
Homes for Rent in Winter Park, FL (339 Rentals)


2804 Dike Rd

3045 Aaron Burr Ave

2948 Antique Oaks Cir

7296 Daniel Webster Dr

123 Oak Grove Rd

5191 Poinsetta Ave
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.

7116 Green Needle Dr

5351 Cypress Dr

2717 Amsden Rd

7413 Fieldcrest Ave

5216 N Indiana Ave

1729 Puritan Ave

7431 Portside Ct

7666 Glenmoor Ln

2631 Ambergate Rd

7145 Timber Dr
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara

2218 Winter Woods Blvd

384 St Dunstan Way

2843 Riddle Dr

630 N Lakemont Ave

7027 Citrus Point Ct

2536 Eastbrook Blvd

1821 Carrigan Ave

423 Ololu Dr

760 Northwood Cir

525 S Lakemont Ave

7417 Daniel Webster Dr
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.

2326 Wellington Blvd

2929 Antique Oaks Cir

1000 S Semoran Blvd

1500 Michigan Ave

7229 Swallow Run

2500 Lee Rd

3007 George Mason Ave

3060 George Mason Ave

3271 Oak Lake Pl
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.

115 Scottsdale Square

7449 Wynnewood Square

225 Lewfield Cir

316 Scottsdale Square

3267 Forest Oaks Ct

3651 N Goldenrod Rd

7328 Forest Hill Ct

7750 Country Pl

1250 S Denning Dr

2941 Antique Oaks Cir

2328 Inagua Way
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 | $1,971 | $1,230 | $4,850 |
Winter Park 3 Bedroom Homes for Rent | $2,700 | $950 | $6,050 |
Winter Park 4 Bedroom Homes for Rent | $4,511 | $1,948 | $10,000+ |
Winter Park 5 Bedroom Homes for Rent | $8,912 | $3,550 | $10,000+ |
Winter Park 6 Bedroom Homes for Rent | $800 | $800 | $800 |
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 299 Apartments for Rent in Winter Park, FL with pricing that ranges from $720 to $6,050. There are also 333 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $720 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 $720 to $25,000 with an average monthly rent of $5,129.
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 $1,099 to $6,050, while Three Bedroom Homes, Condos, and Townhomes for rent range from $950 to $6,050. Four Bedroom Single-Family rentals are also available starting from $1,948 and Four Bedroom Apartments start at $3,150.
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.

How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!

The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.