
2 Bedroom Apartments for Rent in the Downtown Winter Park Neighborhood of Winter Park, FL (28 Rentals)


Paseo at Winter Park Village

Juno Winter Park

Park East - Park Knowles Apartments

Hannibal Square

Village Park Senior

1500 Gay Rd
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.

662 Callahan St

1380 Indiana Ave

1565 Michigan Ave

Lake Killarney Condominiums

The Verandas of Winter Park

542 Shoreview Ave

1546 Minnesota Ave
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

402 W Welbourne Ave

Winter Park Gardens

Douglas Grand at Winter Park

720 N Pennsylvania Ave

125 S Interlachen Ave

Mead Garden Condominiums

1516 Minnesota Ave
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.

470 W New England Ave

400 W Swoope Ave

Chateaux du Lac

El Cortez Apartments

Railroad Avenue Apartments

The Oaks

Gem Lake Apartments
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.
Downtown Winter Park, Winter Park, FL Local Guide

How much does it cost to rent an apartment in Downtown Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Downtown Winter Park Studio Apartments | $1,555 | $1,330 | $1,691 |
| Downtown Winter Park 1 Bedroom Apartments | $1,900 | $1,236 | $2,326 |
Downtown Winter Park 2 Bedroom Apartments | $2,446 | $1,437 | $2,823 |
| Downtown Winter Park 3 Bedroom Apartments | $3,284 | $2,399 | $3,750 |
Browse Apartments in this Neighborhood
There are currently 28 rentals with your search options within a 1 mile radius of the Downtown Winter Park Neighborhood of Winter Park, FL.
See all Apartments in Winter ParkExplore Winter Park
Largest Available Downtown Winter Park 2 Bedroom Apartments
The largest available 2 Bedroom apartment unit in the Downtown Winter Park area of Orlando, FL is found at Village Park Senior and is listed at 1,662 square feet priced from $2,425. Here is today’s list of the largest available 2 Bedroom units in the area:
| Apartment Listing | Model Name | Square Footage | Priced From |
|---|---|---|---|
| Village Park Senior | Virginia (Two Bedroom w/Den) | 1,662 Sq Ft | $2,425 |
| Paseo at Winter Park Village | Vagar | 1,215 Sq Ft | $2,816 |
| Bainbridge Winter Park | B2 | 1,207 Sq Ft | $2,690 |
| Juno Winter Park | Apollo | 1,010 Sq Ft | $2,390 |
| Hannibal Square | 433 2x1 | 741 Sq Ft | $1,750 |
Cheapest Available Downtown Winter Park 2 Bedroom Apartments
Currently the lowest priced 2 Bedroom apartment unit Downtown Winter Park of Orlando, FL is the Two Bedroom Two Bath Model starting from $1,437 at Village Park Senior. The average price for all 2 Bedroom apartments in Downtown Winter Park is currently $2,446. Here is today’s list of the cheapest available 2 Bedroom options in the area:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Village Park Senior | Two Bedroom Two Bath | $1,437 |
| Hannibal Square | 433 2x1 | $1,750 |
| Juno Winter Park | Apollo | $2,390 |
| Paseo at Winter Park Village | Rejuvenecer | $2,550 |
| Bainbridge Winter Park | B3 | $2,602 |
Frequently Asked Questions about 2 Bedroom Downtown Winter Park Apartments
What is the Cheapest apartment in Downtown Winter Park with 2 Bedroom?
Currently the most affordable 2 Bedroom in Downtown Winter Park is at Village Park Senior listed at $1,437.
How much is the average rent for a 2 Bedroom Downtown Winter Park Apartment?
The average rent for a 2 Bedroom Apartment in Downtown Winter Park is $2,446.
What is the largest available 2 Bedroom Downtown Winter Park Apartment for rent?
Today's apartment with the most square footage in Downtown Winter Park is a 1,662 square feet unit starting from $2,425 at Village Park Senior.
What is the average size for Downtown Winter Park 2 Bedroom Apartments for rent?
The average size for a 2 Bedroom rental in Downtown Winter Park is currently 2,461 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
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.

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.

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

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.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.