2 Bedroom Apartments for Rent in Winter Haven, FL (175 Rentals)

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Prose Cypress Pointe
Rent Specials
$1,599 - $1,870
Total Monthly Price

Total Monthly Price

Base Rent
$1,299 - $1,870
Total Monthly Price
$1,299 - $1,870
2 Bedroom Apartments Available Now

Prose Cypress Pointe

3110 Gowan DrWinter Haven, FL 33884
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Renting with Roommates: Realistic Expectations for Shared Lease

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

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property at 5624 Struthers Ct

$1,450

Total Monthly Price

Total Monthly Price

Base Rent
$1,450
Total Monthly Price
$1,450

2 Bedroom, 1 Bath Home for Rent

Available Now

5624 Struthers Ct

Winter HavenFL33884
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 Now

1407 N Lake Shipp Dr SW

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 163 Ave A SE

$1,250

2 Bedroom Rentals

Available Now

163 Ave A SE

Winter HavenFL33880
property at 140 Ave W NW

$1,100

2 Bedroom Rentals

Available Now

140 Ave W NW

Winter HavenFL33881

Renting Smart: Lease Basics Every Renter Needs

Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com

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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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Winter Haven, FL Local Guide

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Winter Haven 2 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: May 24, 2026

There are currently 60 available 2 Bedroom apartment units in Winter Haven, FL neighborhoods that range in price from $1,100 to $2,840. 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 Haven60$1,625$1,100

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. Serenity at Lake Wales in the Hart Lake Hills neighborhood has the second largest 2 Bedroom, which is sized at 1,214 square feet and currently listed start at $2,245. 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
Serenity at Lake WalesSanctuary1,214 Sq Ft$2,245
Briarcrest at Winter HavenThe Hamilton1,194 Sq Ft$1,220
Prose Cypress PointeB11,180 Sq Ft$1,599
Carlton Arms Of Winter Haven(H1A) Townhome1,120 Sq Ft$1,605
The Arbours at Garden GroveTwo Bedrooms/Two Baths1,105 Sq Ft$1,425
Alera at Hunters GlenB41,100 Sq Ft$1,629
The BreezeCPH11,086 Sq Ft$2,225
Dream Winter HavenB31,077 Sq Ft$1,899
RaindanceC-21,058 Sq Ft$2,170

Cheapest Available Winter Haven 2 Bedroom Apartments

As of May 24, 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 The Hamilton Model at Briarcrest at Winter Haven starting at $1,220 in the Graydon Hills neighborhood. The average price for all 2 Bedroom apartments in Winter Haven is currently $1,734. 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
Briarcrest at Winter HavenThe Hamilton$1,220
Central Haven Apartments2 Beds, 1 bath$1,275
Della Vita ApartmentsTwo Bed 1 Bath$1,315
Haven at Lake Deer2 Bedroom$1,325
The Arbours at Garden GroveTwo Bedrooms/Two Baths Reno$1,425
Lakeshore Club2 Bedroom, 2 Bathroom$1,489
Alera at Hunters GlenB3$1,549
Serenity at Lake WalesStarling$1,595

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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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:
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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 $1,734.

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 989 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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