
Apartments for Rent in Winter Park, FL with Swimming Pool (148 Rentals)


Bainbridge Winter Park

Oak Reserve at Winter Park

Elon Winter Park

Seabrook

Central Place At Winter Park

Cranes Landing Apartments

Winter Park Woods Apartments

Seven41 Winter Park

Juno Winter Park
Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities
Why fight Orlando's tourist traffic when you don't have to? Explore the best cities surrounding Orlando for renters, with expert tips on commuting, lifestyle, hidden costs, and where to find the most value.

Paseo at Winter Park Village

Calibre Bend Apartments

Sapphire Winter Park

Summerlin at Winter Park Apartments

Liv at Winter Park Apartment Homes

San Jose Apartments

The Taylor at Winter Park

Berkshire Winter Park

Carlton Arms of Winter Park

Alvista Winter Park
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.

Total Monthly Price
Westmount at Winter Park

POSTE Winter Park

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Atlas at Winter Park

Golden Oaks

Signal Pointe

Total Monthly Price
Solis at Winter Park

The Vista at Winter Park

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Stonecastle Apartment Homes

ARIUM Winter Park

2924 Antique Oaks Cir, Unit 48
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.

1920 Woodcrest Dr, Unit 13

1250 S Denning Dr, Unit 127

1492 Broad Wing Ln

200 St Andrews Blvd, Unit 316

1250 S Denning Dr

5319 N Orange Ave

652 St Johns Ct

205 Lewfield Cir

640 N Park Ave

5354 Lanyard Ct
Top Neighborhoods Near Orlando Major Employers
Learn about the best places to live near major employers in Orlando with original content written by our Local Expert Darla Ferrara

2234 Howard Dr

2500 Lee Rd, Unit 244

The Stratford at Winter Park Condominiums

Lancelot At Winter Park

Lake Killarney Condominiums

Winter Park Villas

Parkview Village

Lake Virginia Condominiums

Mead Garden Condominiums

Winter Park Gardens
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.
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 | $1,615 | $900 | $2,847 |
| Winter Park 1 Bedroom Apartments with Swimming Pool | $1,801 | $250 | $3,409 |
| Winter Park 2 Bedroom Apartments with Swimming Pool | $2,260 | $645 | $5,966 |
| Winter Park 3 Bedroom Apartments with Swimming Pool | $2,892 | $750 | $7,275 |
| Winter Park 4 Bedroom Apartments with Swimming Pool | $1,946 | $1,844 | $2,461 |
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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 Ekos at Lake Shadow listed at $529.
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 $2,416.
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 $1,918 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 665 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

Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities
Written by: Darla Ferrara
When people think of Orlando, FL, the iconic theme parks and buzz of downtown tend to steal the spotlight.

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.

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.

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.
Articles, How-To's, and Tips

Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
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.

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.