2 Bedroom Apartments for Rent in Winter Park, FL (278 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

Renting with Roommates: Realistic Expectations for Shared Lease

Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

Read Article

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.

Read Article

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.

Read Article
property at 1901 Magnolia Ave

$1,150

Total Monthly Price

Total Monthly Price

Base Rent
$1,150
Total Monthly Price
$1,150

2 Bedroom, 1 Bath Home for Rent

Available Now

1901 Magnolia Ave

Winter ParkFL32792
property at 662 Callahan St

$2,408

Total Monthly Price

Total Monthly Price

Base Rent
$2,408
Total Monthly Price
$2,408

2 Bedroom, 1 Bath Home for Rent

Available Nov 25

662 Callahan St

Winter ParkFL32789

Renting Smart: Lease Basics Every Renter Needs

Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com

Read Article

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

Read Article
Showing Results 1-50, Page 1 of 6

Winter Park, FL Local Guide

Photo of Staff Writer - Local Guide Expert
Written By:
Staff Writer
Local Guide Expert

Winter Park 2 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: July 05, 2026

There are currently 61 available 2 Bedroom apartment units in Winter Park, FL neighborhoods that range in price from $1,097 to $3,512. Heres is today's list of the top neighborhoods in Winter Park with the most available 2 Bedroom apartments:

NeighborhoodAvailable UnitsMedian PriceMin Price
Lake Howell61$1,759$1,097

Largest Available Winter Park 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Winter Park, FL is found at Regency Oaks Apartments in the Northeast neighborhood and is 1,800 square feet priced from $1,877. Aurora on the Trail in the Colonial Town Center neighborhood has the second largest 2 Bedroom, which is sized at 1,592 square feet and currently listed start at $2,745. Here is today’s list of the largest available 2 Bedroom units in Winter Park:

Apartment ListingModel NameSquare FootagePriced From
Regency Oaks ApartmentsB5 Townhouse1,800 Sq Ft$1,877
Aurora on the TrailB41,592 Sq Ft$2,745
The Village at Lake LilyB1.21,500 Sq Ft$2,548
Perla Gem LakeB51,439 Sq Ft$3,396
Gables Baldwin ParkB121,405 Sq Ft$4,221
Luna at Lake ShadowB41,299 Sq Ft$2,433
Audubon ParkDuckworth1,263 Sq Ft$2,326
MAA Baldwin ParkDual Level 2x2.5 1214-1248 SF1,248 Sq Ft$2,610
Vintage Winter Park ApartmentsKraft1,229 Sq Ft$2,593
The Cannery at The Packing DistrictB11,118 Sq Ft$2,228

Cheapest Available Winter Park 2 Bedroom Apartments

As of July 05, 2026 the lowest priced 2 Bedroom apartment unit in Winter Park, FL is the 2x2-50 Model starting from $1,141 at Golden Oaks in the The Enclave at Lake Jean neighborhood. The second most affordable Winter Park 2 Bedroom is the 2 Beds, 2 baths Model at Sumerset Apartments starting at $1,195 in the Courtland Street neighborhood. The average price for all 2 Bedroom apartments in Winter Park is currently $2,187. Here is today’s list of the cheapest available 2 Bedroom options in Winter Park:

Apartment ListingModel NamePriced From
Golden Oaks2x2-50$1,141
Sumerset Apartments2 Beds, 2 baths$1,195
Kingswood Apartments2/1$1,200
Spring Tree VillageVilla$1,229
The Park at RialtoB3$1,329
Regency Oaks ApartmentsB2$1,332
Sapphire Winter ParkOnyx$1,349
Eastbrook ApartmentsTwo Bed One Bath$1,350
Birchwood LandingBirchwood B$1,375

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

Read Article
Decorative image

Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

Read Article
Decorative image

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.

decorative image of people with a giant lease agreement

Winter Park Overview

Winter Park, Florida offers something for everyone. This suburban city of over 29,000 people provides historical, cultural, and recreational opportunities. Well-known for its museums, art galleries, and parks, the town is home to Rollins College. Outdoor enthusiasts can enjoy water activities at nearby lakes, or explore local hiking and biking trails. With plenty of options for apartments in Winter Park, find a new home here is easy.

Why live in Winter Park, FL?

If you're unsure about relocating to Winter Park apartments, consider all it has to offer. Its convenient location just northeast of Orlando allows you to reap the benefits of living near a sizeable city while enjoying the amenities of a smaller community. Winter Park apartments provide an impressive selection of housing options. This suburban hamlet offers upscale shopping and dining. A local chain of lakes provides ample opportunities for fishing, swimming, and boating. Rollins College and other post-secondary institutions offer educational opportunities in everything from liberal arts to fine arts. Cultural events and a thriving community center bring residents together.

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

Explore Winter Park, FL Rentals by Map

Decorative image of map

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

View Map
Winter Park, FL Apartments Map
View Map
Winter Park, FL Rental Homes Map

Frequently Asked Questions about 2 Bedroom Winter Park Apartments

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

Currently the most affordable 2 Bedroom in Winter Park is at Golden Oaks listed at $1,141.

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

The average rent for a 2 Bedroom Apartment in Winter Park is $2,187.

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

Today's apartment with the most square footage in Winter Park is a 1,800 square feet unit starting from $1,877 at Regency Oaks Apartments.

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

The average size for a 2 Bedroom rental in Winter Park is currently 1,084 sq ft.

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 Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention article

Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

decorative image for How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide article

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

decorative image for Pet-Friendly Renting: Everything You Need to Know Before You Move article

Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.