
Homes for Rent in Winter Park, FL Under $1,500 (42 Rentals)


5058 Seminole Ave, Unit Seminole Unit 4

5312 Poinsetta Ave, Unit 1

3065 George Mason Ave

1716 Miller Ave

1714 Miller Ave

1434 Minnesota Ave
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.

2942 Antique Oaks Cir

2905 Antique Oaks Cir

3019 Antique Oaks Cir

3014 Antique Oaks Cir

200 St Andrews Blvd

134 Lewfield Cir

1855 Eastbrook Blvd

293 Scottsdale Square

3069 Aaron Burr Ave

261 Scottsdale Square
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.

3035 George Mason Ave

525 S Lakemont Ave

1178 Paseo Del Mar, Unit 1178 c

1400 Lake Shadow Cir

312 Orange St

312 Orange St

312 Orange St

408 Banyon Tree Cir

1073 Princewood Dr

2515 Formosa Ave
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.

2406 Branch Way

1137 Jamajo Blvd

3331 N Westmoreland Dr

5523 Lehigh Ave

4615 Edgewater Dr

860 N Orange Ave

1820 Rogers Ave

631 Shady Ln Dr

524 Georgetown Dr

559 Flemming Way

551 Flemming Way

3008 E Jefferson St
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla F

421 E Kennedy Blvd

416 Lime St

216 Obrien Rd
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 | $2,042 | $950 | $6,800 |
Winter Park 3 Bedroom Homes for Rent | $3,026 | $1,695 | $6,200 |
Winter Park 4 Bedroom Homes for Rent | $3,794 | $2,100 | $7,995 |
Winter Park 5 Bedroom Homes for Rent | $6,931 | $3,495 | $8,650 |
Winter Park 6 Bedroom Homes for Rent | $10,500 | $10,000 | $10,000+ |
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.
Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 290 Apartments for Rent in Winter Park, FL with pricing that ranges from $850 to $18,721. There are also 263 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $800 to $10,500.
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 $800 to $10,500 with an average monthly rent of $4,162.
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 $9,619, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,695 to $6,200. Four Bedroom Single-Family rentals are also available starting from $2,100 and Four Bedroom Apartments start at $2,329.
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.

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.

The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.