1500 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.
1250 S Denning Dr
Winter ParkFL32789
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
851 Miles Ave
Winter ParkFL32789
1500 Gay Rd
Winter ParkFL32789
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
640 N Park 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 | $2,384 | $1,499 | $4,850 |
| Downtown Winter Park 3 Bedroom Homes for Rent | $2,780 | $2,195 | $3,250 |
| Downtown Winter Park 4 Bedroom Homes for Rent | $3,295 | $3,295 | $3,295 |
| Downtown Winter Park 5 Bedroom Homes for Rent | $4,383 | $3,550 | $5,600 |
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 $1,236. 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 | One Bedroom One Bath | 1BR,1BA | $1,236 |
| Hannibal Square | 400 2x1 | 2BR,1BA | $1,500 |
| The Lofts of Winter Park Village | 1BR/1.0BA | 1BR,1BA | $1,595 |
Best Value Apartments for Rent in Downtown Winter Park, FL
As of September 19, 2025 the best value apartment in the Downtown Winter Park area is the $1.74 price per square foot 1BR/1.0BA Model at The Lofts of Winter Park Village in the in the North Orange neighborhood starting from $1,645. The second greatest value Downtown Winter Park apartment is the Bulevar Model at Paseo at Winter Park Village starting at $2,256 with a $2.98 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. |
|---|---|---|---|
| The Lofts of Winter Park Village | 1BR/1.0BA | 1BR,1BA | $1.74 |
| Paseo at Winter Park Village | Bulevar | 1BR,1BA | $2.98 |
| Elon Winter Park | The Tony | 1BR,1BA | $2.16 |
| Bainbridge Winter Park | A1 | 1BR,1BA | $2.47 |
| Hannibal Square | 402 1BD | 1BR,1BA | $2.85 |
| Village Park Senior | Osceola | 1BR,1BA | $2.56 |
| Juno Winter Park | Vest | 1BR,1BA | $2.86 |
Quick Rent Budget Calculator
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Pet Friendly LifestyleDowntown Winter Park, Winter Park, FL
Ranked #7
Among cities in Florida for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
2.5Pet Friendly
Frequently Asked Questions about Downtown Winter Park
What type of rentals are currently available in Downtown Winter Park?
There are currently 55 Apartments for Rent in Downtown Winter Park, FL with pricing that ranges from $1,236 to $3,588. There are also 23 Single Family Homes for rent, Condos, and Townhome rentals currently available in Downtown Winter Park ranging from $1,499 to $5,600.
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 $1,499 to $5,600 with an average monthly rent of $2,993.
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.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.