Luxury Homes for Rent in Winter Park, FL (90 Rentals) Page 2 of 2

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The most luxurious Homes in Winter Park with high-end amenities, features, and finishes.

property at 1513 Woodward St

$2,950

Total Monthly Price

Total Monthly Price

Base Rent
$2,950
Total Monthly Price
$2,950

3 Bedroom, 2.5 Bath Townhome for Rent

Available May 1

1513 Woodward St

OrlandoFL32803

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 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
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
property at 218 Park Lake St

$5,950

Total Monthly Price

Total Monthly Price

Base Rent
$5,950
Total Monthly Price
$5,950

3 Bedroom, 4 Bath Townhome for Rent

Available Now

218 Park Lake St

OrlandoFL32803
property at 758 Highland Ave

$6,500

Total Monthly Price

Total Monthly Price

Base Rent
$6,500
Total Monthly Price
$6,500

3 Bedroom, 5 Bath Townhome for Rent

Available Now

758 Highland Ave

OrlandoFL32803
property at 1224 Alexandra Ct

$12,000

Total Monthly Price

Total Monthly Price

Base Rent
$12,000
Total Monthly Price
$12,000

3 Bedroom, 3.5 Bath Home for Rent

Available Jul 1

1224 Alexandra Ct

OrlandoFL32804
Showing Results 51-90, Page 2 of 2

Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 298 Apartments for Rent in Winter Park, FL with pricing that ranges from $695 to $6,500. There are also 247 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 $3,317.

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 $1,715 to $12,000. 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 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.

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.