Cheap Homes for Rent in Winter Park, FL from $800 (89 Rentals)

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Winter Park, FL Local Guide

Cheapest Neighborhoods for Apartments in Winter Park, FL

Pricing Updated: 07/31/2025

Current apartment rentals in the Winter Park, FL area range in price from to with an overall median price of . Here is today’s list neighborhoods with the lowest median pricing for Winter Park Apartments for rent:

NeighborhoodMedian PriceMin PriceAvailable Units
Lake Howell$3,555$95069

Cheapest Available Winter Park Apartments for Rent

 

The cheapest available apartment rental in Winter Park, FL is a 1 Bed unit found at San Jose Apartments in the Outer East neighborhood priced from $903. Venue At Winter Park in the University Commerce Center neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,050. Here is today’s list of the most affordable Winter Park apartments for rent:

Apartment ListingModel NameBed/BathPriced From
San Jose Apartments1x1 8631BR,1BA$903
Venue At Winter ParkSable1BR,1BA$1,050
Kingswood Apartments1/11BR,1BA$1,050
Sumerset Apartments1 Bed, 1 bath1BR,1BA$1,074
Advenir at MagnoliaS - LilyStudio,1BA$1,099
GOLDEN OAKS3 Bedroom 2 Bathroom3BR,2BA$1,099
District On Baldwin ParkE235xecutive StudioStudio,1BA$1,110
Regency Oaks ApartmentsStudioStudio,2BA$1,112
Hillcrest Hampton HouseStudioStudio,1BA$1,125
Spring Tree VillageStudioStudio,1BA$1,149

Best Value Apartments for Rent in Winter Park, FL

As of August 01, 2025 the best value apartment in the Winter Park area is the $1.31 price per square foot Four Bedroom Model at Lake Weston Point Apartments in the in the Courtland Street neighborhood starting from $1,697. The second greatest value Winter Park apartment is the Onyx+ Model at Sapphire Winter Park starting at $1,849 with a $1.54 price per square foot in the Outer East 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.
Lake Weston Point ApartmentsFour Bedroom4BR,2BA$1.31
Sapphire Winter ParkOnyx+2BR,2BA$1.54
Azalea GardensFloorplan 22BR,2BA$1.46
La Aloma2X22BR,2BA$1.34
GOLDEN OAKS3 Bedroom 2 Bathroom3BR,2BA$1.05
San Jose Apartments2x1 10332BR,1BA$1.05
Shoreview at Baldwin Park2x2A2BR,2BA$1.59
Garden Park Senior LivingTwo Bedroom Two Bath (b)2BR,2BA$1.29
Sumerset Apartments1 Bed, 1 bath1BR,1BA$1.38
Venue At Winter ParkSable1BR,1BA$1.46

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Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 294 Apartments for Rent in Winter Park, FL with pricing that ranges from $900 to $9,567. There are also 294 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $800 to $25,000.

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 $800 to $25,000 with an average monthly rent of $3,176.

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 $9,567, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,695 to $6,000. Four Bedroom Single-Family rentals are also available starting from $2,380 and Four Bedroom Apartments start at $3,060.

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.

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An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent

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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

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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.

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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.