Apartments for Rent with Specials in Winter Park, FL (50 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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Elon Winter Park
Rent Specials
$1,632 - $1,652Special Offer
Discounts Save up to $400 off your move-in costs! - Ask about our Preferred Employer Discounts
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Elon Winter Park

712 Nicolet AveWinter Park, FL 32789
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Seven41 Winter Park
Rent Specials
$1,695 - $3,922Special Offer
Specials Limited-Time Luxury Living Special! Live Elevated. Live Rewarded. For A Limited Time, Enjoy TWO WEEKS 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
$1,299 - $2,460Special 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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The Taylor at Winter Park
Rent Specials
$1,269 - $2,583Special Offer
1 Month Free Move In & Save — Up to 1 Month FREE! Offer available on select homes. Terms apply. Contact us for details.
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The Taylor at Winter Park

2000 Village LnWinter Park, FL 32792
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Berkshire Winter Park
Rent Specials
$1,638 - $4,238Special Offer
1 Month Free ASK US HOW TO GET UP TO HALF A MONTH OFF RENT! *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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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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Alvista Winter Park
Rent Specials
$1,351 - $3,223Special Offer
Specials Summer Savings. Ask us about our look and lease special and get up to 2 weeks free. Restrictions apply.*
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Alvista Winter Park

3935 Sutton Place BlvdWinter Park, FL 32792
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Westmount at Winter Park
Rent Specials
$1,367 - $2,292
Total Monthly Price

Total Monthly Price

Base Rent
$1,367 - $2,292
Total Monthly Price
Varies
Special Offer
Specials Enjoy one month free on all new leases. Restrictions apply, see agent for details.
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Westmount at Winter Park

1701 Lee RdWinter Park, FL 32789
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Signal Pointe
Rent Specials
$1,220 - $2,685Special Offer
1 Month Free Receive 6 weeks FREE when you lease today! *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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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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The Edgewater on Lake Fairview
Rent Specials
$1,747 - $2,942
Total Monthly Price

Total Monthly Price

Base Rent
$1,747 - $2,942
Total Monthly Price
Varies
Special Offer
1 Month Free Take advantage of ONE MONTH FREE. Doors open for touring this month, stay tuned! *applies to base rent, additional fees and res
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The Edgewater on Lake Fairview

2000 Lee RdOrlando, FL 32810
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Inscribe Apartments
Rent Specials
$1,706 - $2,872
Total Monthly Price

Total Monthly Price

Base Rent
$1,706 - $2,872
Total Monthly Price
Varies
Special Offer
2 Months Free Receive Up To 8 WEEKS FREE Base Rent! *Restrictions Apply | Min Terms
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Inscribe Apartments

110 Zora PlOrlando, FL 32810
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Gables Baldwin Park
Rent Specials
$2,265 - $8,315
Total Monthly Price

Total Monthly Price

Base Rent
$2,265 - $8,315
Total Monthly Price
Varies
Special Offer
Specials Don’t miss out – contact our office today to secure your discounted pricing before it is gone!
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Gables Baldwin Park

2050 Jake StOrlando, FL 32814
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Azul Baldwin Park
Rent Specials
$1,925 - $3,913Special 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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The Village at Lake Lily
Rent Specials
$1,677 - $6,249
Total Monthly Price

Total Monthly Price

Base Rent
$1,677 - $6,249
Total Monthly Price
Varies
Special Offer
Specials Preferred Employers Receive Up To 2 Weeks Free Base Rent! Waived App/Admin Fee if Applied Same Day of Touring! Advent Health Prefer
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The Village at Lake Lily

925 S Orlando AveMaitland, FL 32751
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Advenir at Magnolia
Rent Specials
$1,157 - $1,792
Total Monthly Price

Total Monthly Price

Base Rent
$1,157 - $1,792
Total Monthly Price
Varies
Special Offer
1 Month Free One Month Free on Select Units! *Conditions Apply.
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Advenir at Magnolia

210 Welcome WayFern Park, FL 32730
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Newport Colony Apartments in Casselberry
Rent Specials
$1,199 - $2,135Special Offer
Specials End of Summer Special! One Bedroom apartment homes at $1,199! Two Bedroom apartment homes starting at $1,299! When moved in by Aug.
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Newport Colony Apartments in Casselberry

1166 Pointe Newport TerCasselberry, FL 32707
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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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Enders Place at Baldwin Park
Rent Specials
$1,903 - $3,574
Total Monthly Price

Total Monthly Price

Base Rent
$1,903 - $3,574
Total Monthly Price
Varies
Special 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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Shoreview at Baldwin Park
Rent Specials
$1,195 - $2,265Special 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 apartment
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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 - $3,469Special Offer
Specials Receive a Special Lifetime Fitness Membership on Select Apartment Homes! * Conditions apply
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Perla Gem Lake

100 Boucle Jeanne CirMaitland, FL 32751
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The Parker at Maitland Station Apartments
Rent Specials
$1,551 - $4,547Special 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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Courtney At Lake Shadow
Rent Specials
$1,438 - $2,659
Total Monthly Price

Total Monthly Price

Base Rent
$1,438 - $2,659
Total Monthly Price
Varies
Special Offer
Specials LIMITED-TIME MOVE-IN SPECIAL! $1,000 OFF your move-in on select apartments!
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Courtney At Lake Shadow

545 S Keller RdOrlando, FL 32810
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The Baldwin
Rent Specials
$1,545 - $2,406Special Offer
Specials Lease & Save – Limited Homes Available! *Select Homes. Exclusions Apply.
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The Baldwin

