This as-told-to essay is based on a conversation with Keisha Blair, 48, an author and founder of the Institute on Holistic Wealth, an educational self-help platform. She lives in Ottawa, Canada, and owns a villa in Kingston, Jamaica, that she turned into a vacation rental in late 2025. She later converted an unused pool house into a separate 108-square-foot unit on the property. The following has been edited for length and clarity.
When I was 31, my husband died eight weeks after I gave birth to my second child. It felt like lightning had struck — it felt so far off that this rare illness would strike my family.
So I went on a healing journey. I went back to Jamaica on a one-year sabbatical, staying at the three-bedroom home I had purchased with my parents years before.
I never thought this place would ever come back up again in terms of anything related to my business. It was just a place that I went to heal, to cool out, and to get away from it all because I was coping with grief.
My first instinct was to sell the property
The reason I turned the property into a healing retreat was circumstantial.
My father died in April 2025, and I was his main caregiver. My mom called me and said, “You’re going to have to make a decision as to what to do with it.”
At the time, my first instinct was to sell it. It’s this huge one-acre property — I had no idea what to do with it.
I thought about it really long and hard and said, “Let’s try to see how we can open it up on Airbnb so people can visit.”
After all, this was the place that gave me healing. How could I ever part with that without a second thought?
In the time since, I remarried, and my husband and I did a lot of work restoring the property. We spent days and nights down there in the larger villa first, because we weren’t even thinking of converting the pool house yet.
In December 2025, we opened the property up to the public. As soon as we listed it, we got bookings.
Right now, the villa fits six people comfortably, but people started saying, “We want more people to come with us, but you only have three rooms.”
I found myself constantly telling people, “There’s this tiny villa, but it’s not open yet.”
I turned our 108-square-foot pool house into a separate unit
I love the whole movement toward turning unused space into livable, smaller spaces. It gave me the idea for what to do with my space and turn it into a tiny cottage.
If there’s not enough room in the main villa, a couple, a solo traveler, or somebody else can experience that wellness experience in the tiny home as well. And it’s at a lower price point.
The renovation costs for the pool house came in under what I expected, but in some areas, I spent more than I thought I would.
The plumbing was probably the most expensive, because we had to put in a new sewage system, and the labor that went into that was very intensive. So that was the bulk of the cost.
The plumber was also a tiler. We literally ran down to the tiling store, bought the tiles, and he gave me a discount on both jobs, so I didn’t have to spend too much on labor for the tiling work.
A big lesson there was to get multi-skilled contractors who can give you a bundled cost for the different items you need done in your tiny home.
My husband also worked on the project a lot; he worked with the plumber and installed a lot of things as well. We did a lot of the labor ourselves in terms of sourcing materials and getting stuff done.
So I think we saved a lot, budget-wise, by setting up the tiny home ourselves, doing what we could, and negotiating.
The whole property was so healing for me, so renting it out is so meaningful because it means that other people will be able to experience that, too.
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