Cheap Apartments for Rent in the Oakwood Neighborhood of Winter Haven, FL from $500 (35 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

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.

Read Article

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.

Read Article
close
View Me
Lakeside Terrace
1 to 2 Bedroom Apartments

Lakeside Terrace

391 Avenue O NEWinter Haven, FL 33881
Senior Living
  • Utilities Included
close
View Me
Auburn Village
1 to 2 Bedroom Apartments

Auburn Village

3020 Maple DrWinter Haven, FL 33881
Senior Living

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.

Read Article
close
View Me
663 Avenue J Nw
1 to 2 Bedroom Apartments

663 Avenue J Nw

663 Avenue J NwWinter Haven, FL 33881
close
View Me
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.

Read Article
Showing Results 1-35, 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
Central Haven ApartmentsStudio, 1 bathStudio,1BA$1,000
710 Avenue C SW1/11BR,1BA$1,050
Briarcrest at Winter HavenAriana II1BR,1BA$1,090
Haven at Lake Deer1 Bedroom1BR,1BA$1,099
The JadeSunny One1BR,1BA$1,200
Dream Winter HavenA11BR,1BA$1,259

Best Value Apartments for Rent in Oakwood, FL

As of July 16, 2026 the best value apartment in the Oakwood 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 Oakwood apartment is the B1 Model at Elio at Lake Lena starting at $1,785 with a $1.35 price per square foot in the Westwood Villas 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.
Raingarden ApartmentsRaingarden2BR,2.5BA$1.63
Elio at Lake LenaB12BR,2.5BA$1.35
Lakeshore Club2 Bedroom, 2 Bathroom2BR,2BA$1.61
Barrington Place At Winter HavenB12BR,1.5BA$1.29
Briarcrest at Winter HavenAriana II1BR,1BA$1.23
Central Haven Apartments2 Beds, 1 bath2BR,1BA$1.50
Haven at Lake Deer1 Bedroom1BR,1BA$1.73
710 Avenue C SW1/11BR,1BA$1.68
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.

Read Article
Decorative image

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.

Read Article
Decorative image

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.

decorative image of people with a giant lease agreement

Pet Friendly Lifestyle
Oakwood, Winter Haven, FL

Ranked #17

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

Pet Friendliness Lifestyle Score

3.0
Pet Friendly

decorative image of woman handing cat to small boy

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

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 $1,160 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

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

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.

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention article

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.

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

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.

decorative image for Pet-Friendly Renting: Everything You Need to Know Before You Move article

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.