Homes for Rent in Winter Park, FL Under $1,500 (58 Rentals)

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property at 2500 Lee Rd

2500 Lee Rd

Winter ParkFL32789

The Soul of the City Beautiful: What Life in Orlando Is Really Like

Orlando is much more than theme parks. Uncover the city's rich history, diverse neighborhoods like Winter Park and Downtown, and its bustling cultural and culinary life.

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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.

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property at 911 N Orange Ave

911 N Orange Ave

OrlandoFL32801

Top Neighborhoods Near Orlando Major Employers

Learn about the best places to live near major employers in Orlando with original content written by our Local Expert Darla Ferrara

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property at 860 N Orange Ave

860 N Orange Ave

OrlandoFL32801

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.

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property at 5559 Barton Dr

5559 Barton Dr

OrlandoFL32807
property at 2521 Caper Ln

2521 Caper Ln

MaitlandFL32751

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.

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Showing Results 1-50, Page 1 of 2

Winter Park, FL Local Guide

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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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.

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Your Guide to the Perfect Orlando Neighborhood for Student Renters

Learn About the Best Neighborhoods to Rent Near College Campuses in Orlando, FL | Find Orlando Off-Campus Student Housing at ApartmentHomeLiving.com

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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.

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Winter Park, FL Rentals by Map

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See the most popular apartments and homes in Winter Park, FL

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Winter Park, FL Apartments Map
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Winter Park, FL Rental Homes Map

Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 295 Apartments for Rent in Winter Park, FL with pricing that ranges from $900 to $6,992. There are also 363 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $750 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 $750 to $25,000 with an average monthly rent of $4,479.

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 $6,992, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,550 to $6,050. Four Bedroom Single-Family rentals are also available starting from $1,950 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.

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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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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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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.