
Homes for Rent in Winter Garden, FL Under $2,500 (44 Rentals)


14899 Apollo Bond Dr

14454 Prunningwood Pl

8019 Jeremy Joseph Aly

15319 Torpoint Rd

1570 Scarlet Oak Loop

13293 Daniels Landing Cir

13370 Daniels Landing Cir
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.

314 Daniels Pointe Dr

15350 Oak Apple Ct

15327 Oak Apple Ct

326 Daniels Pointe Dr

1007 Butterfly Blvd

13349 Harbor Shore Ln

1000 Dolphin Dr

216 Deepcove Rd
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

1009 Westside Dr

1300 Eastern Pecan Pl

417 Southern Pecan Cir

1535 Broken Oak Dr

430 Southern Pecan Cir

233 Southern Pecan Cir

1066 Dolphin Dr

165 Windtree Ln
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.

508 Varsity St

12506 Westhaven Oak Dr

17102 Heartwood Loop

88 Windtree Ln

203 N Dillard St

502 Dunbar Ave

203 N Dillard St

15267 Honeybell Dr
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.

1800 Demastus Ln

13749 Lensdale Ln

2548 Sweet Viburnum Wy

718 Marotta Loop

2007 Shari Lynn Terrace

Unit

10536 3rd Ave

17321 Promenade Dr
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara

224 10th Ave

14252 Confetti Dr

501 W Herriot Ave

611 N Lakewood Ave
Winter Garden, FL Local Guide

How much does it cost to rent a home in Winter Garden?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winter Garden 2 Bedroom Homes for Rent | $1,999 | $800 | $3,500 |
| Winter Garden 3 Bedroom Homes for Rent | $2,755 | $1,500 | $4,500 |
| Winter Garden 4 Bedroom Homes for Rent | $3,729 | $2,595 | $10,000+ |
| Winter Garden 5 Bedroom Homes for Rent | $6,495 | $2,895 | $10,000+ |
| Winter Garden 6 Bedroom Homes for Rent | $6,600 | $5,800 | $7,500 |
Browse Top Homes for Rent in Winter Garden
Explore Winter Garden
Winter Garden, FL Local Guide
- Winter Garden Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
Your Guide to the Perfect Orlando Neighborhood for Student Renters
Learn About the Best Neighborhoods to Rent Near College Campuses in Orlando, FL | Find Orlando Off-Campus Student Housing at ApartmentHomeLiving.com
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
Best Local Schools in Winter Garden, FL
School data provided by Great Schools
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winter Garden, FL Rentals by Map
See the most popular apartments and homes in Winter Garden, FL
Frequently Asked Questions about Winter Garden
What type of rentals are currently available in Winter Garden?
There are currently 77 Apartments for Rent in Winter Garden, FL with pricing that ranges from $1,350 to $5,914. There are also 189 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Garden ranging from $675 to $18,000.
What is the current price range for Rental Homes in Winter Garden?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winter Garden ranges from $675 to $18,000 with an average monthly rent of $3,872.
How much are larger Three and Four Bedroom Rentals in Winter Garden?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winter Garden range from $1,859 to $4,337, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,500 to $4,500. Four Bedroom Single-Family rentals are also available starting from $2,595 and Four Bedroom Apartments start at $2,615.
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
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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
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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.