Apartments for Rent with Specials in Winter Park, FL (49 Rentals)

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

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Berkshire Winter Park
Rent Specials
$1,492 - $3,921Special Offer
1 Month Free ASK US HOW TO GET YOUR 2nd MONTH RENT FREE * *Restrictions apply/subject to end without notice.
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Berkshire Winter Park

1874 Harmon AveWinter Park, FL 32789
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Juno Winter Park
Rent Specials
$1,850 - $8,297Special 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
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Juno Winter Park

1305 Morgan Stanley AveWinter Park, FL 32789
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Seabrook
Rent Specials
$1,241 - $1,711Special Offer
Specials Save $500 off January 2026 rent. Must move in within 72 hours of application approval . *Select apartments
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Seabrook

3114 Terry Brook DrWinter Park, FL 32792
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The Taylor at Winter Park
Rent Specials
$991 - $2,295Special 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.
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The Taylor at Winter Park

2000 Village LnWinter Park, FL 32792
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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.

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Summerlin at Winter Park Apartments
Rent Specials
$1,286 - $2,996Special Offer
Discounts New Year Special! $2026 OFF MOVE IN Plus Waived Admin and Pet Fees Select Units. Move in by 1/15/2026. Promo Code: MERRYSUMMERLIN
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Summerlin at Winter Park Apartments

3207 Rosebud LnWinter Park, FL 32792
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Park Apartments
Rent Specials
$1,250 - $1,800Special Offer
1 Month Free We are offering 1 MONTH FREE! Call the Leasing Office for more details!
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Park Apartments

7528 Park Promenade DrWinter Park, FL 32792
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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
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The Vista at Winter Park

4704 Lucier CtWinter Park, FL 32792
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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

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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
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The Lofts of Winter Park Village

520 N Orlando AveWinter Park, FL 32789
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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
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Gables Baldwin Park

2050 Jake StOrlando, FL 32814
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Inscribe Apartments
Rent Specials
$1,530 - $2,756Special Offer
2 Months Free Receive Up To 10 WEEKS FREE + Lowered Rates on Select Homes! Ask our team about incentives available for local Eatonville empl
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Inscribe Apartments

110 Zora PlOrlando, FL 32810
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Luna at Lake Shadow
Rent Specials
$1,549 - $4,130Special Offer
2 Months Free Limited Time Only! 8 Weeks Free on Select Apartments if you move in by January 15th, 2026.
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Luna at Lake Shadow

2200 Flagler Promenade WayMaitland, FL 32751
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400 North
Rent Specials
$1,665 - $3,095Special Offer
1 Month Free Receive One Month Free when you move in within 30 days! *Restrictions May Apply
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400 North

400 N Orlando AveMaitland, FL 32751
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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.

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The Village at Lake Lily
Rent Specials
$1,631 - $7,227Special Offer
Discounts Up To $500 Off First Month's Rent + Waived Apps & Admin! *All Applications are Verified Through SNAPPT & CheckPoint ID*
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The Village at Lake Lily

925 S Orlando AveMaitland, FL 32751
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Newport Colony Apartments in Casselberry
Rent Specials
$1,375 - $2,135Special Offer
Specials Limited-Time Pricing! 1BR apartments now starting at $1,299 2BR apartments now starting at $1,349 *Contact leasing office for more
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Newport Colony Apartments in Casselberry

1166 Pointe Newport TerCasselberry, FL 32707
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Adele Place
Rent Specials
$1,363 - $1,766Special Offer
Specials Reduced Rates & Half Off Application Fee! - Limited Time Only! Immediate Move Ins Only!
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Adele Place

7595 Sun Tree CirOrlando, FL 32807
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Azul Baldwin Park
Rent Specials
$1,756 - $3,759Special 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
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Azul Baldwin Park

4460 Lower Park RdOrlando, FL 32814
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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.
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Shoreview at Baldwin Park

1001-1009 Shoreview DrOrlando, FL 32807
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Perla Gem Lake
Rent Specials
$2,012 - $3,763Special Offer
Specials PAY NO RENT UNTIL JANUARY 2026! CALL NOW TO FIND OUT MORE! *Restrictions apply
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Perla Gem Lake

100 Boucle Jeanne CirMaitland, FL 32751
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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.

