Cheap Apartments for Rent in the Oakwood Neighborhood of Winter Haven, FL from $500 (26 Rentals)

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

$1,100

2 Bedroom Rentals

Available Now

140 Ave W NW

Winter HavenFL33881
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Lakeside Terrace
1 to 2 Bedroom Apartments

Lakeside Terrace

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

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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Auburn Village
1 to 2 Bedroom Apartments

Auburn Village

3020 Maple DrWinter Haven, FL 33881
Senior Living
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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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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 1-26, Page 1 of 1

Oakwood, Winter Haven, FL Local Guide

Cheapest Available Oakwood Apartments for Rent

 

The cheapest available apartment rental in the Oakwood area of Lakeland, 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 Oakwood apartments for rent in Lakeland, FL:

Apartment ListingModel NameBed/BathPriced From
The Landings Apartment Homes1 Bedroom - LANDINGS1BR,1BA$899
Lakeview TowerOne Bedroom1BR,1BA$950
Oakcrest Apartments123 Oakcrest1BR,1BA$975
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
The JadeSunny One1BR,1BA$1,200
The BreezeA1Studio,1BA$1,275

Best Value Apartments for Rent in Oakwood, FL

As of May 31, 2026 the best value apartment in the Oakwood area is the $1.61 price per square foot 2 Bedroom, 2 Bathroom Model at Lakeshore Club in the in the Graydon Hills neighborhood starting from $1,625. The second greatest value Oakwood 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 Oakwood apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
Lakeshore Club2 Bedroom, 2 Bathroom2BR,2BA$1.61
501 Avenue L NE501 Avenue L NE2BR,1BA$1.19
330 Avenue G SE, Unit Apartment330 Avenue G SE3BR,1BA$1.75
Briarcrest at Winter HavenAriana II1BR,1BA$1.22
Central Haven Apartments2 Beds, 1 bath2BR,1BA$1.50
Barrington Place At Winter HavenA11BR,1BA$1.43
Haven at Lake Deer1 Bedroom1BR,1BA$1.78
Oakcrest Apartments123 Oakcrest1BR,1BA$1.63
The Landings Apartment Homes1 Bedroom - LANDINGS1BR,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
Oakwood, Winter Haven, FL

Ranked #14

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
Oakwood, Winter Haven, FL

School data provided by Great Schools

Lifestyle Ratings

Our team of engineers and researchers compares millions of points of data to bring you Lifestyle Ratings of rentals and neighborhoods across the USA, including Winter Haven. Our Lifestyle Ratings help you zero-in on the perfect place to call home. This takes in many factors including searching for the best amenities, and the best outdoor access, kid and pet-friendly communities, availability of transit options, and other valuable search options. Use Lifestyle Search in the site filter options on this page - and find your Perfect place!

Frequently Asked Questions about Cheap Oakwood Apartments

What is the Cheapest Studio apartment in Oakwood?

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

How much is rent for a Cheap One Bedroom Oakwood Apartment?

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

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

Today's best deal for a Cheap Two Bedroom Apartment in Oakwood is starting from $1,185 at Briarcrest at Winter Haven.

What is the most affordable Oakwood Three Bedroom Apartment?

The best deal on a cheap Oakwood 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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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.