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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 Winter Park, FL from $800 (86 Rentals)
Search the lowest-cost Homes available for rent right now in Winter Park.
840 Mulberry St
MaitlandFL32751
312 Orange St
MaitlandFL32751
312 Orange St
MaitlandFL32751
2515 Formosa Ave
OrlandoFL32804
407 Shine Ave
OrlandoFL32803
118 Eaton St, Unit 4
118 Eaton St
EatonvilleFL32751
2422 Branch Way, Unit 104
2422 Branch Way
MaitlandFL32751
525 Georgetown Dr
CasselberryFL32707
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.
1000 Lake of the Woods Blvd
Fern ParkFL32730
30 N Primrose Dr
OrlandoFL32803
551 Flemming Way, Unit 201
551 Flemming Way
MaitlandFL32751
1901 Magnolia Ave
Winter ParkFL32792
2505 E Central Blvd
OrlandoFL32803
1695 Lee Rd
Winter ParkFL32789
1008 Meadows Ave
OrlandoFL32804
616 Eola Dr
OrlandoFL32803
1820 Rogers Ave
MaitlandFL32751
385 Lime St
EatonvilleFL32751
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.
385 Lime St
MaitlandFL32751
5319 N Orange Ave
Winter ParkFL32792
2500 Lee Rd, Unit 244
2500 Lee Rd
Winter ParkFL32789
7328 Swallow Run
Winter ParkFL32792
667 Trinidad Ct
Winter ParkFL32792
1411 E Central Blvd
OrlandoFL32801
524 Georgetown Dr
CasselberryFL32707
1125 Lake Shadow Cir, Unit 5-101
1125 Lake Shadow Cir
MaitlandFL32751
1275 Lake Shadow Cir
MaitlandFL32751
1000 S Semoran Blvd
Winter ParkFL32792
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.
3011 George Mason Ave
Winter ParkFL32792
1125 Lake Shadow Cir, Unit Visconti Maitland FL
1125 Lake Shadow Cir
MaitlandFL32751
2500 Lee Rd
Winter ParkFL32789
1154 Paseo Del Sol
CasselberryFL32707
320 Lakeview St
OrlandoFL32804
2942 Antique Oaks Cir
Winter ParkFL32792
860 N Orange Ave
OrlandoFL32801
1000 Lake of the Woods Blvd, Unit Apartment C103
1000 Lake of the Woods Blvd
Fern ParkFL32730
3651 Goldenrod Rd
Winter ParkFL32792
1917 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.
2075 Howell Branch Rd
MaitlandFL32751
151 N Orlando Ave
Winter ParkFL32789
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$1,469Studio Apartments Available Now
1760 Pembrook Dr
1760 Pembrook DrOrlando, FL 32810
2502 Kilgore St
OrlandoFL32803
825 N Primrose Dr
OrlandoFL32803
1507 Legacy Club Dr
MaitlandFL32751
4321 Hargrave St
OrlandoFL32803
639 E Amelia St
OrlandoFL32803
3094 Plaza Terrace Dr
OrlandoFL32803
2407 Branch Way, Unit 105
2407 Branch Way
MaitlandFL32751
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
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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 | $1,859 | $1,150 | $3,200 |
| Winter Park 3 Bedroom Homes for Rent | $2,793 | $1,150 | $6,500 |
| Winter Park 4 Bedroom Homes for Rent | $3,717 | $2,085 | $8,295 |
| Winter Park 5 Bedroom Homes for Rent | $4,581 | $2,395 | $9,500 |
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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- Local Counties
Cheapest Neighborhoods for Apartments in Winter Park, FL
Pricing Updated: 07/04/2026Current 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 | $6,250 | $910 | 152 |
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. Azure Winter Park in the University Commerce Center neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $1,049. 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 |
| Azure Winter Park | Corrine | Studio,1BA | $1,049 |
| Kingswood Apartments | 1/1 | 1BR,1BA | $1,050 |
| Liv at Winter Park Apartment Homes | E1 | Studio,1BA | $1,066 |
| Sumerset Apartments | 1 Bed, 1 bath | 1BR,1BA | $1,074 |
| Regency Oaks Apartments | Studio | Studio,2BA | $1,123 |
| Birchwood Landing | Birchwood A | 1BR,1BA | $1,139 |
| Golden Oaks | 2x2-50 | 2BR,2BA | $1,141 |
| Venue At Winter Park | Sable P | 1BR,1BA | $1,155 |
Best Value Apartments for Rent in Winter Park, FL
As of July 04, 2026 the best value apartment in the Winter Park area is the $1.46 price per square foot Floorplan 2 Model at Azalea Gardens in the in the North Orange neighborhood starting from $1,750. The second greatest value Winter Park apartment is the Daisy (Two Bedroom w/Den) Model at Garden Park Senior Living starting at $1,599 with a $1.36 price per square foot in the Orienta Gardens 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. |
|---|---|---|---|
| Azalea Gardens | Floorplan 2 | 2BR,2BA | $1.46 |
| Garden Park Senior Living | Daisy (Two Bedroom w/Den) | 2BR,2BA | $1.36 |
| The Ivy at Gatehouse | The Palms | 3BR,2BA | $1.50 |
| Seabrook | Plan B2B | 2BR,2BA | $1.56 |
| Serena Winter Park | Eagle | 2BR,2BA | $1.55 |
| Summerlin at Winter Park Apartments | Gardenia | 2BR,2BA | $1.48 |
| Lake Weston Point Apartments | Two Bedroom | 2BR,2BA | $1.50 |
| Signal Pointe | Ponce Inlet | 2BR,1BA | $1.52 |
| Eastbrook Apartments | One Bed One Bath | 1BR,1BA | $1.56 |
| Sumerset Apartments | 1 Bed, 1 bath | 1BR,1BA | $1.38 |
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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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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Explore Winter Park, FL Rentals by Map
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 309 Apartments for Rent in Winter Park, FL with pricing that ranges from $250 to $6,649. There are also 291 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $800 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 $800 to $9,500 with an average monthly rent of $2,610.
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 $750 to $6,649, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,150 to $6,500. Four Bedroom Single-Family rentals are also available starting from $2,085 and Four Bedroom Apartments start at $1,844.
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
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.
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.