2503 Dakota Trail
Fern ParkFL32730
Luxury Homes for Rent in Winter Park, FL (88 Rentals) Page 2 of 2
The most luxurious Homes in Winter Park with high-end amenities, features, and finishes.
2505 Kilgore St
OrlandoFL32803
2704 E Jefferson St
OrlandoFL32803
400 E Colonial Dr
OrlandoFL32803
1504 Mt Vernon St
OrlandoFL32803
437 Shine Ave
OrlandoFL32803
1620 Park Lake St
OrlandoFL32803
3007 E Central Blvd
OrlandoFL32803
10363 Folly Beach Rd
OrlandoFL32827
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara
2165 Ridgewood St
OrlandoFL32803
2662 Derbyshire Rd
MaitlandFL32751
420 Arapaho Trail
MaitlandFL32751
1500 E Ridgewood St
OrlandoFL32803
102 Lago Vista Blvd
CasselberryFL32707
233 Emory Pl
OrlandoFL32804
738 Lake Howell Rd
MaitlandFL32751
2316 E Concord St
OrlandoFL32803
2916 Westchester Ave
OrlandoFL32803
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
641 Brookside Rd
MaitlandFL32751
3707 Pelican Ln
OrlandoFL32803
833 N Fern Creek Ave
OrlandoFL32803
7508 Carolyn Ave
OrlandoFL32807
5489 Baldwin Park St
OrlandoFL32814
1770 Algonquin Trail
MaitlandFL32751
5489 Baldwin Park St
OrlandoFL32814
2406 Shoreham Rd
OrlandoFL32803
544 N Bumby Ave
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.
1733 Prospect Ave
OrlandoFL32814
2054 Brink Alley
OrlandoFL32814
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$4,637
Total Monthly Price
2 Bedroom Apartments Available Jan 26, 2027Total Monthly Price
Base Rent
$4,637
Total Monthly Price
$4,637
102 W King St, Unit SI ID1029870P
102 W King StOrlando, FL 32804
1501 Druid Isle Rd
MaitlandFL32751
266 Park Lake St
OrlandoFL32803
2721 E Marks St
OrlandoFL32803
974 Pinelli St
OrlandoFL32803
703 Fairoaks Ln
MaitlandFL32751
218 Park Lake St
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.
758 Highland Ave
OrlandoFL32803
4230 Lower Park Rd
OrlandoFL32814
Showing Results 51-88, Page 2 of 2
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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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.