Cheap Apartments for Rent in the Winter Park Neighborhood of Orlando, FL from $400 (51 Rentals)

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Cheap Apartments in the Winter Park area of Orlando.

property at 5517 Decatur St

5517 Decatur St

OrlandoFL32807

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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On Baldwin Pond
2 Bedroom Apartments

On Baldwin Pond

829 Lowell BlvdOrlando, FL 32803
  • Utilities Included
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1219 Oregon St
Studio Apartments

1219 Oregon St

1219 Oregon StOrlando, FL 32803
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Bellancia
1 to 3 Bedroom Apartments

Bellancia

7325 Goldenpointe BlvdOrlando, FL 32807
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The Juliette
1 Bedroom Apartments

The Juliette

1225 Moselle AveOrlando, FL 32807

Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.

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Winter Park - One of the Best Affordable Neighborhoods in Orlando

Named as one of the Best Affordable Areas to rent in Orlando by our , Local Expert Darla F. See how it ranks!

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Orlando's Best Affordable Neighborhoods

Learn about Orlando and the best places to live with original content written by our Local Expert Darla F

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Tuscany at Aloma
1 to 3 Bedroom Apartments

Tuscany at Aloma

6999 Aloma AveWinter Park, FL 32792
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El Cortez Apartments
1 to 2 Bedroom Apartments

El Cortez Apartments

210 E Morse BlvdWinter Park, FL 32789
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Golden Oaks
2 to 3 Bedroom Apartments

Golden Oaks

7701 Acorn Woods CirWinter Park, FL 32792
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Sun Bay Apartments
1 Bedroom Apartments

Sun Bay Apartments

7001 Aloma AveWinter Park, FL 32792
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Park East Knowles
Studio to 2 Bedroom Apartments

Park East Knowles

311 N Knowles AveWinter Park, FL 32789
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Azure Winter Park
Studio to 3 Bedroom Apartments

Azure Winter Park

3650 Summer Wind DrWinter Park, FL 32792
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Alvista Winter Park
1 to 2 Bedroom Apartments

Alvista Winter Park

3935 Sutton Place BlvdWinter Park, FL 32792
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Winter Park Oaks
1 to 3 Bedroom Apartments

Winter Park Oaks

325 Balfour DrWinter Park, FL 32792
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Showing Results 1-50, Page 1 of 2

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 District On Baldwin Park priced from $1,110. Hillcrest Hampton House has the second lowest priced unit, which is a Studio apartment currently listed from $1,125. Here are the most affordable Winter Park apartments for rent in Orlando, FL:

Apartment ListingModel NameBed/BathPriced From
District On Baldwin ParkE235xecutive StudioStudio,1BA$1,110
Hillcrest Hampton HouseStudioStudio,1BA$1,125
SeabrookPlan A11BR,1BA$1,191
Summerlin at Winter Park ApartmentsAqua1BR,1BA$1,194
Central Place At Winter ParkA11BR,1BA$1,195
Shoreview at Baldwin ParkStudioStudio,1BA$1,240
Sovereignty at Winter Park ApartmentsA21BR,1BA$1,258
Winter Park WoodsA2-1 Bedroom, 1 Bathroom1BR,1BA$1,265
Azure Winter ParkCorrineStudio,1BA$1,299
The Avenues of Baldwin ParkFern1BR,1BA$1,307

Best Value Apartments for Rent in Winter Park, FL

As of May 02, 2025 the best value apartment in the Winter Park area is the $1.64 price per square foot Heron Model at Cranes Landing Apartments in the in the University Commerce Center neighborhood starting from $1,720. The second greatest value Winter Park apartment is the The Tide Model at Oasis Club starting at $1,336 with a $1.34 price per square foot in the The Enclave at Lake Jean 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.
Cranes Landing ApartmentsHeron2BR,2BA$1.64
Oasis ClubThe Tide2BR,2BA$1.34
The Vista at Winter ParkTown House Renovated2BR,2.5BA$1.77
Bellancia1 Bed | 1 Bath1BR,1BA$1.74
The Avenues of Baldwin ParkFern1BR,1.5BA$1.66
Winter Park WoodsA2-1 Bedroom, 1 Bathroom1BR,1BA$1.67
Sovereignty at Winter Park ApartmentsA21BR,1BA$1.68
Whisper Lake ApartmentsCrescent1BR,1BA$1.90
Summerlin at Winter Park ApartmentsAqua1BR,1BA$1.63
Venue At Winter ParkSable1BR,1BA$1.80

Quick Rent Budget Calculator

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Pet Friendly Lifestyle
Winter Park, Orlando, FL

Ranked #38

Among neighborhoods in Orlando, FL 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

Lifestyle Ratings

ApartmentHomeLiving.com compiles millions of data points to bring you our detailed rental analysis called 'Lifestyle Ratings' - a comparison of neighborhoods, cities and towns, and rental properties across Florida and customized analysis for Orlando, Florida. Our Lifestyle Ratings help you zero-in on the perfect place to call home. This takes in many factors including our Star Ratings to compare for the best proximity to parks and outdoor amenities, luxury amenities, pet-friendly features, places that make kids happy, proximity to transit, in addition to floorplans, availablity, and pricing. Use Lifestyle Search in the site filter options on this page - and find your Perfect place!

Getting Around the Winter Park Neighborhood in Orlando, FL

Walk Score®

75 / 100

Very Walkable

Most errands can be accomplished on foot

Bike Score®

62 / 100

Bikeable

Some bike infrastructure

Transit Score®

26 / 100

Some Transit

A few nearby public transportation options

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about Cheap Winter Park Apartments

What is the Cheapest Studio apartment in Winter Park?

Currently the most affordable Cheap Studio Apartment in Winter Park is at District On Baldwin Park listed at $1,110.

How much is rent for a Cheap One Bedroom Winter Park Apartment?

The lowest price for a Cheap One Bedroom Winter Park Apartment is $1,191 at Seabrook.

What is the lowest price for a Cheap Two Bedroom Winter Park Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Winter Park is starting from $1,336 at Oasis Club.

What is the most affordable Winter Park Three Bedroom Apartment?

The best deal on a cheap Winter Park Three Bedroom Apartment rental is at Venue At Winter Park and starts from $1,741.

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.

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.

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Navigating the Rental Market: Tips for First-Time Renters

Written by: Sandy Baker

Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.

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Rise of Digital Nomads: Remote Work Tips for Apartment Renters

Written by: Brandie Parton

As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.

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Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Written by: Christine Leonard, Esq.

Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.