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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 (78 Rentals)
Search the lowest-cost Homes available for rent right now in Winter Park.
312 Orange St
MaitlandFL32751
312 Orange St
MaitlandFL32751
312 Orange St
MaitlandFL32751
415 Lochmond Dr
Fern ParkFL32730
14 Bel Air St
MaitlandFL32751
118 Eaton St, Unit 4
118 Eaton St
EatonvilleFL32751
525 Georgetown Dr
CasselberryFL32707
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$9751 Bedroom Apartments Available Now
627 E Concord St
627 E Concord StOrlando, FL 32803
2517 Caper Ln
MaitlandFL32751
Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities
Why fight Orlando's tourist traffic when you don't have to? Explore the best cities surrounding Orlando for renters, with expert tips on commuting, lifestyle, hidden costs, and where to find the most value.
5312 Poinsetta Ave, Unit 2
5312 Poinsetta Ave
Winter ParkFL32792
3065 George Mason Ave
Winter ParkFL32792
301 Clark St
EatonvilleFL32751
1000 Lake of the Woods Blvd
Fern ParkFL32730
5587 Lehigh Ave
OrlandoFL32807
2721 Sidney Ave
OrlandoFL32810
551 Flemming Way, Unit 201
551 Flemming Way
MaitlandFL32751
2502 Kilgore St
OrlandoFL32803
7309 Daniel Webster Dr
Winter ParkFL32792
551 Flemming Way
MaitlandFL32751
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.
5319 Sumerset St
OrlandoFL32810
3651 N Goldenrod Rd
Winter ParkFL32792
2500 Lee Rd
Winter ParkFL32789
2075 Howell Branch Rd
MaitlandFL32751
3035 George Mason Ave
Winter ParkFL32792
524 Georgetown Dr
CasselberryFL32707
200 St Andrews Blvd
Winter ParkFL32792
302 Lewfield Cir
Winter ParkFL32792
385 Lime St
MaitlandFL32751
385 Lime St
EatonvilleFL32751
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.
1411 E Central Blvd
OrlandoFL32801
107 E King St
OrlandoFL32804
1000 Lake of the Woods Blvd, Unit C103
1000 Lake of the Woods Blvd
Fern ParkFL32730
1513 Truman Rd
OrlandoFL32807
1000 S Semoran Blvd
Winter ParkFL32792
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$1,379Studio Apartments Available Now
1760 Pembrook Dr
1760 Pembrook DrOrlando, FL 32810
2942 Antique Oaks Cir
Winter ParkFL32792
1600 Indiana Ave
Winter ParkFL32789
115 E Smith St
OrlandoFL32804
655 Trinidad Ct
Winter ParkFL32792
Top Neighborhoods Near Orlando Major Employers
Learn about the best places to live near major employers in Orlando with original content written by our Local Expert Darla Ferrara
1855 Eastbrook Blvd
Winter ParkFL32792
320 Lakeview St
OrlandoFL32804
121 E Evans St
OrlandoFL32804
2406 Branch Way
MaitlandFL32751
2880 Plaza Terrace Dr
OrlandoFL32803
1000 Lake of the Woods Blvd, Unit 204E
1000 Lake of the Woods Blvd
Fern ParkFL32730
5049 Old Cheney Hwy
OrlandoFL32807
1695 Lee Rd
Winter ParkFL32789
911 N Orange Ave
OrlandoFL32801
860 N Orange Ave
OrlandoFL32801
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 | $1,811 | $1,200 | $3,200 |
| Winter Park 3 Bedroom Homes for Rent | $2,711 | $1,645 | $6,450 |
| Winter Park 4 Bedroom Homes for Rent | $3,759 | $2,150 | $8,295 |
| Winter Park 5 Bedroom Homes for Rent | $5,973 | $2,395 | $9,900 |
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: 08/19/2026Current apartment rentals in the Winter Park, FL area range in price from $995 to $4,840 with an overall median price of $1,756. 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 | $1,756 | $995 | 144 |
Cheapest Available Winter Park Apartments for Rent
The cheapest available apartment rental in Winter Park, FL is a 1 Bed unit found at Soraya in the Outer East neighborhood priced from $999. Primrose Orlando in the Downtown Orlando neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,000. Here is today’s list of the most affordable Winter Park apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Soraya | Aries | 1BR,1BA | $999 |
| Primrose Orlando | Upgraded Unit | 1BR,1BA | $1,000 |
| District On Baldwin Park | Executive Studio | Studio,1BA | $1,000 |
| Serena Winter Park | Champions | 1BR,1BA | $1,049 |
| Kingswood Apartments | 1/1 | 1BR,1BA | $1,050 |
| The Ivy at Gatehouse | The Springs | 2BR,2BA | $1,073 |
| Sumerset Apartments | 1 Bed, 1 bath | 1BR,1BA | $1,074 |
| Golden Oaks | 2x2-60 | 2BR,2BA | $1,095 |
| Winter Park Woods Apartments | A1-Studio, 1 Bathroom | 1BR,1BA | $1,107 |
Best Value Apartments for Rent in Winter Park, FL
As of August 19, 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 $1,549 with a $1.31 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 | $1.31 |
| Avenues of Baldwin Park | Meeting (Standard) C1wm | 3BR,2BA | $1.50 |
| Forest Edge | 2BR - 2 | 2BR,2BA | $1.42 |
| Golfside Villas | 2 Beds, 2 Baths | 2BR,2BA | $1.32 |
| San Jose Apartments | 2x1 1033 | 2BR,1BA | $1.17 |
| Summerlin at Winter Park Apartments | Gardenia | 2BR,2BA | $1.48 |
| 2075 Howell Branch Road #101 | 2075 Howell Branch Road #101 - 1 | 2BR,1BA | $1.43 |
| Golden Oaks | 2x2-60 | 2BR,2BA | $1.28 |
| 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.
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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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Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 313 Apartments for Rent in Winter Park, FL with pricing that ranges from $250 to $7,284. There are also 284 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $825 to $9,900.
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 $825 to $9,900 with an average monthly rent of $2,299.
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 $7,284, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,645 to $6,450. Four Bedroom Single-Family rentals are also available starting from $2,150 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
Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities
Written by: Darla Ferrara
When people think of Orlando, FL, the iconic theme parks and buzz of downtown tend to steal the spotlight.
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.
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.
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.
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.
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.
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.