Homes for Rent in Winter Park, FL Under $5,200 (239 Rentals) Page 2 of 5

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property at 7454 Wynnewood Square

$1,950

Total Monthly Price

Total Monthly Price

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

3 Bedroom, 3 Bath Townhome for Rent

Available Now

7454 Wynnewood Square

Winter ParkFL32792
property at 1500 Gay Rd

$1,850

Total Monthly Price

Total Monthly Price

Base Rent
$1,850
Total Monthly Price
$1,850

2 Bedroom, 2 Bath Condo for Rent

Available Now

1500 Gay Rd, Unit 9D

1500 Gay Rd
Winter ParkFL32789
property at 7473 Belle River Ct

$1,800

Total Monthly Price

Total Monthly Price

Base Rent
$1,800
Total Monthly Price
$1,800

3 Bedroom, 3 Bath Townhome for Rent

Available Now

7473 Belle River Ct

Winter ParkFL32792
property at 700 Melrose Ave

$1,650

Total Monthly Price

Total Monthly Price

Base Rent
$1,650
Total Monthly Price
$1,650

1 Bedroom, 1 Bath Condo for Rent

Available Now

700 Melrose Ave

Winter ParkFL32789
property at 2500 Lee Rd

$1,465

Total Monthly Price

Total Monthly Price

Base Rent
$1,465
Total Monthly Price
$1,465

1 Bedroom, 1 Bath Condo for Rent

Available Now

2500 Lee Rd, Unit 244

2500 Lee Rd
Winter ParkFL32789
property at 151 N Orlando Ave

$1,450 - $2,500

1 To 3 Bedroom Rentals

Available Now

151 N Orlando Ave

Winter ParkFL32789
property at 1695 Lee Rd

$1,175 - $1,595

1 To 2 Bedroom Rentals

Available Now

1695 Lee Rd

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 Jun 12

5058 Seminole Ave, Unit Seminole 1

5058 Seminole Ave
Winter ParkFL32792
Showing Results 51-100, Page 2 of 5

Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 307 Apartments for Rent in Winter Park, FL with pricing that ranges from $250 to $6,500. There are also 245 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $795 to $20,000.

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 $795 to $20,000 with an average monthly rent of $3,335.

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 $6,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,495 to $14,000. Four Bedroom Single-Family rentals are also available starting from $1,950 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 An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent article

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.

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.

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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

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.

decorative image for A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back article

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

Written by: Lauren Harrington

I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

decorative image for Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts article

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

decorative image for What Does “Rent Burdened” Mean? How Much Rent Is Too Much article

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.