Cheap Homes for Rent in Winter Park, FL from $700 (90 Rentals)

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property at 860 N Orange Ave

860 N Orange Ave

OrlandoFL32801
property at 911 N Orange Ave

911 N Orange Ave

OrlandoFL32801
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Winter Park, FL Local Guide

Cheapest Neighborhoods for Apartments in Winter Park, FL

Pricing Updated: 09/16/2025

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$1,996$903220

Cheapest Available Winter Park Apartments for Rent

 

The cheapest available apartment rental in Winter Park, FL is a 2 Beds unit found at Ekos at Lake Shadow in the Courtland Street neighborhood priced from $560. San Jose Apartments in the Outer East neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $903. Here is today’s list of the most affordable Winter Park apartments for rent:

Apartment ListingModel NameBed/BathPriced From
Ekos at Lake ShadowB1 302BR,2BA$560
San Jose Apartments1x1 8631BR,1BA$903
Sumerset Apartments1 Bed, 1 bath1BR,1BA$974
Advenir at MagnoliaS - LilyStudio,1BA$1,099
Regency Oaks ApartmentsStudioStudio,2BA$1,112
Birchwood LandingBirchwood A1BR,1BA$1,119
Hillcrest Hampton HouseStudioStudio,1BA$1,125
Garden Park Senior LivingDaisy (Two Bedroom w/Den)2BR,2BA$1,129
Spring Tree VillageStudioStudio,1BA$1,149
Sovereignty at Winter Park ApartmentsA21BR,1BA$1,195

Best Value Apartments for Rent in Winter Park, FL

As of September 16, 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 941 Robinhood Ct Model at 941 Robinhood Ct, Unit 941 Robinhood starting at $1,850 with a $1.47 price per square foot in the Orienta Gardens 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
941 Robinhood Ct, Unit 941 Robinhood941 Robinhood Ct2BR,2BA$1.47
Azalea GardensFloorplan 22BR,2BA$1.50
Sapphire Winter ParkJade+2BR,1BA$1.48
Sumerset Apartments3 Beds, 2 baths3BR,2BA$1.28
SeabrookPlan B2B2BR,2BA$1.44
San Jose Apartments2x1 10332BR,1BA$1.05
Ekos at Lake ShadowB1 302BR,2BA$0.57
La Aloma2X12BR,1BA$1.51
Sovereignty at Winter Park ApartmentsA21BR,1BA$1.59

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

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Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 300 Apartments for Rent in Winter Park, FL with pricing that ranges from $720 to $6,050. There are also 327 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $720 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 $720 to $25,000 with an average monthly rent of $5,386.

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 $1,099 to $6,050, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,450 to $6,050. Four Bedroom Single-Family rentals are also available starting from $2,000 and Four Bedroom Apartments start at $3,150.

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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The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.

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

Written by: Christine Leonard, Esq.

Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.