Homes for Rent in the Downtown Winter Haven Neighborhood of Winter Haven, FL Under $2,000 (52 Rentals)

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property at 711 Avenue B NE
$1,725

Total Monthly Price

Base Rent$1,725
Total Monthly Price$1,725
3 Bedroom, 2 Bath Home for Rent
Available Sep 15

711 Avenue B NE

Winter HavenFL33881
property at 1308 3rd St NE
$1,400

Total Monthly Price

Base Rent$1,400
Total Monthly Price$1,400
2 Bedroom, 1 Bath Home for Rent
Available Oct 1

1308 3rd St NE

Winter HavenFL33881

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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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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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 2405 Ave C SW
$1,325
2 Bedroom Rentals
Available Now
Affordability

2405 Ave C SW

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 248 Avenue L NE
$1,500

Total Monthly Price

Base Rent$1,500
Total Monthly Price$1,500
2 Bedroom, 1 Bath Home for Rent
Available Now

248 Avenue L NE

Winter HavenFL33881
property at 110 Broward Dr
$1,900

Total Monthly Price

Base Rent$1,900
Total Monthly Price$1,900
3 Bedroom, 2 Bath Home for Rent
Available Now

110 Broward Dr

Winter HavenFL33884
property at 333 N Lake Howard Dr
$1,650

Total Monthly Price

Base Rent$1,650
Total Monthly Price$1,650
3 Bedroom, 2 Bath Condo for Rent
Available Now

333 N Lake Howard Dr, Unit 211B

333 N Lake Howard Dr
Winter HavenFL33880
property at 504 Orange Blossom Dr
$1,850

Total Monthly Price

Base Rent$1,850
Total Monthly Price$1,850
2 Bedroom, 3 Bath Townhome for Rent
Available Now
Luxury

504 Orange Blossom Dr

Winter HavenFL33880
Showing Results 1-50, Page 1 of 2

Downtown Winter Haven, Winter Haven, FL Local Guide

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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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
Downtown Winter Haven, Winter Haven, FL

Ranked #11

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

Pet Friendliness Lifestyle Score

3.5
Pet Friendly

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Best Local Schools in
Downtown Winter Haven, Winter Haven, FL

School data provided by Great Schools

Frequently Asked Questions about Downtown Winter Haven

What type of rentals are currently available in Downtown Winter Haven?

There are currently 106 Apartments for Rent in Downtown Winter Haven, FL with pricing that ranges from $850 to $4,701. There are also 64 Single Family Homes for rent, Condos, and Townhome rentals currently available in Downtown Winter Haven ranging from $730 to $3,600.

What is the current price range for Rental Homes in Downtown Winter Haven?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Downtown Winter Haven ranges from $730 to $3,600 with an average monthly rent of $1,666.

How much are larger Three and Four Bedroom Rentals in Downtown Winter Haven?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Downtown Winter Haven range from $1,355 to $4,141, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,550 to $3,600. Four Bedroom Single-Family rentals are also available starting from $1,800 and Four Bedroom Apartments start at $4,701.

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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Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

Written by: Robin Stewart

Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

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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.