
Cheap Gated Apartments for Rent in Winter Park, FL from $400 (40 Rentals)
Search the lowest-cost Apartments available for rent right now in Winter Park.


Total Monthly Price
Atlas at Winter Park

Summerlin at Winter Park Apartments

Alvista Winter Park

ARIUM Winter Park

Bainbridge Winter Park

Calibre Bend Apartments

Seven41 Winter Park
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.

Berkshire Winter Park

Vintage Winter Park Apartments

The Lofts of Winter Park Village

Hannibal Square

District On Baldwin Park

Regency Oaks Apartments

Total Monthly Price
Garden Park Senior Living

Hillcrest Hampton House
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.

Newport Colony Apartments in Casselberry

Steelhouse Orlando

860 North Orange Avenue, Unit Studio, Unit Studio

The Shores at Lake Howell

Infinity off Baldwin Park

The Baldwin

Luna at Lake Shadow

The Cannery at The Packing District
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.

NORA Apartments

Total Monthly Price
The Gallery at Mills Park

Total Monthly Price
The Village at Lake Lily

The Parker at Maitland Station Apartments

Total Monthly Price
Audubon Park

Total Monthly Price
Aurora on the Trail

The Ivy Residences at Health Village Apartment Homes

400 North
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.

The Princeton at College Park

Citron at The Packing District

Azalea Gardens

The Majestic at Downtown Baldwin Park

Maitland City Centre

Total Monthly Price
Inscribe Apartments

Total Monthly Price
Vida at Health Village

Uptown Place Apartments
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.
Winter Park, 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 | $1,669 | $900 | $3,273 |
| Winter Park 1 Bedroom Apartments | $1,797 | $695 | $3,559 |
| Winter Park 2 Bedroom Apartments | $2,212 | $956 | $5,364 |
| Winter Park 3 Bedroom Apartments | $2,750 | $1,082 | $6,500 |
| Winter Park 4 Bedroom Apartments | $1,835 | $1,679 | $2,609 |
Explore Winter Park
Winter Park, FL Local Guide
- Winter Park 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.
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winter Park, FL Rentals by Map
See the most popular apartments and homes in Winter Park, FL
Frequently Asked Questions about Cheap Winter Park Apartments
What is the Cheapest Studio apartment in Winter Park?
Currently the most affordable Cheap Studio Apartment in Winter Park is at Regency Oaks Apartments listed at $1,123.
How much is rent for a Cheap One Bedroom Winter Park Apartment?
The lowest price for a Cheap One Bedroom Winter Park Apartment is $1,000 at Primrose Orlando.
What is the lowest price for a Cheap Two Bedroom Winter Park Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Winter Park is starting from $1,200 at Sumerset Apartments.
What is the most affordable Winter Park Three Bedroom Apartment?
The best deal on a cheap Winter Park Three Bedroom Apartment rental is at Sumerset Apartments and starts from $1,295.
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.