2 Bedroom Apartments for Rent in Winter Haven, FL (122 Rentals)

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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.

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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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Tzadik Brandywyne
2 Bedroom Apartments

Tzadik Brandywyne

411 18th St SEWinter Haven, FL 33884
  • Utilities Included

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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1120 Evergreen Pl
2 Bedroom Apartments

1120 Evergreen Pl

1120 Evergreen PlWinter Haven, FL 33880
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730 W Central Ave
2 Bedroom Apartments

730 W Central Ave

730 W Central AveWinter Haven, FL 33880
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3101 Avenue V NW
2 Bedroom Apartments

3101 Avenue V NW

3101 Avenue V NWWinter Haven, FL 33881
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327 21st St W
2 Bedroom Apartments

327 21st St W

327 21st St WWinter Haven, FL 33880
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669 Avenue B NW
2 Bedroom Apartments

669 Avenue B NW

669 Avenue B NWWinter Haven, FL 33881
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3937 Country Pl
2 Bedroom Apartments

3937 Country Pl

3937 Country PlWinter Haven, FL 33880
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627 Avenue B SW
2 Bedroom Apartments

627 Avenue B SW

627 Avenue B SWWinter Haven, FL 33880

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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151 Avenue C SE
2 Bedroom Apartments

151 Avenue C SE

151 Avenue C SEWinter Haven, FL 33880
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parcel 1
2 Bedroom Apartments

parcel 1

3801 Avenue J NWWinter Haven, FL 33881
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37 Carla Ct
2 Bedroom Apartments

37 Carla Ct

37 Carla CtWinter Haven, FL 33880
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609 NE Sears Ave
2 Bedroom Apartments

609 NE Sears Ave

609 NE Sears AveWinter Haven, FL 33881
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Sunset Apartments
2 Bedroom Apartments

Sunset Apartments

710 Avenue C SWWinter Haven, FL 33880
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Winter Haven, FL Local Guide

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Local Guide Expert

Winter Haven 2 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: January 02, 2026

There are currently 64 available 2 Bedroom apartment units in Winter Haven, FL neighborhoods that range in price from $1,150 to $2,250. Heres is today's list of the top neighborhoods in Winter Haven with the most available 2 Bedroom apartments:

NeighborhoodAvailable UnitsMedian PriceMin Price
Downtown Winter Haven64$1,699$1,150

Largest Available Winter Haven 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Winter Haven, FL is found at The Carlton at Lake Dexter in the Cypress Grove neighborhood and is 1,472 square feet priced from $1,473. Lakeshore Club in the Graydon Hills neighborhood has the second largest 2 Bedroom, which is sized at 1,400 square feet and currently listed start at $1,800. Here is today’s list of the largest available 2 Bedroom units in Winter Haven:

Apartment ListingModel NameSquare FootagePriced From
The Carlton at Lake DexterOxford1,472 Sq Ft$1,473
Lakeshore Club2 Bedroom, 2 Bathroom1,400 Sq Ft$1,800
Briarcrest at Winter HavenThe Hamilton II1,236 Sq Ft$1,230
Serenity at Lake WalesSanctuary1,214 Sq Ft$2,245
Prose Cypress PointeB11,180 Sq Ft$1,599
Mediterranean Villas2 Bed, 2 Bath1,150 Sq Ft$1,438

Cheapest Available Winter Haven 2 Bedroom Apartments

As of January 02, 2026 the lowest priced 2 Bedroom apartment unit in Winter Haven, FL is the The Hamilton II Model starting from $1,230 at Briarcrest at Winter Haven in the Graydon Hills neighborhood. The second most affordable Winter Haven 2 Bedroom is the 2 Beds, 1 bath Model at Central Haven Apartments starting at $1,275 . The average price for all 2 Bedroom apartments in Winter Haven is currently $1,706. Here is today’s list of the cheapest available 2 Bedroom options in Winter Haven:

Apartment ListingModel NamePriced From
Briarcrest at Winter HavenThe Hamilton II$1,230
Central Haven Apartments2 Beds, 1 bath$1,275
The Landings Apartment Homes2 Bedroom - BRANDYWYNE$1,285
Della Vita ApartmentsTwo Bed 1 Bath$1,365
Vista Lake Ned2x1$1,371
The Carlton at Lake DexterWindsor$1,435
Mediterranean Villas2 Bed, 2 Bath$1,438
Haven at Lake Deer2 Bedroom$1,450

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.

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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.

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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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Winter Haven Overview

Living in apartments in Winter Haven, Florida offers you plenty of amenities, outdoor recreation opportunities, and larger cities a short commute away. You get a country feel, while being able to live in a city. The weather is warm throughout most of the year, with only a few months of cooler weather during the winter. Residents enjoy the variety of restaurants and shopping, while there are great work opportunities in nearby Tampa and Orlando. It's a good city to call home, as residents describe it as affordable, relaxing, and quiet.

Why live in Winter Haven, FL?

With an easy commute to Orlando and Tampa, Winter Haven is in an excellent location. It's more affordable than the two nearby cities, and there are a lot of amenities for residents to enjoy. It's a medium-sized city that offers plenty of opportunities for fun, outdoor recreation, dining, shopping, and entertainment. The lakes and canal system are a big draw for residents, and there are many hiking trails throughout the city for those that love nature.

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Winter Haven, FL

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Winter Haven, FL Rentals by Map

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See the most popular apartments and homes in Winter Haven, FL

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Frequently Asked Questions about 2 Bedroom Winter Haven Apartments

What is the Cheapest apartment in Winter Haven with 2 Bedroom?

Currently the most affordable 2 Bedroom in Winter Haven is at Briarcrest at Winter Haven listed at $1,230.

How much is the average rent for a 2 Bedroom Winter Haven Apartment?

The average rent for a 2 Bedroom Apartment in Winter Haven is $1,706.

What is the largest available 2 Bedroom Winter Haven Apartment for rent?

Today's apartment with the most square footage in Winter Haven is a 1,472 square feet unit starting from $1,473 at The Carlton at Lake Dexter.

What is the average size for Winter Haven 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Winter Haven is currently 1,112 sq ft.

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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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.

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How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips

Written by: Justin Habersaat

Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate!