Cheap 2 Bedroom Apartments for Rent in the Winter Park Neighborhood of Orlando, FL from $925 (64 Rentals)

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property at 1419 Virginia Dr

$1,600

2 Bedroom, 1 Bath Home for Rent

Available Now

1419 Virginia Dr

OrlandoFL32803
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On Baldwin Pond
2 Bedroom Apartments

On Baldwin Pond

829 Lowell BlvdOrlando, FL 32803
  • Utilities Included
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Chapel Trace
2 Bedroom Apartments

Chapel Trace

562 Chapel Trace DrOrlando, FL 32807
  • Utilities Included

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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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
2 Bedroom Apartments

Adele Place

7595 Sun Tree CirOrlando, FL 32807
Corporate Housing
property at 2510 Boyd Ave

$1,800 - $1,900

2 Bedroom Rentals

Available Now

2510 Boyd Ave

OrlandoFL32803

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

Looking for the perfect new rental? Learn great ways to spot the perfect apartment for you, identify common red flags, and avoid rental issues and scams with these expert provided actionable tips.

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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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property at 1920 Woodcrest Dr

$1,800

Total Monthly Price

Total Monthly Price

Base Rent
$1,800
Total Monthly Price
$1,800

2 Bedroom, 2 Bath Condo for Rent

Available Now

1920 Woodcrest Dr, Unit 13

1920 Woodcrest Dr
Winter ParkFL32792
property at 1250 S Denning Dr

$1,850

Total Monthly Price

Total Monthly Price

Base Rent
$1,850
Total Monthly Price
$1,850

2 Bedroom, 2 Bath Condo for Rent

Available Now

1250 S Denning Dr, Unit 127

1250 S Denning Dr
Winter ParkFL32789
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Tuscany at Aloma
2 Bedroom Apartments

Tuscany at Aloma

6999 Aloma AveWinter Park, FL 32792
Senior Living
  • Utilities Included

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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El Cortez Apartments
2 Bedroom Apartments

El Cortez Apartments

210 E Morse BlvdWinter Park, FL 32789
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Winter Park Oaks
2 Bedroom Apartments

Winter Park Oaks

325 Balfour DrWinter Park, FL 32792
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Azure Winter Park
2 Bedroom Apartments

Azure Winter Park

3650 Summer Wind DrWinter Park, FL 32792
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Goldenrod Pointe
2 Bedroom Apartments

Goldenrod Pointe

5560 Solidago DrWinter Park, FL 32792
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Golfside Villas
2 Bedroom Apartments

Golfside Villas

1000 S Semoran BlvdWinter Park, FL 32792

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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Winter Park, Orlando, FL Local Guide

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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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

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 Golden Oaks which is listed at $1,095, while the average apartment in Winter Park costs $1,833.

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 60 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 $423 which is $1,410 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.

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.