800 Lombard StOrlando, FL 32807
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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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Vida at Health Village
Rent Specials
$1,747 - $8,136
Total Monthly Price

Total Monthly Price

Base Rent
$1,747 - $8,136
Total Monthly Price
Varies
Special Offer
Specials 60 days of awesome… on the house! Pricing/Special subject to change without notice.
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Vida at Health Village

2680 N Orange AveOrlando, FL 32804
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Village at Baldwin Park
Rent Specials
$1,969 - $2,957
Total Monthly Price

Total Monthly Price

Base Rent
$1,969 - $2,957
Total Monthly Price
Varies
Special Offer
Specials Receive a credit for application + admin fees when you move into select apartment homes.?? Conditions apply.
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Village at Baldwin Park

2055 Lake Baldwin LnOrlando, FL 32814
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Adele Place
Rent Specials
$1,440 - $1,852Special Offer
Specials Save up to $400 Waived Application and Admin Fee For Immediate Move In, Move In By 8/31/26 - Limited Time Only, Must Move In By: 8/
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Adele Place

7595 Sun Tree CirOrlando, FL 32807
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District On Baldwin Park
Rent Specials
$1,000 - $1,700Special Offer
Specials Move in Special Reduced Rent and Look & Lease Special 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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The Ivy at Gatehouse
Rent Specials
$1,436 - $1,945Special Offer
Specials Get 1/2 OFF September rent for all August Move Ins! Look and lease today and get your admin fee waived!
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The Ivy at Gatehouse

7451 Gatehouse CirOrlando, FL 32807
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Audubon Park
Rent Specials
$1,675 - $3,141
Total Monthly Price

Total Monthly Price

Base Rent
$1,675 - $3,141
Total Monthly Price
$1,675 - $3,141
Special Offer
Specials 2 Weeks Free on Select Units - Move in by 8/31
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Audubon Park

990 Warehouse RdOrlando, FL 32803
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The Gallery at Mills Park
Rent Specials
$1,558 - $2,882
Total Monthly Price

Total Monthly Price

Base Rent
$1,558 - $2,882
Total Monthly Price
Varies
Special Offer
Specials Receive up to 4 weeks free base rent on select units! Contact our leasing office for more details. Terms and Conditions Apply.
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The Gallery at Mills Park

1650 N Mills AveOrlando, 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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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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Winter Park, FL Local Guide

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

Specials updated: 08-23-2026

Take advantage of these move-in and rent specials that are ending this month for top Winter Park, FL apartments. Act fast and don’t miss out on an incredible deal on your perfect new place!

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 August 23, 2026

Signal Pointe

Receive 6 weeks FREE when you lease today! *Offers subject to change. Some restrictions apply. Contact office for detailsExpires August 23, 2026

Liv at Winter Park Apartment Homes

One Month Free!Expires August 23, 2026

The Taylor at Winter Park

Move In & Save — Up to 1 Month FREE! Offer available on select homes. Terms apply. Contact us for details.Expires August 23, 2026

POSTE Winter Park

Save on move-in costs! - Student and Preferred Employer savingsExpires August 23, 2026

Elon Winter Park

Save up to $400 off your move-in costs! - Ask about our Preferred Employer DiscountsExpires August 23, 2026

Westmount at Winter Park

Enjoy one month free on all new leases. Restrictions apply, see agent for details.Expires August 23, 2026

Alvista Winter Park

Summer Savings. Ask us about our look and lease special and get up to 2 weeks free. Restrictions apply.*Expires August 23, 2026

Oak Reserve at Winter Park

SPECIAL: Half Off First Full Month's Rent Contact our Leasing Office for Details!Expires August 23, 2026

Central Place At Winter Park

Hot Summer Move-In Specials - Reduced Rent on Select Units & $300 Look & Lease!Expires August 23, 2026

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

Specials updated: 08-23-2026

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.

Liv at Winter Park Apartment Homes

One Month Free!

Rosalia Winter Park 55+ Active Adult Community

Receive 8 weeks free of rent after the first of the month of your lease

Alvista Winter Park

Summer Savings. Ask us about our look and lease special and get up to 2 weeks free. Restrictions apply.*

Oak Reserve at Winter Park

SPECIAL: Half Off First Full Month's Rent Contact our Leasing Office for Details!

Central Place At Winter Park

Hot Summer Move-In Specials - Reduced Rent on Select Units & $300 Look & Lease!

Berkshire Winter Park

ASK US HOW TO GET UP TO HALF A MONTH OFF RENT! *Terms & restrictions apply/subject to end without notice.

Seven41 Winter Park

Limited-Time Luxury Living Special! Live Elevated. Live Rewarded. For A Limited Time, Enjoy TWO WEEKS FREE When You Lease Your New Luxury Apartment Home With Us.

Signal Pointe

Receive 6 weeks FREE when you lease today! *Offers subject to change. Some restrictions apply. Contact office for details

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!

The Taylor at Winter Park

Move In & Save — Up to 1 Month FREE! Offer available on select homes. Terms apply. Contact us for details.

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 $2,345.

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 $2,265 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 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

decorative image for Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities article

Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities

Written by: Darla Ferrara

When people think of Orlando, FL, the iconic theme parks and buzz of downtown tend to steal the spotlight.

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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.

decorative image for Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers article

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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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.

Articles, How-To's, and Tips

decorative image for Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags article

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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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.