2 Bedroom Apartments for Rent in Winter Park, FL with Swimming Pool (110 Rentals) Page 2 of 3

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Orlando's Best Affordable Neighborhoods

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

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Baldwin Harbor
$2,620 - $3,436
Total Monthly Price

Total Monthly Price

Base Rent
$2,049 - $4,376

Total Monthly Price
Varies
2 Bedroom Apartments Available Now

Baldwin Harbor

1771-1887 Jake StOrlando, FL 32814
Affordability
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Renting with Roommates: Realistic Expectations for Shared Lease

Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

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400 North
$2,374 - $3,105
Total Monthly Price

Total Monthly Price

Base Rent
$2,415 - $3,904

Total Monthly Price
Varies
2 Bedroom Apartments Available Sep 9

400 North

400 N Orlando AveMaitland, FL 32751
Luxury
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Aurora on the Trail
Rent Specials
$2,170 - $2,781
Total Monthly Price

Total Monthly Price

Base Rent
$1,615 - $3,266

Total Monthly Price
$1,615 - $3,266
2 Bedroom Apartments Available Aug 8

Aurora on the Trail

825 McCullough AveOrlando, FL 32803
Corporate Housing
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Apartment Common Area Rules: What Renters Need to Know

From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

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Audubon Park
$2,156 - $2,596
Total Monthly Price

Total Monthly Price

Base Rent
$1,781 - $3,653

Total Monthly Price
$1,781 - $3,653
2 Bedroom Apartments Available Now

Audubon Park

990 Warehouse RdOrlando, FL 32803
Corporate Housing
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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

property at 1000 Winderley Pl

$2,200

Total Monthly Price

Total Monthly Price

Base Rent
$2,200

Total Monthly Price
$2,200

2 Bedroom, 2 Bath Condo for Rent

Available Now

1000 Winderley Pl, Unit 128

1000 Winderley Pl
MaitlandFL32751
property at 2912 Plaza Terrace Dr

$2,275

Total Monthly Price

Total Monthly Price

Base Rent
$2,275

Total Monthly Price
$2,275

2 Bedroom, 2 Bath Condo for Rent

Available Sep 1

2912 Plaza Terrace Dr

OrlandoFL32803

The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

Frequently Asked Questions about 2 Bedroom Winter Park Apartments

What is the Cheapest apartment in Winter Park with 2 Bedroom?

Currently the most affordable 2 Bedroom in Winter Park is at Kingswood Apartments listed at $1,200.

How much is the average rent for a 2 Bedroom Winter Park Apartment?

The average rent for a 2 Bedroom Apartment in Winter Park is $2,261.

What is the largest available 2 Bedroom Winter Park Apartment for rent?

Today's apartment with the most square footage in Winter Park is a 1,800 square feet unit starting from $1,877 at Regency Oaks Apartments.

What is the average size for Winter Park 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Winter Park is currently 1,091 sq ft.

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.

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