Apartments for Rent in the Winter Park Neighborhood of Orlando, FL with Swimming Pool (44 Rentals)

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It's time to soak up some sun!

One of the easiest and more obvious ways of enjoying the summer sun is to lounge out by your community pool. Learn a Few Rules to Keep in Mind while at the pool.

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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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Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.

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Winter Park - One of the Best Affordable Neighborhoods in Orlando

Named as one of the Best Affordable Areas to rent in Orlando by our , Local Expert Darla F. See how it ranks!

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151 N Orlando Ave
2 Bedroom Apartments

151 N Orlando Ave

151 N Orlando AveWinter Park, FL 32789
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Park West Condominiums
Studio Apartments

Park West Condominiums

200-300 Carolina AveWinter Park, FL 32789
  • Utilities Included

Orlando's Best Affordable Neighborhoods

Learn about Orlando and the best places to live with original content written by our Local Expert Darla F

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Parkview Village
1 to 2 Bedroom Apartments

Parkview Village

350 S Semoran BlvdWinter Park, FL 32792
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690 Osceola Ave
Studio Apartments

690 Osceola Ave

690 Osceola AveWinter Park, FL 32789
Showing Results 1-44, Page 1 of 1

Winter Park, Orlando, FL Local Guide

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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Pet Friendly Lifestyle
Winter Park, Orlando, FL

Ranked #38

Among neighborhoods in Orlando, FL for Apartment listings with Pet Friendly Amenities

Pet Friendliness Lifestyle Score

3.5
Pet Friendly

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Best Local Schools in
Winter Park, Orlando, FL

School data provided by Great Schools

Getting Around the Winter Park Neighborhood in Orlando, FL

Walk Score®

75 / 100

Very Walkable

Most errands can be accomplished on foot

Bike Score®

62 / 100

Bikeable

Some bike infrastructure

Transit Score®

26 / 100

Some Transit

A few nearby public transportation options

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about Winter Park Apartments with Swimming Pool

What is the Cheapest Swimming Pool apartment in Winter Park?

Currently the most affordable Apartment in Winter Park with Swimming Pool is at Carlton Arms of Winter Park listed at $1,032.

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

The average rent for a Apartment in Winter Park with Swimming Pool is $2,246.

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

Today's Apartment with Swimming Pool and the most square footage in Winter Park is a 1,978 square feet unit starting from $1,937 at Gables Baldwin Park.

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

The average size for a rental with Swimming Pool in Winter Park is currently at 636 sq ft.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

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An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent

Written by: Darla Ferrara

For many, Orlando is the place where you vacation, not live. However, this city, located in the central region of Florida, offers a vibrant tech community, plenty of outdoor activities, and some of the best schools in the country.

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Navigating the Rental Market: Tips for First-Time Renters

Written by: Sandy Baker

Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.

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Rise of Digital Nomads: Remote Work Tips for Apartment Renters

Written by: Brandie Parton

As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.

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Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Written by: Christine Leonard, Esq.

Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.