Homes for Rent in Oakwood Neighborhood of Winter Haven, FL Under $2,000 (86 Rentals)

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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 608 Maggie Cir

$1,600

Total Monthly Price

Total Monthly Price

Base Rent
$1,600
Total Monthly Price
$1,600

3 Bedroom, 2 Bath Home for Rent

Available Now

608 Maggie Cir

Winter HavenFL33880
property at 1407 N Lake Shipp Dr SW

$1,525

Total Monthly Price

Total Monthly Price

Base Rent
$1,525
Total Monthly Price
$1,525

2 Bedroom, 1 Bath Home for Rent

Available Mar 15

1407 N Lake Shipp Dr SW

Winter HavenFL33880

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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property at 1744 Wallace Manor Loop

$1,960

Total Monthly Price

Total Monthly Price

Base Rent
$1,930
Required Monthly Fees
$30
Total Monthly Price
$1,960

3 Bedroom, 2 Bath Rentals

Available Now

1744 Wallace Manor Loop

Winter HavenFL33880
property at 3236 Timberline Rd

$1,885

Total Monthly Price

Total Monthly Price

Base Rent
$1,885
Total Monthly Price
$1,885

3 Bedroom, 2 Bath Rentals

Available Mar 10

3236 Timberline Rd

Winter HavenFL33880
property at 1428 Wallace Manor Pass

$1,845

Total Monthly Price

Total Monthly Price

Base Rent
$1,834
Required Monthly Fees
$11
Total Monthly Price
$1,845

3 Bedroom, 2 Bath Rentals

Available Mar 16

1428 Wallace Manor Pass

Winter HavenFL33880
property at 344 Sand Pine Trail

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$1,970
Required Monthly Fees
$30
Total Monthly Price
$2,000

3 Bedroom, 2 Bath Rentals

Available Apr 20

344 Sand Pine Trail

Winter HavenFL33880
property at 3215 Timberline Rd

$1,509

Total Monthly Price

Total Monthly Price

Base Rent
$1,397
Required Monthly Fees
$112
Total Monthly Price
$1,509

2 Bedroom, 1 Bath Rentals

Available Now

3215 Timberline Rd

Winter HavenFL33880
property at 2390 29th St NW

$1,799

Total Monthly Price

Total Monthly Price

Base Rent
$1,687
Required Monthly Fees
$112
Total Monthly Price
$1,799

4 Bedroom, 2 Bath Rentals

Available Now

2390 29th St NW

Winter HavenFL33881
property at 1405 N Lake Shipp Dr

$1,770

Total Monthly Price

Total Monthly Price

Base Rent
$1,770
Total Monthly Price
$1,770

3 Bedroom, 2 Bath Rentals

Available Now

1405 N Lake Shipp Dr

Winter HavenFL33880

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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property at 3235 Timberline Rd

$1,670

Total Monthly Price

Total Monthly Price

Base Rent
$1,670
Total Monthly Price
$1,670

3 Bedroom, 2 Bath Rentals

Available Now

3235 Timberline Rd

Winter HavenFL33880
property at 3233 Timberline Rd

$1,785

Total Monthly Price

Total Monthly Price

Base Rent
$1,785
Total Monthly Price
$1,785

3 Bedroom, 2 Bath Rentals

Available Now

3233 Timberline Rd

Winter HavenFL33880
property at 606 Patrick Ave

$1,735

Total Monthly Price

Total Monthly Price

Base Rent
$1,735
Total Monthly Price
$1,735

3 Bedroom, 2 Bath Rentals

Available Mar 21

606 Patrick Ave

Winter HavenFL33880

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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property at 2000 15th Ct NW

$1,395 - $1,425

2 Bedroom Rentals

Available Now

2000 15th Ct NW

Winter HavenFL33881
Showing Results 1-50, Page 1 of 2

Oakwood, Winter Haven, FL Local Guide

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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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

Read Article
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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
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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 #9

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

Frequently Asked Questions about Oakwood

What type of rentals are currently available in Oakwood?

There are currently 127 Apartments for Rent in Oakwood, FL with pricing that ranges from $899 to $2,843. There are also 98 Single Family Homes for rent, Condos, and Townhome rentals currently available in Oakwood ranging from $600 to $7,000.

What is the current price range for Rental Homes in Oakwood?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Oakwood ranges from $600 to $7,000 with an average monthly rent of $2,337.

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 Maximizing Your Refund: Essential Tax Tips for Renters article

Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

decorative image for 18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property article

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

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.

decorative image for A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment article

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.