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$6951 Bedroom Apartments Available Now
5530 Old Cheney Hwy, Unit Apartment 3
5530 Old Cheney HwyOrlando, FL 32807
Cheap Homes for Rent in Winter Park, FL from $1,000 (89 Rentals)
Search the lowest-cost Homes available for rent right now in Winter Park.
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$7601 Bedroom Apartments Available Now
5530 Old Cheney Hwy, Unit 2
5530 Old Cheney HwyOrlando, FL 32807
333 Amador Cir
OrlandoFL32810
525 S Lakemont Ave
Winter ParkFL32792
2517 Caper Ln
MaitlandFL32751
1233 Virginia Dr
OrlandoFL32803
1157 Calle del Norte, Unit 1157, Unit 1157
1157 Calle del Norte
CasselberryFL32707
2426 Branch Way, Unit 200, Unit 200
2426 Branch Way
MaitlandFL32751
3075 Aaron Burr Ave
Winter ParkFL32792
301 Clark St
EatonvilleFL32751
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.
138 Lewfield Cir
Winter ParkFL32792
1167 Calle Del Rey
CasselberryFL32707
1695 Lee Rd
Winter ParkFL32789
616 Eola Dr
OrlandoFL32803
1125 Lake Shadow Cir
MaitlandFL32751
5319 N Orange Ave
Winter ParkFL32792
4818 Tangerine Ave
Winter ParkFL32792
1411 E Central Blvd
OrlandoFL32801
2942 Antique Oaks Cir, Unit 82
2942 Antique Oaks Cir
Winter ParkFL32792
320 Lakeview St, Unit 222, Unit 222
320 Lakeview St
OrlandoFL32804
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.
5315 Davisson Ave
OrlandoFL32810
296 Lewfield Cir
Winter ParkFL32792
2905 Villa Dr
OrlandoFL32810
1125 Lake Shadow Cir, Unit Visconti Maitland FL, Unit Visconti Maitland FL
1125 Lake Shadow Cir
MaitlandFL32751
1275 Lake Shadow Cir
MaitlandFL32751
320 Lakeview St
OrlandoFL32804
3032 Antique Oaks Cir
Winter ParkFL32792
121 E Evans St
OrlandoFL32804
320 Lakeview St, Unit 203, Unit 203
320 Lakeview St
OrlandoFL32804
1555 Michigan Ave
Winter ParkFL32789
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.
1000 Lake of the Woods Blvd
Fern ParkFL32730
3651 Goldenrod Rd
Winter ParkFL32792
1913 Truman Rd
OrlandoFL32807
860 N Orange Ave
OrlandoFL32801
2500 Lee Rd, Unit 244, Unit 244
2500 Lee Rd
Winter ParkFL32789
225 E New Hampshire St
OrlandoFL32804
1375 Lake Shadow Cir
MaitlandFL32751
2500 Lee Rd
Winter ParkFL32789
1000 S Semoran Blvd
Winter ParkFL32792
1921 Truman Rd
OrlandoFL32807
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.
7340 Swallow Run
Winter ParkFL32792
360 Eaton St
EatonvilleFL32751
1565 Michigan Ave
Winter ParkFL32789
151 N Orlando Ave
Winter ParkFL32789
911 N Orange Ave
OrlandoFL32801
105 Jergo Rd
Winter ParkFL32792
1140 Lake Maitland Ter
MaitlandFL32751
1225 Lake Shadow Cir
MaitlandFL32751
1608 Legacy Park Dr
MaitlandFL32751
1325 Lake Shadow Cir
MaitlandFL32751
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 a home in Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winter Park 2 Bedroom Homes for Rent | $1,790 | $1,350 | $3,200 |
| Winter Park 3 Bedroom Homes for Rent | $2,788 | $1,500 | $5,950 |
| Winter Park 4 Bedroom Homes for Rent | $4,727 | $1,950 | $10,000+ |
| Winter Park 5 Bedroom Homes for Rent | $10,768 | $2,850 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Homes for Rent in Winter Park
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Winter Park, FL Local Guide
- Winter Park Neighborhoods
- Nearby Cities
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Cheapest Neighborhoods for Apartments in Winter Park, FL
Pricing Updated: 05/18/2026Current apartment rentals in the Winter Park, FL area range in price from to with an overall median price of . Here is today’s list neighborhoods with the lowest median pricing for Winter Park Apartments for rent:
| Neighborhood | Median Price | Min Price | Available Units |
|---|---|---|---|
| Lake Howell | $2,364 | $910 | 189 |
Cheapest Available Winter Park Apartments for Rent
The cheapest available apartment rental in Winter Park, FL is a 1 Bed unit found at Primrose Orlando in the Downtown Orlando neighborhood priced from $1,000. Kingswood Apartments in the Courtland Street neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,050. Here is today’s list of the most affordable Winter Park apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Primrose Orlando | Upgraded Unit | 1BR,1BA | $1,000 |
| Kingswood Apartments | 1/1 | 1BR,1BA | $1,050 |
| Sumerset Apartments | 1 Bed, 1 bath | 1BR,1BA | $1,074 |
| Carlton Arms of Winter Park | Studio Downstairs | Studio,1BA | $1,080 |
| Winter Park Woods Apartments | A1-Studio, 1 Bathroom | 1BR,1BA | $1,093 |
| Azure Winter Park | Corrine | Studio,1BA | $1,099 |
| Solis at Winter Park | A1 | 1BR,1BA | $1,101 |
| Regency Oaks Apartments | Studio | Studio,2BA | $1,123 |
| Garden Park Senior Living | One Bedroom One Bath (b) | 1BR,1BA | $1,139 |
| Birchwood Landing | Birchwood A | 1BR,1BA | $1,139 |
Best Value Apartments for Rent in Winter Park, FL
As of May 18, 2026 the best value apartment in the Winter Park area is the $1.63 price per square foot Quartz Model at Sapphire Winter Park in the in the Outer East neighborhood starting from $2,199. The second greatest value Winter Park apartment is the Floorplan 2 Model at Azalea Gardens starting at $1,750 with a $1.46 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 Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Sapphire Winter Park | Quartz | 3BR,2BA | $1.63 |
| Azalea Gardens | Floorplan 2 | 2BR,2BA | $1.46 |
| Sorrento | 2B 1.5B TOWN | 2BR,1.5BA | $1.31 |
| The Ivy at Gatehouse | The Palms | 3BR,2BA | $1.50 |
| Central Place At Winter Park | B2 | 2BR,2BA | $1.56 |
| Lake Weston Point Apartments | Two Bedroom | 2BR,2BA | $1.37 |
| Garden Park Senior Living | Orchid | 1BR,1BA | $1.65 |
| Eastbrook Apartments | One Bed One Bath | 1BR,1BA | $1.56 |
| Sumerset Apartments | 1 Bed, 1 bath | 1BR,1BA | $1.38 |
| The Grand Reserve at Maitland Park | The Grand A | 1BR,1BA | $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.
Read Article
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
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.
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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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See the most popular apartments and homes in Winter Park, FL
Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 308 Apartments for Rent in Winter Park, FL with pricing that ranges from $250 to $6,500. There are also 226 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $1,050 to $20,000.
What is the current price range for Rental Homes in Winter Park?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winter Park ranges from $1,050 to $20,000 with an average monthly rent of $3,824.
How much are larger Three and Four Bedroom Rentals in Winter Park?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winter Park range from $1,082 to $6,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,500 to $5,950. Four Bedroom Single-Family rentals are also available starting from $1,950 and Four Bedroom Apartments start at $1,679.
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.