Homes for Rent in Winter Park, FL Under $2,000 (96 Rentals)

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Orlando's Best Affordable Neighborhoods

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

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property at 2522 Alexa Ct

2522 Alexa Ct

Winter ParkFL32792
property at 7340 Swallow Run

7340 Swallow Run

Winter ParkFL32792
property at 2500 Lee Rd

2500 Lee Rd

Winter ParkFL32789
property at 1695 Lee Rd

1695 Lee Rd

Winter ParkFL32789
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Winter Park, FL Local Guide

Quick Rent Budget Calculator

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Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 303 Apartments for Rent in Winter Park, FL with pricing that ranges from $820 to $9,609. There are also 201 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $850 to $45,000.

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 $850 to $45,000 with an average monthly rent of $5,661.

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 $1,146 to $9,609, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,750 to $5,800. Four Bedroom Single-Family rentals are also available starting from $2,175 and Four Bedroom Apartments start at $2,414.

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 F

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.

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Renting Smart: Lease Basics Every Renter Needs

Written by: Christine Leonard, Esq.

Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

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Battling the Butts: Your Guide to the Reality of Smoke-Free Renting

Written by: Andrea Lee Negroni, JD

While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.

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Understanding Amenity Fees: Know Where You Might Be Able to Save Money

Written by: Amber Kanuckel

With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.