Apartments for Rent with Specials in Winter Park, FL (47 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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Summerlin at Winter Park Apartments
Rent Specials
$1,361 - $2,394Special Offer
Discounts $1,000 OFF & Reduced Deposit Plus Waived App and Pet Fees!  Subject to change. Optional: Trendy Living & Dining Room Furniture Ava
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Summerlin at Winter Park Apartments

3207 Rosebud LnWinter Park, FL 32792
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Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities

Why fight Orlando's tourist traffic when you don't have to? Explore the best cities surrounding Orlando for renters, with expert tips on commuting, lifestyle, hidden costs, and where to find the most value.

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The Taylor at Winter Park
Rent Specials
$1,246 - $1,824Special Offer
Discounts Receive 50% OFF your first month's rent and enjoy waived app & admin fees when you look & lease today! Terms may apply. Contact th
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The Taylor at Winter Park

2000 Village LnWinter Park, FL 32792
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Berkshire Winter Park
Rent Specials
$1,530 - $3,956Special 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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Alvista Winter Park
Rent Specials
$1,391 - $3,347Special Offer
Specials Receive up to 2 weeks free rent on select apartment homes for move-ins in August or September 2026. Restrictions apply.*
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Alvista Winter Park

3935 Sutton Place BlvdWinter Park, FL 32792
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Signal Pointe
Rent Specials
$1,320 - $2,485Special Offer
1 Month Free Get 1 month FREE on 1 & 2 beds & 2 months FREE 3 bedrooms *Offers subject to change. Some restrictions apply. Contact office fo
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Signal Pointe

2500 Howell Branch RdWinter Park, FL 32792
Corporate Housing
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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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Gables Baldwin Park
Rent Specials
$2,456 - $8,540
Total Monthly Price

Total Monthly Price

Base Rent
$2,456 - $8,540
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

Gables Baldwin Park

2050 Jake StOrlando, FL 32814
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Inscribe Apartments
Rent Specials
$1,718 - $2,718
Total Monthly Price

Total Monthly Price

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

Inscribe Apartments

110 Zora PlOrlando, FL 32810
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Azul Baldwin Park
Rent Specials
$1,888 - $3,744Special 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
Luxury
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Newport Colony Apartments in Casselberry
Rent Specials
$1,299 - $2,135Special Offer
Specials Limited Time Pricing! 1 Bedroom apartments now starting at $1,299, 2 Bedroom apartments starting at $1,349 and 3BR apartments now s
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Newport Colony Apartments in Casselberry

1166 Pointe Newport TerCasselberry, FL 32707
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Evergreen Mills 50
Rent Specials
$1,580 - $2,900Special Offer
1 Month Free ?? LIMITED-TIME MOVE-IN SPECIAL! ?? Get 4 WEEKS FREE on Select Homes PLUS… ?? LOOK & LEASE SPECIAL ??
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Evergreen Mills 50

1647 E Colonial DrOrlando, FL 32803
Corporate Housing
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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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Shoreview at Baldwin Park
Rent Specials
$1,210 - $2,140Special Offer
1 Month Free Enjoy 1-Month FREE! Apply within 24 hours of touring and app/admin fees will be credited at move-in! Valid on vacant apartments
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Shoreview at Baldwin Park

1001-1009 Shoreview DrOrlando, FL 32807
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Perla Gem Lake
Rent Specials
$2,479 - $3,759Special Offer
Specials Lease a 2- Bedroom Today & Receive a Special Lifetime Fitness Membership! * Conditions apply
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Perla Gem Lake

100 Boucle Jeanne CirMaitland, FL 32751
Luxury
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The Parker at Maitland Station Apartments
Rent Specials
$1,365 - $4,563Special Offer
Specials Now offering special pricing on select apartment homes for a limited time. We also have just one A4 floor plan left! Contact our le
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The Parker at Maitland Station Apartments

955 N Orlando AveMaitland, FL 32751
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The Baldwin
Rent Specials
$1,596 - $2,341Special Offer
1 Month Free Save Big with Reduced Rates & 1 Month FREE!* Restrictions Apply.
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The Baldwin

