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Then there were Two St. Augustine Guest Houses 

Wendy and I were in love. Not only with each other but with St. Augustine and we loved being vacation rental hosts. As we were heading out of town, we decided to extend another day and look at a house that was about a 10-minute walk from downtown. We went into this really cute neighborhood with hidden streets and saw a house that had a circular driveway and a Spanish influence and we toured it. Across the street was another house, and leaning against the house was a for sale sign, we were curious. 

Behind the white fence were two dogs, and I bravely opened the gate (they were small dogs), befriended the dogs, and rang the bell. When the woman answered the door, I asked her if her house had just been sold. She said no, it was about to be listed the next day. We asked for a tour of the house and she walked us through and it was amazing. I wasn’t expecting the giant parrot as we opened the door to the backyard when I screamed and we all laughed.  Wendy and I had a plane to catch.  Could we buy this house?  Should we buy this house? We were new to the vacation rental business, but we couldn’t resist the opportunity and we got home and bought the house the next day after seeing it for about 10 minutes. 

This house was amazing and fairly new as it was built 10 years ago in a historic neighborhood.  The concrete block home had been freshly updated with the finest appointments–travertine floors, new carpet, granite, and quartz countertops, LED lighting, a fireplace, custom closets, and so much more. We decided to rent it as a long-term rental for a year while we got our feet wet in the vacation business, learned more about St. Augustine, and got to know the house.  We rented it to a nice family for a year as we continued our St Augustine vacation rental adventures and became a 5* Airbnb Superhost and VRBO Preferred Partner with our downtown guest house. 

It’s been a few years now and people love this house and we love this house. Our family loves this house. Our friends love this house and our guests love this house as it’s so close to the historic district, so close to Francis field where all the festivals are and so close to the Village Inn where they have Free pie on Wednesdays. 

How we found and started the St. Augustine Guesthouse 

Truth be told we had never heard of St. Augustine before coming here in 2015. Wendy and I were at a Florida marketing conference on Amelia Island and we had a free night. We were looking for a place to go for dinner, and we stopped by the table that was promoting St. Augustine as America’s oldest city.  The man at the table suggested we drive an hour down the road and we’d come to St. Augustine, so we did.  Our first stop was Caps on the Water which has the most breathtaking sunsets. After dinner, we went into the historic city for dessert at Cousteau’s Waffle and Milkshake Bar on Hypolita Street during the Nights of Lights Festival.  This wasn’t just any festival. This was the 450th anniversary of St. Augustine and it was spectacular. Where were we? 

After driving around and seeing the thousands and thousands of white lights on the historic buildings, talking to the horse and buggy drivers, seeing and hearing the Holly Jolly Trolley, and seeing people everywhere enjoying the festivities, we had to learn more. Although we had to get back to Amelia Island, our curiosity was piqued. We had just been to one of the most beautiful places we had ever been to, and it was in Florida.   

Shortly after we got back to Boston, we scheduled a trip to St. Augustine and stayed at Casa Monica. We toured the city, went to the beach and we took advantage of their package with the Serenata Beach Club which we now offer to our guests. We walked all around enjoying the music and the food and we decided we needed to find a way to live here, at least part-time.  We decided that we were going to buy a house and start a short-term rental and promote it on Airbnb and VRBO. We visited a few more times with friends and family and stayed at a few vacation rentals in Lincolnville, and one by the Bayfront. We looked and we looked and we couldn’t find a house to buy but we fell in love with the city a little more each time.  We decided to walk back to where it all began on Hypolita Street, in the heart of the historic district. 

As we were walking down the street, we saw an apartment for rent and it was in the most amazing location and the two floors and spiral staircase to the master made it perfect for a guest house. It was above a wine store and across the street from a spice and tea shop and a great location. Could we possibly rent this apartment and turn it into a vacation rental?  We could and we did. We opened the first St Augustine Guest House in March 2018 and after shopping, decorating, marketing, designing, and planning, we loved every minute of it, except one. 

Wendy went down the night before I did and stayed in the future guest house. At about 1:00 AM, I got a phone call and Wendy was a little panicked as the bar next-door had speakers pointed out the windows, and the whole building was shaking.  What had we done? As we had never visited the apartment at night, we didn’t know that the bar was loud and that there were no other neighbors as we were in the commercial district. Did we make a mistake?   

After a few conversations with the neighbors and the landlord, it was agreed that we would buy them an air conditioner, and they would shut their windows and bring the speakers in. We made plans to prepare the house for soundproofing and let the guests know that there was a bar next door.  The vacation rental was a hit from day one and people loved the location being in the middle of it all, and they loved what we did with the place as far as decorating it with fun colors and lots of local art, and we loved being hosts.   

As luck would have it, shortly after we signed the lease, we found a house to buy.