
Cheap Homes for Rent in Winter Park Neighborhood of Orlando, FL from $800 (11 Rentals)
Search the lowest-cost Homes available for rent right now in the Winter Park area of Orlando.


525 S Lakemont Ave

5058 Seminole Ave, Unit Seminole Unit 4

3069 Aaron Burr Ave

261 Scottsdale Square
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla F

293 Scottsdale Square

5559 Barton Dr

1507 Falcon Ct

3035 George Mason Ave

2880 Plaza Terrace Dr
Winter Park
Named as one of the Best Affordable Areas to rent in Orlando by our , Local Expert Darla F. See how it ranks!

7200 Aloma Ave
Winter Park, Orlando, 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 | $1,859 | $850 | $3,000 |
Winter Park 3 Bedroom Homes for Rent | $2,970 | $1,750 | $5,800 |
Winter Park 4 Bedroom Homes for Rent | $5,963 | $2,200 | $10,000+ |
Winter Park 5 Bedroom Homes for Rent | $45,000 | $10,000 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 11 rentals with your search options within a 2 mile radius of the Winter Park Neighborhood of Orlando, FL.
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Winter Park, Orlando, FL Local Guide
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Cheapest Available Winter Park Apartments for Rent
 The cheapest available apartment rental in the Winter Park area of Orlando, FL is a Studio unit found at Hillcrest Hampton House priced from $1,000. District On Baldwin Park has the second lowest priced unit, which is a Studio apartment currently listed from $1,110. Here are the most affordable Winter Park apartments for rent in Orlando, FL:
Apartment Listing | Model Name | Bed/Bath | Priced From |
---|---|---|---|
Hillcrest Hampton House | Studio | Studio,1BA | $1,000 |
District On Baldwin Park | E235xecutive Studio | Studio,1BA | $1,110 |
ARIUM Winter Park | Knight | 1BR,1BA | $1,155 |
Cranes Landing Apartments | Sandpiper | 1BR,1BA | $1,164 |
Seabrook | Plan A1 | 1BR,1BA | $1,170 |
Best Value Apartments for Rent in Winter Park, FL
As of March 28, 2025 the best value apartment in the Winter Park area is the $1.61 price per square foot Meeting Model at The Avenues of Baldwin Park in the in the Colonial Town Center neighborhood starting from $1,834. The second greatest value Winter Park apartment is the Town House Renovated Model at The Vista at Winter Park starting at $1,679 with a $1.75 price per square foot in the University Commerce Center neighborhood. Here is today’s list of the best values for Winter Park apartments based on price per square foot:
Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
---|---|---|---|
The Avenues of Baldwin Park | Meeting | 3BR,2BA | $1.61 |
The Vista at Winter Park | Town House Renovated | 2BR,2.5BA | $1.75 |
Calibre Bend Apartments | Shore Upstairs | 1BR,1BA | $1.71 |
Cranes Landing Apartments | Egret | 1BR,1BA | $1.71 |
Winter Park Woods | A2-1 Bedroom, 1 Bathroom | 1BR,1BA | $1.67 |
Sovereignty at Winter Park Apartments | A2 | 1BR,1BA | $1.82 |
Summerlin at Winter Park Apartments | Aqua | 1BR,1BA | $1.66 |
Venue At Winter Park | Sable | 1BR,1BA | $1.83 |
ARIUM Winter Park | Knight | 1BR,1BA | $1.75 |
7309 Daniel Webster Dr | 7309 Daniel Webster Dr | Studio ,1BA | $1.68 |
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Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 128 Apartments for Rent in Winter Park, FL with pricing that ranges from $1,000 to $9,609. There are also 77 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $850 to $45,000.
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 $850 to $45,000 with an average monthly rent of $11,427.
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 $1,261 to $9,609, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,750 to $5,800. Four Bedroom Single-Family rentals are also available starting from $2,200 and Four Bedroom Apartments start at $3,644.
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.