Apartments for Rent in the Outer East Neighborhood of Winter Park, FL (138 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done
property at 1509 Springtime Loop
$2,695

Total Monthly Price

Base Rent$2,695
Total Monthly Price$2,695
3 Bedroom, 2 Bath Home for Rent
Available Now

1509 Springtime Loop

Winter ParkFL32792
property at 5312 Poinsetta Ave
$1,000

Total Monthly Price

Base Rent$1,000
Total Monthly Price$1,000
1 Bedroom, 1 Bath Home for Rent
Available Now
Furnished

5312 Poinsetta Ave, Unit 2

5312 Poinsetta Ave
Winter ParkFL32792
  • Smoke Free
property at 2038 Ponderosa Ave
$2,250

Total Monthly Price

Base Rent$2,250
Total Monthly Price$2,250
3 Bedroom, 2 Bath Home for Rent
Available Now

2038 Ponderosa Ave

Winter ParkFL32792
  • Smoke Free
property at 2399 Antilles Dr
$1,900

Total Monthly Price

Base Rent$1,900
Total Monthly Price$1,900
2 Bedroom, 1 Bath Townhome for Rent
Available Now
Affordability

2399 Antilles Dr

Winter ParkFL32792

Orlando's Best Affordable Neighborhoods

Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara

Read Article
property at 1840 Bachman Way
$2,550

Total Monthly Price

Base Rent$2,550
Total Monthly Price$2,550
3 Bedroom, 2.5 Bath Home for Rent
Available Now
Luxury

1840 Bachman Way

Winter ParkFL32792
  • Smoke Free

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.

Read Article

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

Read Article

Neighborhood & Market Insights: How to Choose the Right Area to Rent

Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

Read Article

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.

Read Article
Showing Results 1-50, Page 1 of 3

Outer East, Winter Park, FL Local Guide

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.

Read Article
Decorative image

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.

Read Article
Decorative image

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.

Read Article

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.

Read Article
Decorative image

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.

decorative image of people with a giant lease agreement

Pet Friendly Lifestyle
Outer East, Winter Park, FL

Ranked #4

Among cities in Florida for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

3.0
Pet Friendly

decorative image of woman handing cat to small boy

Best Local Schools in
Outer East, Winter Park, FL

School data provided by Great Schools

Lifestyle Ratings

ApartmentHomeLiving.com is proud to bring you our detailed rental analysis called 'Lifestyle Ratings' - a comparison of rentals and neighborhoods across the USA, and customized analysis for Northern Orlando, FL. Our Lifestyle Ratings help you zero-in on the perfect place to call home. This takes in many factors including our Star Ratings to compare for the best proximity to parks and outdoor amenities, luxury amenities, family-friendly amenities, raising pets, transit options, in addition to floorplans, availablity, and pricing. Use Lifestyle Search in the site filter options on this page - and find your Perfect place!

Luxury Living Rating

This area ranks as one of our favorite upscale communities in town, with a score of 3.0 out of 4. Luxury Lifestyle Scoring is based on having high-end community amenities like pools, saunas, workout spaces, concierge services, views, access to parks, and nice home amenities like granite or quartz countertops and stainless steel appliances. Other luxury items often include hardwood floors and fireplaces, sports like tennis and raquetball, and for some communities, even a doorman to greet residents.

Frequently Asked Questions about Outer East

What is the current pricing and availability for apartments for rent in the Outer East area of Winter Park, FL?

As of today, September 11, 2026, there are currently 138 available Outer East apartments priced from $1,002 to $4,840, with an average monthly rent of $1,763.

How much are Studio apartments in Outer East?

There are currently 15 Studio Apartments in Outer East with rent ranges from $1,199 to $2,113 with an average price of $1,318.

What is the current price range for One Bedroom Outer East Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Outer East ranges from $1,002 to $2,431 with an average monthly rent of $1,616.

What does renting a Two Bedroom Apartment in Outer East cost?

The monthly rent prices of Two Bedroom Apartments currently available in Outer East range from $1,076 to $2,522. Today's average rental price for Two Bedrooms here is $1,819.

How expensive are Outer East Three Bedroom Apartments?

There are currently 21 Three Bedroom Apartments listings available in Outer East on ApartmentHomeLiving.com. The pricing ranges from $1,399 to $4,840 - averaging $2,107 for the location.

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

decorative image for Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities article

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

Written by: Darla Ferrara

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

decorative image for The Soul of the City Beautiful: What Life in Orlando Is Really Like article

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.

decorative image for Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers article

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.

decorative image for Your Guide to the Perfect Orlando Neighborhood for Student Renters article

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.

Articles, How-To's, and Tips

decorative image for Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My! article

Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

Written by: Robin Stewart

Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

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

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

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

decorative image for First Apartment Regrets: Real Renters Share What They'd Do Differently article

First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.