square foot in the Graydon Hills neighborhood. Here is today’s list of the best values for Winter Haven apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
The Arbours at Garden GroveTwo Bedrooms/Two Baths2BR,2BA$1.42
501 Avenue L NE501 Avenue L NE2BR,1BA$1.19
The Carlton at Lake DexterBerkeley1BR,1BA$1.41
Villas at Lake Smart Apartments2BR 2BA2BR,2BA$1.10
Briarcrest at Winter HavenAriana II1BR,1BA$1.22
Central Haven Apartments2 Beds, 1 bath2BR,1BA$1.50
Prose Cypress PointeA11BR,1BA$1.56
Barrington Place At Winter HavenA11BR,1BA$1.43
Della Vita Apartments1 Bed 1 Bath1BR,1BA$1.55
The Landings Apartment Homes1 Bedroom - LANDINGS1BR,1BA$1.56

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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Winter Haven Overview

Living in apartments in Winter Haven, Florida offers you plenty of amenities, outdoor recreation opportunities, and larger cities a short commute away. You get a country feel, while being able to live in a city. The weather is warm throughout most of the year, with only a few months of cooler weather during the winter. Residents enjoy the variety of restaurants and shopping, while there are great work opportunities in nearby Tampa and Orlando. It's a good city to call home, as residents describe it as affordable, relaxing, and quiet.

Why live in Winter Haven, FL?

With an easy commute to Orlando and Tampa, Winter Haven is in an excellent location. It's more affordable than the two nearby cities, and there are a lot of amenities for residents to enjoy. It's a medium-sized city that offers plenty of opportunities for fun, outdoor recreation, dining, shopping, and entertainment. The lakes and canal system are a big draw for residents, and there are many hiking trails throughout the city for those that love nature.

Best Local Schools in
Winter Haven, FL

School data provided by Great Schools

Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Winter Haven, FL Rentals by Map

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See the most popular apartments and homes in Winter Haven, FL

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Frequently Asked Questions about Cheap Winter Haven Apartments

What is the Cheapest Studio apartment in Winter Haven?

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

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

The lowest price for a Cheap One Bedroom Winter Haven Apartment is $899 at The Landings Apartment Homes.

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

Today's best deal for a Cheap Two Bedroom Apartment in Winter Haven is starting from $993 at Villas at Lake Smart Apartments.

What is the most affordable Winter Haven Three Bedroom Apartment?

The best deal on a cheap Winter Haven Three Bedroom Apartment rental is at Villas at Lake Smart Apartments and starts from $1,144.

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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Neighborhood and Market Insights: How to Choose the Right Area to Rent

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.

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A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Written by: Lauren Harrington

I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

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Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

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

Written by: Lauren Harrington

This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.