
Homes for Rent in Winter Park, FL (330 Rentals)


2804 Dike Rd

7345 Daniel Webster Dr, Unit D

4854 Tangerine Ave

2560 Galliano Cir

5323 Poinsetta Ave

1900 Erudite Way

779 West Lyman Avenue

1253 Indiana Ave

423 Ololu Dr
The 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.

2948 Antique Oaks Cir

1304 Viburnum Ln

5335 N Orange Ave

7296 Daniel Webster Dr

123 Oak Grove Rd
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara

1399 Miller Ave

1061 Portsmouth Ln

1315 Viburnum Ln

324 Lake Fair Ln

2717 Amsden Rd

1729 Puritan Ave

1601 Aster Dr

5139 Ardmore Dr

7431 Portside Ct

881 Julian St

1427 Broad Wing Ln

630 N Lakemont Ave
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.

2843 Riddle Dr

384 St Dunstan Way

7145 Timber Dr

2536 Eastbrook Blvd

860 N Denning Dr

1855 Eastbrook Blvd

525 S Lakemont Ave

2011 Cornell Ave

200 St Andrews Blvd

2326 Wellington Blvd
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.

134 Lewfield Cir

2929 Antique Oaks Cir

3057 Aaron Burr Ave

1000 S Semoran Blvd

7324 Forest Hill Ct

115 Scottsdale Square

194 Scottsdale Square

7449 Wynnewood Square

3007 George Mason Ave

316 Scottsdale Square

628 Trinidad Ct
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.
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 | $1,898 | $1,200 | $2,950 |
Winter Park 3 Bedroom Homes for Rent | $2,789 | $1,545 | $6,250 |
Winter Park 4 Bedroom Homes for Rent | $5,347 | $2,300 | $10,000+ |
Winter Park 5 Bedroom Homes for Rent | $5,282 | $2,295 | $8,650 |
Browse Top Homes for Rent in Winter Park
Explore Winter Park
Winter Park, FL Local Guide
- Winter Park Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
Quick 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.
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 297 Apartments for Rent in Winter Park, FL with pricing that ranges from $860 to $10,109. There are also 330 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $860 to $25,000.
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 $860 to $25,000 with an average monthly rent of $2,995.
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 $1,261 to $10,109, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,545 to $6,250. Four Bedroom Single-Family rentals are also available starting from $2,300 and Four Bedroom Apartments start at $3,060.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.

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.

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.