
2 Bedroom Homes for Rent in Winter Park, FL (89 Rentals) Page 2 of 2


121 E Evans St

1913 Truman Rd

1375 Lake Shadow Cir

1921 Truman Rd

2075 Howell Branch Rd

1225 Lake Shadow Cir

1325 Lake Shadow Cir

908 Tucker Ave
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.

190 Ventris Ave W

825 N Primrose Dr

1440 Lake Shadow Cir

644 Kenwick Cir

1150 Lake Shadow Cir

2810 Kilgore St

4418 Eli St

636 Kenwick Cir

4521 Edgewater Dr
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

1160 Calle Del Norte

660 Jasmine Rd

8 E Evans St

17 W Winter Park St

2218 Amherst Ave

408 Banyon Tree Cir

2640 Legacy Villas Dr

250 Cedarwood Dr

29 E Spruce St
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

2982 Embassy Ct

1510 Altaloma Ave

2934 Plaza Terrace Dr

3104 Harrison Ave

109 E WINTER PARK St

1003 Sherrywood St

914 Robinhood Ct

1427 Asher Ln

814 Malone Dr
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

2619 E Washington St

2009 E Washington St

16 S Primrose 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 | $1,818 | $1,195 | $3,200 |
| Winter Park 3 Bedroom Homes for Rent | $2,777 | $1,150 | $6,500 |
| Winter Park 4 Bedroom Homes for Rent | $3,852 | $2,049 | $10,000+ |
| Winter Park 5 Bedroom Homes for Rent | $6,318 | $2,445 | $10,000+ |
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 $250 to $6,500. There are also 287 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $795 to $10,900.
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 $10,900 with an average monthly rent of $2,943.
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 $1,150 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

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.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

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.