Cheap Apartments for Rent in the Winter Park Neighborhood of Orlando, FL from $414 (107 Rentals)

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Search the lowest-cost Apartments available for rent right now in the Winter Park area of Orlando.

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

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
Total Monthly Price

Total Monthly Price

Base Rent
$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
Corporate Housing
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  • Customer Reviewed
  • 3D Tour
property at 1419 Virginia Dr

$1,600

2 Bedroom, 1 Bath Home for Rent

Available Now

1419 Virginia Dr

OrlandoFL32803
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Audubon Park
Rent Specials
$1,625 - $3,224
Total Monthly Price

Total Monthly Price

Base Rent
$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
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour

Rent According to Income: A Look at Income-Restricted Rentals

Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.

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Chapel Trace
1 to 3 Bedroom Apartments

Chapel Trace

562 Chapel Trace DrOrlando, FL 32807
  • Utilities Included
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On Baldwin Pond
2 Bedroom Apartments

On Baldwin Pond

829 Lowell BlvdOrlando, FL 32803
  • Utilities Included

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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1219 Oregon St
Studio Apartments

1219 Oregon St

1219 Oregon StOrlando, FL 32803
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The Juliette
1 Bedroom Apartments

The Juliette

1225 Moselle AveOrlando, FL 32807
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Adele Place
1 to 2 Bedroom Apartments

Adele Place

7595 Sun Tree CirOrlando, FL 32807
Corporate Housing
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

Available Now

5555 Barton Dr

OrlandoFL32807

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
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Atlas at Winter Park
$1,323 - $1,913
Total Monthly Price

Total Monthly Price

Base Rent
$1,323 - $1,913
Total Monthly Price
Varies
1 to 3 Bedroom Apartments Available Now

Atlas at Winter Park

3733 N Goldenrod RdWinter Park, FL 32792
Family Friendly
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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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Winter Park, Orlando, FL Local Guide

Cheapest Available Winter Park Apartments for Rent

 

The cheapest available apartment rental in the Winter Park area of Orlando, FL is a Studio unit found at Azure Winter Park priced from $999. District On Baldwin Park has the second lowest priced unit, which is a Studio apartment currently listed from $1,000. Here are the most affordable Winter Park apartments for rent in Orlando, FL:

Apartment ListingModel NameBed/BathPriced From
Azure Winter ParkCorrineStudio,1BA$999
District On Baldwin ParkExecutive StudioStudio,1BA$1,000
Golden Oaks2x2-602BR,2BA$1,095
Winter Park Woods ApartmentsA1-Studio, 1 Bathroom1BR,1BA$1,107
Shoreview at Baldwin Park1x1B1BR,1BA$1,165
Indigo Winter ParkHarmony1BR,1BA$1,199
Venue At Winter ParkSable P1BR,1BA$1,230
The Taylor at Winter ParkA2R1BR,1BA$1,279
Avenues of Baldwin ParkFern (Standard) A1wm1BR,1BA$1,285
Summerlin at Winter Park ApartmentsAqua1BR,1BA$1,299

Best Value Apartments for Rent in Winter Park, FL

As of September 02, 2026 the best value apartment in the Winter Park area is the $1.39 price per square foot St. Clare Model at Chapel Trace in the in the Covered Bridge neighborhood starting from $1,669. The second greatest value Winter Park apartment is the Pelican (Renovated) C1Rwi Model at Cranes Landing Apartments starting at $1,955 with a $1.63 price per square foot in the University Commerce Center neighborhood. Here is today’s list of the best values for Winter Park apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
Chapel TraceSt. Clare3BR,2BA$1.39
Cranes Landing ApartmentsPelican (Renovated) C1Rwi3BR,2BA$1.63
The Ivy at GatehouseThe Palms3BR,2BA$1.50
Park East - Park Knowles Apartments2 Bedroom, 1 Bathroom2BR,1BA$1.59
Golfside Villas2 Beds, 2 Baths2BR,2BA$1.32
Carlton Arms of Winter ParkC2 Upstairs2BR,1BA$1.53
Solis at Winter ParkB12BR,1BA$1.66
Golden Oaks2x2-602BR,2BA$1.64
Goldenrod PointeTwo Bedroom One Bath2BR,1BA$1.59
Avenues of Baldwin ParkFern (Standard) A1wm1BR,1.5BA$1.64

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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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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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.

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Best Local Schools in
Winter Park, Orlando, FL

School data provided by Great Schools

Lifestyle Ratings

ApartmentHomeLiving.com compiles millions of data points to bring you our detailed rental analysis called 'Lifestyle Ratings' - a comparison of neighborhoods, cities and towns, and rental properties across Florida and customized analysis for Orlando, Florida. Our Lifestyle Ratings help you zero-in on the perfect place to call home. This takes in many factors including our Star Ratings to compare for the best proximity to parks and outdoor amenities, luxury amenities, pet-friendly features, places that make kids happy, proximity to transit, in addition to floorplans, availablity, and pricing. Use Lifestyle Search in the site filter options on this page - and find your Perfect place!

Frequently Asked Questions about Cheap Winter Park Apartments

What is a cheap apartment in Winter Park?

A cheap apartment is any apartment up to the 30% percentile of cost for the area, which in Winter Park is under $1,299.

What is the price of a cheap apartment in Winter Park?

The cheapest apartment in Winter Park is District On Baldwin Park which is listed at $1,044, while the average apartment in Winter Park costs $1,859.

What types of apartments are the cheapest in Winter Park?

Student, low-income, and by-the-bed apartments are typically the cheapest rentals in most cities, though they require qualifying criteria to rent. There are 62 regular apartments in Winter Park that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.

How do the prices of cheap apartments compare to the average apartment in Winter Park?

Cheap apartments in Winter Park have an average cost of $418 which is $1,441 cheaper than the average rent for all rentals in Winter Park.

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.

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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.

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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.

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Rent According to Income: A Look at Income-Restricted Rentals

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The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.

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

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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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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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