Apartments for Rent in Winter Park, FL with Swimming Pool (98 Rentals)

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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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1500 Gay Rd
2 Bedroom Apartments

1500 Gay Rd

1500 Gay RdWinter Park, FL 32789
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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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1250 S Denning Dr
2 Bedroom Apartments

1250 S Denning Dr

1250 S Denning DrWinter Park, FL 32789
Showing Results 1-50, Page 1 of 2

Winter Park, FL Local Guide

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Winter Park Overview

Winter Park, Florida offers something for everyone. This suburban city of over 29,000 people provides historical, cultural, and recreational opportunities. Well-known for its museums, art galleries, and parks, the town is home to Rollins College. Outdoor enthusiasts can enjoy water activities at nearby lakes, or explore local hiking and biking trails. With plenty of options for apartments in Winter Park, find a new home here is easy.

Why live in Winter Park, FL?

If you're unsure about relocating to Winter Park apartments, consider all it has to offer. Its convenient location just northeast of Orlando allows you to reap the benefits of living near a sizeable city while enjoying the amenities of a smaller community. Winter Park apartments provide an impressive selection of housing options. This suburban hamlet offers upscale shopping and dining. A local chain of lakes provides ample opportunities for fishing, swimming, and boating. Rollins College and other post-secondary institutions offer educational opportunities in everything from liberal arts to fine arts. Cultural events and a thriving community center bring residents together.

Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Winter Park, FL Rentals by Map

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See the most popular apartments and homes in Winter Park, FL

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Getting Around Winter Park, FL

Walk Score®

71 / 100

Very Walkable

Most errands can be accomplished on foot

Bike Score®

57 / 100

Bikeable

Some bike infrastructure

Transit Score®

22 / 100

Minimal Transit

It may be possible to get on a bus

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 San Jose Apartments listed at $820.

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 $2,411.

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 3,513 square feet unit starting from $2,318 at Lake House.

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 644 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

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Understanding Amenity Fees: Know Where You Might Be Able to Save Money

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With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

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How Your Move-In Inspection Can Protect Your Security Deposit

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If you’re anything like most people, housing costs represent a huge chunk of your monthly budget. On top of that, moving can be both a stressful and expensive affair.

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Signing Your Apartment Lease: The Basics

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When you're about to sign a lease for the first time, it can feel a bit overwhelming. You don’t want to miss any important details hidden in the fine print.