Apartments for Rent with Specials in the Winter Park Neighborhood of Orlando, FL (24 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

Apartments in the Winter Park area of Orlando with special offers and discounts available right now - opportunities to save money or get a month or more of free rent.

close
View Me
Gables Baldwin Park
Rent Specials
$2,075 - $4,731Special Offer
Specials Ring in the New Year 2026 with a Limited-Time Offer! Enjoy up to TWO weeks FREE on select apartment homes. Contact Our Leasing Team
See More

Gables Baldwin Park

2050 Jake StOrlando, FL 32814
Student Housing
  • Verified
  • Customer Reviewed
  • Utilities Included
close
View Me
Azul Baldwin Park
Rent Specials
$1,756 - $3,793Special Offer
Specials MOVE IN DEPOSIT-FREE! We offer a Deposit-Free alternative move in option where no upfront security deposit is required saving you h
See More

Azul Baldwin Park

4460 Lower Park RdOrlando, FL 32814
Affordability
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
Shoreview at Baldwin Park
Rent Specials
$1,085 - $1,850Special Offer
1 Month Free Move-In Special! Enjoy 1-month RENT FREE! Valid on vacant apartments only. *Limited-time offer; terms and conditions apply.
See More

Shoreview at Baldwin Park

1001-1009 Shoreview DrOrlando, FL 32807
Affordability
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
The Baldwin
Rent Specials
$1,651 - $2,380Special Offer
Specials LEASE TODAY AND SAFE UP TO $4,200 IN RENT! Exclusions Apply, Call Us Today For More Info
See More

The Baldwin

800 Lombard StOrlando, FL 32807
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
Adele Place
Rent Specials
$1,313 - $1,746Special Offer
Specials Reduced Rates & Half Off Application Fee! - Limited Time Only! Immediate Move Ins Only!
See More

Adele Place

7595 Sun Tree CirOrlando, FL 32807
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour

The Soul of the City Beautiful: What Life in Orlando Is Really Like

Orlando is much more than theme parks. Uncover the city's rich history, diverse neighborhoods like Winter Park and Downtown, and its bustling cultural and culinary life.

Read Article
close
View Me
Hillcrest Hampton House
Rent Specials
$1,150 - $1,375Special Offer
Discounts NEW YEAR MOVE IN SAVINGS! Choose your special: Option 1 – Studio Special Get $1,500 OFF our studio floor plans • $500 applied to J
See More

Hillcrest Hampton House

2000 Hillcrest StOrlando, FL 32803
Senior Living
  • Verified
  • Customer Reviewed
  • Utilities Included
close
View Me
Audubon Park
Rent Specials
$1,348 - $3,500Special Offer
Specials Up to 2 Months FREE on select units if you move in by 12/5. Call for details
See More

Audubon Park

990 Warehouse RdOrlando, FL 32803
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
Juno Winter Park
Rent Specials
$1,850 - $9,035Special Offer
Specials Enjoy up to 1 month free & $99 App/Admin Special on select 2 or 3 BR units! *Restrictions Apply. Contact our dedicated leasing team
See More

Juno Winter Park

1305 Morgan Stanley AveWinter Park, FL 32789
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour

Top Neighborhoods Near Orlando Major Employers

Learn about the best places to live near major employers in Orlando with original content written by our Local Expert Darla Ferrara

Read Article
close
View Me
The Taylor at Winter Park
Rent Specials
$999 - $2,099Special Offer
2 Months Free Two Months Free on Select Units! Waived App and Admin fees on All Units! *Terms may apply. Contact the office for details.
See More

The Taylor at Winter Park

2000 Village LnWinter Park, FL 32792
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
The Vista at Winter Park
Rent Specials
$1,499 - $1,799Special Offer
1 Month Free Move in special: Up to a full month off the 2nd full month! *Restricted units only* App and Admin special for only $175! Honori
See More

The Vista at Winter Park

4704 Lucier CtWinter Park, FL 32792
Affordability
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
The Lofts of Winter Park Village
Rent Specials
$1,575 - $1,795Special Offer
Specials RENT NOW and receive 6 WEEKS OFF your rent!!! Reduced Security deposit available for qualified applicants! **Free application fee f
See More

The Lofts of Winter Park Village

520 N Orlando AveWinter Park, FL 32789
Affordability
  • Verified
  • Customer Reviewed
  • 3D Tour

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 1-24, Page 1 of 1

Winter Park, Orlando, FL Local Guide

Top Orlando Apartments in the Winter Park Area with Move-In Specials Ending Soon

Specials updated: 01-08-2026

Take advantage of these move-in and rent specials that are ending soon for top Winter Park, FL apartments. Act fast and don’t miss out on an incredible deal on your perfect new place!

