2 Bedroom Apartments for Rent in Winter Park, FL Under $4,400 (123 Rentals) Page 2 of 3

The Parker at Maitland Station Apartments

Onyx Winter Park

The Majestic at Downtown Baldwin Park

Gables Baldwin Park

Inscribe Apartments

Advenir at Magnolia
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

The Shores at Lake Howell

Luna at Lake Shadow

Trelago Apartments

Newport Colony Apartments in Casselberry

400 North

Citron at The Packing District

The Village at Lake Lily

Cortland Lake Howell

The Cannery at The Packing District
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.

Aurora on the Trail

The Princeton at College Park

MAA Baldwin Park

Adele Place

The Ivy Residences at Health Village Apartment Homes

Azul Baldwin Park

The Grand Reserve at Maitland Park

Shoreview at Baldwin Park

Perla Gem Lake
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara

Maitland City Centre

Infinity off Baldwin Park Apartments

Village at Baldwin Park

Courtney At Lake Shadow

Regency Oaks Apartments

The Baldwin

Vida at Health Village

Lake House

Enders Place at Baldwin Park

Avenues of Baldwin Park

District On Baldwin Park

Oasis Club

Garden Park Senior Living

Audubon Park

Steelhouse

The Gallery at Mills Park

Spring Tree Village
Winter Park, FL Local Guide

How much does it cost to rent an apartment in Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winter Park Studio Apartments | $1,521 | $900 | $2,468 |
| Winter Park 1 Bedroom Apartments | $1,793 | $850 | $3,835 |
| Winter Park 2 Bedroom Apartments | $2,100 | $976 | $5,845 |
| Winter Park 3 Bedroom Apartments | $2,632 | $1,099 | $6,050 |
| Winter Park 4 Bedroom Apartments | $3,820 | $3,150 | $4,701 |
Explore Winter Park
Getting Around Winter Park, FL
Walk Score®
71 / 100
Very Walkable
Most errands can be accomplished on foot
Bike Score®
57 / 100
Bikeable
Some bike infrastructure
Transit Score®
22 / 100
Minimal Transit
It may be possible to get on a bus
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 Park Apartments
What is the Cheapest apartment in Winter Park with 2 Bedroom?
Currently the most affordable 2 Bedroom in Winter Park is at San Jose Apartments listed at $1,089.
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 $2,100.
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 $1,977 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 1,091 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

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.

Your Guide to the Perfect Orlando Neighborhood for Student Renters
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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.

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

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Articles, How-To's, and Tips

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.

Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!

The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.








