Cheap Homes for Rent in Winter Park, FL from $700 (93 Rentals)

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

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

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property at 2521 Caper Ln

2521 Caper Ln

MaitlandFL32751

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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property at 5559 Barton Dr

5559 Barton Dr

OrlandoFL32807
property at 860 N Orange Ave

860 N Orange Ave

OrlandoFL32801

The Soul of the City Beautiful: What Life in Orlando Is Really Like

Orlando is much more than theme parks. Uncover the city's rich history, diverse neighborhoods like Winter Park and Downtown, and its bustling cultural and culinary life.

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

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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property at 776 N Orange Ave

776 N Orange Ave

OrlandoFL32801
property at 2500 Lee Rd

2500 Lee Rd

Winter ParkFL32789

Top Neighborhoods Near Orlando Major Employers

Learn about the best places to live near major employers in Orlando with original content written by our Local Expert Darla Ferrara

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Winter Park, FL Local Guide

Cheapest Neighborhoods for Apartments in Winter Park, FL

Pricing Updated: 12/01/2025

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$2,299$903232

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. The Taylor at Winter Park in the Lakeview neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $991. 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
The Taylor at Winter ParkS1RStudio,1BA$991
Winter Park WoodsA1-Studio, 1 BathroomStudio,1BA$999
Regency Oaks ApartmentsStudioStudio,2BA$1,112
Birchwood LandingBirchwood A1BR,1BA$1,119
SorrentoSmall EfficiencyStudio,1BA$1,135
Spring Tree VillageStudioStudio,1BA$1,149
Sumerset Apartments2 Beds, 2 baths2BR,2BA$1,174
Garden Park Senior LivingOne Bedroom One Bath (b)1BR,1BA$1,177

Best Value Apartments for Rent in Winter Park, FL

As of December 01, 2025 the best value apartment in the Winter Park area is the $1.34 price per square foot Quartz Model at Sapphire Winter Park in the in the Outer East neighborhood starting from $1,799. The second greatest value Winter Park apartment is the Four Bedroom Model at Lake Weston Point Apartments starting at $1,697 with a $1.31 price per square foot in the Courtland Street 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.
Sapphire Winter ParkQuartz3BR,2BA$1.34
Lake Weston Point ApartmentsFour Bedroom4BR,2BA$1.31
Oasis ClubThe Palms3BR,2BA$1.50
Sumerset Apartments3 Beds, 2 baths3BR,2BA$1.28
SeabrookPlan B2B2BR,2BA$1.44
San Jose Apartments2x1 10332BR,1BA$1.05
The Vista at Winter ParkTown House Renovated2BR,2.5BA$1.62
The Grand Reserve at Maitland ParkThe Grand A (3rd Floor)1BR,1BA$1.49
Whisper Lake ApartmentsCrescent1BR,1BA$1.60
Sovereignty at Winter Park ApartmentsA21BR,1BA$1.59

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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Your Guide to the Perfect Orlando Neighborhood for Student Renters

Learn About the Best Neighborhoods to Rent Near College Campuses in Orlando, FL | Find Orlando Off-Campus Student Housing at ApartmentHomeLiving.com

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Quick Rent Budget Calculator

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

Explore Winter Park, FL Rentals by Map

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See the most popular apartments and homes in Winter Park, FL

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Winter Park, FL Apartments Map
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Winter Park, FL Rental Homes Map

Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 299 Apartments for Rent in Winter Park, FL with pricing that ranges from $900 to $6,439. There are also 327 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $750 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 $750 to $25,000 with an average monthly rent of $4,542.

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 $6,439, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,425 to $5,650. Four Bedroom Single-Family rentals are also available starting from $2,020 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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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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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.