
Homes for Rent in Winter Park, FL (295 Rentals) Page 5 of 6


3011 Legacy Villas Dr

13 E Winter Park St

385 Lime St

974 Pinelli St

1427 Asher Ln

860 N Orange Ave

4615 Edgewater Dr

2608 E Jefferson St

2406 Musselwhite Ave

2075 Howell Branch Rd

400 E Colonial Dr

1397 Benevolent St

1100 S Orlando Ave

2102 Montana St

1642 Hillcrest St

108 E Hazel St

2408 Corrine Dr

4328 Edgewater Dr

204 Quayside Cir

3602 Upper Union Rd

1350 Chatfield Pl

1811 Park Lake St

1000 Lake of the Woods Blvd

205 E New Hampshire St

316 Georgetown Dr

5039 Old Cheney Hwy

4521 Edgewater Dr

1501 Woodward St

1416 Beatrice Dr

320 Lakeview St

1352 Lake Baldwin Ln

1563 Common Way Rd

2218 Elizabeth Ave

712 Malone Dr

4357 Roush Ave

4809 Thorpe Ave

1225 E Livingston St

5319 Sumerset St

3012 Kilgore St

1225 E Amelia St

1296 Moselle Ave

511 Hillcrest St

226 Georgetown Dr

4478 Twinview Ln

1756 Memphis Ave

3100 E Jefferson St

2330 Mohawk Trail

3104 Harrison Ave

807 Vassar St
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 | $1,809 | $1,175 | $2,750 |
| Winter Park 3 Bedroom Homes for Rent | $2,974 | $1,795 | $9,500 |
| Winter Park 4 Bedroom Homes for Rent | $3,801 | $2,100 | $7,995 |
| Winter Park 5 Bedroom Homes for Rent | $6,331 | $2,395 | $9,900 |
| Winter Park 6 Bedroom Homes for Rent | $10,000 | $10,000 | $10,000+ |
Browse Top Homes for Rent in Winter Park
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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 $529 to $6,500. There are also 285 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $795 to $10,000.
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 $10,000 with an average monthly rent of $2,358.
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 $1,795 to $9,500. Four Bedroom Single-Family rentals are also available starting from $2,100 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
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The Soul of the City Beautiful: What Life in Orlando Is Really Like
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Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers
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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
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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

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.

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.