VRS170 – Practical Vacation Rental Investment with Michael Hamilton

My guest today took his interest and knowledge of real estate investment and has turned it into a vacation rental business. With three properties currently listed on Airbnb & VRBO, Michael Hamilton was about to fly off to North Carolina to close on the fourth, when I was able to talk to him from his San Diego home.

Michael emailed me at the end of last year asking for some feedback on his listing text after he’d studied my ebook, Hypnotic Language for Vacation Rental Listings and Emails. I was interested in his choice of properties and the way he was achieving such great results as evidenced by the Airbnb reviews.

He shares his strategies for purchasing new properties which include his passion for surfing and the outdoors, balancing that against the economic factors of selecting a location.

This is a fascinating glimpse into the world of a practical vacation rental investor – one who has minimal emotional participation in the rental potential of a property but rather sees it as a working entity.

In this interview Michael talks about:

  • How his love of surfing drew him to the North Carolina coastal area
  • The importance of growth indicators to location choice
  • The Airbnb impact on bookings
  • Creating transparency in listings
  • What the About Us page does to increase interest
  • Why he prefers a systems dependent business for managing multiple properties
  • His 3 tips for anyone starting a similar business

Links mentioned in this episode:

Vacation Rental Success Summit

Fortune Builders

Bigger Pockets

Chill Beach and Surf Bungalow

Magical Bungalow OBX

Chill Beach and Surf Pad – San Diego

The E-Myth Real Estate Investor

Enjoyed this episode? Be sure to listen to Part 2 > VRS178

Terry Whyte

Thank you Heather.

Alex Concepcion

Great episode. I love learning more about the investing side of vacation rentals. I think with how fast the industry is going, its inevitable that professional minded business-people will start entering the market. Mike’s surfing business reminds me of a friend of mine who runs wavecation.com, a niche site that specializes in surfing destinations.


    Thanks Alex for the compliments. I have bumped into wavecation as well and I think its a great idea and business model. When we started initially we were considering something similar, we found our that our strengths were really in the real estate acquisition, operational efficiency, communication and creating an outstanding guest experience (and committing to constant improvement) so we decided to focus here.

    We differ from wavecation as we own and operate our properties and also or main clients are not solely folks looking to “surf.” Sure that is an attraction – surfing is sexy! We do get folks on family trips, in town for events and festivals, special personal events and even folks renting for off season holidays. We love to host everyone but surely there is a special connection and a bit more we can offer someone who surfs. Be careful if you pick up a surfboard – it may change your life!!

      Alex Concepcion


      I’d love to connect via email. Mine is alex@vacationtoolbox.com.


        Will do now and you can see our personal website for Live Swell Beach Bungalows at http://www.live-swell.com

One Chic Retreat

Wonderful info! Thank you for this.


    Your welcome and thanks for taking the time to listen in. I think we may have some more interesting topics and perspective in the future!

Gregg Geraghty

Great JOB Mike. I saw this on FB/Face Book but just listened to the interview in it’s entirety. GREAT content, really nice job let’s talk again soon.


    Thanks Gregg. You were one of the first to help me get started and its not been easy but its been worth it.

Capt. Mike

Great info Michael. Awesome that you were able to take your passions of travel and surfing and use them to help shape your business. It’s never work if you do what you love. From the interview it sounds like you are well on your way to a fun, exciting and profitable careeer in the vacation rental business.


    Thanks Michael for the kind words. We have always loved being by the beach and this was an opportunity to recreate the type of experience we love so much for guests. From your screen name my feeling is that you like the ocean and beach to! Heather and I just did a part 2 that is a bit more specific around the investing “mindset,” and technical. Its VRS178 which can be found on CottageBlogger or there is a link on my “Investor” page http://www.live-swell.com/investors and may provide some valuable insights.

Jeff Kluger

Mike Hamilton is the “Real Deal”. I have been privileged to be Mike’s and Maria’s Realtor with their three purchases on the Outer Banks. Normally, I find myself having to educate my clients about the Real Estate buying process and rental market, but with Mike, I feel that I have learned just as much from him as he may have from me. In fact, my wife and I recently purchased our own Outer Banks rental property and I look forward to picking Mike’s brain to help me with what he has learned for my own property. Mike and Maria have Great system in place…..the properties they have purchased and renovations they have made on their homes are amazing and the rental income they have achieved shows that their system works. Looking forward to watching their business continue to grow and prosper on the OBX.

Kristin Silveira

Another great episode Heather! My husband and I have looked at our purchases in a very similar way, it was great to hear the same principals from you Mike! Since we are growing and expanding here in RI, the discussion about systems was particularity interesting. I’m ordering a copy of the e-myth now. I would appreciate any other tips or suggestions!


    Cool feel free to connect mike@live-swell.com – would be happy to chat.

Zach McKinnis

I’m privileged to have Mikey as a good friend of mine. After listening to this podcast I’m really excited and inspired about the opportunity within vacation rentals. I’m not surprised that Mikey has such high level success within his business. His dedication to ethics and integrity as well as his attention to being transparent and upfront with what his rentals provide make booking his rentals a no brainer! Looking forward to seeing your business grow Mikey!

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