521 Ohio St
Winter ParkFL32789
Luxury Homes for Rent in Winter Park, FL (90 Rentals)
The most luxurious Homes in Winter Park with high-end amenities, features, and finishes.
2479 Passamonte Dr
Winter ParkFL32792
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$2,5002 Bedroom Apartments Available Now
522 Holt Ave
522 Holt AveWinter Park, FL 32789
3908 Woodglade Cove
Winter ParkFL32792
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$2,553
Total Monthly Price
2 Bedroom Apartments Available Nov 25Total Monthly Price
Base Rent
$2,553
Total Monthly Price
$2,553
662 Callahan St, Unit SI ID1545989P
662 Callahan StWinter Park, FL 32789
1871 Casselwood St
Winter ParkFL32792
4959 Tangerine Ave
Winter ParkFL32792
2530 Passamonte Dr
Winter ParkFL32792
7423 Antietam Ct E
Winter ParkFL32792
4059 Waterview Loop
Winter ParkFL32792
Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities
Why fight Orlando's tourist traffic when you don't have to? Explore the best cities surrounding Orlando for renters, with expert tips on commuting, lifestyle, hidden costs, and where to find the most value.
5119 Ferncrest Dr
Winter ParkFL32792
2661 Tierra Cir, Unit 09106
2661 Tierra Cir
Winter ParkFL32792
5360 N Lake Burkett Ln
Winter ParkFL32792
1016 Manchester Cir
Winter ParkFL32792
2366 Coldstream Dr
Winter ParkFL32792
1627 Orange Ave
Winter ParkFL32789
1492 Broad Wing Ln
Winter ParkFL32792
1524 Little Wren Ln
Winter ParkFL32792
1351 Merrydale Wy
Winter ParkFL32792
508 Dunblane Dr
Winter ParkFL32792
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
540 W Comstock Ave
Winter ParkFL32789
3463 Arnel Dr
Winter ParkFL32792
8104 Pleasant Pine Cir
Winter ParkFL32792
2817 Bower Rd
Winter ParkFL32792
2252 Howard Dr
Winter ParkFL32789
438 Lakeview Ave
Winter ParkFL32789
1830 Staunton Ave
Winter ParkFL32789
853 W Lyman Ave
Winter ParkFL32789
7039 Pecan Ct
Winter ParkFL32792
7864 Broken Arrow Trail
Winter ParkFL32792
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.
2497 Waving Moss Wy
Winter ParkFL32792
5354 Lanyard Ct
Winter ParkFL32792
1667 Mizell Ave
Winter ParkFL32789
648 Fitzwalter Dr
Winter ParkFL32792
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$5,982
Total Monthly Price
3 Bedroom Apartments Available Oct 1Total Monthly Price
Base Rent
$5,982
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$5,982
2007 Cornell Ave, Unit SI ID1032296P
2007 Cornell AveWinter Park, FL 32789
1403 Michigan Ave
Winter ParkFL32789
2075 Jewell Ave
Winter ParkFL32789
2234 Howard Dr
Winter ParkFL32789
660 Osceola Ave
Winter ParkFL32789
1337 Cumbie St
OrlandoFL32804
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
135 N Lakewood Cir
MaitlandFL32751
561 Hibiscus Rd
CasselberryFL32707
1639 Oakmont Ln
OrlandoFL32804
612 Stetson St
OrlandoFL32804
612 Stetson St
OrlandoFL32804
840 Bethune Dr
OrlandoFL32810
144 Mark David Blvd
CasselberryFL32707
2618 E Central Blvd
OrlandoFL32803
800 Maxwell St
OrlandoFL32804
1726 Diamond Dr
OrlandoFL32807
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
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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.
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Winter Park, FL Local Guide
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Your Guide to the Perfect Orlando Neighborhood for Student Renters
Learn About the Best Neighborhoods to Rent Near College Campuses in Orlando, FL | Find Orlando Off-Campus Student Housing at ApartmentHomeLiving.com
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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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See the most popular apartments and homes in Winter Park, FL
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.