
Apartments for Rent in Winter Park, FL with Swimming Pool (147 Rentals)


Elon Winter Park

Seabrook

Bainbridge Winter Park

Oak Reserve at Winter Park

Cranes Landing Apartments

Seven41 Winter Park

Berkshire Winter Park

Juno Winter Park

Paseo at Winter Park Village
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.

Central Place At Winter Park

Calibre Bend Apartments

Liv at Winter Park Apartment Homes

Summerlin at Winter Park Apartments

Winter Park Woods Apartments

San Jose Apartments

The Taylor at Winter Park

Carlton Arms of Winter Park

POSTE Winter Park

Total Monthly Price
Atlas at Winter Park
Understanding Amenity Fees: Know Where You Might Be Able to Save Money
What are amenity fees and are they optional? This guide breaks down everything you need to know about apartment amenity fees, including when you can opt out and how you might be able to lower your rent.

Signal Pointe

Total Monthly Price
Solis at Winter Park

The Vista at Winter Park

Total Monthly Price
Stonecastle Apartment Homes

Alvista Winter Park

Total Monthly Price
Westmount at Winter Park

Golden Oaks

ARIUM Winter Park

200 Saint Andrews Blvd, Unit 2402

3004 George Mason Ave, Unit George Mason Avenue
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.

700 Melrose Ave

2924 Antique Oaks Cir, Unit 48

223 Sandlewood Trl

2019 Soaring Oak Way

200 St Andrews Blvd, Unit 1607

200 St Andrews Blvd, Unit 1607

3313 Hamlet Loop

1721 Shasta Ct

652 St Johns Ct

1760 Legion Dr
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.

7425 Daniel Webster Dr

2304 Inagua Way

205 Lewfield Cir

3050 Autumn Ct

1843 Shadyhill Terrace

1542 Sugarwood Cir

2344 Woodcrest Dr

1814 Barker Dr

625 Trinidad Ct, Unit 625

2500 Lee Rd, Unit 244
The Soul of the City Beautiful: What Life in Orlando Is Really Like
Orlando is much more than theme parks. Uncover the city's rich history, diverse neighborhoods like Winter Park and Downtown, and its bustling cultural and culinary life.
Winter Park, FL Local Guide

How much does it cost to rent an apartment in Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winter Park Studio Apartments with Swimming Pool | $1,620 | $900 | $3,137 |
| Winter Park 1 Bedroom Apartments with Swimming Pool | $1,834 | $250 | $3,827 |
| Winter Park 2 Bedroom Apartments with Swimming Pool | $2,200 | $956 | $5,169 |
| Winter Park 3 Bedroom Apartments with Swimming Pool | $2,841 | $1,082 | $6,500 |
| Winter Park 4 Bedroom Apartments with Swimming Pool | $2,206 | $1,844 | $3,938 |
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Winter Park, FL Local Guide

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Your Guide to the Perfect Orlando Neighborhood for Student Renters
Learn About the Best Neighborhoods to Rent Near College Campuses in Orlando, FL | Find Orlando Off-Campus Student Housing at ApartmentHomeLiving.com
Read ArticleReal 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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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.
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
See the most popular apartments and homes in Winter Park, FL
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 Kingswood Apartments listed at $900.
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 $2,310.
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 $1,954 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 661 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.
Helpful Local Expert Guides

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.

Your Guide to the Perfect Orlando Neighborhood for Student Renters
Written by: Darla Ferrara
There is never a dull moment in Orlando, Florida. Along with top-tier universities, technical schools, and local colleges, there are world-class entertainment venues, the ocean within driving distance, and lots of sunshine.

Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers
Written by: Darla Ferrara
When I first moved to Orlando, Florida, in the 1990s, one of the things that drew me here was the remarkably low unemployment rates. There was a job for everyone. Two decades later, that fundamental appeal remains.

The Soul of the City Beautiful: What Life in Orlando Is Really Like
Written by: Darla Ferrara
When people think of Orlando, Florida, they dream of theme parks and sunny weather, and rightfully so. It’s that energy that keeps this city a mainstay in the global tourist industry.
Articles, How-To's, and Tips

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.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
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.

Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.