Insights and Strategies for Short-Term Rental Success
Get actionable insights from a vacation rental expert that can help set your business for success.
In this episode of the Hospitable Hosts podcast, we are excited to welcome Annie Holcombe, a co-host on the Alex and Annie Vacation Rental Podcast. Going into its fourth year, the popular podcast for vacation rental professionals is an excellent source of expert insights, industry trends, and inspiring success stories of industry leaders, entrepreneurs, and innovators.
With 30+ years of experience in hospitality and tourism, Annie is an expert in managing owner relations, marketing, and online distribution. After a successful career working with some of the biggest brands in vacation rentals, she launched a consulting business to help hosts and property managers solve the STR puzzle.
In the episode, Annie discusses how to define the right channel mix for vacation rentals. She emphasizes the importance of a direct booking strategy for hosts looking to grow their portfolios. She also shares tips on building trust on your direct booking site, determining the pricing strategy for a new market, delivering outstanding guest experience, and what to consider when starting a property management business.
Press Play now to get actionable insights from a vacation rental expert that can help set your business for success.
If you prefer to read the highlights, we’ve got a summary of the key takeaways below.
Ideal Channel Mix Hosts Should Be Aiming For
Annie points out that when building a strong channel mix for your vacation rentals, choosing the right platforms depends on the number of properties you manage, their characteristics, your location, and your target market. For example, urban hosts in the markets that attract international travelers can benefit from using Booking.com.
“Booking is something that I constantly recommend to people, and I think with the upcoming World Cup coming to Canada, the US, and Mexico, if you're not on Booking.com, you're going to miss out on a huge portion of the market.”
Annie also recommends considering niche sites like Furnished Finder that cater to specific travel types. Annie underlines that managing listings across multiple platforms is hard unless you have a PMS like Hospitable that connects all your booking channels into one centralized system and keeps your calendars in sync.
Direct Booking Strategy
Annie thinks that having a direct booking site, rather than relying on OTAs, is essential for every vacation rental host and property manager looking to grow their business.
“If you have any intention of growing, always have some direct strategy in place and just have it on the back burner as you grow. And you can hone your skills on your content and make sure that these AI tools see you as the expert in your market, and have the information about the attractions and those things on your site. And then if you do grow, you have something to fall back on, and you're not dependent on any one channel.”
Annie points out that having a direct booking site is a great way to build a unique brand identity and show it to your target audience. “Make sure that you have your logos and the information about your company in place,” she recommends.
Annie also shares ways to effectively build trust among your potential guests that can help you increase direct bookings:
Ask guests to leave you reviews on Google or Trustpilot that you can post on your website
Make sure your pricing is consistent across your channels
Be transparent and honest in your communications.
“I think it's always about you telling your story,” Annie notes. “People want that human connection, even more so with AI. You want to feel like you have some connection, and hospitality is a connection at the end of the day.”
Getting Started with the Pricing Strategy
“If you own the property, you have a little bit more flexibility than if you're dealing with it for a particular owner, because a lot of times they'll say, I need a bare minimum of X for a night or a month that I need to make,” Annie points out.
She recommends starting by developing your pricing strategy through market research and by exploring the website you plan to list on. “Look at Booking.com, Airbnb, Vrbo, whatever those are, and look at comparable properties. That is a great way to start, and then you'll find out your baseline based on your cost of doing business, cleaning services, maintenance, and other expenses. But I think looking at your competitive set and setting that up from the beginning is important,” Annie says.
Becoming a Professional STR Property Manager
Speaking about transitioning from self-managing your own properties to managing vacation rentals for other people, Annie emphasizes the importance of having a PMS that you can grow with. “Having a system in place where you can house your details and connect to a lot of channels is important.”
Annie recommends finding a mentor whom you could reach out to and connect with. “One thing that's great about this business is people want to share their learnings, and help people avoid some of the mistakes,” she points out.
Another recommendation is to join vacation rental alliances or associations that can provide educational resources. “I am on the board for VRMA, and one of the things that we've discussed is how to provide access to education for someone who is starting. And so that they know that they could always go to VRMA to access information, ask questions, go to road shows or educational webinars,” Annie explains.
Annie also talks about some red flags that a property manager should be looking out for when deciding whether a property owner is the right fit for their business, gives advice on how to assess a property’s potential, and shares how to scale a cleaning team to ensure smooth operations as you expand your portfolio.
Listen to the full episode of the Hospitable Hosts podcast to learn about effective strategies that can help you build a thriving STR business.



