Apartments for Rent in Winter Haven, FL with Swimming Pool (70 Rentals)

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Prose Cypress Pointe
Rent Specials
$1,299 - $1,649

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
Affordability
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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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property at 700 Mirror Ter NW
$1,400

Total Monthly Price

Base Rent$1,400
Total Monthly Price$1,400
1 Bedroom, 2 Bath Condo for Rent
Available Now
Furnished

700 Mirror Ter NW, Unit 705

700 Mirror Ter NW
Winter HavenFL33881
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Apartment Common Area Rules: What Renters Need to Know

From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

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property at 1938 Sarah St
$2,150

Total Monthly Price

Base Rent$2,150
Total Monthly Price$2,150
4 Bedroom, 3 Bath Home for Rent
Available Now

1938 Sarah St

Winter HavenFL33884
property at 679 Lake Dexter Cir
$2,300

Total Monthly Price

Base Rent$2,300
Total Monthly Price$2,300
2 Bedroom, 2 Bath Home for Rent
Available Now
Luxury

679 Lake Dexter Cir

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 1026 Medinah Dr
$1,500

Total Monthly Price

Base Rent$1,500
Total Monthly Price$1,500
2 Bedroom, 2 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

1026 Medinah Dr

Winter HavenFL33884
property at 715 Magnolia Pl
$1,700

Total Monthly Price

Base Rent$1,700
Total Monthly Price$1,700
2 Bedroom, 2 Bath Condo for Rent
Available Now
Luxury

715 Magnolia Pl, Unit 715

715 Magnolia Pl
Winter HavenFL33884
property at 8402 Waterview Way
$1,200

Total Monthly Price

Base Rent$1,200
Total Monthly Price$1,200
2 Bedroom, 2 Bath Condo for Rent
Available Now
Furnished

8402 Waterview Way, Unit 8402

8402 Waterview Way
Winter HavenFL33884
property at 407 Eagle Pond Dr
$1,400

Total Monthly Price

Base Rent$1,400
Total Monthly Price$1,400
2 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

407 Eagle Pond Dr, Unit 4F

407 Eagle Pond Dr
Winter HavenFL33884
property at 687 Lake Dexter Cir
$1,900

Total Monthly Price

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

687 Lake Dexter Cir

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
property at 8302 Waterview Way
$1,400

Total Monthly Price

Base Rent$1,400
Total Monthly Price$1,400
2 Bedroom, 2 Bath Condo for Rent
Available Now
Luxury

8302 Waterview Way

Winter HavenFL33884

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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Winter Haven, FL Local Guide

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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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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.

Best Local Schools in
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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Frequently Asked Questions about Winter Haven Apartments with Swimming Pool

What is the Cheapest Swimming Pool apartment in Winter Haven?

Currently the most affordable Apartment in Winter Haven with Swimming Pool is at Carlton Arms Of Winter Haven listed at $959.

How much is the average rent for Winter Haven Apartments with Swimming Pool?

The average rent for a Apartment in Winter Haven with Swimming Pool is $1,558.

What is the largest Winter Haven Apartment for rent with Swimming Pool?

Today's Apartment with Swimming Pool and the most square footage in Winter Haven is a 1,933 square feet unit starting from $1,475 at Lakeshore Club.

What is the average size for Winter Haven Apartments for rent with Swimming Pool?

The average size for a rental with Swimming Pool in Winter Haven is currently at 743 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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How Commercial-to-Residential Property Conversions Help the Housing Crisis

Written by: Robin Stewart

Many housing markets throughout America share a common complaint: a lack of affordable rental properties.

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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.