1915 Taylor Ave
Winter ParkFL32792
Homes for Rent in Winter Park, FL (293 Rentals)
2383 Sun Valley Cir, Unit Winter Park
2383 Sun Valley Cir
Winter ParkFL32792
276 Cambridge Blvd
Winter ParkFL32789
200 Saint Andrews Blvd
Winter ParkFL32792
2865 Euston Rd
Winter ParkFL32789
1509 Springtime Loop
Winter ParkFL32792
2038 Ponderosa Ave
Winter ParkFL32792
2399 Antilles Dr
Winter ParkFL32792
5312 Poinsetta Ave, Unit 2
5312 Poinsetta Ave
Winter ParkFL32792
2924 Antique Oaks Cir, Unit 48
2924 Antique Oaks Cir
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.
151 N Orlando Ave, Unit 262
151 N Orlando Ave
Winter ParkFL32789
1250 S Denning Dr, Unit 127
1250 S Denning Dr
Winter ParkFL32789
1920 Woodcrest Dr, Unit 13
1920 Woodcrest Dr
Winter ParkFL32792
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$2,715
Total Monthly Price
Base Rent$2,715
Total Monthly Price$2,715
662 Callahan St, Unit SI ID1545989P
662 Callahan StWinter Park, FL 32789
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$4,586
Total Monthly Price
Base Rent$4,586
Total Monthly Price$4,586
2007 Cornell Ave, Unit SI ID1032296P
2007 Cornell AveWinter Park, FL 32789
5206 Tangerine Ave
Winter ParkFL32792
333 Cornwall Rd
Winter ParkFL32792
1250 S Denning Dr
Winter ParkFL32789
2772 Prism Pt
Winter ParkFL32792
3362 Bougainvillea Dr
Winter ParkFL32792
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.
1710 Puritan Ave
Winter ParkFL32792
151 N Orlando Ave, Unit 207
151 N Orlando Ave
Winter ParkFL32789
162 Moyses Rd
Winter ParkFL32792
3016 Village Hill Pl
Winter ParkFL32792
4040 Waterview Loop
Winter ParkFL32792
7039 Pecan Ct
Winter ParkFL32792
659 Montego Bay Ct
Winter ParkFL32792
3628 Datura Ct
Winter ParkFL32792
200 St Andrews Blvd, Unit 316
200 St Andrews Blvd
Winter ParkFL32792
7423 Antietam Ct E
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.
2866 Euston Rd
Winter ParkFL32789
7336 Forest Hill Ct
Winter ParkFL32792
3465 Balsam Dr
Winter ParkFL32792
2545 Madeline Ave
Winter ParkFL32789
1939 Gunn Rd
Winter ParkFL32792
1620 Palm Ave
Winter ParkFL32789
2918 Antique Oaks Cir
Winter ParkFL32792
4874 Tangerine Ave
Winter ParkFL32792
920 Aragon Ave
Winter ParkFL32789
2510 Roxbury Rd
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
2481 Tahoe Cir
Winter ParkFL32792
1431 Broad Wing Ln
Winter ParkFL32792
5454 Bracken Ct
Winter ParkFL32792
2704 Tortoise Cv
Winter ParkFL32792
2700 Tortoise Cv
Winter ParkFL32792
1812 Killarney Dr
Winter ParkFL32789
3068 Autumn Ct
Winter ParkFL32792
1403 Michigan Ave
Winter ParkFL32789
7338 Swallow Run
Winter ParkFL32792
2719 Merrie Oaks Rd
Winter ParkFL32792
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
Showing Results 1-50, Page 1 of 6
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 | $1,802 | $1,200 | $2,750 |
| Winter Park 3 Bedroom Homes for Rent | $2,831 | $1,750 | $6,300 |
| Winter Park 4 Bedroom Homes for Rent | $3,935 | $1,900 | $8,900 |
| Winter Park 5 Bedroom Homes for Rent | $6,118 | $2,395 | $9,900 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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Winter Park, FL Local Guide
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A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.
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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.
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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
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Real 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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Remember the 3 Rules of Real Estate:Location, Location, Location!
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 315 Apartments for Rent in Winter Park, FL with pricing that ranges from $529 to $6,500. There are also 295 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $795 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 $795 to $9,900 with an average monthly rent of $2,360.
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 $6,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,750 to $6,300. Four Bedroom Single-Family rentals are also available starting from $1,900 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.