2 Bedroom Apartments for Rent in Winter Park, FL (283 Rentals)

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Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities

Why fight Orlando's tourist traffic when you don't have to? Explore the best cities surrounding Orlando for renters, with expert tips on commuting, lifestyle, hidden costs, and where to find the most value.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Looking for the perfect new rental? Learn great ways to spot the perfect apartment for you, identify common red flags, and avoid rental issues and scams with these expert provided actionable tips.

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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 1920 Woodcrest Dr

$1,800

Total Monthly Price

Total Monthly Price

Base Rent
$1,800
Total Monthly Price
$1,800

2 Bedroom, 2 Bath Condo for Rent

Available Now

1920 Woodcrest Dr, Unit 13

1920 Woodcrest Dr
Winter ParkFL32792
property at 622 St Johns Ct

$1,900

Total Monthly Price

Total Monthly Price

Base Rent
$1,900
Total Monthly Price
$1,900

2 Bedroom, 2 Bath Home for Rent

Available Now

622 St Johns Ct

Winter ParkFL32792
property at 1250 S Denning Dr

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000
Total Monthly Price
$2,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

1250 S Denning Dr, Unit 127

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 662 Callahan St

$2,415

Total Monthly Price

Total Monthly Price

Base Rent
$2,415
Total Monthly Price
$2,415

2 Bedroom, 1 Bath Home for Rent

Available Nov 25

662 Callahan St

Winter ParkFL32789
property at 1695 Lee Rd

$1,450 - $1,800

2 Bedroom Rentals

Available Now

1695 Lee Rd

Winter ParkFL32789

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.

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Winter Park, FL Local Guide

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Written By:
Staff Writer
Local Guide Expert

Winter Park 2 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: August 19, 2026

There are currently 61 available 2 Bedroom apartment units in Winter Park, FL neighborhoods that range in price from $1,208 to $2,970. 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$1,847$1,208

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. Perla Gem Lake in the Courtland Street neighborhood has the second largest 2 Bedroom, which is sized at 1,439 square feet and currently listed start at $3,426. 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
Perla Gem LakeB51,439 Sq Ft$3,426
Gables Baldwin ParkB121,405 Sq Ft$4,100
The Village at Lake LilyB2.21,365 Sq Ft$2,317
Hannibal Square558 -2bd/2bath1,365 Sq Ft$2,400
The Majestic at Downtown Baldwin ParkShaldon1,280 Sq Ft$2,700
Audubon ParkDuckworth1,263 Sq Ft$2,236
Maitland City CentreB51,261 Sq Ft$2,659
MAA Baldwin ParkTraditional 2x2 1141-1291 SF1,141 Sq Ft$2,375
The Cannery at The Packing DistrictB11,118 Sq Ft$2,381

Cheapest Available Winter Park 2 Bedroom Apartments

As of August 19, 2026 the lowest priced 2 Bedroom apartment unit in Winter Park, FL is the 2x2-60 Model starting from $1,095 at Golden Oaks in the The Enclave at Lake Jean neighborhood. The second most affordable Winter Park 2 Bedroom is the 2/1 Model at Kingswood Apartments starting at $1,200 in the Courtland Street neighborhood. The average price for all 2 Bedroom apartments in Winter Park is currently $2,163. Here is today’s list of the cheapest available 2 Bedroom options in Winter Park:

Apartment ListingModel NamePriced From
Golden Oaks2x2-60$1,095
Kingswood Apartments2/1$1,200
San Jose Apartments2x1 1033$1,208
Spring Tree VillageVilla$1,229
Sapphire Winter ParkJade$1,249
SorayaLynx$1,249
2075 Howell Branch Road #1012075 Howell Branch Road #101 - 1$1,250
Sumerset Apartments2 Beds, 2 baths$1,274
Newport Colony Apartments in CasselberryTwo Bedroom Patio$1,299
Avenues of Baldwin ParkAnson (Standard) B1wm$1,300

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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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.

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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

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

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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 $1,095.

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 $2,163.

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 1,089 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

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When people think of Orlando, FL, the iconic theme parks and buzz of downtown tend to steal the spotlight.

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

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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.

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

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Articles, How-To's, and Tips

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

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