
Cheap 2 Bedroom Apartments for Rent in the Winter Park Neighborhood of Orlando, FL from $956 (50 Rentals)


Shoreview at Baldwin Park

Avenues of Baldwin Park

The Ivy at Gatehouse

Bellancia Apartments

On Baldwin Pond

1913 Truman Rd

1921 Truman Rd

5516 Charleston St

908 Tucker Ave
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.

6003 Oleander Dr

Golden Oaks

Winter Park Woods Apartments

Carlton Arms of Winter Park

Summerlin at Winter Park Apartments

La Aloma

Cranes Landing Apartments

The Taylor at Winter Park

Total Monthly Price
Solis at Winter Park

Total Monthly Price
Atlas at Winter Park
Renting with Roommates: Realistic Expectations for Shared Lease
Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

Village Park Senior

The Vista at Winter Park

ARIUM Winter Park

Seabrook

Central Place At Winter Park

Calibre Bend Apartments

Hannibal Square

Park East - Park Knowles Apartments

Tuscany at Aloma

El Cortez Apartments
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.

Winter Park Oaks

Mizell at Winter Park

Sovereignty at Winter Park Apartments

Venue At Winter Park

Goldenrod Pointe

1000 S Semoran Blvd

3651 Goldenrod Rd

7340 Swallow Run

7328 Swallow Run

7429 Daniel Webster Dr
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

Azure Winter Park

3651 N Goldenrod Rd

2911 Antique Oaks Cir

7004 Mills Rd

3011 George Mason Ave

7338 Swallow Run

Whisper Lake Apartments

4968 Tangerine Ave

1941 Lanier Ct

614 St Johns Ct
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
Winter Park, Orlando, FL Local Guide

How much does it cost to rent an apartment in Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winter Park Studio Apartments | $1,752 | $1,000 | $2,685 |
| Winter Park 1 Bedroom Apartments | $1,779 | $695 | $4,135 |
Winter Park 2 Bedroom Apartments | $2,213 | $956 | $5,042 |
| Winter Park 3 Bedroom Apartments | $2,959 | $1,082 | $5,667 |
| Winter Park 4 Bedroom Apartments | $3,938 | $3,938 | $3,938 |
Explore Orlando
Winter Park, Orlando, FL Local Guide
- Nearby Orlando neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
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.
Read ArticleYour 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
Read ArticleReal 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.
Read ArticleQuick Rent Budget Calculator
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.
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 $1,295.
What is the price of a cheap apartment in Winter Park?
The cheapest apartment in Winter Park is Summerlin at Winter Park Apartments which is listed at $1,332, while the average apartment in Winter Park costs $3,938.
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 46 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 $356 which is $3,582 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

An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent
Written by: Darla Ferrara
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.

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.

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.

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.
Articles, How-To's, and Tips

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
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.