Luxury Homes for Rent in Winter Park, FL (100 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

The most luxurious Homes in Winter Park with high-end amenities, features, and finishes.

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.

Read Article

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.

Read Article
property at 690 Osceola Ave

690 Osceola Ave

Winter ParkFL32789

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.

Read Article

Orlando's Best Affordable Neighborhoods

Learn about Orlando and the best places to live with original content written by our Local Expert Darla F

Read Article
Showing Results 1-50, Page 1 of 2

Winter Park, FL Local Guide

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.

decorative image of people with a giant lease agreement

Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 292 Apartments for Rent in Winter Park, FL with pricing that ranges from $850 to $18,721. There are also 264 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 $4,161.

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 $9,543, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,695 to $5,750. 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.

decorative image for An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent article

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.

decorative image for Roommate Matching: Finding the Right Fit and Avoiding Pitfalls article

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.

decorative image for The Art of the Rental Viewing: What to look for during a property tour article

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.

decorative image for Know Your Budget: Calculating What You Can Realistically Afford When Renting article

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.