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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
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The Baldwin

800 Lombard StOrlando, FL 32807
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Lake House
Rent Specials
$1,772 - $7,764Special Offer
Specials Limited Time Special: UP TO TWO months FREE on select apartment homes!
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Lake House

295 NE Ivanhoe BlvdOrlando, FL 32804
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Hillcrest Hampton House
Rent Specials
$1,150 - $1,550Special 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
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Hillcrest Hampton House

2000 Hillcrest StOrlando, FL 32803
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Garden Park Senior Living
Rent Specials
$1,177 - $1,682Special Offer
Discounts Senior Living at its Finest! $300 Off Move-In Costs on Select 2 Bedroom with Den Apartment Homes* *Must move in by 1/16/26. Restri
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Garden Park Senior Living

361-365 Garden Edge PtFern Park, FL 32730
Senior Living
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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.

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Audubon Park
Rent Specials
$1,598 - $3,714Special Offer
Specials Up to 2 Months FREE on select units if you move in by 12/5. Call for details
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Audubon Park

990 Warehouse RdOrlando, FL 32803
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Showing Results 1-49, Page 1 of 1

Winter Park, FL Local Guide

Top Apartments in Winter Park, FL with Move-In Specials Ending Soon

Specials updated: 01-03-2026

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!

Stonecastle Apartment Homes

One month free with a new lease. Restrictions apply, see agent for details.Expires 01-02-2026

Village Park Senior

Senior Living at its Finest! $250 Move-In Costs on Select 1 and 2 Bedroom Apartment Homes. App Fee only $30!* *Must move in by 1/9/26. Restrictions apply, contact leasing office for details.Expires 01-02-2026

Juno Winter Park

Enjoy up to 1 month free & $99 App/Admin Special on select 2 or 3 BR units! *Restrictions Apply. Contact our dedicated leasing team for more details!Expires 01-03-2026

Paseo at Winter Park Village

We are Currently Available for In-person and Virtual Interactions - Schedule Your Tour Today!Expires 01-03-2026

Berkshire Winter Park

ASK US HOW TO GET YOUR 2nd MONTH RENT FREE * *Restrictions apply/subject to end without notice.Expires 01-03-2026

Seabrook

Save $500 off January 2026 rent. Must move in within 72 hours of application approval . *Select apartmentsExpires 01-03-2026

Summerlin at Winter Park Apartments

New Year Special! $2026 OFF MOVE IN Plus Waived Admin and Pet Fees Select Units. Move in by 1/15/2026. Promo Code: MERRYSUMMERLIN Subject to change.Expires 01-03-2026

Rosalia Winter Park 55+ Active Adult Community

Receive 6 weeks free rent upon the first of the month of your leaseExpires 01-03-2026

Oak Reserve at Winter Park

SPECIAL: Select Units starting at $1395 Contact our Leasing Office for Details!Expires 01-03-2026

Liv at Winter Park Apartment Homes

Up To Six Weeks Free!Expires 01-03-2026

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

Specials updated: 01-03-2026

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

Cranes Landing Apartments

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

Park Apartments

We are offering 1 MONTH FREE! Call the Leasing Office for more details!Expires 02-28-2026

Summerlin at Winter Park Apartments

New Year Special! $2026 OFF MOVE IN Plus Waived Admin and Pet Fees Select Units. Move in by 1/15/2026. Promo Code: MERRYSUMMERLIN Subject to change.Expires 01-03-2026

Rosalia Winter Park 55+ Active Adult Community

Receive 6 weeks free rent upon the first of the month of your leaseExpires 01-03-2026

Juno Winter Park

Enjoy up to 1 month free & $99 App/Admin Special on select 2 or 3 BR units! *Restrictions Apply. Contact our dedicated leasing team for more details!Expires 01-03-2026

Paseo at Winter Park Village

We are Currently Available for In-person and Virtual Interactions - Schedule Your Tour Today!Expires 01-03-2026

Berkshire Winter Park

ASK US HOW TO GET YOUR 2nd MONTH RENT FREE * *Restrictions apply/subject to end without notice.Expires 01-03-2026

Seven41 Winter Park

Move into luxury and save. Get up to $750 off your new apartment home!Expires 01-03-2026

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.

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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.

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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.

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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

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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.

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Winter Park, FL Rentals by Map

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See the most popular apartments and homes in Winter Park, FL

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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 Kingswood Apartments listed at $900.

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 $2,263.

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 3,513 square feet unit starting from $1,772 at Lake House.

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 645 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.

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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.

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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.

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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

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How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips

Written by: Justin Habersaat

Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

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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.

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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.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate!