VRS458 - Building a unique short-term rental business with minimal investment with Kelly Cronin of Cronin's Castles

Investing in property in three very diverse markets, mostly off-grid, and in wildly different locations may not be unusual, but doing it simultaneously, and on a small budget, requires a very unique perspective.  And when the investors' motto is Plan Less – Live More, you may wonder how this all comes about.

In her day job, Kelly Cronin provides multi-site support to veterinary emergency and specialty centers.  Outside of this, and with very little capital, she was able to fund purchases in Puerto Rico, Utah and Alaska – a collection that has become Cronin’s Castles.

With the help of her multi-talented, 11-year old, marketing director-daughter, Kelly is achieving a mostly direct-book business and in this episode, she shares how the business came about, what makes it tick along, and what’s next in the works.

You’ll hear about:

  • How Kelly got into the real estate and short-term rental business.
  • Where she found the properties and her philosophy on buying diverse real estate
  • What makes unique properties so desirable in today’s market
  • The marketing platforms that work the best and why she aims for direct booking as the primary driver for her business
  • The ways one-eyed Willie, the rooster, wild horses, and an iguana appeal to her demographic
  • How to create effective barter arrangements with influencers and photographers
  • The technology platforms that make her business more effective and easier to manage
  • Creative ways to employ good staff and how to work with vendors effectively
  • Kelly’s advice for any new investor in the STR market

Links mentioned:

Cronin’s Castles

Facebook: Cronins Castles

                  Vieques Seahouse (Puerto Rico)

                  Inn a Nutshell (Alaska)


Izzy: Video of Vieques Seahouse

Airbnb listings:

Inn a Nutshell

Vieques Seahouse




Dorian Sanders Photography