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$6001 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 $1,100 (43 Rentals)
Search the lowest-cost Homes available for rent right now in the Winter Park area of Orlando.
5587 Lehigh Ave
OrlandoFL32807
7309 Daniel Webster Dr
Winter ParkFL32792
1000 S Semoran Blvd
Winter ParkFL32792
3004 George Mason Ave
Winter ParkFL32792
1513 Truman Rd
OrlandoFL32807
4874 Tangerine Ave
Winter ParkFL32792
3651 N Goldenrod Rd
Winter ParkFL32792
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.
1756 Memphis Ave
OrlandoFL32807
5049 Old Cheney Hwy
OrlandoFL32807
5515 Decatur St
OrlandoFL32807
5555 Barton Dr
OrlandoFL32807
200 Saint Andrews Blvd
Winter ParkFL32792
5122 Old Cheney Hwy
OrlandoFL32807
3374 Cedar Springs Pl
Winter ParkFL32792
2918 Antique Oaks Cir
Winter ParkFL32792
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.
3225 Oak Lawn Pl
Winter ParkFL32792
2911 Antique Oaks Cir
Winter ParkFL32792
7338 Swallow Run
Winter ParkFL32792
3370 Cedar Springs Pl
Winter ParkFL32792
200 St Andrews Blvd, Unit 316
200 St Andrews Blvd
Winter ParkFL32792
2404 Gallery View Dr
Winter ParkFL32792
5039 Old Cheney Hwy
OrlandoFL32807
659 Montego Bay Ct
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.
4968 Tangerine Ave
Winter ParkFL32792
7336 Forest Hill Ct
Winter ParkFL32792
612 Trinidad Ct
Winter ParkFL32792
0000 Undisclosed
AlomaFL32792
7446 Wynnewood Square
Winter ParkFL32792
731 W Comstock Ave
Winter ParkFL32789
3367 Riverview Way
Winter ParkFL32792
759 Antonette Ave
Winter ParkFL32789
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
2924 Antique Oaks Cir, Unit 48
2924 Antique Oaks Cir
Winter ParkFL32792
2808 Plaza Terrace Dr
OrlandoFL32803
1250 S Denning Dr
Winter ParkFL32789
2934 Plaza Terrace Dr
OrlandoFL32803
3220 Oak Lawn Pl
Winter ParkFL32792
5730 Oleander Dr
OrlandoFL32807
1708 Garvin St
OrlandoFL32803
937 Aragon Ave
Winter ParkFL32789
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.
3629 Hedgewood Dr
Winter ParkFL32792
783 Eldridge St
OrlandoFL32803
6867 Belmar Dr
OrlandoFL32807
Showing Results 1-43, 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 | $1,772 | $1,300 | $2,400 |
| Winter Park 3 Bedroom Homes for Rent | $3,332 | $1,795 | $9,500 |
| Winter Park 4 Bedroom Homes for Rent | $3,590 | $2,100 | $7,995 |
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 43 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
- Nearby Orlando neighborhoods
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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 Studio unit found at District On Baldwin Park priced from $1,000. Winter Park Woods Apartments has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,107. Here are the most affordable Winter Park apartments for rent in Orlando, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| District On Baldwin Park | Executive Studio | Studio,1BA | $1,000 |
| Winter Park Woods Apartments | A1-Studio, 1 Bathroom | 1BR,1BA | $1,107 |
| Golden Oaks | 3x2-60 | 3BR,2BA | $1,170 |
| Atlas at Winter Park | Palm | 1BR,1BA | $1,184 |
| Shoreview at Baldwin Park | 1x1B | 1BR,1BA | $1,185 |
| Central Place At Winter Park | A1 | 1BR,1BA | $1,195 |
| La Aloma Apartments | 2 Bedrooms, 1 Bathroom | 2BR,1BA | $1,200 |
| Venue At Winter Park | Sable P | 1BR,1BA | $1,208 |
| Seabrook | Plan A1 | 1BR,1BA | $1,254 |
| Avenues of Baldwin Park | Fern (Standard) A1wm | 1BR,1BA | $1,285 |
Best Value Apartments for Rent in Winter Park, FL
As of September 13, 2026 the best value apartment in the Winter Park area is the $1.33 price per square foot Central Model at Azure Winter Park in the in the University Commerce Center neighborhood starting from $1,849. The second greatest value Winter Park apartment is the St. Bernadette Model at Chapel Trace starting at $1,452 with a $1.32 price per square foot in the Covered Bridge 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. |
|---|---|---|---|
| Azure Winter Park | Central | 3BR,2BA | $1.33 |
| Chapel Trace | St. Bernadette | 2BR,2BA | $1.32 |
| The Ivy at Gatehouse | The Palms | 3BR,2BA | $1.50 |
| Golfside Villas | 2 Beds, 2 Baths | 2BR,2BA | $1.32 |
| La Aloma Apartments | 2 Bedrooms, 1.5 Bathrooms | 2BR,1.5BA | $1.65 |
| Summerlin at Winter Park Apartments | Gardenia | 2BR,2BA | $1.43 |
| Carlton Arms of Winter Park | C2 Upstairs | 2BR,1BA | $1.53 |
| Golden Oaks | 2x2-60 | 2BR,2BA | $1.64 |
| Goldenrod Pointe | Two Bedroom One Bath | 2BR,1BA | $1.59 |
| 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 ArticleNavigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
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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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 135 Apartments for Rent in Winter Park, FL with pricing that ranges from $600 to $5,092. There are also 104 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $1,100 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 $1,100 to $9,500 with an average monthly rent of $2,624.
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.
Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.
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.