1555 Michigan Ave
Winter ParkFL32789
Cheap Homes for Rent in Downtown Winter Park Neighborhood of Winter Park, FL from $1,400 (5 Rentals)
Search the lowest-cost Homes available for rent right now in the Downtown Winter Park area of Winter Park.
1565 Michigan Ave
Winter ParkFL32789
1250 S Denning Dr
Winter ParkFL32789
1399 Miller Ave
Winter ParkFL32789
1433 Indiana Ave
Winter ParkFL32789
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla F
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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 | $2,164 | $1,575 | $3,000 |
| Downtown Winter Park 3 Bedroom Homes for Rent | $4,098 | $2,200 | $5,800 |
| Downtown Winter Park 5 Bedroom Homes for Rent | $45,000 | $10,000 | $10,000+ |
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 The Adeline priced from $1,582. Hannibal Square has the second lowest priced unit, which is a 2 Beds apartment currently listed from $1,600. Here are the most affordable Downtown Winter Park apartments for rent in Orlando, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| The Adeline | A1 | 1BR,1BA | $1,582 |
| Hannibal Square | 400 2x1 | 2BR,1BA | $1,600 |
| The Village at Lake Lily | A3 | 1BR,1BA | $1,609 |
Best Value Apartments for Rent in Downtown Winter Park, FL
As of March 27, 2025 the best value apartment in the Downtown Winter Park area is the $2.28 price per square foot B3 Model at Perla Gem Lake in the in the Courtland Street neighborhood starting from $2,836. The second greatest value Downtown Winter Park apartment is the B3 Model at Bainbridge Winter Park starting at $2,447 with a $2.10 price per square foot in the Courtland Street 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. |
|---|---|---|---|
| Perla Gem Lake | B3 | 2BR,2BA | $2.28 |
| Bainbridge Winter Park | B3 | 2BR,2BA | $2.10 |
| The Ivy Residences at Health Village Apartment Homes | Formosa | 1BR,1BA | $2.20 |
| The Village at Lake Lily | A4 | 1BR,1BA | $2.16 |
| Maitland City Centre | A4 | 1BR,1BA | $2.22 |
| Vida at Health Village | A9 | 1BR,1BA | $2.76 |
| The Lofts of Winter Park Village | 1BR/1.0BA | 1BR,1BA | $2.03 |
| Paseo at Winter Park Village | Bulevar | 1BR,1BA | $2.64 |
| The Adeline | A2 | 1BR,1BA | $2.46 |
| Hannibal Square | 402 1BD | 1BR,1BA | $3.00 |
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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 59 Apartments for Rent in Downtown Winter Park, FL with pricing that ranges from $1,578 to $7,373. There are also 19 Single Family Homes for rent, Condos, and Townhome rentals currently available in Downtown Winter Park ranging from $1,450 to $45,000.
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 $1,450 to $45,000 with an average monthly rent of $13,178.
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 F
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.
Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.
Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.
Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.