Cheap Homes for Rent in Winter Park, FL from $700 (58 Rentals)

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

property at 648 Kenwick Cir

$1,000

Total Monthly Price

Total Monthly Price

Base Rent
$1,000
Total Monthly Price
$1,000

1 Bedroom, 1 Bath Condo for Rent

Available May 1

648 Kenwick Cir, Unit 102

648 Kenwick Cir
CasselberryFL32707

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 1008 Maltby Ave

$1,200

Total Monthly Price

Total Monthly Price

Base Rent
$1,200
Total Monthly Price
$1,200

1 Bedroom, 1 Bath Townhome for Rent

Available Now

1008 Maltby Ave

OrlandoFL32803
property at 2517 Caper Ln

$999 - $1,200

1 Bedroom Rentals

Available Now

2517 Caper Ln

MaitlandFL32751
property at 2520 Caper Ln

$1,300

Total Monthly Price

Total Monthly Price

Base Rent
$1,300
Total Monthly Price
$1,300

1 Bedroom, 1 Bath Condo for Rent

Available Now

2520 Caper Ln, Unit 102

2520 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 2500 Lee Rd

$1,375

Total Monthly Price

Total Monthly Price

Base Rent
$1,375
Total Monthly Price
$1,375

2 Bedroom, 1 Bath Condo for Rent

Available Now

2500 Lee Rd, Unit 212

2500 Lee Rd
Winter ParkFL32789

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 2500 Lee Rd

$1,465

Total Monthly Price

Total Monthly Price

Base Rent
$1,465
Total Monthly Price
$1,465

1 Bedroom, 1 Bath Condo for Rent

Available Now

2500 Lee Rd

Winter ParkFL32789
property at 911 N Orange Ave

$1,495

Total Monthly Price

Total Monthly Price

Base Rent
$1,495
Total Monthly Price
$1,495

1 Bedroom, 1 Bath Condo for Rent

Available Now

911 N Orange Ave

OrlandoFL32801

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 911 N Orange Ave

$1,475 - $2,000

1 To 2 Bedroom Rentals

Available Now

911 N Orange Ave

OrlandoFL32801
property at 860 N Orange Ave

$1,225 - $2,000

Studio To 2 Bedroom Rentals

Available Now

860 N Orange Ave

OrlandoFL32801

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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Showing Results 1-50, Page 1 of 2

Winter Park, FL Local Guide

Cheapest Neighborhoods for Apartments in Winter Park, FL

Pricing Updated: 04/01/2026

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$3,499$80059

Cheapest Available Winter Park Apartments for Rent

 

The cheapest available apartment rental in Winter Park, FL is a Studio unit found at District On Baldwin Park in the Colonial Town Center neighborhood priced from $1,000. 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
District On Baldwin ParkE235xecutive StudioStudio,1BA$1,000
Kingswood Apartments1/11BR,1BA$1,050
Regency Oaks ApartmentsStudioStudio,2BA$1,123
Liv at Winter Park Apartment HomesE1Studio,1BA$1,129
Birchwood LandingBirchwood A1BR,1BA$1,139
Garden Park Senior LivingOne Bedroom One Bath (b)1BR,1BA$1,139
Shoreview at Baldwin Park1x1B1BR,1BA$1,170
SorrentoLarge EfficiencyStudio,1BA$1,170
SeabrookPlan A11BR,1BA$1,173
Spring Tree VillageStudioStudio,1BA$1,179

Best Value Apartments for Rent in Winter Park, FL

As of April 01, 2026 the best value apartment in the Winter Park area is the $1.30 price per square foot Four Bedroom Model at Lake Weston Point Apartments in the in the Courtland Street neighborhood starting from $1,679. The second greatest value Winter Park apartment is the 2815 E Washington St Model at 2815 E Washington St, Unit 2815 starting at $2,000 with a $1.60 price per square foot in the Downtown Orlando 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$1.30
2815 E Washington St, Unit 28152815 E Washington St2BR,2BA$1.60
Azalea GardensFloorplan 22BR,2BA$1.46
Ekos at Lake ShadowC1 60 & 703BR,2BA$1.50
The Ivy at GatehouseThe Palms3BR,2BA$1.50
Park East - Park Knowles Apartments2 Bedroom, 1 Bathroom2BR,1BA$1.59
Sumerset Apartments3 Beds, 2 baths3BR,2BA$1.33
Cranes Landing ApartmentsIbis (Standard) b1wi2BR,2BA$1.57
Carlton Arms of Winter ParkC1A Downstairs2BR,1BA$1.62
Eastbrook ApartmentsOne Bed One Bath1BR,1BA$1.56

10 Hidden Costs of Renting You Should Budget for Before Signing a Lease

Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.

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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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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 $695 to $6,250. There are also 237 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $760 to $19,000.

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 $760 to $19,000 with an average monthly rent of $2,972.

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 $6,250, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,585 to $10,000. Four Bedroom Single-Family rentals are also available starting from $2,085 and Four Bedroom Apartments start at $1,697.

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

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 Your Guide to the Perfect Orlando Neighborhood for Student Renters article

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.

decorative image for Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers article

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.

decorative image for The Soul of the City Beautiful: What Life in Orlando Is Really Like article

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 Maximizing Your Refund: Essential Tax Tips for Renters article

Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

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.