2252 Howard Dr
Winter ParkFL32789
3 Bedroom Homes for Rent in Winter Park, FL (111 Rentals) Page 2 of 3
1830 Staunton Ave
Winter ParkFL32789
2497 Waving Moss Wy
Winter ParkFL32792
1667 Mizell Ave
Winter ParkFL32789
648 Fitzwalter Dr
Winter ParkFL32792
660 Osceola Ave
Winter ParkFL32789
1627 Orange Ave
Winter ParkFL32789
3463 Arnel Dr
Winter ParkFL32792
612 Stetson St
OrlandoFL32804
612 Stetson St
OrlandoFL32804
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara
840 Bethune Dr
OrlandoFL32810
1733 Prospect Ave
OrlandoFL32814
31 Bel Air St
EatonvilleFL32751
215 Lochmond Dr
Fern ParkFL32730
144 Mark David Blvd
CasselberryFL32707
414 Sonesta Ct
CasselberryFL32707
508 Zinnia Dr
CasselberryFL32707
5415 Alloway St
OrlandoFL32810
1725 Durock Ct
OrlandoFL32807
7508 Carolyn Ave
OrlandoFL32807
Renting with Roommates: Realistic Expectations for Shared Lease
Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.
5489 Baldwin Park St
OrlandoFL32814
5214 2nd St
OrlandoFL32810
1 E King St
OrlandoFL32804
1141 Exceller Ct
CasselberryFL32707
310 Kentia Rd
CasselberryFL32707
1322 Carlson Dr
OrlandoFL32804
2114 Winnebago Trail
CasselberryFL32730
911 Robinhood Ct
MaitlandFL32751
520 Seneca Trail
MaitlandFL32751
7480 Azalea Cove Cir
Azalea ParkFL32807
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
2102 Montana St
OrlandoFL32803
2608 E Jefferson St
OrlandoFL32803
1413 Carlson Dr
OrlandoFL32804
602 Desoto Dr
CasselberryFL32707
2 W Yale St
OrlandoFL32804
4177 N Orange Blossom Trl
OrlandoFL32804
1908 Bobtail Dr
MaitlandFL32751
1838 Illinois St
OrlandoFL32803
1337 Cumbie St
OrlandoFL32804
2618 E Central Blvd
OrlandoFL32803
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.
200 S Glenwood Ave
OrlandoFL32803
2505 Kilgore St
OrlandoFL32803
2704 E Jefferson St
OrlandoFL32803
1504 Mt Vernon St
OrlandoFL32803
437 Shine Ave
OrlandoFL32803
3007 E Central Blvd
OrlandoFL32803
2165 Ridgewood St
OrlandoFL32803
102 Lago Vista Blvd
CasselberryFL32707
2316 E Concord St
OrlandoFL32803
2916 Westchester Ave
OrlandoFL32803
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.
Showing Results 51-100, Page 2 of 3
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 | $1,872 | $1,150 | $3,200 |
| Winter Park 3 Bedroom Homes for Rent | $2,801 | $1,645 | $9,500 |
| Winter Park 4 Bedroom Homes for Rent | $3,606 | $2,070 | $8,295 |
| Winter Park 5 Bedroom Homes for Rent | $4,898 | $2,395 | $8,600 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Homes for Rent in Winter Park
Explore Winter Park
Let everyone know!
Do you know the Winter Park area?
If you’re an expert on all things Winter Park, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 310 Apartments for Rent in Winter Park, FL with pricing that ranges from $250 to $7,275. There are also 286 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $825 to $9,500.
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 $825 to $9,500 with an average monthly rent of $2,677.
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 $7,275, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,645 to $9,500. Four Bedroom Single-Family rentals are also available starting from $2,070 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
Written by: Darla Ferrara
When people think of Orlando, FL, the iconic theme parks and buzz of downtown tend to steal the spotlight.
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.
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.
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.
Articles, How-To's, and Tips
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.
Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.
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.