700 Melrose Ave
Winter ParkFL32789
Condos for Rent in Winter Park, FL (54 Rentals)
1500 Gay Rd, Unit 9D, Unit 9D
1500 Gay Rd
Winter ParkFL32789
2942 Antique Oaks Cir, Unit 82
2942 Antique Oaks Cir
Winter ParkFL32792
1695 Lee Rd
Winter ParkFL32789
4818 Tangerine Ave
Winter ParkFL32792
3032 Antique Oaks Cir
Winter ParkFL32792
3651 Goldenrod Rd
Winter ParkFL32792
2500 Lee Rd
Winter ParkFL32789
1000 S Semoran Blvd
Winter ParkFL32792
7340 Swallow Run
Winter ParkFL32792
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.
151 N Orlando Ave
Winter ParkFL32789
3651 N Goldenrod Rd
Winter ParkFL32792
2911 Antique Oaks Cir
Winter ParkFL32792
3011 George Mason Ave
Winter ParkFL32792
625 Trinidad Ct
Winter ParkFL32792
4968 Tangerine Ave
Winter ParkFL32792
1941 Lanier Ct
Winter ParkFL32792
205 Lewfield Cir
Winter ParkFL32792
3050 Autumn Ct
Winter ParkFL32792
110 Killarney Bay Ct
Winter ParkFL32789
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.
2530 Passamonte Dr
Winter ParkFL32792
782 S Pennsylvania Ave
Winter ParkFL32789
2500 Lee Rd, Unit 244, Unit 244
2500 Lee Rd
Winter ParkFL32789
320 Lakeview St, Unit 222, Unit 222
320 Lakeview St
OrlandoFL32804
2426 Branch Way, Unit 200, Unit 200
2426 Branch Way
MaitlandFL32751
1125 Lake Shadow Cir, Unit Visconti Maitland FL, Unit Visconti Maitland FL
1125 Lake Shadow Cir
MaitlandFL32751
1408 Lake Shadow Cir, Unit 1105, Unit 1105
1408 Lake Shadow Cir
MaitlandFL32751
1157 Calle del Norte, Unit 1157, Unit 1157
1157 Calle del Norte
CasselberryFL32707
320 Lakeview St, Unit 203, Unit 203
320 Lakeview St
OrlandoFL32804
860 N Orange Ave, Unit 268, Unit 268
860 N Orange Ave
OrlandoFL32801
Top Neighborhoods Near Orlando Major Employers
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860 N Orange Ave, Unit 860 N Orange Ave UNIT 464, Unit 860 N Orange Ave UNIT 464
860 N Orange Ave
OrlandoFL32801
360 Eaton St
EatonvilleFL32751
2517 Caper Ln
MaitlandFL32751
1125 Lake Shadow Cir
MaitlandFL32751
1275 Lake Shadow Cir
MaitlandFL32751
1375 Lake Shadow Cir
MaitlandFL32751
1325 Lake Shadow Cir
MaitlandFL32751
1225 Lake Shadow Cir
MaitlandFL32751
1140 Lake Maitland Ter
MaitlandFL32751
1140 S Orlando Ave
MaitlandFL32751
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.
1150 Lake Shadow Cir
MaitlandFL32751
1475 Lake Shadow Cir
MaitlandFL32751
1100 Lake Shadow Cir
MaitlandFL32751
1175 Lake Shadow Cir
MaitlandFL32751
1167 Calle Del Rey
CasselberryFL32707
1141 Exceller Ct
CasselberryFL32707
1166 Carmel Cir
CasselberryFL32707
320 Lakeview St
OrlandoFL32804
860 N Orange Ave
OrlandoFL32801
1921 Truman Rd
OrlandoFL32807
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.
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 | $1,781 | $1,350 | $3,200 |
| Winter Park 3 Bedroom Homes for Rent | $2,783 | $1,500 | $5,950 |
| Winter Park 4 Bedroom Homes for Rent | $4,861 | $1,950 | $10,000+ |
| Winter Park 5 Bedroom Homes for Rent | $6,722 | $2,495 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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Winter Park, FL Local Guide
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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
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Real 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.
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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.
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See the most popular apartments and homes in Winter Park, FL
Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 307 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 $947 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 $947 to $20,000 with an average monthly rent of $3,171.
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 $1,844.
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.
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
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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.
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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.
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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.