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About Us

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Meet the Team

Drew

Drew is a seasoned vacation rental manager with a decade of experience in the industry. As the founder and owner of South End Hospitality, Drew has established expertise in optimizing operations and delivering exceptional guest experiences. Prior to venturing into property management, Drew managed restaurants, honing valuable skills in guest service and team leadership. With a solid background in both hospitality and property management, Drew possesses a unique perspective and a knack for seamlessly merging the two industries. With a passion for creating memorable stays, Drew is dedicated to ensuring guests have unforgettable vacation experiences. Drew lives in Jamaica Plain with his two cats Olive & Saffron.

Nicole

Nicole, a 30+ year property management pro, sold her 3000-door long term property company in 2018 to enter the vacation rental industry. Her diverse experience spans long-term rentals, commercial spaces, student housing, and short-term accommodations, and she excels at operations management, budgeting, financial analysis, process improvement, and team leadership. Nicole leverages her expertise to maximize property efficiency and profitability. She’s also an animal lover with two cats and a lively puppy/team mascot, Ringo.

Tyler

Tyler is a highly experienced property management professional with over 5 years of expertise in the vacation rental industry. Drawing from his background as a skilled cyclist and mechanic, his attention to detail and hands-on approach make him an invaluable asset in ensuring the smooth operation of properties. By combining his technical expertise with a passion for guest satisfaction, Tyler excels at providing exceptional experiences for visitors. Residing on beautiful Cape Cod, he is well-acquainted with the local attractions and can offer valuable insights to enhance guests’ stays. With a commitment to ensuring memorable getaways, Tyler goes above and beyond to deliver outstanding service in the vacation rental space.

Our team is the foundation of our success, and we are grateful for each member’s contribution. You’ll have the opportunity to connect with Pia, Angel-Nicole, Karen, Hazel, Ivy, Dee, Catherine, Bea, Nicole, and Rovern, all of whom are eagerly awaiting your arrival. We are excited to offer you a warm welcome and make sure your stay is unforgettable.

History of South End Hospitality

We started Home Shar​ing on Airbnb by using a spare bedroom in one of our own South End apartments, to make some extra cash. We welcomed guests from the US and all over world, including France, Australia, and India. Sometimes we bring our guests with us to parties or share a bottle of wine with them after work. Listening to our guests’ stories, sharing our backgrounds, and helping them learn about the great city of Boston really makes the Airbnb experience special and unique.

We turned this passion for hospitality into a full service Airbnb management company, launching South End Hospitality in September of 2015.Our first contract was for complete management services for a small studio apartment in South Boston. Our business is growing, as we have added multiple listings in Boston and Cambridge, all using our signature Hand Us The Keys Service.

Whether you’re looking for complete Airbnb management services or just help with your Airbnb reservations, South End Hospitality wants to be your trusted partner. With over ten years of experience in the hospitality industry, you can count on us to maximize your profits and take good care of your guests.
Whether you’re looking for complete Airbnb management services or just help with your Airbnb reservations, South End Hospitality wants to be your trusted partner. With over ten years of experience in the hospitality industry, you can count on us to maximize your profits and take good care of your guests.

Recent Guest Reviews

The apartment is well located, spacious and well kept. Everything…

July 2021
5star rating
The apartment is well located, spacious and well kept. Everything was well spelled out and there were no issues with our stay. We enjoyed our stay and will be back!

The unit is exactly as described. Very clean and well…

June 2024
5star rating
The unit is exactly as described. Very clean and well furnished. The kitchen has everything you need. A very comfortable bed, crisp linens. The TV has everything you need. Washer/dryer just outside the entry door of the unit. Plenty of dress…

Great place to accommodate a large group. Close to fun…

October 2024
5star rating
Great place to accommodate a large group. Close to fun activities as well

This place was awesome for a ski weekend at Butternut.…

February 2023
5star rating
This place was awesome for a ski weekend at Butternut. My three brothers and I, all in our 30’s and 40’s, loved the house, which was really fantastic for just hanging out in the evening after skiing. Great vibe, great space, great times. Don’t hes…

Mike and Silvana were excellent hosts during our stay. They…

April 2021
5star rating
Mike and Silvana were excellent hosts during our stay. They were incredibly responsive and the place was great. Everyone really enjoyed how convenient it was to get to restaurants, coffee shops, and other stores around Southie.

Great stay at a great location. Will be back again…

January 2025
5star rating
Great stay at a great location. Will be back again next time we are in GB.

Lucas’s place was perfect for 12 of us. The house…

February 2023
5star rating
Lucas’s place was perfect for 12 of us. The house was spacious and clean. The kitchen was fully stocked. They left coffee for us which was a nice touch! There was no TV on the main floor which I think was made known on the listing. I didn’t …

Excellent location. Very roomy townhouse with a wonderful great room/kitchen…

December 2021
5star rating
Excellent location. Very roomy townhouse with a wonderful great room/kitchen area as seen in the pictures.

Drew’s place was in a great location for our time…

April 2025
5star rating
Drew’s place was in a great location for our time in Boston. The neighborhood was very walkable, felt safe, and very convenient to restaurants, coffee shops, and the airport shuttle bus stop was within walking distance. I was so pleased with ho…