
Cheap Apartments for Rent in Winter Park, FL from $529 with Washer/Dryer (86 Rentals) Page 2 of 2
Search the lowest-cost Apartments available for rent right now in Winter Park.


The Ivy at Gatehouse

Lake Weston Point Apartments

5049 Old Cheney Hwy

Steelhouse Orlando

Grand Reserve at Maitland Park

1700 Van Ness St

119 Georgetown Dr, Unit 119 D Georgetown

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The Gallery at Mills 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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Aurora on the Trail

Infinity off Baldwin Park

The Cannery at The Packing District

The Baldwin

Evergreen Mills 50

1172 Calle Del Rey, Unit A

5301 Andrus Ave

Citron at The Packing District

NORA Apartments
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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The Village at Lake Lily

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Inscribe Apartments

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Audubon Park

312 Orange St

Gem Lake Apartments

Fountain Place Apartment Homes

The Park at Rialto

On Baldwin Pond

2424 Kilgore St
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.

The Fairview

The Juliette

Adele Place

1756 Memphis Ave

1000 Lake of the Woods Blvd, Unit 204E

5555 Barton Dr

1000 Lake of the Woods Blvd, Unit 201

627 Shady Ln Dr

Camden North Quarter
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.
Winter Park, FL Local Guide

How much does it cost to rent an apartment in Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winter Park Studio Apartments | $1,592 | $900 | $2,790 |
| Winter Park 1 Bedroom Apartments | $1,780 | $529 | $3,781 |
| Winter Park 2 Bedroom Apartments | $2,173 | $645 | $4,567 |
| Winter Park 3 Bedroom Apartments | $2,689 | $750 | $6,500 |
| Winter Park 4 Bedroom Apartments | $2,250 | $1,844 | $6,109 |
Browse Top Apartments in Winter Park
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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 Azure Winter Park listed at $949.
How much is rent for a Cheap One Bedroom Winter Park Apartment?
The lowest price for a Cheap One Bedroom Winter Park Apartment is $1,044 at District On Baldwin Park.
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 $1,175 at 2075 Howell Branch Road #101.
What is the most affordable Winter Park Three Bedroom Apartment?
The best deal on a cheap Winter Park Three Bedroom Apartment rental is at Golden Oaks and starts from $1,170.
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

Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities
Written by: Darla Ferrara
When people think of Orlando, FL, the iconic theme parks and buzz of downtown tend to steal the spotlight.

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.

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.

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.
Articles, How-To's, and Tips

Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
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.

First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
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.

Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
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.