Apartments for Rent in the Winter Park Neighborhood of Orlando, FL (232 Rentals)

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Gables Baldwin Park
Rent Specials
$2,248 - $8,315
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$2,248 - $8,315
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Studio to 3 Bedroom Apartments Available Now

Gables Baldwin Park

2050 Jake StOrlando, FL 32814
Student Housing
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Baldwin Harbor
$1,895 - $4,939
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$1,895 - $4,939
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1 to 3 Bedroom Apartments Available Now

Baldwin Harbor

1771-1887 Jake StOrlando, FL 32814
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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.

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Aurora on the Trail
$1,483 - $3,173
Total Monthly Price

Total Monthly Price

Base Rent
$1,483 - $3,173
Total Monthly Price
$1,483 - $3,173
Studio to 3 Bedroom Apartments Available Now

Aurora on the Trail

825 McCullough AveOrlando, FL 32803
Corporate Housing
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Audubon Park
Rent Specials
$1,640 - $3,141
Total Monthly Price

Total Monthly Price

Base Rent
$1,640 - $3,141
Total Monthly Price
$1,640 - $3,141
1 to 3 Bedroom Apartments Available Now

Audubon Park

990 Warehouse RdOrlando, FL 32803
Corporate Housing
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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.

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property at 1513 Truman Rd

$1,350

Total Monthly Price

Total Monthly Price

Base Rent
$1,350
Total Monthly Price
$1,350

1 Bedroom, 1 Bath Home for Rent

Available Now

1513 Truman Rd

OrlandoFL32807

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.

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property at 1419 Virginia Dr

$1,600

2 Bedroom, 1 Bath Home for Rent

Available Sep 1

1419 Virginia Dr

OrlandoFL32803

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

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property at 2510 Boyd Ave

$1,800 - $1,900

2 Bedroom Rentals

Available Now

2510 Boyd Ave

OrlandoFL32803

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.

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Winter Park, Orlando, FL Local Guide

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.

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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.

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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

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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.

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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.

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Best Local Schools in
Winter Park, Orlando, FL

School data provided by Great Schools

Lifestyle Ratings

Our team is proud to bring you comprehensive Lifestyle Ratings of rentals and neighborhoods across the USA, including Winter Park, Orlando, and the greater Orlando area. 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, kid and pet-friendly communities, availability of transit options, in addition to floorplans, availablity, and pricing. Find Lifestyle Search in the filter options (above). Happy Searching!

Luxury Living Rating

This area of town is one of our favorite upscale neighborhoods in town, with a score of 3.5 out of 4. Luxury Lifestyle Scoring is based on having high-end community amenities like olympic-sized pools, concierge services, park access, and quartz countertops in the kitchen with high-end appliances. Luxury submarkets also often offer wood-burning fireplaces, raquetball courts, and for some communities, even a doorman to greet residents.

Frequently Asked Questions about Winter Park

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

As of today, August 25, 2026, there are currently 232 available Winter Park apartments priced from $600 to $4,920, with an average monthly rent of $2,001.

How much are Studio apartments in Winter Park?

There are currently 37 Studio Apartments in Winter Park with rent ranges from $1,000 to $2,790 with an average price of $1,755.

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 $600 to $3,021 with an average monthly rent of $1,749.

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 $925 to $4,082. Today's average rental price for Two Bedrooms here is $2,119.

How expensive are Winter Park Three Bedroom Apartments?

There are currently 49 Three Bedroom Apartments listings available in Winter Park on ApartmentHomeLiving.com. The pricing ranges from $1,307 to $4,920 - averaging $2,479 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 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.

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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

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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.

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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.

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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.

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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.