
Top Rated Apartments for Rent in Winter Park, FL Under $2,000 (38 Rentals)
Apartments in Winter Park with the best features, newest construction, and richest amenities.


Elon Winter Park

Vintage Winter Park Apartments

Paseo at Winter Park Village

Bainbridge Winter Park

Berkshire Winter Park

Central Place At Winter Park

Stonecastle Apartment Homes
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.

Inscribe Apartments

Onyx Winter Park

Alexan Mills 50

The Majestic at Downtown Baldwin Park

The Village at Lake Lily
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.

Luna at Lake Shadow

The Cannery at The Packing District

Lake House

MAA Baldwin Park

The Ivy Residences at Health Village Apartment Homes

Azul Baldwin Park

Jefferson Lake Howell
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.

Maitland City Centre

Infinity off Baldwin Park Apartments

Courtney At Lake Shadow

Perla Gem Lake

400 North Apartments

Vida at Health Village

Aurora on the Trail

The Princeton at College Park

The Parker at Maitland Station Apartments

Steelhouse
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla F

The Gallery at Mills Park

Enders Place at Baldwin Park
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 | $2,449 | $900 | $10,000+ |
Winter Park 1 Bedroom Apartments | $2,136 | $850 | $10,000+ |
Winter Park 2 Bedroom Apartments | $2,575 | $1,089 | $10,000+ |
Winter Park 3 Bedroom Apartments | $2,975 | $1,261 | $9,543 |
Winter Park 4 Bedroom Apartments | $3,628 | $2,214 | $7,866 |
Explore Winter Park
Winter Park, FL Local Guide
- Winter Park Neighborhoods
- Nearby Cities
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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.
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 Winter Park
How much are Studio apartments in Winter Park?
There are currently 38 Studio Apartments in Winter Park with rent ranges from $876 to $13,982 with an average price of $3,551.
What is the current price range for One Bedroom Winter Park Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Winter Park ranges from $850 to $16,538 with an average monthly rent of $2,136.
What does renting a Two Bedroom Apartment in Winter Park cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winter Park range from $1,089 to $18,788. Today's average rental price for Two Bedrooms here is $2,575.
How expensive are Winter Park Three Bedroom Apartments?
There are currently 93 Three Bedroom Apartments listings available in Winter Park on ApartmentHomeLiving.com. The pricing ranges from $1,261 to $9,543 - averaging $2,975 for the location.
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.

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.

The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.