Cheap Homes for Rent in Winter Park, FL from $800 (78 Rentals) Page 2 of 2

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Search the lowest-cost Homes available for rent right now in Winter Park.

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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property at 5555 Barton Dr

$1,495

Total Monthly Price

Total Monthly Price

Base Rent
$1,495
Total Monthly Price
$1,495

2 Bedroom, 1 Bath Home for Rent

Available Now

5555 Barton Dr

OrlandoFL32807
property at 2407 Branch Way

$1,500

Total Monthly Price

Total Monthly Price

Base Rent
$1,500
Total Monthly Price
$1,500

2 Bedroom, 1 Bath Condo for Rent

Available Now

2407 Branch Way, Unit 105

2407 Branch Way
MaitlandFL32751

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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property at 1000 Lake of the Woods Blvd

$1,550

Total Monthly Price

Total Monthly Price

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

2 Bedroom, 2 Bath Condo for Rent

Available Now

1000 Lake of the Woods Blvd, Unit 201

1000 Lake of the Woods Blvd
Fern ParkFL32730
property at 860 N Orange Ave

$1,550

Total Monthly Price

Total Monthly Price

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

1 Bedroom, 1 Bath Condo for Rent

Available Aug 31

860 N Orange Ave

OrlandoFL32801

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

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Showing Results 51-78, Page 2 of 2

Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 312 Apartments for Rent in Winter Park, FL with pricing that ranges from $250 to $6,500. There are also 295 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $825 to $9,900.

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 $825 to $9,900 with an average monthly rent of $2,277.

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 $750 to $6,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,645 to $6,450. Four Bedroom Single-Family rentals are also available starting from $1,950 and Four Bedroom Apartments start at $1,844.

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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Rent According to Income: A Look at Income-Restricted Rentals

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The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.

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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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First Apartment Regrets: Real Renters Share What They'd Do Differently

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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.

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Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.