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Gather your favorite people and stay at the Windsor Island Resort

  • Writer: alexa estevez
    alexa estevez
  • Apr 22, 2024
  • 4 min read

Updated: Jun 5, 2024


Photo by Windsor Island Resort Page



It was a Friday afternoon in the middle of March when my parents drove from Miami to Lakeland and picked my friends and me up at our college in a 15-passenger, gray, Mercedes van. It was the weekend of my twenty-first birthday and we headed to an Airbnb community called Windsor Island Resort in Davenport, Fla. 

Excited to enter the resort, we were stopped by security check-in because a few people’s names were not on the guest list. With the owner of the Airbnb on the phone, it took us 20 minutes for the issue to be resolved. To ensure a smooth check-in at Windsor, make sure you have all the guest's names pre-registered, and if you have any extras guests get a separate pass at the clubhouse. 

We were welcomed into the house with the decor of a modern beach house. Baby blue, wooden oars were holstered on the clean, white walls, with a painting of a beach with waves crashing on the shoreline. With the aesthetic was a long, white wooden-legged, farm table placed in the middle of the house alongside the gray marbled kitchen counter. The house had two floors with nine bedrooms. Two of the bedrooms had a theme, one being Spongebob and the other Mickey Mouse. The upstairs floor were carpeted and to prevent it from being dirtied, shoes lined up alongside the door. 



After we settled in, it was around six p.m. and we headed over to the clubhouse to discover the amenities. As we walked there, the community looked like a movie set, with all the same houses that went on for miles over the hills. Since the pool closed at seven p.m. we checked out golf clubs and played a round of miniature golf on the other side of the pool gate. There were eight holes and since we had 15 people, we shared clubs and would go two at a time. My brother was impatient with the group and ended up using his foot as a “club”, which everyone thought was funny. 



The night ended with my dad's chicken wings and salad which was followed by some of us upstairs playing Pac-Man on the arcade machine and others JackBox on the TV. Jackbox is a video game that has multiple options. Our favorite one is Quiplash, which is where everyone writes an answer to a prompt and votes for their favorite. 

As the next morning came, we were ready to spend time at the pool. With a lazy river, two water slides, and a sand volleyball court, we dressed quickly, ate blueberry pancakes and walked over. To begin the pool day, I started at the waterslides. As I waited in line, I observed the people who rode before me to determine if the blue or green slide was faster. I chose the blue one because after I saw people push themselves down the slide they already splashed into the water below. 

Once I was submerged in the water, I drifted into the lazy river that was attached to the exit of it and floated in a circle around the waterslide. 

The rest of the afternoon was filled with competitive sand volleyball with a short intermission for lunch to eat red-sauce meatball pasta at the house. While we ate, we also played Monopoly Deal, a fast-paced card version of Monopoly. 

When night approached I dared all my friends to plunge into the pool at our house before they showered. The catch? The pool was unheated and was not in direct sunlight, so it was ice cold. At the count of three, we jumped in and immediately raced out because of how frigid it was. 

After we warmed up with a shower, we gathered around the marbled kitchen counter and sang Happy Birthday. Once I blew out the candles we ate flowered-shaped iced cupcakes made by Sweets By Sandra. When I bit into the cupcake, there was a pleasant palate surprise of dulce de leche. 



Throughout the night we continued to eat cupcakes and played Family Feud, a gameshow hosted by Steve Harvey in which players guess the results of audience survey questions. It's funny to watch and was even funnier to play. We broke off into teams of boys versus girls and my dad, who religiously watches the game every night, pretended to be Steve Harvey. With the accent and mannerisms, he nailed the role. 



As the game went on, we realized the boys had cheated. One of the guys tried to answer but messed up the wording. Then my brother, with his phone on his lap, explained what he meant which proceeded with a confirmation from my friend saying, “I read the sentence wrong off the phone.” 

When three a.m. hit, our eyes began to shut and we headed to bed. With five hours of sleep, I was surprised we all got up in the morning for croissants and muffins with enough time to spare to check out. 

The three-day weekend at Windsor Island Resort was the perfect place to celebrate my twenty-first birthday. Not only did I enjoy it and feel loved, but my friends mentioned when we got back that Airbnb rentals for birthdays should be our new tradition.

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