800 Lombard StOrlando, FL 32807
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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 Now

Aurora on the Trail

825 McCullough AveOrlando, FL 32803
Corporate Housing
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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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Lake House
Rent Specials
$1,894 - $4,579Special Offer
Specials $1,000.00 Special on select floorplans. Call agent for details.
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Lake House

295 NE Ivanhoe BlvdOrlando, FL 32804
Luxury
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Hillcrest Hampton House
Rent Specials
$1,250 - $1,550Special Offer
Discounts July 2026 Summer Savings! Move into a 1 bedroom apartment by July 31st and receive $500 off August & September 2026 Rent!
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Hillcrest Hampton House

2000 Hillcrest StOrlando, FL 32803
Senior Living
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Adele Place
Rent Specials
$1,365 - $1,874Special Offer
Specials Up to $600 in Savings for Immediate Move In, Move In By 7/15/26 - Limited Time Only, Must Move In By: 7/15/26
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Adele Place

7595 Sun Tree CirOrlando, FL 32807
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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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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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Winter Park, FL Local Guide

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

Specials updated: 07-09-2026

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!

Elon Winter Park

SAVE UP TO $800 OFF YOUR MOVE IN COSTS! - *Move In By 7/31!Expires 07-09-2026

Oak Reserve at Winter Park

SPECIAL: Half Off First Full Month's Rent Contact our Leasing Office for Details!Expires 07-09-2026

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 07-09-2026

Seven41 Winter Park

Limited-Time Luxury Living Special! Live Elevated. Live Rewarded. For A Limited Time, Enjoy ONE MONTH FREE When You Lease Your New Luxury Apartment Home With UsExpires 07-09-2026

Alvista Winter Park

Receive up to 2 weeks free rent on select apartment homes for move-ins in August or September 2026. Restrictions apply.*Expires 07-09-2026

The Lofts of Winter Park Village

Rent by June 15th and Get $750 Off Your First Month + a Super Low $350 Security Deposit!!!Expires 07-09-2026

Summerlin at Winter Park Apartments

$1,000 OFF & Reduced Deposit Plus Waived App and Pet Fees!  Subject to change. Optional: Trendy Living & Dining Room Furniture Available! Ask Us How!Expires 07-09-2026

The Taylor at Winter Park

Receive 50% OFF your first month's rent and enjoy waived app & admin fees when you look & lease today! Terms may apply. Contact the office for detailsExpires 07-09-2026

Signal Pointe

Get 1 month FREE on 1 & 2 beds & 2 months FREE 3 bedrooms *Offers subject to change. Some restrictions apply. Contact office for detailsExpires 07-09-2026

Liv at Winter Park Apartment Homes

Up to One Month Free!Expires 07-09-2026

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

Specials updated: 07-09-2026

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.

Cranes Landing Apartments

Lease Today and Receive up to Six Weeks Free!Expires 07-31-2026

Liv at Winter Park Apartment Homes

Up to One Month Free!Expires 07-09-2026

Rosalia Winter Park 55+ Active Adult Community

Receive 8 weeks free of rent after the first of the month of your leaseExpires 07-09-2026

POSTE Winter Park

Save up to $300 off move in - Student and Preferred Employer savingsExpires 07-09-2026

Central Place At Winter Park

Limited Time Summer Special - Reduced Rent on Select Units + $300 Look & Lease!Expires 07-09-2026

Elon Winter Park

SAVE UP TO $800 OFF YOUR MOVE IN COSTS! - *Move In By 7/31!Expires 07-09-2026

Oak Reserve at Winter Park

SPECIAL: Half Off First Full Month's Rent Contact our Leasing Office for Details!Expires 07-09-2026

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 07-09-2026

Seven41 Winter Park

Limited-Time Luxury Living Special! Live Elevated. Live Rewarded. For A Limited Time, Enjoy ONE MONTH FREE When You Lease Your New Luxury Apartment Home With UsExpires 07-09-2026

Alvista Winter Park

Receive up to 2 weeks free rent on select apartment homes for move-ins in August or September 2026. Restrictions apply.*Expires 07-09-2026

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 $2,204.

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 $1,894 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 642 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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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.