
Homes for Rent in Winter Park, FL (245 Rentals) Page 4 of 5


1225 Lake Shadow Cir

492 Banyon Tree Cir

400 Banyon Tree Cir

1140 S Orlando Ave

1140 Lake Maitland Ter

2444 Legacy Lake Dr

210 N East St

824 Town Cir

2119 Shadow View Cir

206 Quayside Cir

1224 Trust Ln

1511 E Horatio Ave

2120 Deloraine Trail

1430 Lone Feather Trail

1420 Lyndale Blvd

301 Clark St

106 People St

1000 Lake of the Woods Blvd

1159 Calle Del Norte

220 Sunshower Ct

208 Wilshire Dr

1162 Carmel Cir

2977 Lowell Ct

610 Wilshire Dr

348 Georgetown Dr

1212 Jamajo Blvd

5469 Decatur St

5514 Decatur St

320 Lakeview St

108 E Winter Park St

2505 E Central Blvd

121 E Evans St

1000 W Par St

1418 Beatrice Dr

1319 Oregon St

5517 Decatur St

2880 Plaza Terrace Dr

2619 Marble Ave

911 N Orange Ave

860 N Orange Ave

1626 Roosevelt Ave

2507 E Central Blvd

908 Tucker Ave

225 E New Hampshire St

1024 Manor Dr

5533 Decatur St

1023 E Amelia St

1413 Woodward St

2810 Kilgore 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 | $1,767 | $1,175 | $2,900 |
| Winter Park 3 Bedroom Homes for Rent | $3,036 | $1,585 | $10,000+ |
| Winter Park 4 Bedroom Homes for Rent | $3,872 | $2,085 | $10,000+ |
| Winter Park 5 Bedroom Homes for Rent | $6,442 | $2,345 | $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 301 Apartments for Rent in Winter Park, FL with pricing that ranges from $695 to $6,250. There are also 237 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $760 to $19,000.
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 $760 to $19,000 with an average monthly rent of $2,972.
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 $1,099 to $6,250, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,585 to $10,000. Four Bedroom Single-Family rentals are also available starting from $2,085 and Four Bedroom Apartments start at $1,697.
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

An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent
Written by: Darla Ferrara
For many, Orlando is the place where you vacation, not live. However, this city, located in the central region of Florida, offers a vibrant tech community, plenty of outdoor activities, and some of the best schools in the country.

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.

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.

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.
Articles, How-To's, and Tips

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.