
Homes for Rent in Winter Park, FL (272 Rentals) Page 4 of 6


758 Canovia Ave

1811 Oregon St

3907 Kiawa Dr

1614 Ferris Ave

5536 Kingswood Dr

416 Lime St

421 E Kennedy Blvd

2815 Shadow View Cir

551 Flemming Way

559 Flemming Way

1820 Rogers Ave

1225 Lake Shadow Cir

2407 Branch Way

1100 Lake Shadow Cir

1375 Lake Shadow Cir

1420 Lake Shadow Cir

1325 Lake Shadow Cir

1948 Legacy Cove Dr

581 E Horatio Ave

1817 Shadow View Cir

227 Lochmond Dr

824 Town Cir

1347 Benevolent St

2113 Shadow View Cir

1440 Lake Shadow Cir

1967 Legacy Cove Dr

530 Ventris Ct

100 Whitecaps Cir

821 Gamewell Ave

2490 Lauder Dr

2120 Deloraine Trail

2514 Tuscarora Trail

201 Cedarwood Dr

216 Obrien Rd

206 Diamond Cove

630 Kenwick Cir

642 Kenwick Cir

228 Everest Point

1165 Paseo De Las Flores Apt C

518 Polaris Loop

2021 Schuller Way

220 Wilshire Dr

1150 Carmel Cir

121 Springwind Way

5846 Willow Leaf Ct

104 Madrid Dr

2787 Willow Bay Terrace

348 Georgetown Dr

1233 Virginia Dr
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 | $1,924 | $950 | $3,650 |
Winter Park 3 Bedroom Homes for Rent | $2,867 | $1,695 | $6,200 |
Winter Park 4 Bedroom Homes for Rent | $3,536 | $2,550 | $6,000 |
Winter Park 5 Bedroom Homes for Rent | $6,200 | $3,750 | $8,650 |
Winter Park 6 Bedroom Homes for Rent | $3,695 | $3,695 | $3,695 |
Browse Top Homes for Rent in Winter Park
Explore Winter Park
Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 299 Apartments for Rent in Winter Park, FL with pricing that ranges from $695 to $10,885. There are also 272 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $800 to $8,650.
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 $800 to $8,650 with an average monthly rent of $3,014.
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 $1,261 to $10,885, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,695 to $6,200. Four Bedroom Single-Family rentals are also available starting from $2,550 and Four Bedroom Apartments start at $2,450.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.

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.

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.