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

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.