Cheap Apartments for Rent in Winter Park, FL from $400 with Swimming Pool (32 Rentals)
Search the lowest-cost Apartments available for rent right now in Winter Park.

San Jose Apartments

Carlton Arms of Winter Park

Winter Park Woods

Venue At Winter Park
It's time to soak up some sun!
One of the easiest and more obvious ways of enjoying the summer sun is to lounge out by your community pool. Learn a Few Rules to Keep in Mind while at the pool.

Sovereignty at Winter Park Apartments

Solis at Winter Park

ARIUM Winter Park

Park Apartments

Central Place At Winter Park

Cranes Landing Apartments

Indigo Winter Park

The Taylor at Winter Park

Signal Pointe
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.

Liv at Winter Park Apartment Homes

Summerlin at Winter Park Apartments

Westmount at Winter Park

Seabrook

Sapphire Winter Park

Kingswood 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.

District On Baldwin Park

Birchwood Landing

Regency Oaks Apartments

The Park at Rialto

Shoreview at Baldwin Park

Onyx Winter Park

The Avenues of Baldwin Park

Newport Colony Apartments in Casselberry
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.
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 | $2,485 | $900 | $10,000+ |
Winter Park 1 Bedroom Apartments | $2,117 | $850 | $10,000+ |
Winter Park 2 Bedroom Apartments | $2,597 | $1,089 | $10,000+ |
Winter Park 3 Bedroom Apartments | $2,983 | $1,261 | $9,543 |
Winter Park 4 Bedroom Apartments | $3,570 | $2,214 | $7,866 |
Explore Winter Park
Winter Park, FL Local Guide
- Winter Park Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
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 Cheap Winter Park Apartments
What is a cheap apartment in Winter Park?
A cheap apartment is any apartment up to the 30% percentile of cost for the area, which in Winter Park is under $1,199.
What is the price of a cheap apartment in Winter Park?
The cheapest apartment in Winter Park is San Jose Apartments which is listed at $903, while the average apartment in Winter Park costs $2,329.
What types of apartments are the cheapest in Winter Park?
Student, low-income, and by-the-bed apartments are typically the cheapest rentals in most cities, though they require qualifying criteria to rent. There are 5 regular apartments in Winter Park that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.
How do the prices of cheap apartments compare to the average apartment in Winter Park?
Cheap apartments in Winter Park have an average cost of $544 which is $1,785 cheaper than the average rent for all rentals in Winter Park.
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.