Cheap Apartments for Rent in the Winter Park Neighborhood of Orlando, FL from $400 (81 Rentals)

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

property at 1008 Maltby Ave

$1,200

Total Monthly Price

Total Monthly Price

Base Rent
$1,200
Total Monthly Price
$1,200

1 Bedroom, 1 Bath Townhome for Rent

Available Now

1008 Maltby Ave

OrlandoFL32803

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

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Aurora on the Trail
$1,496 - $3,126
Total Monthly Price

Total Monthly Price

Base Rent
$1,496 - $3,126
Total Monthly Price
$1,496 - $3,126
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
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Audubon Park
$1,542 - $3,134
Total Monthly Price

Total Monthly Price

Base Rent
$1,542 - $3,134
Total Monthly Price
$1,542 - $3,134
1 to 3 Bedroom Apartments Available Now

Audubon Park

990 Warehouse RdOrlando, FL 32803
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

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On Baldwin Pond
2 Bedroom Apartments

On Baldwin Pond

829 Lowell BlvdOrlando, FL 32803
  • Utilities Included
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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

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

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property at 5793 Oleander Dr

$1,650

Total Monthly Price

Total Monthly Price

Base Rent
$1,650
Total Monthly Price
$1,650

2 Bedroom, 1 Bath Home for Rent

Available Now

5793 Oleander Dr

OrlandoFL32807
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Atlas at Winter Park
$1,183 - $2,278
Total Monthly Price

Total Monthly Price

Base Rent
$1,183 - $2,278
Total Monthly Price
$1,183 - $2,278
1 to 3 Bedroom Apartments Available Now

Atlas at Winter Park

3733 N Goldenrod RdWinter Park, FL 32792
Family Friendly
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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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Solis at Winter Park
Rent Specials
$1,295 - $1,664
Total Monthly Price

Total Monthly Price

Base Rent
$1,295 - $1,664
Total Monthly Price
$1,295 - $1,664
1 to 2 Bedroom Apartments Available Now

Solis at Winter Park

7502 Sun Key BlvdWinter Park, FL 32792
Student Housing
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  • Customer Reviewed
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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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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 1 Bed unit found at Winter Park Woods Apartments priced from $1,058. Golden Oaks has the second lowest priced unit, which is a 3 Beds apartment currently listed from $1,082. Here are the most affordable Winter Park apartments for rent in Orlando, FL:

Apartment ListingModel NameBed/BathPriced From
Winter Park Woods ApartmentsA2-1 Bedroom, 1 Bathroom1BR,1BA$1,058
Golden Oaks3x2-503BR,2BA$1,082
SeabrookPlan A11BR,1BA$1,138
Atlas at Winter ParkPalm1BR,1BA$1,183
Shoreview at Baldwin ParkStudioStudio,1BA$1,195
Hillcrest Hampton HouseStudioStudio,1BA$1,200
Venue At Winter ParkSable P1BR,1BA$1,204
Village Park SeniorOne Bedroom One Bath1BR,1BA$1,236
Azure Winter ParkMills1BR,1BA$1,249
Central Place At Winter ParkA11BR,1BA$1,255

Best Value Apartments for Rent in Winter Park, FL

As of April 12, 2026 the best value apartment in the Winter Park area is the $1.50 price per square foot The Palms Model at The Ivy at Gatehouse in the in the The Enclave at Lake Jean neighborhood starting from $1,645. The second greatest value Winter Park apartment is the 2 Bedroom, 1 Bathroom Model at Park East - Park Knowles Apartments starting at $1,750 with a $1.59 price per square foot in the North Orange 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.
The Ivy at GatehouseThe Palms3BR,2BA$1.50
Park East - Park Knowles Apartments2 Bedroom, 1 Bathroom2BR,1BA$1.59
Golden Oaks3x2-503BR,2BA$1.03
Azure Winter ParkPark2BR,2BA$1.67
Cranes Landing ApartmentsIbis (Standard) b1wi2BR,2BA$1.57
Carlton Arms of Winter ParkC1A Downstairs2BR,1BA$1.63
Bellancia ApartmentsOne Bedroom1BR,1BA$1.75
Avenues of Baldwin ParkFern (Standard) A1wm1BR,1.5BA$1.66
Winter Park Woods ApartmentsA2-1 Bedroom, 1 Bathroom1BR,1BA$1.40
Whisper Lake ApartmentsCrescent1BR,1BA$1.73

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

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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

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

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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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Best Local Schools in
Winter Park, Orlando, FL

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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 $1,255.

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

The cheapest apartment in Winter Park is Winter Park Woods Apartments which is listed at $1,058, while the average apartment in Winter Park costs $3,944.

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 88 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 $420 which is $3,524 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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An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent

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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.

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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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Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers

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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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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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This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

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Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

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A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.