How I booked a room at a historic hotel on Airbnb for half the price

Next spring, I’m cruising out of Puerto Rico with my sister. Our itinerary includes some southern islands that I’ve never visited before. We decided to stay 3 nights in San Juan prior to our cruise to explore the area (and to ensure we actually make it on the cruise in case of flight cancellations/delays, etc).

I’ve been to Puerto Rico before, but it was on a work trip (my old corporate job). I didn’t get to do or see anything remotely cool while there.

Initially, I was going to use some Hyatt points to stay at either Hyatt Place San Juan, Hyatt House San Juan or Hyatt Regency Grand Reserve Puerto Rico. I know several readers have had great stays at Hyatt Regency Grand Reserve. And honestly, any of those 3 hotels would have worked fine for our stay.

But the FOMO (fear of missing out) part of me wanted to stay in Old San Juan. How glorious would it be to walk outside your door and see this?

Old San Juan. Photo by Yajnas on Unsplash

So, I started exploring hotels in Old San Juan.

Hotel El Convento

My online searches brought me to Hotel El Convento. This historic hotel was built in 1646 and, as its name suggests, it was originally a convent. It’s the oldest member of the Historic Hotels of America.

I was drawn to the location, amenities and the aesthetics of this boutique hotel.

Photo credit: Hotel El Convento

It’s within walking distance of everything in Old San Juan, including the cruise port. It has a rooftop pool, fitness center and beach club access at its sister hotel (Courtyard Isla Verde Beach Resort).

However, for 3 nights in a room with 2 beds, the price was almost $1200:

For the location and quality of the hotel, that’s probably not a bad price. It’s just that my other choices were free on points.

Searching Airbnb

So, I decided to see if I could find any cute apartment rentals in Old San Juan on Airbnb. Yes, there were a lot available at a lower price. One in particular caught my eye: Hotel El Convento!

To my surprise, I could get the same room on Airbnb for the same number of nights for $505.o6, including all taxes and fees. That’s less than half the price of booking through the hotel directly! And, I could still cancel the booking up to the day before our stay.

I thought for sure this must be a scam. However, I noticed that other boutique hotels in Old San Juan also had listings on Airbnb.

I contacted the airbnb host to confirm that this listing was for a room inside the hotel with two beds. Next, I booked online through Airbnb. And lastly, I contacted the hotel directly to make sure this Airbnb listing was legitimate. The hotel confirmed my reservation.

While our hotel stay isn’t quite as free or cheap as staying at one of those Hyatt hotels, I still could use some Capital One miles to offset the charge.

I’m excited to experience this unique, historic hotel!

But Why?

Why is this hotel and other hotels selling rooms on Airbnb for less money? I’ve come up with no solid answers. Maybe they rarely sell out through direct bookings and figured they would capture some of the Airbnb clients. I really wish I knew the motivation. But, I suppose it doesn’t matter.

Have you booked a hotel room through Airbnb? What was your experience?

How does my family travel so much? We use miles and points from credit card bonuses. See my Travel Hacking 101 post as well as current credit card offers here.

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