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Rent Specials
$2,110 - $4,846Special Offer
1 Month Free Up to 1 Month Free on Select Apartment Homes!
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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 (27 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
$1,625 - $5,765Special Offer
Specials Lease Now, monthly rent has been reduced -$100! Certain exclusions may apply.
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MAA Baldwin Park
4688 New Broad StOrlando, FL 32814
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Rent Specials
$1,257 - $1,851Special Offer
Discounts Reduced Rates & Saving up to $300 Off at Move-In!* - Limited Time Only! Immediate Move Ins Only!
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Adele Place
7595 Sun Tree CirOrlando, FL 32807
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Rent Specials
$1,768 - $3,776Special 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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Rent Specials
$1,205 - $1,915Special 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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Rent Specials
$1,553 - $2,325Special Offer
Specials Look and Lease Special! Call Us Today For Rent Specials
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The Baldwin
800 Lombard StOrlando, FL 32807
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
$1,436 - $1,645Special Offer
Specials Reduced rent on select apartment units!
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Oasis Club
7451 Gatehouse CirOrlando, FL 32807
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Rent Specials
$1,625 - $3,514Special Offer
2 Months Free Move in within 30 days and enjoy up to 2 months FREE! *Restrictions May Apply
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Enders Place at Baldwin Park
4220 New Broad StOrlando, FL 32814
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Rent Specials
$1,294 - $3,294Special Offer
Specials Holiday Cheer Starts Here! Unwrap big savings this season with no full rent payment until January 2026! Move in now and celebrate t
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The Avenues of Baldwin Park
5800 Auvers BlvdOrlando, FL 32807
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Rent Specials
$1,350 - $1,650Special Offer
Specials $100 off monthly rent with a 12-month lease AND 1 month FREE! Call today to learn more about this limited time special!
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Hillcrest Hampton House
2000 Hillcrest StOrlando, FL 32803
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Rent Specials
$1,110 - $1,825Special 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
$1,515 - $3,117Special 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
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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Rent Specials
$1,607 - $2,820Special Offer
Specials Receive Up To One Month Free, Plus Lease within 48 hours of touring and get your App and Admin Fees Waived!
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The Gallery at Mills Park
1650 N Mills AveOrlando, FL 32803
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Rent Specials
$1,454 - $4,336Special Offer
1 Month Free Up to 6 Weeks Free! Act Now and receive 6 weeks free on a two-bedroom floor plan or one month free on a one-bedroom floor plan.
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Vintage Winter Park Apartments
7490 Dwell Well WayWinter Park, FL 32792
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Rent Specials
$2,170 - $6,445Special Offer
Specials We are Currently Available for In-person and Virtual Interactions - Schedule Your Tour Today!
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Paseo at Winter Park Village
940 W Canton AveWinter Park, FL 32789
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Rent Specials
$1,211 - $1,556Special Offer
Specials Save $800 off December & January rent, $99 app/admin. 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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Rent Specials
$1,874 - $7,569Special 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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Rent Specials
$1,383 - $2,158Special Offer
Specials Holiday Cheer Starts Here! Unwrap big savings this season with no full rent payment until January 2026! Move in now and celebrate t
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Cranes Landing Apartments
3440 N Goldenrod RdWinter Park, FL 32792
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
$1,475 - $2,075Special Offer
Specials SPECIAL: Select Units starting at $1395 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
$1,205 - $2,075Special Offer
Specials Fall into Savings! Reduced Rent on Select Units & Up One Month Free!
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Central Place At Winter Park
7000 University BlvdWinter Park, FL 32792
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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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Rent Specials
$1,293 - $2,874Special Offer
Discounts NO RENT UNTIL JAN 1ST ON SELECT 3BR UNITS. $500 Off Move In on Select Units! Offer Subject to Change.
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Summerlin at Winter Park Apartments
3207 Rosebud LnWinter Park, FL 32792
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Rent Specials
$999 - $1,760Special Offer
Specials 2 MONTH FREE rent for immediate move in, call today!
