Luxury Homes for Rent in Winter Park, FL (59 Rentals)

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

Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.

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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 1806 Bobtail Dr

1806 Bobtail Dr

MaitlandFL32751
Showing Results 1-50, Page 1 of 2

Winter Park, FL Local Guide

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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 $9,543. There are also 209 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $950 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 $950 to $10,500 with an average monthly rent of $3,459.

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 $9,543, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,300 to $5,800. Four Bedroom Single-Family rentals are also available starting from $2,000 and Four Bedroom Apartments start at $2,355.

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.

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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.

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Rise of Digital Nomads: Remote Work Tips for Apartment Renters

Written by: Brandie Parton

As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.

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Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Written by: Christine Leonard, Esq.

Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.

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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.