What We’re Using to Grow our Vacation Rental Management Business in 2023

I can’t believe another year has ended and we are already in 2023.  As a father of 4 young and crazy kiddos, each year seems to go by faster and faster.  And our vacation rental management business and digital welcome book start-up continues to grow, it’s important to keep up with the best platforms available.

We’ve had the opportunity to research, test, and implement some great tools to help to grow our businesses.  So here are some tools and platforms you should highly consider using in 2023.

Disclaimer:  There are many good software platforms and resources available.  This is not a comprehensive list of tools / platforms we use or recommend.  But a few that have delivered tremendous value to our small vacation rental management businesses.

Dynamic Pricing

If you have more than one property, increase the likelihood you’ll achieve an optimal nightly rate for your space, by using a dynamic pricing tool like Pricelabs or Wheelhouse.  These pricing tools will help with automatically adjusting prices for seasonal fluctuations, special area events, and other demand factors.  Take time to learn how to create more complex rule sets and you’ll be sure to capture more booking revenue.

Dynamic pricing tools are not set-and-forget it.  The best property managers will go in daily to make manual price adjustments to specific nights or time periods.  Currently, there is no software replacement for a host’s unique understanding of their neighborhood and space.

There are other great pricing solutions we have tested and used at one time but Pricelabs or Wheelhouse offer the best overall value.  Each have development teams that regularly release updates and new features. Both have monthly fees starting at $20 per property.

Message Automation

Three years ago we opened our 1st short-term rental in downtown Detroit.  At the time I really had no idea what it would take to be successful and all the challenges that come with a being a host.  But from my 20 years of being a web developer, I knew automating as much of the businesses was fundamental to operations and scaling.

One of the first tools I researched and evaluated was a messaging tool.  A friend, who had 3 cabins in the Smokies, shared with me how he responded to each and every one of his messages.  At the time I remembering saying, “Wow, that seems like a lot to work…there’s got to be a tool that can help reduce the amount of back-and-forth communication…”

And still today we use a messaging tool called Hospitable (formerly Smartbnb).  There are property management platforms with integrated messaging but we love Hospitable for the following reasons:

  • Intuitive and easy to use user experience
  • Great mobile design
  • Team / Cleaner notifications and calendar
  • Smart messaging to answer common questions
  • Automate door codes with Schlage Encode or Remote Lock

Our team uses messaging automation to streamline our guest communication but this does not replace the necessary personal attention each guest deserves.  And won’t account for every possible question or scenario. 

Guest messages should be short and simple.  Want to see an example?  Download our messaging template and customize for your properties.

Download Messaging Template (PDF)

Virtual Assistants

Eventually we grew to a point where building out a support team would be key to optimizing operations and win back a ton of time.  Creating a great guest support experience allows us to focus more on growing the vacation rental business and Everhost startup.  Luckily, with years in the online space, we had experience working with overseas contractors before outsourcing became such popular option.

20 years ago we were working with developers in India, China, and the Philippines.  If you have ever tried to work with overseas contractors you know the challenges of creating a functional team.  Today it is still a challenging and back then it was much more difficult. 

Based on these experiences we chose to hire virtual assistants from the Philippines.  Without getting into all the challenges and nuances of other work cultures, below are a few competitive advantages our virtual assistant team offers:

  • Great English (spoken and written)
  • Familiar with western style work culture and expectations
  • Affordable ($300-$900 per month for 30-40 hrs / week)
  • All our VA’s are former Airbnb claim specialists
  • 3 VA’s on 8 hour shifts offering 24×7 guest support
  • Social media marketing when not supporting guests
  • Willing to work weekends

We feel extremely fortunate to have built a small VA team with deep customer support experience in the vacation rental industry.  Part of our success is because we treat our team very well. When interviewing VA’s we shared our number one priority was to provide amazing guest services and if they had to spend 2-3 hours helping out one guest, then we would be very happy.  Surprisingly, a number of VA’s shared with us their experience working for other vacation rental management companies.  Detailing how they didn’t feel valued, working long hours in demanding environments, leaving little time for even a bathroom break, in addition to getting paid below average wages.

Using a different metric for success and paying above average has helped us attract hard working, professional, and reliable talent.

If your business is ready for a VA, start your search for a great Filipino virtual assistant using https://onlinejobs.ph/

Guest Welcome Book & Area Guide

As the short-term rental industry continues to mature and new players continue to enter the space, one of the most important aspects of being a 5-star host that does not get enough attention is the guest experience.   Immediately after booking guests should have the best experience possible but even with large operators like Expedia, Booking.com, and premium resort / hotel brands all a guest receives is 1 or 2 emails providing booking details for their trip.

Based on what our guests have shared with us over the years, here are some the most valued aspects to the start of a great stay.

  • Easy access to all info. needed for their stay
  • Helpful tips, advice, and details about property
  • Want local experiences and recommendations
  • Curious to know about neighborhood and local conveniences like grocery stores, transportation, etc…
  • Having access to support from hosts when there is a problem

So how can smaller hosts, with limited resources and time, create a memorable experience immediately after a guest books?  Create an amazing guest welcome book and area guide. Developing a welcome book is one of the easiest ways to elevate your guest experience and if done right, delivers tremendous value to current and future guests.  

When researching different digital welcome book solutions we wanted a platform that not only gave us the ability to provide information to guests but could be an extension of our local knowledge.  We love being in areas like Detroit and want to encourage visitors to go out and explore our favorite places.  There are a handful of great digital welcome books available but none focused on connecting the guest experience with the local community and businesses.

So we decided to build our own called Everhost.

Some of the features that make Everhost unique are:

  • Curated local places based on property’s address
  • Help guests skip the tourist traps and highlight your favorite places
  • Highly customizable
  • Easy setup and use
  • Deals and discounts (in development)
  • Measurable Impact / Analytics (in development)
  • Create welcome books for up to 10 properties, at no cost


Here’s a checklist we use for our cleaning team.  We put this list into a binder and is a great tool for training new cleaners.

Download Cleaner Checklist (PDF)

Get Started Today!

Create a 5-star guest experience immediately after each guest books.  Save time and eliminate the back and forth communication.  Make more money by making it super easy for guests to book again!

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