Cheap Homes for Rent in Winter Park, FL from $700 (91 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 860 N Orange Ave

$1,095 - $1,995

Studio To 2 Bedroom Rentals

Available Now

860 N Orange Ave

OrlandoFL32801

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

$1,295

1 Bedroom, 1 Bath Home for Rent

Available Now

5559 Barton Dr

OrlandoFL32807

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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property at 1250 S Denning Dr

$1,350 - $2,150

1 To 2 Bedroom Rentals

Available Now

1250 S Denning Dr

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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property at 2500 Lee Rd

$1,465

1 Bedroom, 1 Bath Condo for Rent

Available Now

2500 Lee Rd

Winter ParkFL32789

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

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

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Winter Park, FL Local Guide

Cheapest Neighborhoods for Apartments in Winter Park, FL

Pricing Updated: 02/01/2026

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$2,700$92567

Cheapest Available Winter Park Apartments for Rent

 

The cheapest available apartment rental in Winter Park, FL is a Studio unit found at Winter Park Woods in the University Commerce Center neighborhood priced from $999. Kingswood Apartments in the Courtland Street neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,050. Here is today’s list of the most affordable Winter Park apartments for rent:

Apartment ListingModel NameBed/BathPriced From
Winter Park WoodsA1-Studio, 1 BathroomStudio,1BA$999
Kingswood Apartments1/11BR,1BA$1,050
Hillcrest Hampton HouseStudioStudio,1BA$1,075
The Taylor at Winter ParkA1R1BR,1BA$1,099
Regency Oaks ApartmentsStudioStudio,2BA$1,112
Birchwood LandingBirchwood A1BR,1BA$1,119
Garden Park Senior LivingOne Bedroom One Bath (b)1BR,1BA$1,159
The Grand Reserve at Maitland ParkThe Grand A (3rd Floor)1BR,1BA$1,175
Spring Tree VillageStudioStudio,1BA$1,179

Best Value Apartments for Rent in Winter Park, FL

As of February 01, 2026 the best value apartment in the Winter Park area is the $1.57 price per square foot The Grand D Model at The Grand Reserve at Maitland Park in the in the Courtland Street neighborhood starting from $2,179. The second greatest value Winter Park apartment is the 2 Bed 1 Bath Model at Virginia Drive Apartments starting at $1,500 with a $1.11 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.
The Grand Reserve at Maitland ParkThe Grand D3BR,2BA$1.57
Virginia Drive Apartments2 Bed 1 Bath2BR,1BA$1.11
Oasis ClubThe Palms3BR,2BA$1.50
Sumerset Apartments3 Beds, 2 baths3BR,2BA$1.19
Golden Oaks3x2-603BR,2BA$1.31
Azure Winter ParkPark2BR,2BA$1.46
Lake Weston Point ApartmentsTwo Bedroom2BR,2BA$1.38
Garden Park Senior LivingOrchid1BR,1BA$1.62
Eastbrook ApartmentsOne Bed One Bath1BR,1BA$1.56
2920 E Jefferson St2920 E Jefferson St1BR,1BA$1.43

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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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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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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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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Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 301 Apartments for Rent in Winter Park, FL with pricing that ranges from $650 to $6,050. There are also 297 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $750 to $20,000.

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 $20,000 with an average monthly rent of $4,725.

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 $1,749 to $11,500. Four Bedroom Single-Family rentals are also available starting from $2,075 and Four Bedroom Apartments start at $1,995.

Expert Rental Resources

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.

Helpful Local Expert Guides

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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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Your Guide to the Perfect Orlando Neighborhood for Student Renters

Written by: Darla Ferrara

There is never a dull moment in Orlando, Florida. Along with top-tier universities, technical schools, and local colleges, there are world-class entertainment venues, the ocean within driving distance, and lots of sunshine.

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Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers

Written by: Darla Ferrara

When I first moved to Orlando, Florida, in the 1990s, one of the things that drew me here was the remarkably low unemployment rates. There was a job for everyone. Two decades later, that fundamental appeal remains.

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

Written by: Darla Ferrara

When people think of Orlando, Florida, they dream of theme parks and sunny weather, and rightfully so. It’s that energy that keeps this city a mainstay in the global tourist industry.

Articles, How-To's, and Tips

decorative image for 18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property article

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.

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A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

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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.