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Winter Park Woods
349 Scottsdale SqWinter Park, FL 32792
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Rent Specials
$1,777 - $2,691Special Offer
1 Month Free Receive 6 weeks free rent upon the first of the month of your lease
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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
$1,489 - $1,857Special Offer
Specials Save up to $800 on move-in costs! - Limited time move in by 11/15
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POSTE Winter Park
800 Semoran Park DrWinter Park, FL 32792
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Rent Specials
$1,399 - $1,899Special Offer
Discounts Move in special:$1,000 off!
*Restricted units only*
Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurs
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The Vista at Winter Park
4704 Lucier CtWinter Park, FL 32792
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Rent Specials
$1,600 - $1,850Special 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
Showing Results 1-27, 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 | $1,578 | $991 | $2,175 |
| Winter Park 1 Bedroom Apartments | $1,799 | $1,139 | $2,995 |
| Winter Park 2 Bedroom Apartments | $2,203 | $976 | $5,859 |
| Winter Park 3 Bedroom Apartments | $2,742 | $1,099 | $4,846 |
| Winter Park 4 Bedroom Apartments | $3,514 | $3,514 | $3,514 |
Browse Apartments in this Neighborhood
There are currently 27 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: 11-16-2025Take 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!
Gables Baldwin Park
Up to 1 Month Free on Select Apartment Homes!Expires 11-16-2025
Audubon Park
Up to 2 Months FREE on select units if you move in by 12/5. Call for detailsExpires 11-16-2025
Enders Place at Baldwin Park
Move in within 30 days and enjoy up to 2 months FREE! *Restrictions May ApplyExpires 11-16-2025
Oak Reserve at Winter Park
SPECIAL: Select Units starting at $1395 Contact our Leasing Office for Details!Expires 11-16-2025
Rosalia Winter Park 55+ Active Adult Community
Receive 6 weeks free rent upon the first of the month of your leaseExpires 11-16-2025
Oasis Club
Reduced rent on select apartment units!Expires 11-16-2025
MAA Baldwin Park
Lease Now, monthly rent has been reduced -$100! Certain exclusions may apply.Expires 11-16-2025
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 11-16-2025
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 11-16-2025
Summerlin at Winter Park Apartments
NO RENT UNTIL JAN 1ST ON SELECT 3BR UNITS. $500 Off Move In on Select Units! Offer Subject to Change.Expires 11-16-2025
Newly Listed Move-In Specials offers for Apartments in Winter Park, FL
Specials updated: 11-16-2025Here 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
The Vista at Winter Park
Move in special:$1,000 off! *Restricted units only* Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!Expires 11-30-2025
Winter Park Woods
2 MONTH FREE rent for immediate move in, call today!Expires 12-31-2025
Hillcrest Hampton House
$100 off monthly rent with a 12-month lease AND 1 month FREE! Call today to learn more about this limited time special!Expires 11-30-2025
Cranes Landing Apartments
Holiday Cheer Starts Here! Unwrap big savings this season with no full rent payment until January 2026! Move in now and celebrate the season stress-free! Contact your Leasing & Live It! Specialist today for full details. Dont wait this offer is limited! Now open Sundays from 1 PM to 5 PM!Expires 12-31-2025
The Avenues of Baldwin Park
Holiday Cheer Starts Here! Unwrap big savings this season with no full rent payment until January 2026! Move in now and celebrate the season stress-free! Contact your Leasing & Live It! Specialist today for full details. Dont wait this offer is limited! Now open Sundays from 1 PM to 5 PM!Expires 12-31-2025
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
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 ArticleYour 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 ArticleQuick 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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Pet Friendly LifestyleWinter Park, Orlando, FL
Ranked #54
Among cities in Florida for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.5Pet Friendly
Best Local Schools in Winter Park, Orlando, FL
School data provided by Great Schools
Getting Around the Winter Park Neighborhood in Orlando, FL
Walk Score®
75 / 100
Very Walkable
Most errands can be accomplished on foot
Bike Score®
62 / 100
Bikeable
Some bike infrastructure
Transit Score®
26 / 100
Some Transit
A few nearby public transportation options
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 The Taylor at Winter Park listed at $991.
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 $2,176.
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 $2,110 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 657 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.
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.
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.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
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.