Apartments for Rent with Specials in Winter Park, FL (57 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
$1,535 - $5,520Special 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
$1,883 - $6,506Special 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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Elon Winter Park
Rent Specials
$1,599 - $1,629Special Offer
Discounts SAVE UP TO $800 OFF YOUR MOVE IN COSTS! - Must move in by 9/30
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Elon Winter Park

712 Nicolet AveWinter Park, FL 32789
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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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Seabrook
Rent Specials
$1,293 - $1,815Special Offer
Specials Save $800 off October 2025 rent + $99 app/admin fee. Must move in within 72 hours, upon 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
$1,351 - $2,454Special Offer
1 Month Free Limited Time Offer: One Month Free On Select Homes. Terms may apply. Please contact the office for details.
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The Taylor at Winter Park

2000 Village LnWinter Park, FL 32792
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POSTE Winter Park
Rent Specials
$1,489 - $1,805Special Offer
Specials Limited Time Only Receive $800 Off Move-in - Select Apartment Homes Move-in by 9/30
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POSTE Winter Park

800 Semoran Park DrWinter Park, FL 32792
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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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Signal Pointe
Rent Specials
$1,245 - $2,675Special Offer
Specials Get October & December rent FREE with a move-in by 9/30/25! *Offers subject to change. Some restrictions apply. Contact office for
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Signal Pointe

2500 Howell Branch RdWinter Park, FL 32792
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The Vista at Winter Park
Rent Specials
$1,499 - $1,899Special Offer
1 Month Free Enjoy your 2nd full month completely on us! *Restricted units only* Special prices for application fees! Honoring Heroes: $35 M
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The Vista at Winter Park

4704 Lucier CtWinter Park, FL 32792
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The Lofts of Winter Park Village
Rent Specials
$1,595 - $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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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 Parker at Maitland Station Apartments
Rent Specials
$1,608 - $3,874Special Offer
Specials Limited-Time Move-In Special!  Move In by September 24th and Get October Rent-Free! Dont miss this early fall dealschedule your tou
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The Parker at Maitland Station Apartments

955 N Orlando AveMaitland, FL 32751
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Inscribe Apartments
Rent Specials
$1,586 - $2,977Special 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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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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Perla Gem Lake
Rent Specials
$1,989 - $3,764Special Offer
1 Month Free Get 1 Month Free on Select Layouts and Waived Application Fees!
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Perla Gem Lake

100 Boucle Jeanne CirMaitland, FL 32751
Luxury
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400 North
Rent Specials
$1,720 - $2,306Special Offer
1 Month Free Move in by September 30th and get one month FREE! *Restrictions May Apply
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400 North

400 N Orlando AveMaitland, FL 32751
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Newport Colony Apartments in Casselberry
Rent Specials
$1,350 - $2,135Special Offer
Specials Move in to selected apartment homes by 09/31 and get December's rent free!  **Restrictions apply contact the leasing team for more
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Newport Colony Apartments in Casselberry

1166 Pointe Newport TerCasselberry, FL 32707
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The Village at Lake Lily
Rent Specials
$1,480 - $6,840Special Offer
Discounts Enjoy Up To $1,500 Off Your First Month's Rent On Select Homes!* *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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Luna at Lake Shadow
Rent Specials
$1,736 - $4,023Special Offer
1 Month Free Limited Time Only! 6 Weeks Free on Select Apartments if you move in by September 30th, 2025.
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Luna at Lake Shadow

2200 Flagler Promenade WayMaitland, 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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Adele Place
Rent Specials
$1,426 - $1,903Special Offer
Discounts 2 Beds Up To $500 Off At Move-In!* App Fee 1/2 Off! - Call TODAY To Schedule Your Tour! *Select homes, Must move in by 9/30/25.
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Adele Place

7595 Sun Tree CirOrlando, FL 32807
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Azul Baldwin Park
Rent Specials
$1,853 - $3,972Special 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
$1,305 - $1,900Special 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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The Milk Stacks: Boutique Luxury Living
Rent Specials
$1,829Special Offer
1 Month Free Lease your brand-new apartment home and receive 1 MONTH FREE RENT!! Call today for details on how to claim your 1 YEAR FREE GYM
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The Milk Stacks: Boutique Luxury Living

221 S Bumby AveOrlando, FL 32803
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Courtney At Lake Shadow
Rent Specials
$1,409 - $3,109Special Offer
Specials Summer Still on Fire! Look and Lease within the 48 hours of your tour and we'll waive your application and administration fee
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Courtney At Lake Shadow

545 S Keller RdOrlando, FL 32810
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Lake House
Rent Specials
$1,718 - $7,070Special Offer
Specials Limited Time Special: UP TO SIX WEEKS FREE on select apartment homes!
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Lake House

295 NE Ivanhoe BlvdOrlando, FL 32804
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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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Winter Park, FL Local Guide

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

Specials updated: 09-19-2025

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!

Central Place At Winter Park

Reduced Rent on Select Apartment Homes + $500 OFF When You Look & Lease!Expires 09-19-2025

The Taylor at Winter Park

Limited Time Offer: One Month Free On Select Homes. Terms may apply. Please contact the office for details.Expires 09-19-2025

Oak Reserve at Winter Park

SPECIAL: Select nits starting at $1295 Contact our Leasing Office for Details!Expires 09-19-2025

Summerlin at Winter Park Apartments

$500 Off Move In on Select Units! Offer Subject to Change.Expires 09-19-2025

Bainbridge Winter Park

Limited Time: Enjoy a WAIVED Admin Fee and $250 Gift Card on SELECT Units!Expires 09-19-2025

Rosalia Winter Park 55+ Active Adult Community

Receive 6 weeks free rent upon the first of the month of your leaseExpires 09-19-2025

Seabrook

Save $800 off October 2025 rent & $99 app/admin fee. Must move in within 72 hours, upon approval. *Select apartmentsExpires 09-19-2025

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 09-19-2025

Paseo at Winter Park Village

We are Currently Available for In-person and Virtual Interactions - Schedule Your Tour Today!Expires 09-19-2025

Berkshire Winter Park

ASK US HOW TO GET YOUR 2nd MONTH RENT FREE * *Restrictions apply/subject to end without notice.Expires 09-19-2025

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

Specials updated: 09-19-2025

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.

Park Apartments

We are offering 1 MONTH FREE! Call the Leasing Office for more details!Expires 12-31-2025

The Vista at Winter Park

Enjoy your 2nd full month completely on us! *Restricted units only* Special prices for application fees! Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!Expires 09-30-2025

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

Summerlin at Winter Park Apartments

$500 Off Move In on Select Units! Offer Subject to Change.Expires 09-19-2025

Bainbridge Winter Park

Limited Time: Enjoy a WAIVED Admin Fee and $250 Gift Card on SELECT Units!Expires 09-19-2025

Rosalia Winter Park 55+ Active Adult Community

Receive 6 weeks free rent upon the first of the month of your leaseExpires 09-19-2025

Winter Park Woods

2 MONTH FREE rentExpires 10-31-2025

Central Place At Winter Park

Reduced Rent on Select Apartment Homes + $500 OFF When You Look & Lease!Expires 09-19-2025

The Taylor at Winter Park

Limited Time Offer: One Month Free On Select Homes. Terms may apply. Please contact the office for details.Expires 09-19-2025

Oak Reserve at Winter Park

SPECIAL: Select nits starting at $1295 Contact our Leasing Office for Details!Expires 09-19-2025

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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Winter Park, FL Apartments Map
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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 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 $2,303.

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 $1,718 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 664 sq ft.

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.

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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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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.