747 Maryland Ave
Winter ParkFL32789
Luxury Homes for Rent in Winter Park, FL (91 Rentals)
The most luxurious Homes in Winter Park with high-end amenities, features, and finishes.
1839 Blaine Ter
Winter ParkFL32792
3313 Hamlet Loop
Winter ParkFL32792
5563 Pats Point
Winter ParkFL32792
504 St Dunstan Way
Winter ParkFL32792
2887 Clever Ln
Winter ParkFL32792
7500 Waunatta Ct
Winter ParkFL32792
1947 Summerfield Rd
Winter ParkFL32792
3465 Balsam Dr
Winter ParkFL32792
2530 Passamonte Dr
Winter ParkFL32792
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.
1546 Peruvian Ln
Winter ParkFL32792
1721 Shasta Ct, Unit 6310
1721 Shasta Ct
Winter ParkFL32792
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$2,767
Total Monthly Price
3 Bedroom Apartments Available Jul 17Total Monthly Price
Base Rent
$2,767
Total Monthly Price
$2,767
2007 Cornell Ave, Unit SI ID1032296P
2007 Cornell AveWinter Park, FL 32789
1761 Indiana Ave
Winter ParkFL32789
4190 Bear Gully Rd
Winter ParkFL32792
2817 Bright Bird Ln
Winter ParkFL32792
1951 Canny Cv
Winter ParkFL32792
540 W Comstock Ave
Winter ParkFL32789
2233 Shadowland Lp
Winter ParkFL32792
223 Sandlewood Trl
Winter ParkFL32789
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.
5360 N Lake Burkett Ln
Winter ParkFL32792
3463 Arnel Dr
Winter ParkFL32792
7 Carver Ct
Winter ParkFL32789
3651 Oak Vista Ln
Winter ParkFL32792
1415 Harmon Ave
Winter ParkFL32789
1351 Merrydale Wy
Winter ParkFL32792
640 N Park Ave
Winter ParkFL32789
438 Lakeview Ave
Winter ParkFL32789
1843 Shadyhill Terrace
Winter ParkFL32792
853 W Lyman Ave
Winter ParkFL32789
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.
1137 S Pennsylvania Ave
Winter ParkFL32789
2806 Summerfield Rd
Winter ParkFL32792
7864 Broken Arrow Trail
Winter ParkFL32792
1542 Sugarwood Cir
Winter ParkFL32792
1667 Mizell Ave
Winter ParkFL32789
1625 Tioga Trail
Winter ParkFL32789
2344 Woodcrest Dr
Winter ParkFL32792
1119 S Pennsylvania Ave
Winter ParkFL32789
2335 Coldstream Dr
Winter ParkFL32792
782 S Pennsylvania Ave
Winter ParkFL32789
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
2019 Soaring Oak Way
Winter ParkFL32792
784 S Pennsylvania Ave
Winter ParkFL32789
2075 Jewell Ave
Winter ParkFL32789
1760 Legion Dr
Winter ParkFL32789
1814 Barker Dr
Winter ParkFL32789
1760 Alabama Dr
Winter ParkFL32789
602 Desoto Dr
CasselberryFL32707
1219 Lake Highland Dr
OrlandoFL32803
612 Stetson St
OrlandoFL32804
612 Stetson St
OrlandoFL32804
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.
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 | $1,837 | $1,250 | $3,200 |
| Winter Park 3 Bedroom Homes for Rent | $2,867 | $1,150 | $10,000+ |
| Winter Park 4 Bedroom Homes for Rent | $4,182 | $2,049 | $10,000+ |
| Winter Park 5 Bedroom Homes for Rent | $5,522 | $2,445 | $10,000+ |
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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The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
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Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winter Park, FL Rentals by Map
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 301 Apartments for Rent in Winter Park, FL with pricing that ranges from $250 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 $20,000.
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 $20,000 with an average monthly rent of $2,885.
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 $1,082 to $6,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,150 to $10,900. Four Bedroom Single-Family rentals are also available starting from $2,049 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
An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent
Written by: Darla Ferrara
For many, Orlando is the place where you vacation, not live. However, this city, located in the central region of Florida, offers a vibrant tech community, plenty of outdoor activities, and some of the best schools in the country.
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.
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.
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.
Articles, How-To's, and Tips
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.
Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.
Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.