Zen and the Art of Real Estate Investing with Jonathan Greene

116: All of the Short-Term Rental Insights You Can Handle with Kenny Bedwell


The short-term rental market is far from dead, and with the right marketing, systems, and data, it can be a more lucrative investment than long-term rentals.

On this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Kenny Bedwell, founder and CEO of STR Insights. Kenny uses data to find the best places, prices, and markets in the short-term rental market. His predictions using data-backed analysis have helped him create a lucrative personal investing career and a successful company helping others do the same. Kenny is also the co-host of the STRonomics podcast.

While data may not be the first thing that comes to mind when considering a short-term rental investment, Kenny Bedwell explains why it should be at the forefront of your analysis. Jonathan and Kenny break down the origin story behind STR Insights, some of the nuances of property management in the short-term rental market world, and how you can remove the guesswork from what your renters can expect from a stay at your property. He also explains why these investments are 100% a part of the hospitality industry, and Kenny offers five key metrics he uses to analyze assets before buying them. You’ll hear why understanding that short-term rentals are seasonal matters, the signs of an emerging market ripe for investment, and the best metric for consumers to use to gauge whether or not an STR is a good one.

Kenny Bedwell is a short-term rental expert with experience and data to help you get the most bang for your buck in the market.

In this episode, you will hear:

  • When data analytics became most important to Kenny Bedwell’s business
  • Kenny’s interest in real estate and why it piqued his interest as an adult
  • Using data to predict real estate prices and where to target your investing
  • The origin story behind STR Insights
  • His first investment property—a long-term rental—and why finding it boring propelled him toward short-term rentals
  • Implementing data and research into your investment property searches
  • The nuances of property management in the short-term rental market
  • Taking the guesswork out of what your renters can expect out of a stay at your property
  • Why short-term rentals are 100% part of the hospitality industry
  • The five key metrics to analyze before buying a short-term rental investment
  • Understanding the seasonal nature of short-term rentals
  • Identifying the signs of an emerging market
  • The problem with purchasing a short-term rental with a fallback plan as a long-term rental
  • Why STRs aren’t dead and are still a profitable asset class
  • The best metric for a consumer to gauge whether or not an STR is good
  • Avoiding burnout and setting up systems that work
  • Must-have amenities for your rentals and how to market them

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If you enjoyed this episode, we’ve created a PDF that has all of the key information for you from the episode. Just go to the episode page at to download it.

Supporting Resources:

STR Insights website –

STR Inisghts on YouTube –

Find Kenny Bedwell on Instagram –

STR Insights on Instagram –

Connect with Kenny on LinkedIn –

STRonomics Podcast –

Website –

YouTube –

Instagram –

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TikTok –

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Bigger Pockets –

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