252 Balfour Dr
Winter ParkFL32792
Luxury Homes for Rent in Winter Park, FL (90 Rentals)
The most luxurious Homes in Winter Park with high-end amenities, features, and finishes.
7508 Glenmoor Ln
Winter ParkFL32792
2029 Taylor Ave
Winter ParkFL32792
3628 Datura Ct
Winter ParkFL32792
110 Killarney Bay Ct
Winter ParkFL32789
1137 Oaks Blvd
Winter ParkFL32789
2530 Passamonte Dr
Winter ParkFL32792
2887 Clever Ln
Winter ParkFL32792
6877 Jackman Blvd
Winter ParkFL32792
1589 Viburnum Ln
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.
1813 E Cheryl Dr
Winter ParkFL32792
2141 Ridge Dr
Winter ParkFL32792
1721 Shasta Ct
Winter ParkFL32792
7518 Aloma Pines Ct
Winter ParkFL32792
1947 Summerfield Rd
Winter ParkFL32792
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$2,7103 Bedroom Apartments Available Jun 8
2007 Cornell Ave, Unit SI ID1032296P
2007 Cornell AveWinter Park, FL 32789
5219 Ardmore Dr
Winter ParkFL32792
1868 Lake Spier Dr
Winter ParkFL32789
2372 Shadowland Lp
Winter ParkFL32792
524 Byron Rd
Winter ParkFL32792
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
540 W Comstock Ave
Winter ParkFL32789
1891 Oglesby Ave
Winter ParkFL32789
2011 Howard Dr
Winter ParkFL32789
504 St Dunstan Way
Winter ParkFL32792
1351 Merrydale Way
Winter ParkFL32792
1830 Staunton Ave
Winter ParkFL32789
1886 Demetree Dr
Winter ParkFL32789
438 Lakeview Ave
Winter ParkFL32789
1850 Whitehall Dr
Winter ParkFL32789
2115 Sycamore Dr
Winter ParkFL32789
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.
1313 Buckingham Rd
Winter ParkFL32789
1667 Mizell Ave
Winter ParkFL32789
1815 Barker Dr
Winter ParkFL32789
1580 Oakhurst Ave
Winter ParkFL32789
1026 S Lakemont Ave
Winter ParkFL32792
870 Carver St
Winter ParkFL32789
782 S Pennsylvania Ave
Winter ParkFL32789
1776 Mondrian Cir
Winter ParkFL32789
1441 Oneco Ave
Winter ParkFL32789
2075 Jewell Ave
Winter ParkFL32789
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.
311 E Morse Blvd
Winter ParkFL32789
1814 Barker Dr
Winter ParkFL32789
1041 Tuscany Pl
Winter ParkFL32789
1742 Temple Dr
Winter ParkFL32789
1221 Richmond Rd
Winter ParkFL32789
7915 Chartreux Ln
MaitlandFL32751
540 Central Ave
MaitlandFL32751
1408 E Ridgewood St
OrlandoFL32801
5015 Santee St
OrlandoFL32804
612 Stetson St
OrlandoFL32804
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
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 | $1,798 | $1,175 | $3,400 |
| Winter Park 3 Bedroom Homes for Rent | $3,078 | $1,715 | $10,000+ |
| Winter Park 4 Bedroom Homes for Rent | $4,356 | $2,085 | $10,000+ |
| Winter Park 5 Bedroom Homes for Rent | $7,923 | $2,345 | $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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10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
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Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash 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.
Read ArticleYour 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
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
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 298 Apartments for Rent in Winter Park, FL with pricing that ranges from $695 to $6,500. There are also 247 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $795 to $19,000.
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 $19,000 with an average monthly rent of $3,317.
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 $1,715 to $12,000. Four Bedroom Single-Family rentals are also available starting from $2,085 and Four Bedroom Apartments start at $1,679.
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
Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.