Luxury Apartments for Rent in the Winter Park Neighborhood of Orlando, FL (55 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

The most luxurious Apartments in the Winter Park area of Orlando with high-end amenities, features, and finishes.

close
View Me
Gables Baldwin Park
Rent Specials
$2,230 - $7,714
Total Monthly Price

Total Monthly Price

Base Rent
$2,230 - $7,714
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

Gables Baldwin Park

2050 Jake StOrlando, FL 32814
Student Housing
  • Verified
  • Customer Reviewed
  • Utilities Included
close
View Me
Baldwin Harbor
$2,190 - $4,498
Total Monthly Price

Total Monthly Price

Base Rent
$2,190 - $4,498
Total Monthly Price
Varies
1 to 3 Bedroom Apartments Available Now

Baldwin Harbor

1771-1887 Jake StOrlando, FL 32814
Affordability
  • Verified
  • Customer Reviewed
  • 3D Tour

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

Read Article
close
View Me
Aurora on the Trail
$1,700 - $3,266
Total Monthly Price

Total Monthly Price

Base Rent
$1,700 - $3,266
Total Monthly Price
$1,700 - $3,266
Studio to 3 Bedroom Apartments Available Now

Aurora on the Trail

825 McCullough AveOrlando, FL 32803
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
Audubon Park
$1,708 - $3,599
Total Monthly Price

Total Monthly Price

Base Rent
$1,708 - $3,599
Total Monthly Price
$1,708 - $3,599
1 to 3 Bedroom Apartments Available Now

Audubon Park

990 Warehouse RdOrlando, FL 32803
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour
property at 1733 Prospect Ave

$4,100

Total Monthly Price

Total Monthly Price

Base Rent
$4,100
Total Monthly Price
$4,100

3 Bedroom, 3.5 Bath Townhome for Rent

Available Oct 1

1733 Prospect Ave

OrlandoFL32814

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.

Read Article
property at 2721 E Marks St

$5,800

Total Monthly Price

Total Monthly Price

Base Rent
$5,800
Total Monthly Price
$5,800

3 Bedroom, 2 Bath Home for Rent

Available Now

2721 E Marks St

OrlandoFL32803

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.

Read Article
property at 779 West Lyman Avenue

$2,950

Total Monthly Price

Total Monthly Price

Base Rent
$2,950
Total Monthly Price
$2,950

3 Bedroom, 2 Bath Home for Rent

Available Now

779 West Lyman Avenue

Winter ParkFL32789
property at 130 N Center St

$1,295 - $2,500

1 Bedroom Rentals

Available Now

130 N Center St

Winter ParkFL32789

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.

Read Article
property at 662 Callahan St

$2,536

Total Monthly Price

Total Monthly Price

Base Rent
$2,536
Total Monthly Price
$2,536

2 Bedroom, 1 Bath Home for Rent

Available Nov 25

662 Callahan St

Winter ParkFL32789

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.

Read Article
Showing Results 1-50, Page 1 of 2

Winter Park, Orlando, FL Local Guide

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 Article
Decorative image

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.

Read Article
Decorative image

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.

decorative image of people with a giant lease agreement

Best Local Schools in
Winter Park, Orlando, FL

School data provided by Great Schools

Lifestyle Ratings

ApartmentHomeLiving brings you Lifestyle Ratings of rentals and neighborhoods across the USA, and customized analysis for North Central Orlando. Lifestyle Ratings show you the best fit for your needs and interests. This takes in many factors including rankings of the best places for the best outdoor access, luxury amenities, transit availability, pet-friendly communities, family-friendly amenities, and much more. These search options are in the site filters at the top of this page.

Luxury Living Rating

Winter Park is known as amongst the finest high-end communities in town, with a score of 3.5 out of 4. Luxury Lifestyle Scoring is based on having high-end community amenities like saunas, pools, sport courts, proximity to great shopping areas, park access, and quartz countertops in the kitchen with high-end appliances. Luxury communities also often offer tile or hardwood floors, tennis courts, and for some communities, even a doorman to greet residents.

Frequently Asked Questions about Winter Park

How much are Studio apartments in Winter Park?

There are currently 38 Studio Apartments in Winter Park with rent ranges from $1,000 to $2,790 with an average price of $1,772.

What is the current price range for One Bedroom Winter Park Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Winter Park ranges from $740 to $3,006 with an average monthly rent of $1,781.

What does renting a Two Bedroom Apartment in Winter Park cost?

The monthly rent prices of Two Bedroom Apartments currently available in Winter Park range from $1,141 to $4,097. Today's average rental price for Two Bedrooms here is $2,173.

How expensive are Winter Park Three Bedroom Apartments?

There are currently 47 Three Bedroom Apartments listings available in Winter Park on ApartmentHomeLiving.com. The pricing ranges from $1,307 to $4,498 - averaging $2,797 for the location.

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

decorative image for An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent article

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.

decorative image for Your Guide to the Perfect Orlando Neighborhood for Student Renters article

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.

decorative image for Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers article

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.

decorative image for The Soul of the City Beautiful: What Life in Orlando Is Really Like article

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

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

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.

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention article

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.

decorative image for How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide article

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.

decorative image for Pet-Friendly Renting: Everything You Need to Know Before You Move article

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.