Our First Experience with Airbnb: St. Augustine, Fl

As many nights as I have spent in hotels, I have accumulated some rewards points to show for it. In my past life, I was flying charter and I spent many more nights away from home than I did at home. I accrued quite a few rewards points during those years and I have many of them left in my Hilton Honors account. The beautiful thing about these points is I can use them to vacation with my family and have free hotel stays.

The negative side of hotel stays is we can not bring our dog, Teddy. While some hotels do allow dogs, many are very restrictive on what you are allowed to do with your dog during your stay. For example, some hotels will permit dogs but they require them to be caged if you are not in the room with them. My dog is so well behaved, we have never even purchased a cage for him and I think the experience would be too traumatic to risk.


So recently when we decided to go on vacation, I opted to not use my hotel points but rather I settled on giving Airbnb a try. The obvious advantage for us was that many Airbnb hosts will allow pets with no restrictions.

Our vacation mission was to spend a night in St. Augustine with our dog and our toddler. I settled on an apartment on Cuna Street, right next door to The Gourmet Hut – a quick walk to the Castillo De San Marcos on the bay. Our usual central location during our stays in St. Augustine is near the Castillo De San Marcos, George Street, and the many shops and restaurants near the bay.

When I reserved the room, I was able to do so right from my smartphone. I selected the night I wished to stay, entered my passport number and photo, and paid to reserve right from the app. I was able to communicate with my “host”, or the owner of the apartment we planned to stay in quite easily.


If you are familiar at all with St. Augustine, you will understand me when I say parking is limited downtown. When my wife was going to school at Flagler College, she did not have the benefit of the lovely new parking garage. Don’t get her started on the meter maids… When we arrived at the apartment, all was as advertised. We were able to unload our car from the narrow Cuna Street and then I parked at the parking garage while my wife got settled. I totally grabbed an Uber ride back from the parking garage, to save myself a walk on a very hot Florida summer afternoon.

The price was on par with a hotel room in town, but we had total privacy, amazing location, and best of all we had a welcoming place to keep our dog during our stay. It was a quick trip, but we still hit all our major favorites, like Osteen’s Restaurant, Crucial Coffee, The Gourmet Hut, and many of the shops along George Street. Perhaps someday we will own our own property in St. Augustine so we can stay there anytime we want!