Cheap Apartments for Rent in the Oakwood Neighborhood of Winter Haven, FL from $539 (38 Rentals)

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

Rent According to Income: A Look at Income-Restricted Rentals

Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.

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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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Auburn Village
1 to 2 Bedroom Apartments

Auburn Village

3020 Maple DrWinter Haven, FL 33881
Senior Living

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

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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1800 3rd Ct SE
1 to 3 Bedroom Apartments

1800 3rd Ct SE

1800 3rd Ct SEWinter Haven, FL 33880
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663 Avenue J Nw
1 Bedroom Apartments

663 Avenue J Nw

663 Avenue J NwWinter Haven, FL 33881
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710 Avenue C SW
1 to 2 Bedroom Apartments

710 Avenue C SW

710 Avenue C SWWinter Haven, FL 33880

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

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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property at 202 Polk St

$1,100

1 Bedroom Rentals

Available Now

202 Polk St

AuburndaleFL33823

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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Showing Results 1-38, 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 1800 3rd Ct SE priced from $925. 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
1800 3rd Ct SE1BR/1.0BA1BR,1BA$925
Lakeview TowerOne Bedroom1BR,1BA$950
663 Avenue J Nw1 Beds, 1 Baths1BR,1BA$950
Oakcrest Apartments123 Oakcrest1BR,1BA$975
710 Avenue C SW1/11BR,1BA$975
The Landings Apartment Homes1 Bedroom - LANDINGS1BR,1BA$979
Briarcrest at Winter HavenThe Ariana1BR,1BA$997
Central Haven ApartmentsStudio, 1 bathStudio,1BA$1,000
Haven at Lake DeerStudioStudio,1BA$1,099

Best Value Apartments for Rent in Oakwood, FL

As of August 30, 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 C-2 Model at Raindance starting at $1,895 with a $1.79 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.
Raingarden ApartmentsRaingarden2BR,2.5BA$1.63
RaindanceC-22BR,2BA$1.79
Lakeshore Club2 Bedroom, 2 Bathroom2BR,2BA$1.61
Central Haven Apartments2 Beds, 1 bath2BR,1BA$1.50
Briarcrest at Winter HavenThe Ariana1BR,1BA$1.26
1800 3rd Ct SE1BR/1.0BA1BR,1BA$1.45
710 Avenue C SW1/11BR,1BA$1.56
Oakcrest Apartments123 Oakcrest1BR,1BA$1.63
The Landings Apartment Homes1 Bedroom - LANDINGS1BR,1BA$1.70
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 $925 at 1800 3rd Ct SE.

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 $1,220 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 $1,355.

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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Rent According to Income: A Look at Income-Restricted Rentals

Written by: Robin Stewart

The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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.