Apartments for Rent in the Winter Park Neighborhood of Orlando, FL (211 Rentals)

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Baldwin Harbor
$1,819 - $4,872
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$1,819 - $4,872
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1 to 3 Bedroom Apartments Available Now

Baldwin Harbor

1771-1887 Jake StOrlando, FL 32814
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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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Aurora on the Trail
$1,496 - $3,126
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Total Monthly Price

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$1,496 - $3,126
Total Monthly Price
$1,496 - $3,126
Studio to 3 Bedroom Apartments Available Now

Aurora on the Trail

825 McCullough AveOrlando, FL 32803
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Audubon Park
$1,542 - $3,134
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$1,542 - $3,134
Total Monthly Price
$1,542 - $3,134
1 to 3 Bedroom Apartments Available Now

Audubon Park

990 Warehouse RdOrlando, FL 32803
Corporate Housing
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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 1008 Maltby Ave

$1,200

Total Monthly Price

Total Monthly Price

Base Rent
$1,200
Total Monthly Price
$1,200

1 Bedroom, 1 Bath Townhome for Rent

Available Now

1008 Maltby Ave

OrlandoFL32803
property at 912 La Salle Ave

$1,780

Total Monthly Price

Total Monthly Price

Base Rent
$1,780
Total Monthly Price
$1,780

2 Bedroom, 1 Bath Home for Rent

Available Now

912 La Salle Ave

OrlandoFL32803
property at 2510 Boyd Ave

$1,900 - $1,950

1 Bedroom Rentals

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2510 Boyd Ave

OrlandoFL32803

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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Orlando's Best Affordable Neighborhoods

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

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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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Winter Park, Orlando, FL Local Guide

10 Hidden Costs of Renting You Should Budget for Before Signing a Lease

Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.

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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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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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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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How a Move-In Inspection Can Protect Your Security Deposit

Learn How a Move-In Inspection Can Protect Your Security Deposit from the Renter University at AparmentHomeLiving.com.

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Quick Rent Budget Calculator

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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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Best Local Schools in
Winter Park, Orlando, FL

School data provided by Great Schools

Lifestyle Ratings

Our team is proud to bring you comprehensive Lifestyle Ratings of rentals and neighborhoods across the USA, including Winter Park, Orlando, and the greater Orlando area. Lifestyle Ratings show you the best fit for your needs and interests. This takes in many factors including rankings of the best places for the best outdoor access, luxury amenities, kid and pet-friendly communities, availability of transit options, in addition to floorplans, availablity, and pricing. Find Lifestyle Search in the filter options (above). Happy Searching!

Luxury Living Rating

This area of town is one of our favorite upscale neighborhoods in town, with a score of 3.5 out of 4. Luxury Lifestyle Scoring is based on having high-end community amenities like olympic-sized pools, concierge services, park access, and quartz countertops in the kitchen with high-end appliances. Luxury submarkets also often offer wood-burning fireplaces, raquetball courts, and for some communities, even a doorman to greet residents.

Frequently Asked Questions about Winter Park

How much are Studio apartments in Winter Park?

There are currently 55 Studio Apartments in Winter Park with rent ranges from $1,000 to $2,685 with an average price of $1,712.

What is the current price range for One Bedroom Winter Park Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Winter Park ranges from $695 to $5,937 with an average monthly rent of $1,854.

What does renting a Two Bedroom Apartment in Winter Park cost?

The monthly rent prices of Two Bedroom Apartments currently available in Winter Park range from $956 to $5,750. Today's average rental price for Two Bedrooms here is $2,069.

How expensive are Winter Park Three Bedroom Apartments?

There are currently 64 Three Bedroom Apartments listings available in Winter Park on ApartmentHomeLiving.com. The pricing ranges from $1,082 to $5,723 - averaging $2,797 for the location.

Expert Rental Resources

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.

Helpful Local Expert Guides

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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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Your Guide to the Perfect Orlando Neighborhood for Student Renters

Written by: Darla Ferrara

There is never a dull moment in Orlando, Florida. Along with top-tier universities, technical schools, and local colleges, there are world-class entertainment venues, the ocean within driving distance, and lots of sunshine.

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Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers

Written by: Darla Ferrara

When I first moved to Orlando, Florida, in the 1990s, one of the things that drew me here was the remarkably low unemployment rates. There was a job for everyone. Two decades later, that fundamental appeal remains.

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

Written by: Darla Ferrara

When people think of Orlando, Florida, they dream of theme parks and sunny weather, and rightfully so. It’s that energy that keeps this city a mainstay in the global tourist industry.

Articles, How-To's, and Tips

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What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Written by: Lauren Harrington

This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

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Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.

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A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.