Apartments for Rent with Specials in Winter Park, FL (46 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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Seven41 Winter Park
Rent Specials
$1,585 - $3,922Special Offer
Specials Limited-Time Luxury Living Special! Live Elevated. Live Rewarded. For A Limited Time, Enjoy ONE MONTH FREE When You Lease Your New
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Seven41 Winter Park

741 Clay StWinter Park, FL 32789
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Berkshire Winter Park
Rent Specials
$1,550 - $5,148Special Offer
1 Month Free ASK US HOW TO GET UP TO ONE MONTH FREE ON SELECT APARTMENTS * *Terms & restrictions apply/subject to end without notice.
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Berkshire Winter Park

1874 Harmon AveWinter Park, FL 32789
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The Taylor at Winter Park
Rent Specials
$1,235 - $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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Summerlin at Winter Park Apartments
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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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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Signal Pointe
Rent Specials
$1,115 - $2,575Special Offer
1 Month Free Get 1 month FREE on a 12-15 month lease! *Offers subject to change. Some restrictions apply. Contact office for details
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Signal Pointe

2500 Howell Branch RdWinter Park, FL 32792
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Solis at Winter Park
Rent Specials
$1,065 - $1,684
Total Monthly Price

Total Monthly Price

Base Rent
$1,065 - $1,684
Total Monthly Price
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1 to 2 Bedroom Apartments Available Now

Solis at Winter Park

7502 Sun Key BlvdWinter 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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Gables Baldwin Park
Rent Specials
$2,218 - $4,449
Total Monthly Price

Total Monthly Price

Base Rent
$2,218 - $4,449
Total Monthly Price
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Studio to 3 Bedroom Apartments Available Now

Gables Baldwin Park

2050 Jake StOrlando, FL 32814
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Inscribe Apartments
Rent Specials
$1,629 - $2,535
Total Monthly Price

Total Monthly Price

Base Rent
$1,629 - $2,535
Total Monthly Price
Varies
1 to 3 Bedroom Apartments Available Now

Inscribe Apartments

110 Zora PlOrlando, FL 32810
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Luna at Lake Shadow
Rent Specials
$1,836 - $3,667Special Offer
2 Months Free 2 Months Free on Select 2- and 3-bedroom apartments. Other specials do apply.
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Luna at Lake Shadow

2200 Flagler Promenade WayMaitland, FL 32751
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Advenir at Magnolia
Rent Specials
$1,157 - $1,742
Total Monthly Price

Total Monthly Price

Base Rent
$1,157 - $1,742
Total Monthly Price
Varies
Studio to 2 Bedroom Apartments Available Now

Advenir at Magnolia

210 Welcome WayFern Park, FL 32730
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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 3BR apartments now starting at $1
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Newport Colony Apartments in Casselberry

1166 Pointe Newport TerCasselberry, FL 32707
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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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Evergreen Mills 50
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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Azul Baldwin Park
Rent Specials
$1,908 - $3,670Special 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
$1,195 - $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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Perla Gem Lake
Rent Specials
$1,977 - $3,675Special Offer
2 Months Free Now Offering up to 2-Months Free on Select Floor plans! Call Today to Find out More!
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Perla Gem Lake

100 Boucle Jeanne CirMaitland, FL 32751
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Steelhouse Orlando
Rent Specials
$1,455 - $2,515Special Offer
1 Month Free Get 1 Month Free and Zero Deposit on All units! Plus $500 Gift card on Select Units! Please call us for details!
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Steelhouse Orlando

750 N Orange AveOrlando, FL 32801
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Vida at Health Village
Rent Specials
$1,718 - $8,139
Total Monthly Price

Total Monthly Price

Base Rent
$1,718 - $8,139
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

Vida at Health Village

2680 N Orange AveOrlando, FL 32804
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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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Aurora on the Trail
Rent Specials
$1,700 - $3,255
Total Monthly Price

Total Monthly Price

Base Rent
$1,700 - $3,255
Total Monthly Price
$1,700 - $3,255
Studio to 3 Bedroom Apartments Available Jun 7

Aurora on the Trail

825 McCullough AveOrlando, FL 32803
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The Ivy at Gatehouse
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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Adele Place
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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Hillcrest Hampton House
Rent Specials
$1,200 - $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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Audubon Park
Rent Specials
$1,718 - $2,996
Total Monthly Price

Total Monthly Price

Base Rent
$1,718 - $2,996
Total Monthly Price
$1,718 - $2,996
1 to 3 Bedroom Apartments Available Now

Audubon Park

990 Warehouse RdOrlando, FL 32803
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Primrose Orlando
Rent Specials
$1,000 - $1,250Special Offer
Specials Now is the perfect time to save with our lower rental price specials, for a limited time only. These limited-time reduced prices ma
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Primrose Orlando

2716 E Washington StOrlando, FL 32803
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Orlando's Best Affordable Neighborhoods

Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara

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property at 237 Emory Pl

$1,850

Total Monthly Price

Total Monthly Price

Base Rent
$1,850
Total Monthly Price
$1,850

1 Bedroom, 1 Bath Home for Rent

Available Jun 1

237 Emory Pl

OrlandoFL32804
Showing Results 1-46, Page 1 of 1

Winter Park, FL Local Guide

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

Specials updated: 05-24-2026

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!

Berkshire Winter Park

ASK US HOW TO GET UP TO ONE MONTH FREE ON SELECT APARTMENTS * *Terms & restrictions apply/subject to end without notice.Expires 05-24-2026

Liv at Winter Park Apartment Homes

Up to One Month Free!Expires 05-24-2026

Rosalia Winter Park 55+ Active Adult Community

Receive 8 weeks free of rent after the first of the month of your leaseExpires 05-24-2026

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 05-24-2026

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 05-24-2026

Oak Reserve at Winter Park

SPECIAL: Half Off First Full Month's Rent Contact our Leasing Office for Details!Expires 05-24-2026

Juno Winter Park

2 weeks freeExpires 05-24-2026

Central Place At Winter Park

Reduced Rates on Select Apartment Homes + $500 Look & Lease Special!Expires 05-24-2026

Elon Winter Park

Save up to $500 on your move-in costs! - Move in by 6/15Expires 05-24-2026

The Lofts of Winter Park Village

Rent by June 1st and Get $1000 Off Your First Month + a Super Low $350 Security Deposit!!!Expires 05-24-2026

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

Specials updated: 05-24-2026

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.

Stonecastle Apartment Homes

Enjoy one month free on all new leases. Restrictions apply, see agent for details.Expires 05-25-2026

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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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 $2,217.

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 631 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

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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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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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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.

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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.

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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.

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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.