From Paper Calendars to Algorithms: How the Holiday Rental Industry Has Changed Since 1996

When we began managing holiday homes in 1996, things looked very different. There were no apps, no Airbnb, no automated check-ins — and most guests found us through newspaper ads or word of mouth. The internet was just starting for public use and dial up was the thing.

Fast-forward to today, and the short-term rental industry is unrecognisable.

Then vs Now – A Snapshot

1996Today
Ads in local papersMulti-channel digital marketing
Guestbooks & handwritten notesInstant guest messaging, SMS & reviews
Cash-on-arrival paymentsSecure, automated online bookings
House keys hand deliveredKey safes & smart locks
Family-owned holiday homesMixed with investment portfolios
Limited regulationStrict NSW STRA & compliance laws

What’s Changed?

1. The Rise of Platforms

Airbnb, Stayz, Booking.com, and direct booking sites have reshaped the industry. While this gives owners and guests more reach, it’s also created more competition — and more complexity. Dynamic pricing, guest screening, calendar syncing… it’s no longer a side hobby.

2. Regulation & Compliance

Holiday letting has become formalised, especially in NSW. STRA registration, safety standards, and even strata by-laws now govern how properties can be used. Owners must meet minimum standards and stay updated on changes — or risk fines or bans.

3. Guest Expectations

Today’s guests expect hotel-level presentation with home comforts. Fast Wi-Fi, spotless linen, 24/7 support, and self check-in are the norm. A professional touch is no longer a bonus — it’s expected.

4. The Rise of Investors

What was once dominated by owner-occupied holiday homes is now shared and even monopolised with investor portfolios. This can drive income growth, but it also means guests have more choices — so presentation, pricing, and management quality are more important than ever.

What Hasn’t Changed?

  • People still want to feel at home when they travel
  • Owners still want peace of mind and reliable returns
  • Properties that are well cared for still outperform those that aren’t
  • Trust, service, and consistency still matter more than scale

Why Our Experience Matters

At My Holiday Home Manager (and Lakeshores Accommodation) we’ve seen it all — from faxes and phone bookings to algorithm-powered dynamic pricing. Our local knowledge, hands-on management style, and genuine relationships with owners have remained at the heart of everything we do.

We haven’t followed the trend of rapid expansion just to sell off a portfolio. Instead, we’ve chosen to grow sustainably, focusing on quality over quantity — and that’s what makes us different. We love what we do, it isnt just a job to us. We get satisfaction from our happy owners and guests.


Thinking About Listing Your Property?

Whether you’re new to the idea or considering switching managers, we’re happy to share insights and guide you through the process. We know what works, what’s changed — and what still matters most.

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