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Rent Specials
$2,218 - $4,594
Total Monthly Price
Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
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$2,218 - $4,594
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Gables Baldwin Park
2050 Jake StOrlando, FL 32814
Apartments for Rent with Specials in the Winter Park Neighborhood of Orlando, FL (23 Rentals)
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.
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Rent Specials
$1,604 - $2,870Special Offer
1 Month Free GET 6 WEEKS FREE ON SELECT HOMES — LIMITED TIME ONLY! ****LOOK & LEASE SPECIAL — GET A FREE 75"TV ****
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Evergreen Mills 50
1647 E Colonial DrOrlando, FL 32803
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Rent Specials
$1,349 - $1,979Special Offer
Specials One-Bedroom Apartments: Get your first month’s rent free – must move in by 5/31.
$99 Security Deposit!!!! Call for details.
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Bellancia Apartments
7325 Goldenpointe BlvdOrlando, FL 32807
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Rent Specials
$1,715 - $6,930Special Offer
Specials Lease Now, monthly rent has been reduced -$115! Certain exclusions may apply.
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MAA Baldwin Park
4688 New Broad StOrlando, FL 32814
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Rent Specials
$1,804 - $3,274Special Offer
1 Month Free Elevate Your Move: Enjoy One Month Free & move-in within 30 days *Restrictions May Apply
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Enders Place at Baldwin Park
4220 New Broad StOrlando, FL 32814
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Rent Specials
$1,190 - $2,280Special Offer
1 Month Free Enjoy 1-Month FREE! Plus, apply within 24 hours of touring for waived application fees! *Limited-time offer; terms and conditio
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Shoreview at Baldwin Park
1001-1009 Shoreview DrOrlando, FL 32807
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Rent Specials
$1,908 - $3,606Special 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
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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Rent Specials
$1,700 - $3,255
Total Monthly Price
Studio to 3 Bedroom Apartments Available Jun 7Total Monthly Price
Base Rent
$1,700 - $3,255
Total Monthly Price
$1,700 - $3,255
Aurora on the Trail
825 McCullough AveOrlando, FL 32803
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Rent Specials
$1,436 - $1,745Special Offer
Discounts Elevated living is waiting for you at Ivy at Gatehouse. Sophisticated interiors and top-tier amenities are just the beginning. Sec
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The Ivy at Gatehouse
7451 Gatehouse CirOrlando, FL 32807
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Rent Specials
$1,331 - $1,854Special Offer
Specials Up to $600 in Savings for Immediate Move In, Move In By 5/30/26 - Limited Time Only, Must Move In By: 5/30/26
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Adele Place
7595 Sun Tree CirOrlando, FL 32807
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Rent Specials
$1,000 - $1,700Special Offer
Specials Move in Special Reduced Rent and Application and Admin fee reduced to $99
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District On Baldwin Park
5590 Baldwin Park StOrlando, FL 32807
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Rent Specials
$1,225 - $1,525Special Offer
Discounts May 2026 Special: Move in by May 31st and receive $500 off June Rent for 1 bedrooms. Studios will receive $500 off June & July !
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Hillcrest Hampton House
2000 Hillcrest StOrlando, FL 32803
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Rent Specials
$1,752 - $2,996
Total Monthly Price
1 to 3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$1,752 - $2,996
Total Monthly Price
$1,752 - $2,996
Audubon Park
990 Warehouse RdOrlando, FL 32803
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Rent Specials
$1,638 - $3,227
Total Monthly Price
Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$1,638 - $3,227
Total Monthly Price
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The Gallery at Mills Park
1650 N Mills AveOrlando, FL 32803
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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Rent Specials
$1,818 - $6,627Special Offer
Specials 2 weeks free
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Juno Winter Park
1305 Morgan Stanley AveWinter Park, FL 32789
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Rent Specials
$1,295 - $2,075Special Offer
Specials SPECIAL: Half Off First Full Month's Rent Contact our Leasing Office for Details!
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Oak Reserve at Winter Park
541 Oak Reserve LnWinter Park, FL 32792
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Rent Specials
$1,250 - $2,040Special Offer
Specials Reduced Rates on Select Apartment Homes + $500 Look & Lease Special!
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Central Place At Winter Park
7000 University BlvdWinter Park, FL 32792
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Rent Specials
$1,244 - $2,411Special Offer
2 Months Free Limited-Time Offer: Get 2 Months Free on select units—move in by 4/20/26! Terms may apply. Please contact the office for more
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The Taylor at Winter Park
2000 Village LnWinter Park, FL 32792
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Rent Specials
$1,332 - $2,445Special Offer
Discounts $1,000 OFF & Reduced Deposit Plus Waived App and Pet Fees! Move in by May 15th Subject to change. Optional: Trendy Living & Dinin
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Summerlin at Winter Park Apartments
3207 Rosebud LnWinter Park, FL 32792
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Rent Specials
$1,330 - $1,960Special Offer
1 Month Free 1 MONTH FREE RENT!!! Call NOW for information on move-in specials!!!
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Park East - Park Knowles Apartments
311 N Knowles AveWinter Park, FL 32789
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Rent Specials
$1,917 - $2,806
Total Monthly Price
1 to 2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$1,917 - $2,806
Total Monthly Price
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Rosalia Winter Park 55+ Active Adult Community
3045 Aloma AveWinter Park, FL 32792
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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Rent Specials
$1,123 - $1,672
Total Monthly Price
1 to 2 Bedroom Apartments Available NowTotal Monthly Price
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$1,123 - $1,672
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Solis at Winter Park
7502 Sun Key BlvdWinter Park, FL 32792
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Rent Specials
$1,675Special Offer
Specials Rent by June 1st and Get $1000 Off Your First Month + a Super Low $350 Security Deposit!!!
