Apartments for Rent in Winter Haven, FL (481 Rentals)

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Prose Cypress Pointe
Rent Specials
$1,299 - $1,649
Total Monthly Price

Total Monthly Price

Base Rent
$1,299 - $1,649
Total Monthly Price
$1,299 - $1,649
1 to 2 Bedroom Apartments Available Now

Prose Cypress Pointe

3110 Gowan DrWinter Haven, FL 33884
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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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Neighborhood & Market Insights: How to Choose the Right Area to Rent

Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

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property at 711 Avenue B NE

$1,795

Total Monthly Price

Total Monthly Price

Base Rent
$1,795
Total Monthly Price
$1,795

3 Bedroom, 2 Bath Home for Rent

Available Now

711 Avenue B NE

Winter HavenFL33881
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 2756 San Marco Way

$2,100

Total Monthly Price

Total Monthly Price

Base Rent
$2,100
Total Monthly Price
$2,100

4 Bedroom, 2 Bath Home for Rent

Available Now

2756 San Marco Way

Winter HavenFL33884

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 1108 29th St NW

$2,150

Total Monthly Price

Total Monthly Price

Base Rent
$2,150
Total Monthly Price
$2,150

4 Bedroom, 2 Bath Home for Rent

Available Jun 27

1108 29th St 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 4766 Osprey Way

$2,180

Total Monthly Price

Total Monthly Price

Base Rent
$2,180
Total Monthly Price
$2,180

4 Bedroom, 2 Bath Rentals

Available Now

4766 Osprey Way

Winter HavenFL33881
property at 4878 St James Ln

$2,515

Total Monthly Price

Total Monthly Price

Base Rent
$2,515
Total Monthly Price
$2,515

5 Bedroom, 3 Bath Rentals

Available Now

4878 St James Ln

Winter HavenFL33881
Showing Results 1-50, Page 1 of 10

Winter Haven, FL Local Guide

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A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.

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

Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.

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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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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.

What is the history of Winter Haven?

The city of Winter Haven saw an increase of settlers in the 1880's, at a time when there were no roads and sand trails throughout the area. Winter Haven was named in 1911, when it was incorporated. It had a local bank, movie theater, and news outlets. In 1930, the first Publix was opened in Winter Haven by owner George Jenkins. In 1936, Cypress Gardens was opened by Dick and Julie Pope, and this was the start of the tourist industry in Winter Haven.

How is the weather in Winter Haven?

In the summer months, you can expect hot, humid weather in Winter Haven, and the summer temperatures extend into the spring and fall months. The winters are cool, and rarely does the weather get below freezing. In January, average high temperatures are 71 F, and lows are 52 F. In June, the average high temperatures are 90 F, with 72 F for a low. The most precipitation throughout the year occurs in June, July and August. 

How do I get around town?

Many people prefer to have a car to get around Winter Haven, especially for their work commute. There is train service through SunRail Poinciana, and local bus transit throughout Winter Haven with Citrus Connection. While there is a municipal airport in Winter Haven, there are major airports in nearby Tampa and Orlando to find flights throughout the world. 

What is the Winter Haven commute like?

Many residents in Winter Haven work in either nearby Tampa, or Orlando. Both are roughly a 25-minute commute by car, and there is both a train and bus system to get you to work if necessary. Traffic during high commute times tends to be mild to moderate. Major highways in Winter Haven include SR 540 and SR 549. US-17 is another major highway that goes across Florida, beginning at the Georgia border.

What are the local media outlets?

There are a number of popular media outlets that residents of Winter Haven turn to. WESH 2 news out of Daytona Beach is the local NBC station, WKMG 6 is the CBS station out of Orlando, and WEDQ is on channel 16, the PBS channel out of Tampa. WPCV 97.5 is a country music station in Winter Haven, WSIR 1490 is an AM gospel station, and WFLZ 93.3 offers top 40 music. The Winter Haven Sun is a local newspaper written for residents.

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.

What Winter Haven landmarks should I see?

Winter Haven is known for it's Chain of Lakes, and the waterside parks, restaurants and nature trails that surround the lakes. The Chain of Lakes park is a well-visited attraction, and historical sites include Cypress Gardens, Panther Point Trail, Box Tower Gardens, and Benjamin Franklin Holland House are popular. You can take a walk at South Lake Howard Nature Park, or enjoy a show at Ritz Theatre 100.

What is there to do around Winter Haven?

LEGOLAND Florida is one of the main attractions in Winter Haven that bring tourists from all over to the area. It's a fun place for residents to enjoy, especially when the tourist season is slow. Cypress Gardens is another favorite, while Willowbrook Golf Course and Cypresswood Golf & County Club offer plenty of bike trails, hiking, and golf. The Chain of Lakes is a long series of at least 26 lakes that are combined using a canal system. Apartments in Winter Haven are close to amenities and make it possible to get out and enjoy time in nature.

Any annual festivals or Winter Haven events to know?

Winter Haven offers a consistent weekly Farmers Market every Saturday morning. The market offers live music, is pet friendly, and includes at least 40 curated vendors. There is an annual Art Fest held every April, a community wide festival in March, and local music venues. The Bloomin' Arts festival is another popular event the first weekend of March in nearby Bartow.

Where are the nearby vacation spots?

There are many vacation opportunities within driving distance of Winter Haven, Florida. From nearby Orlando with Disney World, Universal Studios and Sea World, to Tampa with beautiful beaches, a casino, and Major League Baseball, there is plenty of places to go for a vacation. A bit further Northeast is Daytona Beach, where you can spend the week driving on the beach, playing, and enjoying the Daytona 500. Kennedy Space Center is another favorite to visit. Miami Beach and the top of the Florida Keys are also popular vacation spots.

Where is the best place to move in Winter Haven?

Terranova is a gated community in Winter Haven that is only minutes from LEGOLAND, while Madison Lake Ned has luxury apartments in Winter Haven to rent. Apartments near Lake Deer are also an excellent place to live.  If you have a pet, you will want to look for an apartment that is close to a dog park, and allows pets on the premises. The Ruby Lake and Winterset neighborhoods offer good apartment options in the city.

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Remember the 3 Rules of Real Estate:
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Frequently Asked Questions about Winter Haven

How much are Studio apartments in Winter Haven?

There are currently 36 Studio Apartments in Winter Haven with rent ranges from $959 to $1,385 with an average price of $1,107.

What is the current price range for One Bedroom Winter Haven Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Winter Haven ranges from $950 to $2,045 with an average monthly rent of $1,389.

What does renting a Two Bedroom Apartment in Winter Haven cost?

The monthly rent prices of Two Bedroom Apartments currently available in Winter Haven range from $993 to $3,250. Today's average rental price for Two Bedrooms here is $1,705.

How expensive are Winter Haven Three Bedroom Apartments?

There are currently 46 Three Bedroom Apartments listings available in Winter Haven on ApartmentHomeLiving.com. The pricing ranges from $1,144 to $3,045 - averaging $1,946 for the location.

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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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

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There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

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For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

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Creative Ways Developers Reimagine Retail Spaces as Residential Units

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Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.