Cheap Homes for Rent in Winter Park, FL from $800 (48 Rentals)

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property at 312 Orange St

312 Orange St

MaitlandFL32751

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

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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property at 1695 Lee Rd

1695 Lee Rd

Winter ParkFL32789

Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.

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property at 7340 Swallow Run

7340 Swallow Run

Winter ParkFL32792

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, FL Local Guide

Cheapest Neighborhoods for Apartments in Winter Park, FL

Pricing Updated: 05/18/2025

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$2,329$820160

Cheapest Available Winter Park Apartments for Rent

 

The cheapest available apartment rental in Winter Park, FL is a 1 Bed unit found at Kingswood Apartments in the Courtland Street neighborhood priced from $1,050. Advenir at Magnolia in the Montacino Hearthstone neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $1,058. Here is today’s list of the most affordable Winter Park apartments for rent:

Apartment ListingModel NameBed/BathPriced From
Kingswood Apartments1/11BR,1BA$1,050
Advenir at MagnoliaSR - Lily RStudio,1BA$1,058
Garden Park Senior LivingOne Bedroom One Bath (b)1BR,1BA$1,086
District On Baldwin ParkE235xecutive StudioStudio,1BA$1,110
Birchwood LandingBirchwood A1BR,1BA$1,119
Hillcrest Hampton HouseStudioStudio,1BA$1,125
Spring Tree VillageStudioStudio,1BA$1,149

Best Value Apartments for Rent in Winter Park, FL

As of May 18, 2025 the best value apartment in the Winter Park area is the $1.63 price per square foot 4177 N Orange Blossom Trail Model at 4177 N Orange Blossom Trail, Unit 304 in the in the Downtown Orlando neighborhood starting from $2,695. The second greatest value Winter Park apartment is the Quartz Model at Sapphire Winter Park starting at $2,149 with a $1.60 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.
4177 N Orange Blossom Trail, Unit 3044177 N Orange Blossom Trail3BR,2BA$1.63
Sapphire Winter ParkQuartz3BR,2BA$1.60
Lake Weston Point ApartmentsFour Bedroom4BR,2BA$1.31
Azalea GardensFloorplan 22BR,2BA$1.46
5321 Davisson Ave5321 Davisson Ave2BR,1BA$1.54
Affinity at Winter Park ApartmentsB12BR,1BA$1.16
Sumerset Apartments3 Beds, 2 baths3BR,2BA$1.37
Central Place At Winter ParkB12BR,1BA$1.49
Garden Park Senior LivingOne Bedroom One Bath (b)1BR,1BA$1.35
2920 E Jefferson St2920 E Jefferson St1BR,1BA$1.43

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Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 306 Apartments for Rent in Winter Park, FL with pricing that ranges from $820 to $18,788. There are also 219 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $825 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 $825 to $10,500 with an average monthly rent of $4,509.

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 $1,146 to $9,543, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,845 to $5,800. Four Bedroom Single-Family rentals are also available starting from $2,100 and Four Bedroom Apartments start at $2,214.

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 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.

decorative image for Know Your Budget: Calculating What You Can Realistically Afford When Renting article

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.

decorative image for The Freedom of Short-Term Leases: Exploring the Advantages for Renters article

The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.

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Navigating the Rental Market: Tips for First-Time Renters

Written by: Sandy Baker

Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.