Cheap Homes for Rent in Winter Park Neighborhood of Orlando, FL from $800 (11 Rentals)

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Search the lowest-cost Homes available for rent right now in the Winter Park area of Orlando.

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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Winter Park

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

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Winter Park, Orlando, FL Local Guide

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 ListingModel NameBed/BathPriced From
Hillcrest Hampton HouseStudioStudio,1BA$1,000
District On Baldwin ParkE235xecutive StudioStudio,1BA$1,110
ARIUM Winter ParkKnight1BR,1BA$1,155
Cranes Landing ApartmentsSandpiper1BR,1BA$1,164
SeabrookPlan A11BR,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 ListingModel NameBed/BathPrice Per Sq.Ft.
The Avenues of Baldwin ParkMeeting3BR,2BA$1.61
The Vista at Winter ParkTown House Renovated2BR,2.5BA$1.75
Calibre Bend ApartmentsShore Upstairs1BR,1BA$1.71
Cranes Landing ApartmentsEgret1BR,1BA$1.71
Winter Park WoodsA2-1 Bedroom, 1 Bathroom1BR,1BA$1.67
Sovereignty at Winter Park ApartmentsA21BR,1BA$1.82
Summerlin at Winter Park ApartmentsAqua1BR,1BA$1.66
Venue At Winter ParkSable1BR,1BA$1.83
ARIUM Winter ParkKnight1BR,1BA$1.75
7309 Daniel Webster Dr7309 Daniel Webster DrStudio ,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.

decorative image for An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent article

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.

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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.

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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.

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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.