Cheap Homes for Rent in Winter Park Neighborhood of Orlando, FL from $1,000 (53 Rentals)

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Search the lowest-cost Homes available for rent right now in the Winter Park area of Orlando.

property at 5559 Barton Dr

5559 Barton Dr

OrlandoFL32807

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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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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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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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, Orlando, FL Local Guide

Cheapest Available Winter Park Apartments for Rent

 

The cheapest available apartment rental in the Winter Park area of Orlando, FL is a Studio unit found at The Taylor at Winter Park priced from $991. Winter Park Woods has the second lowest priced unit, which is a Studio apartment currently listed from $999. Here are the most affordable Winter Park apartments for rent in Orlando, FL:

Apartment ListingModel NameBed/BathPriced From
The Taylor at Winter ParkS1RStudio,1BA$991
Winter Park WoodsA1-Studio, 1 BathroomStudio,1BA$999
Atlas at Winter ParkPalm1BR,1BA$1,177
Venue At Winter ParkSable P1BR,1BA$1,183
Sovereignty at Winter Park ApartmentsA21BR,1BA$1,195
Whisper Lake ApartmentsCrescent1BR,1BA$1,199
Central Place At Winter ParkA11BR,1BA$1,205
SeabrookPlan A11BR,1BA$1,211
Village Park SeniorOne Bedroom One Bath1BR,1BA$1,236
Adele PlaceThe Royal1BR,1BA$1,257

Best Value Apartments for Rent in Winter Park, FL

As of November 16, 2025 the best value apartment in the Winter Park area is the $1.50 price per square foot The Palms Model at Oasis Club in the in the The Enclave at Lake Jean neighborhood starting from $1,645. The second greatest value Winter Park apartment is the 2 Bed | 2 Bath Model at Bellancia starting at $1,566 with a $1.42 price per square foot in the Eastmar Commons 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.
Oasis ClubThe Palms3BR,2BA$1.50
Bellancia2 Bed | 2 Bath2BR,2BA$1.42
Golden Oaks3x2-603BR,2BA$1.31
Azure Winter ParkPark2BR,2BA$1.52
The Vista at Winter ParkTown House Renovated2BR,2.5BA$1.67
Shoreview at Baldwin Park2x12BR,1BA$1.58
The Avenues of Baldwin ParkFern1BR,1.5BA$1.65
Whisper Lake ApartmentsCrescent1BR,1BA$1.60
Sovereignty at Winter Park ApartmentsA21BR,1BA$1.59
Winter Park WoodsA1-Studio, 1 BathroomStudio ,1BA$1.67

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

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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Pet Friendly Lifestyle
Winter Park, Orlando, FL

Ranked #54

Among cities in Florida for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

3.5
Pet Friendly

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Best Local Schools in
Winter Park, Orlando, FL

School data provided by Great Schools

Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 124 Apartments for Rent in Winter Park, FL with pricing that ranges from $976 to $5,859. There are also 120 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $1,000 to $22,500.

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 $1,000 to $22,500 with an average monthly rent of $3,757.

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.