612 Stetson St
OrlandoFL32804
Luxury Homes for Rent in Winter Park, FL (91 Rentals) Page 2 of 2
The most luxurious Homes in Winter Park with high-end amenities, features, and finishes.
712 Malone Dr
OrlandoFL32810
1100 S Orlando Ave
MaitlandFL32751
1397 Benevolent St
MaitlandFL32751
2505 Kilgore St
OrlandoFL32803
1811 Park Lake St
OrlandoFL32803
2704 E Jefferson St
OrlandoFL32803
200 S Glenwood Ave
OrlandoFL32803
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara
2503 Dakota Trail
Fern ParkFL32730
310 E Vanderbilt St, Unit 3
310 E Vanderbilt St
OrlandoFL32804
812 Harwood St
OrlandoFL32803
2330 Mohawk Trail
MaitlandFL32751
3012 Kilgore St
OrlandoFL32803
2607 Elizabeth Ave
OrlandoFL32804
1629 Ferris Ave
OrlandoFL32803
1448 Cumbie St
OrlandoFL32804
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.
2483 E Jefferson St
OrlandoFL32803
809 N Hyer Ave
OrlandoFL32803
420 Arapaho Trail
MaitlandFL32751
102 Lago Vista Blvd
CasselberryFL32707
2408 Corrine Dr
OrlandoFL32803
3306 Eagle Blvd
OrlandoFL32804
4020 Ibis Dr
OrlandoFL32803
1642 Hillcrest St
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.
1296 Moselle Ave
OrlandoFL32807
7524 Marietta St
OrlandoFL32807
7508 Carolyn Ave
OrlandoFL32807
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$3,781
Total Monthly Price
Base Rent$3,781
Total Monthly Price$3,781
2710 Amherst Ave, Unit SI ID1018188P
2710 Amherst AveOrlando, FL 32804
4357 Roush Ave
OrlandoFL32803
1350 Chatfield Pl
OrlandoFL32814
1352 Lake Baldwin Ln
OrlandoFL32814
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$3,939
Total Monthly Price
Base Rent$3,939
Total Monthly Price$3,939
102 W King St, Unit SI ID1029870P
102 W King StOrlando, FL 32804
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.
544 N Bumby Ave
OrlandoFL32803
1563 Common Way Rd
OrlandoFL32814
1965 Osprey Ave
OrlandoFL32814
4478 Twinview Ln
OrlandoFL32814
1501 Druid Isle Rd
MaitlandFL32751
1425 Chatfield Pl
OrlandoFL32814
974 Pinelli St
OrlandoFL32803
2721 E Marks 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.
3602 Upper Union Rd
OrlandoFL32814
Showing Results 51-91, 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 | $1,821 | $1,175 | $2,750 |
| Winter Park 3 Bedroom Homes for Rent | $2,909 | $1,795 | $9,500 |
| Winter Park 4 Bedroom Homes for Rent | $3,627 | $2,100 | $7,995 |
| Winter Park 5 Bedroom Homes for Rent | $6,331 | $2,395 | $9,900 |
| Winter Park 6 Bedroom Homes for Rent | $10,000 | $10,000 | $10,000+ |
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
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Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 313 Apartments for Rent in Winter Park, FL with pricing that ranges from $529 to $6,500. There are also 288 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $795 to $10,000.
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 $10,000 with an average monthly rent of $2,338.
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 $6,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,795 to $9,500. Four Bedroom Single-Family rentals are also available starting from $2,100 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
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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
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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
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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.
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Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
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Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
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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.