807 Vassar St
OrlandoFL32804
Homes for Rent in Winter Park, FL Under $2,000 (134 Rentals) Page 3 of 3
5555 Barton Dr
OrlandoFL32807
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$1,469Studio Apartments Available Now
1760 Pembrook Dr
1760 Pembrook DrOrlando, FL 32810
1917 Truman Rd
OrlandoFL32807
4321 Hargrave St
OrlandoFL32803
2880 Plaza Terrace Dr
OrlandoFL32803
5049 Old Cheney Hwy
OrlandoFL32807
3022 Plaza Terrace Dr
OrlandoFL32803
121 E Evans St
OrlandoFL32804
1000 Lake of the Woods Blvd, Unit Apartment C103
1000 Lake of the Woods Blvd
Fern ParkFL32730
2502 Kilgore St
OrlandoFL32803
825 N Primrose Dr
OrlandoFL32803
320 Lakeview St
OrlandoFL32804
860 N Orange Ave
OrlandoFL32801
2075 Howell Branch Rd
MaitlandFL32751
1411 E Central Blvd
OrlandoFL32801
107 E King St
OrlandoFL32804
385 Lime St
EatonvilleFL32751
385 Lime St
MaitlandFL32751
616 Eola Dr
OrlandoFL32803
468 Banyon Tree Cir, Unit 202
468 Banyon Tree Cir
MaitlandFL32751
524 Georgetown Dr
CasselberryFL32707
5587 Lehigh Ave
OrlandoFL32807
551 Flemming Way, Unit 201
551 Flemming Way
MaitlandFL32751
30 N Primrose Dr
OrlandoFL32803
301 Clark St
EatonvilleFL32751
2422 Branch Way, Unit 104
2422 Branch Way
MaitlandFL32751
525 Georgetown Dr
CasselberryFL32707
14 Bel Air St
MaitlandFL32751
2517 Caper Ln
MaitlandFL32751
118 Eaton St, Unit 4
118 Eaton St
EatonvilleFL32751
312 Orange St
MaitlandFL32751
312 Orange St
MaitlandFL32751
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$7601 Bedroom Apartments Available Now
5530 Old Cheney Hwy, Unit 2
5530 Old Cheney HwyOrlando, FL 32807
Showing Results 101-134, Page 3 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 | $1,873 | $1,150 | $3,200 |
| Winter Park 3 Bedroom Homes for Rent | $2,784 | $1,575 | $9,500 |
| Winter Park 4 Bedroom Homes for Rent | $3,558 | $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.
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Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 311 Apartments for Rent in Winter Park, FL with pricing that ranges from $250 to $7,275. There are also 292 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 $2,665.
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 $1,575 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.