Airbnbs on the Road: Down South

Jessica M. Castillo
8 min readFeb 1, 2021

A young woman stays at Airbnbs in the southeastern U.S. while on her road trip across America.

This story was originally published on on May 17, 2018.

My first Airbnb on this road trip, and the first one after my ill-fated trip to Palm Desert last year, was with Allie and Bronson, Allie’s big lovable mixed-breed rescue pup, in her three-bedroom house in St. Augustine. The house has a wild open yard and Airbnb listing description proclaiming, “Bronson’s the head honcho here, we’re both kooky mutts who like making new friends.”

Allie, who is originally from Buffalo and is half Indian-American and half Italian, and her home were awesome. Bohemian, quirky, inviting. With doors left unlocked and the pair of guys who rent the attached efficiency unit hanging outside, smoking with friends, it was an easygoing vibe, people coming and going, lives sliding past and in between. The rooms and living spaces were tastefully filled with unique knickknacks and treasures. A wall of spiritual masks, an old-timey record player, collections of devil figurines, vinyl records, vintage paperback books, instruments, decorative skulls, mythical creatures and other unique oddities.

I settled in after a long day of sightseeing and reminiscing in Gainesville earlier that day, and a couple hours’ of driving over to St. Augustine. I sat in one of Allie’s big easy chairs by the window in the living room, as Bronson sat perched on the futon sofa to my right looking out the window at Allie in the garden tending her herbs, vegetables and flowers. The late afternoon sun melted into the big open room as Allie’s underground eclectic music played, and I felt at ease and at home.

It’s funny how it’s such a human thing to be curious about and want to connect to people from different backgrounds. A yearning for the exotic, foreign, different. I could sense that Allie was like that, though I could feel some of her trepidation about going out into the world to explore it. She has made friends with wonderful people with interesting stories and backgrounds from all over the world through hosting for Airbnb and Couchsurfing, but she herself has never couchsurfed at someone else’s place (and I don’t think she’s Airbnb’d at someone else’s place either). At 27, with her first-ever passport newly minted, she was preparing for her first trip abroad, to meet a friend — who she met through Couchsurfing — in Mexico, where they’d hang at the beach and go free diving. She’s a soft soul, a big open spirit who is genuinely interested in learning about other people and cultures, and she felt like a kindred spirit.

Images of some scenes from my Airbnb in St. Augustine, Florida.

I stayed at Allie’s place for just the night, and a quiet Spanish couple from the Canary Islands stayed in the second Airbnb room in the house. I didn’t interact much with the couple, but I loved and appreciated the different lives coming together and living under one roof for even just one night. The beauty of the world lies in its diversity, and when that diversity comes together, it’s magical.

My next Airbnb was with Daniel in his two-bedroom condo in a renovated house next to the train tracks along King Street, half way between Charleston and North Charleston. The place was almost the opposite from Allie’s, but each so cool and funky in their own ways. He was so sweet and great, extremely helpful, clean and organized and just overall on top of it. He was born and raised in Charleston and works as an independent entrepreneur, has recently picked up boxing, and is dreaming of taking a one-way flight to Cuba and/or Hispaniola in the Caribbean. He’s a great guy.

Images of some scenes from my Airbnb in Charleston, South Carolina.

Everything I needed in the condo was labeled, from breakfast items and coffee filters to towels, linens and toilet paper. The space was so modern and chic. I think he pumped lavender through the air vents. I felt like I was in a spa. In the bathroom, there was a toilet stool to raise your legs, and the toilet even had a motion-detected and light-sensitive blue night light. Everything in the condo was so well thought out. Daniel offers his guests brochures of tours and things to see and do in Charleston, his recommendations for eateries, and home rules and instructions all typed up in sheet protectors. True southern hospitality.

The next Airbnb was a stopover in North Carolina, making my way up through the South. It was very different from the others yet again. It’s called the Tuck Inn and it’s an old bungalow just northwest of downtown Charlotte, near the Smallwood, Seversville and Wesley Heights neighborhoods. The house has three rentable rooms and is owned and operated by a small community nonprofit, QC Family Tree. The profit it makes from renting three of the rooms goes to supporting youth leadership and community development. The living areas in the house are used as safe and welcoming spaces for learning, making art, and holding gatherings of spiritual connection, such as bible study sessions and practicing yoga. Plus, I loved that they added this to the Airbnb listing description: “We didn’t think we would have to include this note, but apparently we do: If you are concerned with sharing a neighborhood with people of color, you should seek therapy and also find a different Airbnb listing.”

Images of some scenes from my Airbnb in Charlotte, North Carolina. I stayed in the Nina Simone room.

I was the only one there when I stayed the night and, truth be told, I did wonder to myself if the old pre-war house was haunted, with its hidden closets and creaky wooden floors. But it was clean, had wi-fi and all I needed for a night. The house was right next door to a local community church and, as it was Friday night, there was a lively church party going on right outside my bedroom window. It died down by 11pm or so. The next morning, there was another gathering at the church: kids playing after the Saturday service, I imagine. It was all very comforting actually. I felt the strong community feeling hugging the house and dispelling any hidden ghosts.

My last Airbnb in the south, before moving up into the mid-Atlantic, was in Roanoke. It was a lovely little cottage home on a main road in a blue collar neighborhood. The host, Victoria, was out of town for the weekend so I never met her, but she was so kind and very responsive over the Airbnb app. I needed the room for just one night as it was another stopover en route to Shenandoah National Park, but the day before she had offered me an extra free night and I would have the whole house to myself. It was so kind of her to offer.

Images of some scenes from my Airbnb in Roanoke, Virginia.

I think she was Jehovah’s Witness, based on some of the books that I saw around the house. Also, I’m not sure if this was for religious reasons, but there was no cable or wi-fi (I assume she uses Airbnb through cell service on her phone). A whiteboard in the bedroom detailing home instructions explained “No cable or wi-fi :( but there are plenty of movies in the cabinet under the TV in the living room.” The TV was older, from the mid- to late-1990s, boxy with a rounded screen, and it sat atop a cabinet filled with drawers of old VHS tapes, mostly animated Disney movies. It was quirky, sweet and warm.

The Airbnbs I’ve stayed in so far have all been so wonderful and unique. It’s been what I want from an Airbnb — getting a glimpse into different, diverse lives that make up this beautiful pale, blue dot. This is what I feel like Airbnb is all about. Yes, it’s a cheaper place to stay for a traveler, and a way to make some extra cash for a homeowner, but at the end of the day, I feel people use Airbnb for this fundamental purpose — to connect with and learn from others seemingly different than ourselves. I know that’s my main reason for using it.



Jessica M. Castillo

A writer and photographer living in Miami. Lover of reading, writing, photography, art, music, nature, philosophy, science and almond croissants.