Homes for Rent in Winter Park, FL Under $2,000 (134 Rentals)

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property at 1250 S Denning Dr

$2,000

Total Monthly Price

Total Monthly Price

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

2 Bedroom, 2 Bath Condo for Rent

Available Now

1250 S Denning Dr, Unit 127

1250 S Denning Dr
Winter ParkFL32789
property at 1920 Woodcrest Dr

$1,950

Total Monthly Price

Total Monthly Price

Base Rent
$1,950
Total Monthly Price
$1,950

2 Bedroom, 2 Bath Condo for Rent

Available Now

1920 Woodcrest Dr, Unit 13

1920 Woodcrest Dr
Winter ParkFL32792

Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities

Why fight Orlando's tourist traffic when you don't have to? Explore the best cities surrounding Orlando for renters, with expert tips on commuting, lifestyle, hidden costs, and where to find the most value.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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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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property at 151 N Orlando Ave

$1,450 - $2,750

1 To 2 Bedroom Rentals

Available Now

151 N Orlando Ave

Winter ParkFL32789
property at 1695 Lee Rd

$1,400 - $1,745

1 To 3 Bedroom Rentals

Available Now

1695 Lee Rd

Winter ParkFL32789
property at 2500 Lee Rd

$1,350

Total Monthly Price

Total Monthly Price

Base Rent
$1,350
Total Monthly Price
$1,350

1 Bedroom, 1 Bath Condo for Rent

Available Now

2500 Lee Rd, Unit 244

2500 Lee Rd
Winter ParkFL32789

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 1901 Magnolia Ave

$1,150

Total Monthly Price

Total Monthly Price

Base Rent
$1,150
Total Monthly Price
$1,150

2 Bedroom, 1 Bath Home for Rent

Available Now

1901 Magnolia Ave

Winter ParkFL32792
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

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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Showing Results 1-50, Page 1 of 3

Winter Park, FL Local Guide

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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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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Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 311 Apartments for Rent in Winter Park, FL with pricing that ranges from $250 to $7,275. There are also 292 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $825 to $9,500.

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 $825 to $9,500 with an average monthly rent of $2,665.

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 $750 to $7,275, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,575 to $9,500. Four Bedroom Single-Family rentals are also available starting from $2,070 and Four Bedroom Apartments start at $1,844.

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

decorative image for Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities article

Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities

Written by: Darla Ferrara

When people think of Orlando, FL, the iconic theme parks and buzz of downtown tend to steal the spotlight.

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.

decorative image for Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers article

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 Your Guide to the Perfect Orlando Neighborhood for Student Renters article

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.

Articles, How-To's, and Tips

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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.