1250 S Denning Dr
Winter ParkFL32789
Cheap Homes for Rent in Downtown Winter Park Neighborhood of Winter Park, FL from $1,800 (5 Rentals)
Search the lowest-cost Homes available for rent right now in the Downtown Winter Park area of Winter Park.
851 Miles Ave
Winter ParkFL32789
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
1500 Gay Rd
Winter ParkFL32789
1399 Miller Ave
Winter ParkFL32789
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
936 Aragon Ave
Winter ParkFL32789
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Downtown Winter Park, Winter Park, FL Local Guide
How much does it cost to rent a home in Downtown Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Downtown Winter Park 2 Bedroom Homes for Rent | $2,332 | $1,865 | $3,500 |
| Downtown Winter Park 3 Bedroom Homes for Rent | $3,549 | $2,700 | $6,000 |
| Downtown Winter Park 4 Bedroom Homes for Rent | $3,500 | $3,500 | $3,500 |
| Downtown Winter Park 5 Bedroom Homes for Rent | $4,975 | $3,750 | $6,200 |
Browse Homes for Rent in this Neighborhood
There are currently 5 rentals with your search options within a 1 mile radius of the Downtown Winter Park Neighborhood of Winter Park, FL.
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Downtown Winter Park, Winter Park, FL Local Guide
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Cheapest Available Downtown Winter Park Apartments for Rent
The cheapest available apartment rental in the Downtown Winter Park area of Orlando, FL is a 1 Bed unit found at Village Park Senior priced from $1,207. Hannibal Square has the second lowest priced unit, which is a 2 Beds apartment currently listed from $1,500. Here are the most affordable Downtown Winter Park apartments for rent in Orlando, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Village Park Senior | 1 Bed 1 Bath | 1BR,1BA | $1,207 |
| Hannibal Square | 400 2x1 | 2BR,1BA | $1,500 |
| Elon Winter Park | The Tony | 1BR,1BA | $1,564 |
Best Value Apartments for Rent in Downtown Winter Park, FL
As of August 03, 2025 the best value apartment in the Downtown Winter Park area is the $2.25 price per square foot Apollo Model at Juno Winter Park in the in the Courtland Street neighborhood starting from $2,271. The second greatest value Downtown Winter Park apartment is the 1BR/1.0BA Model at The Lofts of Winter Park Village starting at $1,625 with a $1.84 price per square foot in the North Orange neighborhood. Here is today’s list of the best values for Downtown Winter Park apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Juno Winter Park | Apollo | 2BR,2BA | $2.25 |
| The Lofts of Winter Park Village | 1BR/1.0BA | 1BR,1BA | $1.84 |
| Bainbridge Winter Park | A3 | 1BR,1BA | $2.55 |
| Paseo at Winter Park Village | Bulevar | 1BR,1BA | $2.65 |
| Elon Winter Park | The Tony | 1BR,1BA | $2.11 |
| Hannibal Square | 402 1BD | 1BR,1BA | $2.85 |
| Village Park Senior | 1 Bed 1 Bath | 1BR,1BA | $1.84 |
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Frequently Asked Questions about Downtown Winter Park
What type of rentals are currently available in Downtown Winter Park?
There are currently 54 Apartments for Rent in Downtown Winter Park, FL with pricing that ranges from $1,207 to $6,231. There are also 19 Single Family Homes for rent, Condos, and Townhome rentals currently available in Downtown Winter Park ranging from $1,865 to $6,200.
What is the current price range for Rental Homes in Downtown Winter Park?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Downtown Winter Park ranges from $1,865 to $6,200 with an average monthly rent of $3,589.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.
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.
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.