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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

Very walkable and easy access to the train station. The

May 2025
5star rating
Very walkable and easy access to the train station. The location was ideal for my group’s trip.

Lucas’s place is gorgeous, I travel constantly throughout the year

February 2019
5star rating
Lucas’s place is gorgeous, I travel constantly throughout the year for work and this Airbnb has taken the cake for it’s accommodations, cleanliness, location, style, space, and anything else you can think of! Highly recommend. A++

My family of 5 adults had a wonderful stay at

July 2021
5star rating
My family of 5 adults had a wonderful stay at this house. EASY walk to downtown Great Barrington. Lots of space, very clean, filled with light and a great view from the large balcony. I’d stay here again for sure.

The place was beautiful and looked exactly like the photos.

June 2026
5star rating
The place was beautiful and looked exactly like the photos. It was in the perfect area for us and walkable. There is a Dunkin Donuts a block down from the Airbnb, our fav coffee. New York Pizza is down the block as well, enjoyed the convenience of…

Marathon Monday in the South End

April 2025
5star rating
A wonderful place to stay – one mile walk to finish of marathon so you could get to the finish easily but return to a less stress and less crowded environment. So many lovely restaurants close by. We felt like we were in a cozy neighborhood. Ou…

Drews place was lovely , came as advertised and very

June 2024
5star rating
Drews place was lovely , came as advertised and very good communication

Wedding

October 2023
5star rating
Wonderful great location

נהננו מאד לשהות בדירה של דרו. הכל היה בדיוק כפי

June 2026
5star rating
נהננו מאד לשהות בדירה של דרו. הכל היה בדיוק כפי שהבטיח . לכל שאלה ובקשה נתן מענה מיידי. המטבח מאובזר היטב, הכל נקי. הגינה מאד יפה . אזור מצוין, רגוע, ביתי . ממליצה מאד על הדירה הזאת ובשמחה הייתי מבקרת בה שוב

Had an excellent stay thanks to Drew’s gracious, friendly and

May 2025
5star rating
Had an excellent stay thanks to Drew’s gracious, friendly and prompt help. Much appreciated!

We stayed at Lucas’s place weekend of Oct 25-27. From

October 2024
5star rating
We stayed at Lucas’s place weekend of Oct 25-27. From the time I chose to book the place until we left, communication was seamless. Lucas was very responsive. The place…i cannot stop to rave about it. Best airbnb we have stayed at. My adult kids l…