543. The 3 Questions Every Smart STR Host Is Asking Right Now

Thanks For Visiting

Airbnb Superhosts Annette Grant & Sarah Karakaian

Education, Business, Society & Culture, Places & Travel, Investing, How To

4.9 • 589 Ratings

🗓️ 19 March 2026

⏱️ 31 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

If you’re hosting in 2026, chances are you’ve asked yourself at least one of these questions:

Am I underpriced if my calendar is filling faster than everyone else’s?

Should I switch to midterm rentals during the slow season?

Why is my listing cheaper than the competition but still not getting booked?

In this episode, Sarah and Annette break down three real questions from hosts inside the Priced and Profitable Bootcamp VIP coaching sessions—questions that many hosts are quietly struggling with right now.

They unpack what these questions reveal about pricing strategy, market positioning, listing trust, and the mindset shifts required to actually build a profitable short-term rental business.

You’ll learn why being the most booked property isn’t always a win, how slow seasons should really be approached, and why lowering your price can actually hurt your bookings instead of helping them.

If you’re serious about optimizing your STR business in today’s market, this episode will help you ask better questions—and make better decisions.

Transcript

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0:00.0	You're listening to the thanks for visiting podcast.
0:08.3	We believe hosting with heart is at the core of every short-term rental.
0:12.2	With Annette's background in business operation and Sarah's extensive hospitality management
0:17.4	and interior design experience, we have welcomed thousands of guests from over 30
0:22.2	countries earning us over a million dollars and garnering us thousands of five-star reviews.
0:28.0	We love sharing creative ways for your listing to stand out, serve your guests, and be profitable.
0:34.9	Each episode, we will have knowledgeable guests who bring value to the short-term
0:38.7	rental industry, or we will share our stories of our own experiences so you can implement
0:43.7	actual improvements to your rentals. Whether you're experienced new or nervous to start your own
0:50.3	short-term rental, we promise you'll feel right at home.
1:10.4	Hello, welcome back to another great episode. My name is Sarah Caracan. I'm Annette Grant,
1:12.2	and together we are. Thanks for visiting. Let's start this episode like we do each and every week and that is showcasing one of you,
1:16.7	our listeners. All you have to do is go to head over to sDR share.com. Share everything you can
1:22.6	about your short-term rental so we can share you here on the podcast. And who are we sharing this week? This week we are
1:28.8	sharing at Urban Pines, AL. Urban Pines, A.L. And they are in Boas, Alabama. What I love about this
1:38.7	property is they are just, I think they're continuing to develop on their land. They have three properties
1:45.9	around a small, I guess a lake pond maybe. I'm not sure the exact size of it. But what I want
1:54.6	you to check out when you go to their feed is they're very different properties. They have a nice mix of a new bill, but they're all
2:06.0	tiny homes. So I like their staying niche in what they do. And one thing that I saw that I think is
2:13.4	really interesting and for all of you wanting to build out your portfolio, potentially you have
2:18.4	some land and you can continue to put houses on it is I did see some reviews of folks renting
2:24.5	out all of them, each tiny home for a family trip. And that is really when you can start to
	...

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