118 Eaton St, Unit 4
118 Eaton St
EatonvilleFL32751
Cheap Condos for Rent in Winter Park, FL from $900 (34 Rentals)
Search the lowest-cost Condos available for rent right now in Winter Park.
525 Georgetown Dr
CasselberryFL32707
1000 Lake of the Woods Blvd
Fern ParkFL32730
551 Flemming Way, Unit 201
551 Flemming Way
MaitlandFL32751
551 Flemming Way
MaitlandFL32751
5319 Sumerset St
OrlandoFL32810
3651 N Goldenrod Rd
Winter ParkFL32792
3035 George Mason Ave
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.
2075 Howell Branch Rd
MaitlandFL32751
524 Georgetown Dr
CasselberryFL32707
200 St Andrews Blvd
Winter ParkFL32792
302 Lewfield Cir
Winter ParkFL32792
1000 Lake of the Woods Blvd, Unit C103
1000 Lake of the Woods Blvd
Fern ParkFL32730
1000 S Semoran Blvd
Winter ParkFL32792
115 E Smith St
OrlandoFL32804
2942 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.
655 Trinidad Ct
Winter ParkFL32792
1855 Eastbrook Blvd
Winter ParkFL32792
320 Lakeview St
OrlandoFL32804
2880 Plaza Terrace Dr
OrlandoFL32803
1000 Lake of the Woods Blvd, Unit 204E
1000 Lake of the Woods Blvd
Fern ParkFL32730
1695 Lee Rd
Winter ParkFL32789
860 N Orange Ave
OrlandoFL32801
911 N Orange Ave
OrlandoFL32801
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.
805 Vassar St
OrlandoFL32804
3004 George Mason Ave
Winter ParkFL32792
1375 Lake Shadow Cir
MaitlandFL32751
1100 Lake Shadow Cir
MaitlandFL32751
2407 Branch Way, Unit 105
2407 Branch Way
MaitlandFL32751
4328 Edgewater Dr
OrlandoFL32804
860 N Orange Ave
OrlandoFL32801
1000 Lake of the Woods Blvd, Unit 201
1000 Lake of the Woods Blvd
Fern ParkFL32730
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
1420 Lake Shadow Cir
MaitlandFL32751
5301 Andrus Ave
OrlandoFL32810
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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 Condos for Rent | $1,753 | $1,200 | $2,695 |
| Winter Park 3 Bedroom Condos for Rent | $2,386 | $1,645 | $2,800 |
| Winter Park 4 Bedroom Condos for Rent | $2,500 | $2,500 | $2,500 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Condos for Rent in Winter Park
Explore Winter Park
Winter Park, FL Local Guide
- Winter Park Neighborhoods
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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 314 Apartments for Rent in Winter Park, FL with pricing that ranges from $250 to $7,284. There are also 285 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $950 to $2,800.
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 $950 to $2,800 with an average monthly rent of $1,708.
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 $2,800. Four Bedroom Single-Family rentals are also available starting from $2,500 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
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.
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.