2 Bedroom Apartments for Rent in Winter Haven, FL (127 Rentals)

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Prose Cypress Pointe
Rent Specials
$1,549 - $2,032
Total Monthly Price

Total Monthly Price

Base Rent
$1,299 - $1,890
Required Monthly Fees
$142
Total Monthly Price
$1,441 - $2,032
2 Bedroom Apartments Available Now

Prose Cypress Pointe

3110 Gowan DrWinter Haven, FL 33884
Family Friendly
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The Breeze
Rent Specials
$1,995 - $2,328
Total Monthly Price

Total Monthly Price

Base Rent
$1,275 - $2,253
Required Monthly Fees
$75
Total Monthly Price
$1,350 - $2,328
2 Bedroom Apartments Available Now

The Breeze

265 Ave E SWWinter Haven, FL 33880
Student Living
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Dream Winter Haven
Rent Specials
$1,529 - $1,999
Total Monthly Price

Total Monthly Price

Base Rent
$1,260 - $2,060
Required Monthly Fees
$39
Total Monthly Price
$1,299 - $2,099
2 Bedroom Apartments Available Now

Dream Winter Haven

5004 Dream DrWinter Haven, FL 33881
Corporate Housing
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Raindance
Rent Specials
$1,925 - $2,383
Total Monthly Price

Total Monthly Price

Base Rent
$1,428 - $2,308
Required Monthly Fees
$75
Total Monthly Price
$1,503 - $2,383
2 Bedroom Apartments Available Now

Raindance

200 Avenue C SWWinter Haven, FL 33880
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour

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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617 Sears Ave NE
$1,250
Total Monthly Price

Total Monthly Price

Base Rent
$1,250
Total Monthly Price
$1,250
2 Bedroom Apartment Available Now

617 Sears Ave NE

617 Sears Ave NEWinter Haven, FL 33881
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660 24th St NW, Unit # B
$1,235
Total Monthly Price

Total Monthly Price

Base Rent
$1,235
Total Monthly Price
$1,235
2 Bedroom Apartment Available Now

660 24th St NW, Unit # B

660 24th St NWWinter Haven, FL 33880
Affordability
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property at 140 Ave W NW

$1,499

2 Bedroom Rentals

Available Now

140 Ave W NW

Winter HavenFL33881

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 163 Ave A SE

$1,300

2 Bedroom Rentals

Available Now

163 Ave A SE

Winter HavenFL33880
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Tzadik Brandywyne
2 Bedroom Apartments

Tzadik Brandywyne

411 18th St SEWinter Haven, FL 33884
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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

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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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
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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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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
Showing Results 1-50, Page 1 of 3

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: February 23, 2026

There are currently 59 available 2 Bedroom apartment units in Winter Haven, FL neighborhoods that range in price from $1,150 to $2,916. 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 Haven59$1,598$1,150

Largest Available Winter Haven 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Winter Haven, FL is found at Lakeshore Club in the Graydon Hills neighborhood and is 1,400 square feet priced from $1,700. The Carlton at Lake Dexter in the Cypress Grove neighborhood has the second largest 2 Bedroom, which is sized at 1,279 square feet and currently listed start at $1,435. Here is today’s list of the largest available 2 Bedroom units in Winter Haven:

Apartment ListingModel NameSquare FootagePriced From
Lakeshore Club2 Bedroom, 2 Bathroom1,400 Sq Ft$1,700
The Carlton at Lake DexterWindsor1,279 Sq Ft$1,435
Serenity at Lake WalesSanctuary1,214 Sq Ft$2,245
Prose Cypress PointeB11,180 Sq Ft$1,691
Alera at Hunters GlenB41,100 Sq Ft$1,699
The BreezeCPH11,086 Sq Ft$2,250

Cheapest Available Winter Haven 2 Bedroom Apartments

As of February 23, 2026 the lowest priced 2 Bedroom apartment unit in Winter Haven, FL is the 2BR 2BA Model starting from $993 at Villas at Lake Smart Apartments in the Brandywyne neighborhood. The second most affordable Winter Haven 2 Bedroom is the 2 Beds, 1 bath Model at Central Haven Apartments starting at $1,275 in the Graydon Hills neighborhood. The average price for all 2 Bedroom apartments in Winter Haven is currently $1,727. Here is today’s list of the cheapest available 2 Bedroom options in Winter Haven:

Apartment ListingModel NamePriced From
Villas at Lake Smart Apartments2BR 2BA$993
Central Haven Apartments2 Beds, 1 bath$1,275
The Landings Apartment Homes2 Bedroom - BRANDYWYNE$1,285
510 Avenue K NW2b/2b$1,350
Della Vita ApartmentsTwo Bed 1 Bath$1,365
Haven at Lake Deer2 Bedroom$1,385
Vista Lake Ned2x1$1,397

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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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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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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 Villas at Lake Smart Apartments listed at $993.

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 $1,727.

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 1,400 square feet unit starting from $1,700 at Lakeshore Club.

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 1,024 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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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.

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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.

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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.