Apartments for Rent in the Oakwood Neighborhood of Winter Haven, FL (222 Rentals)

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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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property at 3960 Avenue U NW

$1,800

Total Monthly Price

Total Monthly Price

Base Rent
$1,800
Total Monthly Price
$1,800

4 Bedroom, 2 Bath Home for Rent

Available Now

3960 Avenue U NW

Winter HavenFL33881
property at 101 Lake Sears Dr

$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

101 Lake Sears Dr

Winter HavenFL33880
property at 1536 Axel Cir

$1,875

Total Monthly Price

Total Monthly Price

Base Rent
$1,875
Total Monthly Price
$1,875

4 Bedroom, 2 Bath Home for Rent

Available Now

1536 Axel Cir

Winter HavenFL33880

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

Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

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property at 4766 Osprey Way

$2,025

Total Monthly Price

Total Monthly Price

Base Rent
$2,025
Total Monthly Price
$2,025

4 Bedroom, 2 Bath Rentals

Available Now

4766 Osprey Way

Winter HavenFL33881

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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Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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Showing Results 1-50, Page 1 of 5

Oakwood, Winter Haven, FL Local Guide

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

Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.

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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.

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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 #12

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

This website compares millions of points of data to bring you comprehensive Lifestyle Ratings of neighborhoods, areas, and rental properties across Florida, including Winter Haven. Lifestyle Ratings show you the best fit for your needs and interests. This takes in many factors including rankings of the best places for outdoor amenities like tennis courts, luxury amenities, apartment communities for the kids, raising pets, transit options, and other valuable search options. Find Lifestyle Search in the filter options (above). Happy Searching!

Frequently Asked Questions about Oakwood

What is the current pricing and availability for apartments for rent in the Oakwood area of Winter Haven, FL?

As of today, August 19, 2026, there are currently 222 available Oakwood apartments priced from $850 to $3,250, with an average monthly rent of $1,500.

What is the current price range for One Bedroom Oakwood Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Oakwood ranges from $850 to $1,785 with an average monthly rent of $1,351.

What does renting a Two Bedroom Apartment in Oakwood cost?

The monthly rent prices of Two Bedroom Apartments currently available in Oakwood range from $995 to $3,250. Today's average rental price for Two Bedrooms here is $1,618.

How expensive are Oakwood Three Bedroom Apartments?

There are currently 14 Three Bedroom Apartments listings available in Oakwood on ApartmentHomeLiving.com. The pricing ranges from $1,355 to $2,200 - averaging $1,616 for the location.

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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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.

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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.