Apartments for Rent in the Winter Park Neighborhood of Orlando, FL Under $2,000 (110 Rentals)

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Baldwin Harbor
$1,958 - $5,002
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$1,958 - $5,002
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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
$1,520 - $3,177
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Total Monthly Price

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$1,520 - $3,177
Total Monthly Price
$1,520 - $3,177
Studio to 3 Bedroom Apartments Available Now

Aurora on the Trail

825 McCullough AveOrlando, FL 32803
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Audubon Park
Rent Specials
$1,625 - $3,224
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Total Monthly Price

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$1,625 - $3,224
Total Monthly Price
$1,625 - $3,224
1 to 3 Bedroom Apartments Available Now

Audubon Park

990 Warehouse RdOrlando, FL 32803
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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

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 1419 Virginia Dr

$1,600

2 Bedroom, 1 Bath Home for Rent

Available Now

1419 Virginia Dr

OrlandoFL32803

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 2510 Boyd Ave

$1,800 - $1,900

2 Bedroom Rentals

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2510 Boyd Ave

OrlandoFL32803
property at 5555 Barton Dr

$1,495

Total Monthly Price

Total Monthly Price

Base Rent
$1,495
Total Monthly Price
$1,495

2 Bedroom, 1 Bath Home for Rent

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5555 Barton Dr

OrlandoFL32807
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Adele Place
1 to 2 Bedroom Apartments

Adele Place

7595 Sun Tree CirOrlando, FL 32807
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The Juliette
1 Bedroom Apartments

The Juliette

1225 Moselle AveOrlando, FL 32807

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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1219 Oregon St
Studio Apartments

1219 Oregon St

1219 Oregon StOrlando, FL 32803
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On Baldwin Pond
2 Bedroom Apartments

On Baldwin Pond

829 Lowell BlvdOrlando, FL 32803
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Chapel Trace
1 to 3 Bedroom Apartments

Chapel Trace

562 Chapel Trace DrOrlando, FL 32807
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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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Showing Results 1-50, Page 1 of 3

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

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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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Best Local Schools in
Winter Park, Orlando, FL

School data provided by Great Schools

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 $1,680.

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 $2,935 with an average monthly rent of $1,734.

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 $4,107. Today's average rental price for Two Bedrooms here is $2,128.

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 $5,002 - averaging $2,828 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

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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.

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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.

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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.