My First Airbnb Experience: Old San Juan


Airbnb Old San Juan is part of the Despacito! TPOL Moves to Puerto Rico Trip Report.

In April 2018, I visited Puerto Rico. In April 2018, I decided to move to Puerto Rico. In June 2018, I left Scottsdale, where I had just moved the prior December (see TPOL Moves to Scottsdale: My Drive to the Desert) and needed a place to stay while conducting my House Hunters PR Adventure. For all my traveling, I had never stayed at an Airbnb. Why pay for Airbnb when points are free?

Even with points, there was no way I could afford to stay at the Hyatt House San Juan for months on end. At the same time, the prices on Airbnb seemed a bit outrageous. 2k a month was a bit steep for a furnished rental. Luckily, I read an old post from MileValue (Three Ways to Save Money on Airbnb) and negotiated a decent rate of $1300 per month with utilities included for a one bedroom in Old San Juan.

Living in Old San Juan had its perks. My place was on Calle del Sol, only a few paces from Calle San Sebastian, home to the San Sebastian Street Festival which takes place every January. I was also within walking distance to the grocery store and plenty of restaurants. More importantly, living in OSJ for two months was a good way of deciding whether I could live there permanently (see House Hunters Puerto Rico: Old San Juan, America’s Most Beautiful City).

The place was nice enough though it is was a new experience to have what can best be described as ‘open ventilation’ in the living room. Mosquitoes and I became very good friends. Overall, I prefer the amenities of a hotel to an Airbnb but since my new strategy is to stay in places for months, not days (see TPOL’s Travel Philosophy), I’m going to have to get better at 1) identifying quality Airbnbs via reviews and photos 2) negotiating better rates.

My home for 2 months.
One of the few places in OSJ with parking spaces.

Mosquito Haven 

Living Room 

Moving in


Bad water pressure and not much hot water. While that’s fine for a few days, it got old quickly.


For life, all I need is a comfortable bed, great a/c, Wi-Fi, and a hot shower. Here, the bed and the a/c were on point, but the Wi-Fi was not good. 

Perfectly dark room


Great place to drink a coffee and watch the people go by

The Neighborhood 

Old San Juan is like nowhere else in the US. It is America’s most beautiful city.


The best part of living here was my new best friend that I cleverly named ‘gato negro.’ It was sad to leave him behind. 

Are you an avid Airbnber? Or would you rather just MS your way to PH stays?

So long Airbnb.

Addendum: @boilernuke on Twitter commented, “Unfortunately Airbnb is changing Old San Juan by displacing long time residents and replacing them with investor-owned “deconstructed hotels.” I see the appeal to travelers but the business model is destroying neighborhoods across the globe.” I heard the same thing from my host who runs an owner occupied Airbnb in OSJ. Her hospitality made the experience and for what it’s worth, I would recommend staying in an owner occupied unit.


  1. You sure do move a lot. Michigan, Mongolia, New York, Nebraska, Puerto Rico, Arizona. I love to travel but really like having a home to come back to. Do you think Puerto Rico is it for some years or just another stepping stone?

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