
Cheap Homes for Rent in Winter Park, FL from $1,000 (88 Rentals) Page 2 of 2
Search the lowest-cost Homes available for rent right now in Winter Park.


3651 N Goldenrod Rd

1408 Lake Shadow Cir, Unit 1105, Unit 1105

2507 E Central Blvd

1150 Lake Shadow Cir

2810 Kilgore St

3011 George Mason Ave

908 Tucker Ave

12 Herring Ct
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

1519 Lake Baldwin Ln

5306 Satel Dr

644 Kenwick Cir

4418 Eli St

2523 Alexa Ct

3012 Patel Dr

1475 Lake Shadow Cir

Total Monthly Price
2710 Amherst Ave, Unit SI ID1018188P

1100 Lake Shadow Cir
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.

625 Trinidad Ct

643 Woodward St

700 Melrose Ave

190 Ventris Ave W

701 Kings Cove Ct

6003 Oleander Dr

4968 Tangerine Ave

660 Jasmine Rd

3283 Oak Lake Pl
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

7429 Daniel Webster Dr

1941 Lanier Ct

2304 Inagua Way

17 W Winter Park St

4521 Edgewater Dr

1798 Shadow View Cir

1618 Legacy Park Dr

205 Lewfield Cir

1141 Exceller Ct
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara

7473 Belle River Ct

435 Meadowood Blvd
Winter Park, FL Local Guide

How much does it cost to rent a home in Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winter Park 2 Bedroom Homes for Rent | $1,790 | $1,350 | $3,200 |
| Winter Park 3 Bedroom Homes for Rent | $2,788 | $1,500 | $5,950 |
| Winter Park 4 Bedroom Homes for Rent | $4,727 | $1,950 | $10,000+ |
| Winter Park 5 Bedroom Homes for Rent | $10,768 | $2,850 | $10,000+ |
Browse Top Homes for Rent in Winter Park
Explore Winter Park
Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 306 Apartments for Rent in Winter Park, FL with pricing that ranges from $250 to $6,500. There are also 237 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $1,050 to $20,000.
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 $1,050 to $20,000 with an average monthly rent of $3,824.
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 $1,082 to $6,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,500 to $5,950. Four Bedroom Single-Family rentals are also available starting from $1,950 and Four Bedroom Apartments start at $1,679.
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

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.

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.

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.

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

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.

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.

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.

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.