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The Lofts of Winter Park Village
520 N Orlando AveWinter Park, FL 32789
Showing Results 1-23, Page 1 of 1
Winter Park, Orlando, 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 | $1,745 | $1,000 | $2,685 |
| Winter Park 1 Bedroom Apartments | $1,784 | $695 | $4,111 |
| Winter Park 2 Bedroom Apartments | $2,209 | $956 | $5,013 |
| Winter Park 3 Bedroom Apartments | $2,976 | $1,082 | $5,652 |
| Winter Park 4 Bedroom Apartments | $3,938 | $3,938 | $3,938 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Apartments in this Neighborhood
There are currently 23 rentals with your search options within a 2 mile radius of the Winter Park Neighborhood of Orlando, FL.
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Winter Park, Orlando, FL Local Guide
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Top Orlando Apartments in the Winter Park Area with Move-In Specials Ending Soon
Specials updated: 05-27-2026Take 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!
Shoreview at Baldwin Park
Enjoy 1-Month FREE! Plus, apply within 24 hours of touring for waived application fees! *Limited-time offer; terms and conditions apply.Expires 05-28-2026
Gables Baldwin Park
Don’t miss out – contact our office today to secure your discounted pricing before it is gone!Expires 05-28-2026
The Lofts of Winter Park Village
Rent by June 1st and Get $1000 Off Your First Month + a Super Low $350 Security Deposit!!!Expires 05-28-2026
Summerlin at Winter Park Apartments
$1,000 OFF & Reduced Deposit Plus Waived App and Pet Fees! Move in by May 15th Subject to change. Optional: Trendy Living & Dining Room Furniture Available! Ask Us How!Expires 05-28-2026
The Ivy at Gatehouse
Elevated living is waiting for you at Ivy at Gatehouse. Sophisticated interiors and top-tier amenities are just the beginning. Secure your new apartment today and enjoy $500 OFF May rent! Whether you are working from home or relaxing by the pool, life is better here. Reach out to us for a tour and let us get you moved in.Expires 05-28-2026
MAA Baldwin Park
Lease Now, monthly rent has been reduced -$115! Certain exclusions may apply.Expires 05-28-2026
The Gallery at Mills Park
Receive Up To FOUR WEEKS Free Base Rent, Plus Lease within 48 hours of touring and get your App and Admin Fees Waived! Terms and Conditions Apply.Expires 05-28-2026
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 05-28-2026
Rosalia Winter Park 55+ Active Adult Community
Receive 8 weeks free of rent after the first of the month of your leaseExpires 05-28-2026
The Taylor at Winter Park
Limited-Time Offer: Get 2 Months Free on select units—move in by 4/20/26! Terms may apply. Please contact the office for more details.Expires 05-28-2026
Newly Listed Move-In Specials offers for Apartments in Winter Park, FL
Specials updated: 05-27-2026Here 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.
Hillcrest Hampton House
May 2026 Special: Move in by May 31st and receive $500 off June Rent for 1 bedrooms. Studios will receive $500 off June & July !Expires 05-31-2026
Bellancia Apartments
One-Bedroom Apartments: Get your first month’s rent free – must move in by 5/31. $99 Security Deposit!!!! Call for details.Expires 05-31-2026
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 05-28-2026
Rosalia Winter Park 55+ Active Adult Community
Receive 8 weeks free of rent after the first of the month of your leaseExpires 05-28-2026
The Taylor at Winter Park
Limited-Time Offer: Get 2 Months Free on select units—move in by 4/20/26! Terms may apply. Please contact the office for more details.Expires 05-28-2026
Audubon Park
First Full Month FREE on 13 month leases who move in by 6/12/2026Expires 05-28-2026
Enders Place at Baldwin Park
Elevate Your Move: Enjoy One Month Free & move-in within 30 days *Restrictions May ApplyExpires 05-28-2026
Solis at Winter Park
Start Summer Smart! ?? Move in by May 30th and receive a Gift Card valued at 2 weeks of free rent in July when you sign a 12–15 month lease! *Restrictions ApplyExpires 05-28-2026
Adele Place
Up to $600 in Savings for Immediate Move In, Move In By 5/30/26 - Limited Time Only, Must Move In By: 5/30/26Expires 05-28-2026
Central Place At Winter Park
Reduced Rates on Select Apartment Homes + $500 Look & Lease Special!Expires 05-28-2026
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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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.
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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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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 District On Baldwin Park listed at $1,000.
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 $2,140.
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 $2,218 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 599 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
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.
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.
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.
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
A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.
Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.