close
View Me
$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 Neighborhood of Orlando, FL from $1,000 (28 Rentals)
Search the lowest-cost Homes available for rent right now in the Winter Park area of Orlando.
close
View Me
$7801 Bedroom Apartments Available Now
5530 Old Cheney Hwy, Unit 2
5530 Old Cheney HwyOrlando, FL 32807
5058 Seminole Ave, Unit Seminole Unit 2, Unit Seminole Unit 2
5058 Seminole Ave
Winter ParkFL32792
525 S Lakemont Ave
Winter ParkFL32792
5469 Decatur St
OrlandoFL32807
1008 Maltby Ave
OrlandoFL32803
3075 Aaron Burr Ave
Winter ParkFL32792
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.
1232 Linda Ln
Azalea ParkFL32807
4818 Tangerine Ave
Winter ParkFL32792
3651 N Goldenrod Rd
Winter ParkFL32792
5514 Decatur St
OrlandoFL32807
2942 Antique Oaks Cir, Unit 82
2942 Antique Oaks Cir
Winter ParkFL32792
3032 Antique Oaks Cir
Winter ParkFL32792
1319 Oregon St
OrlandoFL32803
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.
2619 Marble Ave
OrlandoFL32803
1227 Minnesota St
OrlandoFL32803
3020 Antique Oaks Cir
Winter ParkFL32792
1416 Granville Ln
OrlandoFL32803
851 Miles Ave
Winter ParkFL32789
2911 Antique Oaks Cir
Winter ParkFL32792
908 Tucker Ave
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.
1024 Manor Dr
OrlandoFL32807
5533 Decatur St
OrlandoFL32807
5793 Oleander Dr
OrlandoFL32807
1000 S Semoran Blvd
Winter ParkFL32792
2936 Antique Oaks Cir
Winter ParkFL32792
1413 Woodward St
OrlandoFL32803
4968 Tangerine Ave
Winter ParkFL32792
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.
Showing Results 1-28, Page 1 of 1
Winter Park, Orlando, 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 | $1,768 | $1,175 | $2,695 |
| Winter Park 3 Bedroom Homes for Rent | $3,466 | $1,800 | $8,950 |
| Winter Park 4 Bedroom Homes for Rent | $3,167 | $2,099 | $4,300 |
| Winter Park 5 Bedroom Homes for Rent | $11,013 | $3,040 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 28 rentals with your search options within a 2 mile radius of the Winter Park Neighborhood of Orlando, FL.
Explore Orlando
Winter Park, Orlando, FL Local Guide
- Nearby Orlando neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
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 Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Winter Park Woods Apartments | A2-1 Bedroom, 1 Bathroom | 1BR,1BA | $1,058 |
| Golden Oaks | 3x2-50 | 3BR,2BA | $1,082 |
| Seabrook | Plan A1 | 1BR,1BA | $1,138 |
| Atlas at Winter Park | Palm | 1BR,1BA | $1,183 |
| Shoreview at Baldwin Park | Studio | Studio,1BA | $1,195 |
| Hillcrest Hampton House | Studio | Studio,1BA | $1,200 |
| Venue At Winter Park | Sable P | 1BR,1BA | $1,204 |
| Village Park Senior | One Bedroom One Bath | 1BR,1BA | $1,236 |
| Azure Winter Park | Mills | 1BR,1BA | $1,249 |
| Central Place At Winter Park | A1 | 1BR,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 Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| The Ivy at Gatehouse | The Palms | 3BR,2BA | $1.50 |
| Park East - Park Knowles Apartments | 2 Bedroom, 1 Bathroom | 2BR,1BA | $1.59 |
| Golden Oaks | 3x2-50 | 3BR,2BA | $1.03 |
| Azure Winter Park | Park | 2BR,2BA | $1.67 |
| Cranes Landing Apartments | Ibis (Standard) b1wi | 2BR,2BA | $1.57 |
| Carlton Arms of Winter Park | C1A Downstairs | 2BR,1BA | $1.63 |
| Bellancia Apartments | One Bedroom | 1BR,1BA | $1.75 |
| Avenues of Baldwin Park | Fern (Standard) A1wm | 1BR,1.5BA | $1.66 |
| Winter Park Woods Apartments | A2-1 Bedroom, 1 Bathroom | 1BR,1BA | $1.40 |
| Whisper Lake Apartments | Crescent | 1BR,1BA | $1.73 |
10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
Read Article
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 ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash 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.
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 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.
Let everyone know!
Do you know the Winter Park area?
If you’re an expert on all things Winter Park, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Best Local Schools in Winter Park, Orlando, FL
School data provided by Great Schools
Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 129 Apartments for Rent in Winter Park, FL with pricing that ranges from $695 to $5,937. There are also 82 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $1,000 to $19,000.
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 $1,000 to $19,000 with an average monthly rent of $4,156.
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 $5,723, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,800 to $8,950. Four Bedroom Single-Family rentals are also available starting from $2,099 and Four Bedroom Apartments start at $3,944.
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
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.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
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.