Cheap 2 Bedroom Apartments for Rent in Winter Park, FL from $956 (98 Rentals) Page 2 of 2

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Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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property at 1408 Lake Shadow Cir

$1,575

Total Monthly Price

Total Monthly Price

Base Rent
$1,575
Total Monthly Price
$1,575

2 Bedroom, 2 Bath Condo for Rent

Available Jun 30

1408 Lake Shadow Cir, Unit 1105, Unit 1105

1408 Lake Shadow Cir
MaitlandFL32751
property at 643 Woodward St

$1,650

Total Monthly Price

Total Monthly Price

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

2 Bedroom, 1 Bath Townhome for Rent

Available Now

643 Woodward St

OrlandoFL32803

Renting Smart: Lease Basics Every Renter Needs

Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com

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Smith Street Condo
2 Bedroom Apartments

Smith Street Condo

113 E Smith StOrlando, FL 32804
  • Utilities Included
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The Oaks Apartments
2 Bedroom Apartments

The Oaks Apartments

3222 Clay AveOrlando, FL 32804
  • Utilities Included
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Forest Edge
2 Bedroom Apartments

Forest Edge

2271 Weston LnOrlando, FL 32810
  • Utilities Included
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On Baldwin Pond
2 Bedroom Apartments

On Baldwin Pond

829 Lowell BlvdOrlando, FL 32803
  • Utilities Included
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La Bella Vida
2 Bedroom Apartments

La Bella Vida

3308-3310 Clay StOrlando, FL 32804
  • Utilities Included
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Harwood Street
2 Bedroom Apartments

Harwood Street

714 E Harwood StOrlando, FL 32803

The Soul of the City Beautiful: What Life in Orlando Is Really Like

Orlando is much more than theme parks. Uncover the city's rich history, diverse neighborhoods like Winter Park and Downtown, and its bustling cultural and culinary life.

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Top Neighborhoods Near Orlando Major Employers

Learn about the best places to live near major employers in Orlando with original content written by our Local Expert Darla Ferrara

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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.

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The Fairview
2 Bedroom Apartments

The Fairview

1700 Van Ness StOrlando, FL 32810
  • Utilities Included
Showing Results 51-98, Page 2 of 2

Frequently Asked Questions about Cheap Winter Park Apartments

What is the Cheapest Studio apartment in Winter Park?

Currently the most affordable Cheap Studio Apartment in Winter Park is at Sumerset Apartments listed at $1,200.

How much is rent for a Cheap One Bedroom Winter Park Apartment?

The lowest price for a Cheap One Bedroom Winter Park Apartment is $1,200 at Sumerset Apartments.

What is the lowest price for a Cheap Two Bedroom Winter Park Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Winter Park is starting from $1,200 at Sumerset Apartments.

What is the most affordable Winter Park Three Bedroom Apartment?

The best deal on a cheap Winter Park Three Bedroom Apartment rental is at Sumerset Apartments and starts from $1,200.

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.

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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 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.

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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.

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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.