Apartments for Rent in Winter Park, FL (592 Rentals) Page 7 of 12

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property at 316 Georgetown Dr
$1,650 - $1,699
2 Bedroom Rentals
Available Now
Cost Per Sq.Ft.

316 Georgetown Dr

CasselberryFL32707
property at 860 N Orange Ave
$1,300 - $1,900
Studio To 2 Bedroom Rentals
Available Now
Affordability

860 N Orange Ave

OrlandoFL32801
property at 320 Lakeview St
$1,325 - $1,400
Studio To 1 Bedroom Rentals
Available Now
Affordability

320 Lakeview St

OrlandoFL32804
property at 911 N Orange Ave
$1,400 - $2,200
1 To 2 Bedroom Rentals
Available Now
Furnished

911 N Orange Ave

OrlandoFL32801
Showing Results 301-350, Page 7 of 12

Frequently Asked Questions about Winter Park

What is the current pricing and availability for apartments for rent in Winter Park, FL?

As of today, September 18, 2026, there are currently 592 available Winter Park apartments priced from $529 to $6,500, with an average monthly rent of $2,033.

What Winter Park neighborhoods have the most available apartments?

There are 7 neighborhoods in the Winter Park area with available listings as of today. The three neighborhoods with the most options are I Drive Orlando with 1,134 listings, North Orlando with 817 listings, and East Orlando with 421 listings.

How much are Studio apartments in Winter Park?

There are currently 90 Studio Apartments in Winter Park with rent ranges from $900 to $2,790 with an average price of $1,573.

What is the current price range for One Bedroom Winter Park Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Winter Park ranges from $529 to $3,798 with an average monthly rent of $1,769.

What does renting a Two Bedroom Apartment in Winter Park cost?

The monthly rent prices of Two Bedroom Apartments currently available in Winter Park range from $645 to $4,405. Today's average rental price for Two Bedrooms here is $2,174.

How expensive are Winter Park Three Bedroom Apartments?

There are currently 109 Three Bedroom Apartments listings available in Winter Park on ApartmentHomeLiving.com. The pricing ranges from $750 to $6,500 - averaging $2,632 for the location.

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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Articles, How-To's, and Tips

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

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Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.