
Homes for Rent in Winter Park, FL (270 Rentals) Page 4 of 6


312 Orange St

1028 Yates St

523 Oak Ave

2161 Fennell St

120 Waverly Dr

800 Maxwell St

450 Iris Rd

1930 Shoshonee Trail

2500 Carver Ave

912 Neuse Ave

611 Hewett Dr

12 Herring Ct

470 Sunnyview Cir

5730 Oleander Dr

2517 Caper Ln

1275 Lake Shadow Cir

1375 Lake Shadow Cir

1507 Legacy Club Dr

1225 Lake Shadow Cir

1608 Legacy Park Dr

1325 Lake Shadow Cir

1140 S Orlando Ave

1140 Lake Maitland Ter

190 Ventris Ave W

1150 Lake Shadow Cir

408 Banyon Tree Cir

250 Cedarwood Dr

932 Robinhood Ct

914 Robinhood Ct

916 Robinhood Ct

1175 Lake Shadow Cir

520 Seneca Trail

2430 Deloraine Trail

301 Clark St

310 Clark St

16 Eaton St

644 Kenwick Cir

1160 Calle Del Norte

636 Kenwick Cir

660 Jasmine Rd

1141 Exceller Ct

435 Meadowood Blvd

2982 Embassy Ct

1177 Paseo Del Mar

2401 Harleyford Pl

1166 Carmel Cir

6 Carriage Hill Cir

102 Lago Vista Blvd

1220 Linda Ln
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 | $1,824 | $1,250 | $3,200 |
| Winter Park 3 Bedroom Homes for Rent | $2,757 | $1,495 | $6,500 |
| Winter Park 4 Bedroom Homes for Rent | $4,817 | $2,049 | $10,000+ |
| Winter Park 5 Bedroom Homes for Rent | $7,789 | $2,495 | $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 304 Apartments for Rent in Winter Park, FL with pricing that ranges from $250 to $6,500. There are also 269 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $795 to $20,000.
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 $20,000 with an average monthly rent of $3,357.
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 $1,082 to $6,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,495 to $6,500. Four Bedroom Single-Family rentals are also available starting from $2,049 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

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

Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.