2449 Grand Teton Cir
Winter ParkFL32792
Homes for Rent in Winter Park, FL Under $2,000 (141 Rentals)
2648 Galliano Cir
Winter ParkFL32792
937 Aragon Ave
Winter ParkFL32789
1201 Springview Run
Winter ParkFL32792
825 Driver Ave
Winter ParkFL32789
1618 Indiana Ave
Winter ParkFL32789
3036 Patel Dr
Winter ParkFL32792
5139 Oak Hill Dr
Winter ParkFL32792
1250 S Denning Dr
Winter ParkFL32789
1500 Gay Rd, Unit 25B
1500 Gay Rd
Winter ParkFL32789
Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities
Why fight Orlando's tourist traffic when you don't have to? Explore the best cities surrounding Orlando for renters, with expert tips on commuting, lifestyle, hidden costs, and where to find the most value.
2399 Antilles Dr
Winter ParkFL32792
3220 Oak Lawn Pl
Winter ParkFL32792
162 Moyses Rd
Winter ParkFL32792
2510 Roxbury Rd
Winter ParkFL32789
2924 Antique Oaks Cir, Unit 48
2924 Antique Oaks Cir
Winter ParkFL32792
2481 Tahoe Cir
Winter ParkFL32792
7446 Wynnewood Square
Winter ParkFL32792
5415 Peaco Pl
Winter ParkFL32792
3367 Riverview Way
Winter ParkFL32792
2772 Prism Pt
Winter ParkFL32792
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
731 W Comstock Ave
Winter ParkFL32789
2404 Gallery View Dr
Winter ParkFL32792
1720 Miller Ave
Winter ParkFL32789
612 Trinidad Ct
Winter ParkFL32792
276 Cambridge Blvd
Winter ParkFL32789
205 Lewfield Cir
Winter ParkFL32792
7336 Forest Hill Ct
Winter ParkFL32792
4968 Tangerine Ave
Winter ParkFL32792
659 Montego Bay Ct
Winter ParkFL32792
2704 Tortoise Cv
Winter ParkFL32792
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.
3370 Cedar Springs Pl
Winter ParkFL32792
200 St Andrews Blvd, Unit 316
200 St Andrews Blvd
Winter ParkFL32792
7338 Swallow Run
Winter ParkFL32792
1695 Lee Rd
Winter ParkFL32789
2918 Antique Oaks Cir
Winter ParkFL32792
3225 Oak Lawn Pl
Winter ParkFL32792
3374 Cedar Springs Pl
Winter ParkFL32792
2530 Kamnic Ct
Winter ParkFL32792
200 Saint Andrews Blvd
Winter ParkFL32792
3254 Howell Branch Rd
Winter ParkFL32792
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
1434 Minnesota Ave
Winter ParkFL32789
3043 Antique Oaks Cir
Winter ParkFL32792
3651 N Goldenrod Rd
Winter ParkFL32792
4874 Tangerine Ave
Winter ParkFL32792
3004 George Mason Ave
Winter ParkFL32792
1600 Indiana Ave
Winter ParkFL32789
2500 Lee Rd
Winter ParkFL32789
7309 Daniel Webster Dr
Winter ParkFL32792
1000 S Semoran Blvd
Winter ParkFL32792
5312 Poinsetta Ave, Unit 2
5312 Poinsetta Ave
Winter ParkFL32792
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.
Showing Results 1-50, Page 1 of 3
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 | $1,824 | $1,300 | $2,600 |
| Winter Park 3 Bedroom Homes for Rent | $2,740 | $1,795 | $5,800 |
| Winter Park 4 Bedroom Homes for Rent | $3,265 | $2,100 | $6,350 |
| Winter Park 5 Bedroom Homes for Rent | $4,547 | $2,395 | $6,700 |
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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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.
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.
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Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winter Park, FL Rentals by Map
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 312 Apartments for Rent in Winter Park, FL with pricing that ranges from $529 to $6,500. There are also 216 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $825 to $6,700.
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 $6,700 with an average monthly rent of $2,205.
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 $1,795 to $5,800. Four Bedroom Single-Family rentals are also available starting from $2,100 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
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.