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$7601 Bedroom Apartments Available Now
5530 Old Cheney Hwy, Unit 2
5530 Old Cheney HwyOrlando, FL 32807
Cheap Homes for Rent in the Winter Park Neighborhood of Orlando, FL from $1,000 (21 Rentals)
Search the lowest-cost Homes available for rent right now in the Winter Park area of Orlando.
5058 Seminole Ave, Unit Seminole 1
5058 Seminole Ave
Winter ParkFL32792
3035 George Mason Ave
Winter ParkFL32792
5587 Lehigh Ave
OrlandoFL32807
1000 S Semoran Blvd
Winter ParkFL32792
3011 George Mason Ave
Winter ParkFL32792
825 N Primrose Dr
OrlandoFL32803
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.
2942 Antique Oaks Cir
Winter ParkFL32792
3022 Plaza Terrace Dr
OrlandoFL32803
3651 N Goldenrod Rd
Winter ParkFL32792
2880 Plaza Terrace Dr
OrlandoFL32803
1917 Truman Rd
OrlandoFL32807
4321 Hargrave St
OrlandoFL32803
151 N Orlando Ave
Winter ParkFL32789
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.
200 St Andrews Blvd
Winter ParkFL32792
3094 Plaza Terrace Dr
OrlandoFL32803
7340 Swallow Run
Winter ParkFL32792
5555 Barton Dr
OrlandoFL32807
7338 Swallow Run
Winter ParkFL32792
908 Tucker Ave
OrlandoFL32807
2942 Plaza Terrace Dr
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.
Showing Results 1-21, 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 | $1,948 | $1,395 | $3,150 |
| Winter Park 3 Bedroom Homes for Rent | $3,134 | $1,665 | $9,500 |
| Winter Park 4 Bedroom Homes for Rent | $3,515 | $2,350 | $5,800 |
| Winter Park 5 Bedroom Homes for Rent | $6,122 | $2,745 | $9,500 |
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 21 rentals with your search options within a 2 mile radius of the Winter Park Neighborhood of Orlando, FL.
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Winter Park, Orlando, FL Local Guide
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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 Shoreview at Baldwin Park priced from $1,200. Central Place At Winter Park has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,215. Here are the most affordable Winter Park apartments for rent in Orlando, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Shoreview at Baldwin Park | 1x1A | 1BR,1BA | $1,200 |
| Central Place At Winter Park | A1 | 1BR,1BA | $1,215 |
| Venue At Winter Park | Sable P | 1BR,1BA | $1,217 |
| Azure Winter Park | Mills | 1BR,1BA | $1,249 |
| Winter Park Woods Apartments | A3-1 Bedroom, 1 Bathroom | 1BR,1BA | $1,274 |
Best Value Apartments for Rent in Winter Park, FL
As of July 19, 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 Baldwin Park neighborhood starting from $1,645. The second greatest value Winter Park apartment is the Dunes Downstairs Model at Calibre Bend Apartments starting at $1,844 with a $1.73 price per square foot in the University Commerce Center 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 |
| Calibre Bend Apartments | Dunes Downstairs | 2BR,2BA | $1.73 |
| Seabrook | Plan B2B | 2BR,2BA | $1.58 |
| Azure Winter Park | Park+ | 2BR,2BA | $1.62 |
| Golfside Villas | 2 Beds, 2 Baths | 2BR,2BA | $1.33 |
| La Aloma Apartments | 2 Bedrooms, 1.5 Bathrooms | 2BR,1.5BA | $1.56 |
| Golden Oaks | 2x2-60 | 2BR,2BA | $1.64 |
| Goldenrod Pointe | Two Bedroom One Bath | 2BR,1BA | $1.69 |
| Cranes Landing Apartments | Egret (Renovated) A2Rwi | 1BR,1BA | $1.68 |
| Avenues of Baldwin Park | Fern (Standard) A1wm | 1BR,1.5BA | $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.
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.
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Best Local Schools in Winter Park, Orlando, FL
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Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 138 Apartments for Rent in Winter Park, FL with pricing that ranges from $740 to $4,498. There are also 95 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $1,000 to $9,500.
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 $9,500 with an average monthly rent of $3,231.
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
Rent According to Income: A Look at Income-Restricted Rentals
Written by: Robin Stewart
The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.
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.
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.
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.