2 Bedroom Apartments for Rent in Winter Garden, FL (82 Rentals)

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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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Winter Garden, FL Local Guide

Winter Garden 2 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: August 04, 2025

There are currently 41 available 2 Bedroom apartment units in Winter Garden, FL neighborhoods that range in price from $1,544 to $3,180. Heres is today's list of the top neighborhoods in Winter Garden with the most available 2 Bedroom apartments:

NeighborhoodAvailable UnitsMedian PriceMin Price
West Orlando41$2,161$1,544

Largest Available Winter Garden 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Winter Garden, FL is found at The Lodge at Hamlin in the Southbridge Village Townhomes neighborhood and is 1,616 square feet priced from $3,280. The Alibi at Lake Lilly in the Ashton Park neighborhood has the second largest 2 Bedroom, which is sized at 1,575 square feet and currently listed start at $3,070. Here is today’s list of the largest available 2 Bedroom units in Winter Garden:

Apartment ListingModel NameSquare FootagePriced From
The Lodge at HamlinB51,616 Sq Ft$3,280
The Alibi at Lake LillyEllington B6T1,575 Sq Ft$3,070
The OverlookNewport 2-Car Garage Townhome1,553 Sq Ft$3,095
The Haven at Lake BrittSanctuary D1 Two-Car Townhome1,553 Sq Ft$3,310
Ascend Waterleigh VillageB41,476 Sq Ft$2,625
Addison At WindermereThe Kaiden1,398 Sq Ft$2,430
Windermere at Lakes Edge ApartmentsDuval Key1,397 Sq Ft$1,928
Birchstone WaterleighB41,365 Sq Ft$2,525
Solay Horizon WestB21,305 Sq Ft$2,474
Apollo ApartmentsSunrise1,269 Sq Ft$2,179

Cheapest Available Winter Garden 2 Bedroom Apartments

As of August 04, 2025 the lowest priced 2 Bedroom apartment unit in Winter Garden, FL is the Cypress Renovated Model starting from $1,544 at Advenir at The Oaks in the Ashton Park neighborhood. The second most affordable Winter Garden 2 Bedroom is the Two Bed/ Two Bath Model at Inland Seas Apartments starting at $1,640 in the Deer Island neighborhood. The average price for all 2 Bedroom apartments in Winter Garden is currently $2,332. Here is today’s list of the cheapest available 2 Bedroom options in Winter Garden:

Apartment ListingModel NamePriced From
Advenir at The OaksCypress Renovated$1,544
Inland Seas ApartmentsTwo Bed/ Two Bath$1,640
Garden City ApartmentsTwo Bed/1.5 Bath Standard$1,650
Palm CrossingValencia$1,678
Country GardensTwo Bedroom Two Bath$1,750
Arya at WindermereSapphire$1,776
IMT Sonoma HillsB1$1,880
Windermere CaySagamore$1,901
Prose Avalon PointeB1$1,909
Serenza at Ocoee Village ApartmentsB3$1,916

Quick Rent Budget Calculator

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Pet Friendly Lifestyle
Winter Garden, FL

Ranked #33

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

Pet Friendliness Lifestyle Score

2.5
Pet Friendly

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Best Local Schools in
Winter Garden, FL

School data provided by Great Schools

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

Explore Winter Garden, FL Rentals by Map

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

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Getting Around Winter Garden, FL

Walk Score®

40 / 100

Car-Dependent

Most errands require a car

Bike Score®

46 / 100

Somewhat Bikeable

Minimal bike infrastructure

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 2 Bedroom Winter Garden Apartments

What is the Cheapest apartment in Winter Garden with 2 Bedroom?

Currently the most affordable 2 Bedroom in Winter Garden is at Advenir at The Oaks listed at $1,544.

How much is the average rent for a 2 Bedroom Winter Garden Apartment?

The average rent for a 2 Bedroom Apartment in Winter Garden is $2,332.

What is the largest available 2 Bedroom Winter Garden Apartment for rent?

Today's apartment with the most square footage in Winter Garden is a 1,616 square feet unit starting from $3,280 at The Lodge at Hamlin.

What is the average size for Winter Garden 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Winter Garden is currently 1,086 sq ft.

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

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

Written by: Christine Leonard, Esq.

Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.

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

Written by: Christine Leonard, Esq.

Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.