Places to Stay

My Favorite Airbnb: Two Homes on One Lush Property in the Florida Keys

This resort-style rental was the perfect Florida getaway for a summer group trip.
An outdoor pool and bar.
Courtesy Airbnb

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The late Jimmy Buffett’s popular song “Margaritaville” was based on his time in Key West. Although Margaritaville was a fictional oasis (turned restaurant and resort) where people operated on island time, the Florida Keys is a real-life sanctuary where the sun sets in the west and it's always five o’clock. It's also a great place for a group trip. I hadn’t been on one of this magnitude since my high school marching band and I bombarded the staff at Kalahari. During the week-long vacation with 14 friends, I was most interested in going to the beach, enjoying the pool, and napping in the sun (lathered in sunscreen, of course) without a care in the world.

Everyone in the group flew into Miami International Airport and piled into four rental cars to make the two-hour drive to Marathon, a city in the middle of the Keys. We knew we’d be met with esteemed Florida views at some point on the drive, but we couldn’t have anticipated the crisp blue skies and coastal sights we would get from each bridge we crossed. On each narrow street, we were but yards away from the Gulf of Mexico—it was both serene and scary.

The beauty continued when we reached our accommodation: It’s one thing to see the gorgeous photos online, but the sheer size of the property was unbelievable. It felt like a playground and we had no problem ping-ponging back and forth between the two homes for all our wants and needs. The first house had a standard bedroom and a primary bedroom with a bathroom attached. The lack of bedrooms in the first house was made up for in its entertainment spaces. The open living room had a long, gray couch that doubled as a pull-out bed, a TV that was used mostly for gaming, and a basket full of board games from Monopoly to Uno. After making your way through the kitchen, there was a wooden dining table that could seat six people and another comfortable couch that could double as a bed if needed. The dining room became the hub for dinners and late-night card games throughout the week.

Outside, there was a small pool, a bar area with a neon pink “Welcome to The Keys” sign, and a hot tub in the corner that had strong jets. Hammocks and floaties could be found all over the garden. Beyond a set of big wooden doors, you’d find a shed with more than five bikes, kayaks, life vests, and surfboards for all the outdoor activities that could be found around Marathon. The next house (both of which were rented together) had three bedrooms, another sofa bed, a hot tub, a volleyball court, a firepit, and a patio where we spent most of our mornings and nights discussing what we wanted to do that day and what we enjoyed the most from the vacation so far.

The only thing bigger than the property itself is the sheer number of amenities made available to us. Our days were spent kayaking in the morning and biking around the neighborhood. When we didn’t feel like leaving the property, we had plenty of household amenities to choose from—whether it was relaxing in one of two hot tubs on the property, enjoying some competition on the full-size volleyball court, or making our own cocktails at the tiki bar, the possibilities seemed endless. We felt as though we were in a world all our own. It was truly a magical place for friends new and old to come together and experience the sheer tranquility of The Keys. As an extrovert who still looks for moments of solitude, I found that I could still find some seclusion within the two full houses.

Kayaking was made easy with a public dock less than half a mile from the house. In town, everything that we could possibly want to do was within driving distance. We made our way to Sombrero Beach but realized that the short distance would be more tolerable in the car than trying to walk or bike there. One morning, we booked spots on a charter fishing boat, The Marathon Lady. For many of us, it was the first time we had gone fishing, and all together the group caught 51 fish—even those who weren’t so patient when it came to the process. Our fish were then filleted for us and we were told of the numerous restaurants in town that would cook our fish if we made a reservation.

Marathon gave each of us time away from our busy schedules to sit down and breathe, reconnect with old friends, and create new relationships. It also gave us a moment to step out of our comfort zones and spend more time on the water and relaxing in the sun than we're accustomed to living in the city. Leaving Marathon, I have a newfound appreciation for the simpler life—the recently-added Jimmy Buffet songs on my playlists can prove it.