Homes for Rent in Winter Park Neighborhood of Orlando, FL (91 Rentals)

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property at 2912 Plaza Terrace Dr

$2,695

Total Monthly Price

Total Monthly Price

Base Rent
$2,695
Total Monthly Price
$2,695

2 Bedroom, 2 Bath Condo for Rent

Available Sep 1

2912 Plaza Terrace Dr

OrlandoFL32803
property at 1610 N Goldenrod Rd

$3,991

Total Monthly Price

Total Monthly Price

Base Rent
$3,991
Total Monthly Price
$3,991

3 Bedroom, 1 Bath Home for Rent

Available Now

1610 N Goldenrod Rd

OrlandoFL32807

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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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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property at 2721 E Marks St

$5,800

Total Monthly Price

Total Monthly Price

Base Rent
$5,800
Total Monthly Price
$5,800

3 Bedroom, 2 Bath Home for Rent

Available Now

2721 E Marks St

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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property at 2810 Sandwell Dr

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000
Total Monthly Price
$2,000

3 Bedroom, 2 Bath Home for Rent

Available Now

2810 Sandwell Dr

Winter ParkFL32792
property at 7 Carver Ct

$3,000

Total Monthly Price

Total Monthly Price

Base Rent
$3,000
Total Monthly Price
$3,000

3 Bedroom, 2 Bath Home for Rent

Available Now

7 Carver Ct

Winter ParkFL32789
property at 5058 Seminole Ave

$1,000

Total Monthly Price

Total Monthly Price

Base Rent
$1,000
Total Monthly Price
$1,000

1 Bedroom, 1 Bath Home for Rent

Available Now

5058 Seminole Ave, Unit Seminole 1

5058 Seminole Ave
Winter ParkFL32792
property at 1629 N Goldenrod Rd

$3,938

Total Monthly Price

Total Monthly Price

Base Rent
$3,938
Total Monthly Price
$3,938

4 Bedroom, 2 Bath Home for Rent

Available Jul 9

1629 N Goldenrod Rd

Azalea ParkFL32807

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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Neighborhood & Market Insights: How to Choose the Right Area to Rent

Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

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Showing Results 1-50, Page 1 of 2

Winter Park, Orlando, FL Local Guide

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.

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

Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.

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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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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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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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Best Local Schools in
Winter Park, Orlando, FL

School data provided by Great Schools

Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 133 Apartments for Rent in Winter Park, FL with pricing that ranges from $695 to $5,224. There are also 91 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $1,000 to $10,900.

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 $1,000 to $10,900 with an average monthly rent of $4,100.

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 $1,082 to $5,224, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,150 to $5,800. Four Bedroom Single-Family rentals are also available starting from $2,075 and Four Bedroom Apartments start at $3,938.

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.

decorative image for The Soul of the City Beautiful: What Life in Orlando Is Really Like article

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

decorative image for How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide article

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

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Creative Ways Developers Reimagine Retail Spaces as Residential Units

Written by: Robin Stewart

Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

decorative image for Neighborhood and Market Insights: How to Choose the Right Area to Rent article

Neighborhood and Market Insights: How to Choose the Right Area to Rent

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.