Apartments for Rent in the Downtown Winter Park Neighborhood of Winter Park, FL (76 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
property at 151 N Orlando Ave

$2,300

Total Monthly Price

Total Monthly Price

Base Rent
$2,300
Total Monthly Price
$2,300

1 Bedroom, 1 Bath Condo for Rent

Available Now

151 N Orlando Ave, Unit 262

151 N Orlando Ave
Winter ParkFL32789
property at 1250 S Denning Dr

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000
Total Monthly Price
$2,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

1250 S Denning Dr, Unit 127

1250 S Denning Dr
Winter ParkFL32789

Orlando's Best Affordable Neighborhoods

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

Read Article
property at 151 N Orlando Ave

$2,100 - $2,750

1 To 2 Bedroom Rentals

Available Now

151 N Orlando Ave

Winter ParkFL32789

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
close
View Me
Park West Condominiums
Studio Apartments

Park West Condominiums

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

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
close
View Me
400 W Swoope Ave
2 Bedroom Apartments

400 W Swoope Ave

400 W Swoope AveWinter Park, FL 32789
close
View Me
600 N Park Ave
1 Bedroom Apartments

600 N Park Ave

600 N Park AveWinter Park, FL 32789
close
View Me
The Landmark
Studio Apartments

The Landmark

140 E Morse BlvdWinter Park, FL 32789
close
View Me
141 E Swoope Ave
Studio Apartments

141 E Swoope Ave

141 E Swoope AveWinter Park, FL 32789

Neighborhood & Market Insights: How to Choose the Right Area to Rent

Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

Read Article
close
View Me
THE CLOISTERS
Studio Apartments

THE CLOISTERS

200 S Interlachen AveWinter Park, FL 32789
close
View Me
THE CLOISTERS
Studio Apartments

THE CLOISTERS

100 S Interlachen AveWinter Park, FL 32789
close
View Me
Villa Siena
Studio Apartments

Villa Siena

315 E New England AveWinter Park, FL 32789
close
View Me
THE CLOISTERS
Studio Apartments

THE CLOISTERS

106 S Interlachen AveWinter Park, FL 32789

The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

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

Frequently Asked Questions about Downtown Winter Park

What is the current pricing and availability for apartments for rent in the Downtown Winter Park area of Winter Park, FL?

As of today, August 21, 2026, there are currently 76 available Downtown Winter Park apartments priced from $1,330 to $3,669, with an average monthly rent of $2,269.

How much are Studio apartments in Downtown Winter Park?

There are currently 17 Studio Apartments in Downtown Winter Park with rent ranges from $1,330 to $1,965 with an average price of $1,672.

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

Today's rental pricing for One Bedroom Apartments in Downtown Winter Park ranges from $1,400 to $2,500 with an average monthly rent of $1,963.

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

The monthly rent prices of Two Bedroom Apartments currently available in Downtown Winter Park range from $1,475 to $3,431. Today's average rental price for Two Bedrooms here is $2,608.

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 Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities article

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.

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.

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 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.

Articles, How-To's, and Tips

decorative image for Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags article

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

decorative image for First Apartment Regrets: Real Renters Share What They'd Do Differently article

First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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.