The History Behind our Cottages

Learn More About How these Vacation Homes in Destin Began

Believe it or not, the Cottages by the Bay have a rich history. They not only have served as a wonderful spot for families to vacation but also were home to many different Destin locals throughout the years. Each plot of land was individually owned until they were purchased and turned into the Cottages by the Bay.

To book your 2021 vacation at the Cottages by the Bay, click here. To learn more about how this beautiful piece of land came to be, continue reading!

The first purchase made to begin the set of Cottages was 118 Calhoun Avenue in August 2015. The home was originally built in 1952 and was occupied by the Smith family, however now we call it Something Blue. The entire Calhoun side of the property became a place for the Smith family to call home. His mother lived in a small cottage that was later torn down. Then, Mr. Smith built the properties that are named Better Together, Peace, and Tranquility. The Smith family decided to sell the land and move to Pensacola. They sold it to Mr. Braden in 1959 and you will never guess what he decided to build on the property…a barbeque pit.

Fun Fact: Mr. Smith’s son stopped by the Cottages by the Bay while they were being renovated and shared some interesting stores about the time he lived there. While he lived there, he kept three horses, Susie, Midnight, and Rusty, in a corral with a makeshift barn between Tranquility and Something Blue. Can you imagine driving down the road in Destin, FL and seeing three horses?

Just as the Calhoun side of the property has an interesting history, so does the Sibert side. The Okaloosa County “Under Sherriff” once called this land home. His daughter, Ms. Joanne Wells is who we bought the property from. The oldest structure on Sibert Avenue is Love Letter. It was originally built in 1935 and when we started the renovation process, we discovered some interesting characteristics about the house. The structure was originally sitting on cypress tree stumps instead of concrete blocks. Also, the ceiling height was a bit shorter than the average eight feet that builders use today.

Humble and Kind and Family Tradition also has interesting facts about how they came to be. To read more about their history, visit our website! We hope this brief rundown of how these vacation homes in Destin came to be will give you a little insight into how special this piece of property is!

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