Oak Reserve at Winter Park

SPECIAL: Select Units starting at $1395 Contact our Leasing Office for Details!Expires 01-09-2026

Audubon Park

Up to 2 Months FREE on select units if you move in by 12/5. Call for detailsExpires 01-09-2026

Enders Place at Baldwin Park

For a limited time, move-in within 30 days and enjoy one month free! *Restrictions May ApplyExpires 01-09-2026

Gables Baldwin Park

Ring in the New Year 2026 with a Limited-Time Offer! Enjoy up to TWO weeks FREE on select apartment homes. Contact Our Leasing Team for Details.Expires 01-09-2026

MAA Baldwin Park

Lease Now, monthly rent has been reduced -$40! Certain exclusions may apply.Expires 01-09-2026

The Gallery at Mills Park

Receive Up To One Month Free, Plus Lease within 48 hours of touring and get your App and Admin Fees Waived!Expires 01-09-2026

The Taylor at Winter Park

Two Months Free on Select Units! Waived App and Admin fees on All Units! *Terms may apply. Contact the office for details.Expires 01-09-2026

Adele Place

Reduced Rates & Half Off Application Fee! - Limited Time Only! Immediate Move Ins Only!Expires 01-09-2026

Azul Baldwin Park

MOVE IN DEPOSIT-FREE! We offer a Deposit-Free alternative move in option where no upfront security deposit is required saving you hundreds of dollars on move-in costs.Expires 01-09-2026

Shoreview at Baldwin Park

Move-In Special! Enjoy 1-month RENT FREE! Valid on vacant apartments only. *Limited-time offer; terms and conditions apply.Expires 01-09-2026

Newly Listed Move-In Specials offers for Apartments in Winter Park, FL

Specials updated: 01-08-2026

Here are the most recently added special offers for renters looking to find the best deals on apartments in Winter Park, FL. Be sure to take advantage of some of the area’s top offers.

The Lofts of Winter Park Village

RENT NOW and receive 6 WEEKS OFF your rent!!! Reduced Security deposit available for qualified applicants! **Free application fee for Active and Retired Military**Expires 01-31-2026

Hillcrest Hampton House

NEW YEAR MOVE IN SAVINGS! Choose your special: Option 1 – Studio Special Get $1,500 OFF our studio floor plans • $500 applied to January, February & March rent Option 2 – 1 Bedroom Special Enjoy February rent FREE with a move in by January 31st Offers cannot be combined. $1,500 off special applies to studio apartments only.Expires 01-15-2026

Avenues of Baldwin Park

6 WEEKS FREE!!!! MOVE IN NOW!!!Expires 01-31-2026

The Vista at Winter Park

Move in special: Up to a full month off the 2nd full month! *Restricted units only* App and Admin special for only $175! Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!Expires 01-31-2026

The Majestic at Downtown Baldwin Park

Limited time offer - 1 month free on select floorplans!Expires 01-31-2026

Cranes Landing Apartments

Lease Today and Receive up to One Month Free!Expires 01-31-2026

Oak Reserve at Winter Park

SPECIAL: Select Units starting at $1395 Contact our Leasing Office for Details!Expires 01-09-2026

Audubon Park

Up to 2 Months FREE on select units if you move in by 12/5. Call for detailsExpires 01-09-2026

Enders Place at Baldwin Park

For a limited time, move-in within 30 days and enjoy one month free! *Restrictions May ApplyExpires 01-09-2026

Gables Baldwin Park

Ring in the New Year 2026 with a Limited-Time Offer! Enjoy up to TWO weeks FREE on select apartment homes. Contact Our Leasing Team for Details.Expires 01-09-2026

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

Read Article
Decorative image

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

Read Article
Decorative image

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

Read Article
Decorative image

Your Guide to the Perfect Orlando Neighborhood for Student Renters

Learn About the Best Neighborhoods to Rent Near College Campuses in Orlando, FL | Find Orlando Off-Campus Student Housing at ApartmentHomeLiving.com

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

Best Local Schools in
Winter Park, Orlando, FL

School data provided by Great Schools

Frequently Asked Questions about Rent Specials Winter Park Apartments

What is the Cheapest Rent Specials apartment in Winter Park?

Currently the most affordable Rent Specials Apartment in Winter Park is at The Taylor at Winter Park listed at $999.

How much is the average rent for a Rent Specials Winter Park Apartment?

The average rent for a Rent Specials Apartment in Winter Park is $2,228.

What is the largest Rent Specials Winter Park Apartment for rent?

Today's Rent Specials apartment with the most square footage in Winter Park is a 1,978 square feet unit starting from $2,075 at Gables Baldwin Park.

What is the average size for Winter Park Rent Specials Apartments for rent?

The average size for a Rent Specials rental in Winter Park is currently at 629 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

decorative image for An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent article

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.

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.

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 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.

Articles, How-To's, and Tips

decorative image for A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment article

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.

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

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.

decorative image for Apartment Common Area Rules: What Renters Need to Know article

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.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate!