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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

Great value, perfect for a group or a few couples.

July 2022
5star rating
Great value, perfect for a group or a few couples. Quiet neighborhood, well stocked kitchen and working grill! Lovely to have breakfast on the patio and AC in each room!

Our family had a great stay at Lucas’s house in

January 2025
5star rating
Our family had a great stay at Lucas’s house in Great Barrington. We were close enough to town to enjoy the amenities and also a short trip to butternut, where we had a great day of skiing with a group of mixed skiing experience. The house was com…

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…

House was spacious and very clean. The lot is large

May 2024
5star rating
House was spacious and very clean. The lot is large and off road. Would definitely rent again

Loved staying here! Amazing location, and the space is just

July 2025
5star rating
Loved staying here! Amazing location, and the space is just beautiful. Will be back again for sure!

Thank you

July 2023
5star rating
My family and I really enjoyed our time at your home. Everything was perfect. Thank you

First and foremost, Lucas IS a super host. Down to

November 2020
5star rating
First and foremost, Lucas IS a super host. Down to every detail and no question was too trite. The house was immaculate, clean, and cozy. The beds were unusually comfortable which is so rare in rentals; the wifi was incredibly fast which was impor…

This is a truly amazing 3-bedroom home in a residential

March 2025
5star rating
This is a truly amazing 3-bedroom home in a residential area in Great Barrington which is centrally located to the stores and great restaurants. The house is situated in a quiet, safe residential area. The house is well designed with modern applia…

The apartment was great. Communication good. They allowed us to

May 2026
5star rating
The apartment was great. Communication good. They allowed us to check in early which was very welcoming. The stairs down to the basement were a little precarious with heavy suitcases but otherwise we were pleased. Thank you.

Great getaway

December 2022
5star rating
Clean, lots of natural light, well stocked and great location. We would rent again!