Cheap Homes for Rent in Winter Park, FL from $800 (56 Rentals)

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The Art of the Rental Viewing: What to look for during a property tour

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Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

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Orlando's Best Affordable Neighborhoods

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Winter Park, FL Local Guide

Cheapest Neighborhoods for Apartments in Winter Park, FL

Pricing Updated: 06/24/2025

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$2,445$903149

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. GOLDEN OAKS in the Baldwin Park neighborhood has the second lowest priced unit, which is a 3 Beds apartment currently listed from $984. 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
GOLDEN OAKS3 Bedroom 2 Bathroom3BR,2BA$984
Kingswood Apartments1/11BR,1BA$1,050
District On Baldwin ParkE235xecutive StudioStudio,1BA$1,110
Birchwood LandingBirchwood A1BR,1BA$1,119
Hillcrest Hampton HouseStudioStudio,1BA$1,125
Advenir at MagnoliaS - LilyStudio,1BA$1,130
Spring Tree VillageStudioStudio,1BA$1,149
Summerlin at Winter Park ApartmentsAqua1BR,1BA$1,216
Solis at Winter ParkA11BR,1BA$1,237

Best Value Apartments for Rent in Winter Park, FL

As of June 24, 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 Floorplan 2 Model at Azalea Gardens starting at $1,750 with a $1.46 price per square foot in the North Orange 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
Azalea GardensFloorplan 22BR,2BA$1.46
Ekos at Lake ShadowC1 60 & 703BR,2BA$1.27
La Aloma2X22BR,2BA$1.34
Sumerset Apartments3 Beds, 2 baths3BR,2BA$1.37
Calibre Bend ApartmentsDunes Downstairs2BR,2BA$1.60
GOLDEN OAKS3 Bedroom 2 Bathroom3BR,2BA$0.94
San Jose Apartments2x1 10332BR,1BA$1.05
Venue At Winter ParkMaple2BR,2BA$1.47
Cranes Landing ApartmentsIbis2BR,2BA$1.59

Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 292 Apartments for Rent in Winter Park, FL with pricing that ranges from $850 to $9,692. There are also 252 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $800 to $10,500.

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 $10,500 with an average monthly rent of $4,042.

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 $9,692, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,695 to $6,200. Four Bedroom Single-Family rentals are also available starting from $2,495 and Four Bedroom Apartments start at $2,329.

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

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.

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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.

decorative image for The Art of the Rental Viewing: What to look for during a property tour article

The Art of the Rental Viewing: What to look for during a property tour

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.