Homes for Rent in Winter Park, FL Under $5,200 (231 Rentals) Page 2 of 5

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done
property at 151 N Orlando Ave

$1,799

Total Monthly Price

Total Monthly Price

Base Rent
$1,799
Total Monthly Price
$1,799

2 Bedroom, 1 Bath Condo for Rent

Available Now

151 N Orlando Ave, Unit 101

151 N Orlando Ave
Winter ParkFL32789
property at 1500 Gay Rd

$1,750

Total Monthly Price

Total Monthly Price

Base Rent
$1,750
Total Monthly Price
$1,750

2 Bedroom, 2 Bath Condo for Rent

Available Now

1500 Gay Rd

Winter ParkFL32789

Orlando's Best Affordable Neighborhoods

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

Read Article
property at 1695 Lee Rd

$1,400 - $1,800

1 To 3 Bedroom Rentals

Available Now

1695 Lee Rd

Winter ParkFL32789
property at 1695 Lee Rd

$1,550

Total Monthly Price

Total Monthly Price

Base Rent
$1,550
Total Monthly Price
$1,550

2 Bedroom, 1 Bath Condo for Rent

Available Now

1695 Lee Rd, Unit B106

1695 Lee Rd
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

Winter ParkFL32789
property at 2500 Lee Rd

$1,375

Total Monthly Price

Total Monthly Price

Base Rent
$1,375
Total Monthly Price
$1,375

2 Bedroom, 1 Bath Condo for Rent

Available Now

2500 Lee Rd, Unit 212

2500 Lee Rd
Winter ParkFL32789
property at 266 Park Lake St

$4,600

Total Monthly Price

Total Monthly Price

Base Rent
$4,600
Total Monthly Price
$4,600

3 Bedroom, 5 Bath Townhome for Rent

Available Now

266 Park Lake St

OrlandoFL32803
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 302 Apartments for Rent in Winter Park, FL with pricing that ranges from $695 to $6,307. There are also 244 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $795 to $19,000.

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 $19,000 with an average monthly rent of $3,139.

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 $6,250, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,850 to $10,000. Four Bedroom Single-Family rentals are also available starting from $2,085 and Four Bedroom Apartments start at $1,679.

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.

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.

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 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 Maximizing Your Refund: Essential Tax Tips for Renters article

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.

decorative image for 18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property article

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.

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

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.

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.