1733 Prospect Ave
OrlandoFL32814
Homes for Rent in the Winter Park Neighborhood of Orlando, FL (94 Rentals)
2912 Plaza Terrace Dr
OrlandoFL32803
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$7601 Bedroom Apartments Available Now
5530 Old Cheney Hwy, Unit 2
5530 Old Cheney HwyOrlando, FL 32807
1725 Durock Ct
OrlandoFL32807
5489 Baldwin Park St
OrlandoFL32814
7508 Carolyn Ave
OrlandoFL32807
1726 Diamond Dr
OrlandoFL32807
4230 Lower Park Rd
OrlandoFL32814
2054 Brink Alley
OrlandoFL32814
5489 Baldwin Park St
OrlandoFL32814
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.
4249 Corrine Dr
OrlandoFL32814
1917 Truman Rd
OrlandoFL32807
1782 Carley Ct
OrlandoFL32807
2510 Boyd Ave
OrlandoFL32803
3707 Pelican Ln
OrlandoFL32803
2934 Plaza Terrace Dr
OrlandoFL32803
2880 Plaza Terrace Dr
OrlandoFL32803
2882 Plaza Terrace Dr
OrlandoFL32803
10363 Folly Beach Rd
OrlandoFL32827
974 Pinelli St
OrlandoFL32803
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.
5587 Lehigh Ave
OrlandoFL32807
2916 Westchester Ave
OrlandoFL32803
2102 Montana St
OrlandoFL32803
5122 Old Cheney Hwy
OrlandoFL32807
4321 Hargrave St
OrlandoFL32803
5049 Old Cheney Hwy
OrlandoFL32807
825 N Primrose Dr
OrlandoFL32803
908 Tucker Ave
OrlandoFL32807
833 N Fern Creek Ave
OrlandoFL32803
1620 Park Lake St
OrlandoFL32803
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.
1407 Park Lake St
OrlandoFL32803
1222 Illinois St
OrlandoFL32803
1509 Woodward St
OrlandoFL32803
6879 Belmar Dr
OrlandoFL32807
5555 Barton Dr
OrlandoFL32807
2721 E Marks St
OrlandoFL32803
1920 Woodcrest Dr, Unit 13
1920 Woodcrest Dr
Winter ParkFL32792
530 Byron Rd
Winter ParkFL32792
2810 Sandwell Dr
Winter ParkFL32792
2924 Antique Oaks Cir, Unit 48
2924 Antique Oaks Cir
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
1250 S Denning Dr, Unit 127
1250 S Denning Dr
Winter ParkFL32789
151 N Orlando Ave, Unit 262
151 N Orlando Ave
Winter ParkFL32789
3373 Cedar Springs Pl
Winter ParkFL32792
5058 Seminole Ave, Unit Seminole 1
5058 Seminole Ave
Winter ParkFL32792
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$2,5002 Bedroom Apartments Available Now
522 Holt Ave
522 Holt AveWinter Park, FL 32789
659 Montego Bay Ct
Winter ParkFL32792
200 St Andrews Blvd, Unit 316
200 St Andrews Blvd
Winter ParkFL32792
7423 Antietam Ct E
Winter ParkFL32792
1250 S Denning Dr
Winter ParkFL32789
853 W Lyman Ave
Winter ParkFL32789
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.
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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 | $1,824 | $1,250 | $3,000 |
| Winter Park 3 Bedroom Homes for Rent | $3,053 | $1,645 | $9,500 |
| Winter Park 4 Bedroom Homes for Rent | $4,447 | $2,295 | $8,295 |
| Winter Park 5 Bedroom Homes for Rent | $5,637 | $2,675 | $8,600 |
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 94 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
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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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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 137 Apartments for Rent in Winter Park, FL with pricing that ranges from $740 to $7,064. There are also 96 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $1,000 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 $1,000 to $9,500 with an average monthly rent of $3,301.
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
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.
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.