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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

This place FAR exceeded our expectations and it looks even

February 2018
5star rating
This place FAR exceeded our expectations and it looks even better in person than the pictures. It was slightly hard to find at first, but the host had provided clear instructions at first which helped ensure we didn’t have any issues. The place is…

Awesome place! Well cleaned, great communication easy to get in

March 2025
5star rating
Awesome place! Well cleaned, great communication easy to get in

Perfect for my bachelorette party! Easy walk into town for

August 2023
5star rating
Perfect for my bachelorette party! Easy walk into town for coffee, shopping, or drinks. 10 minute walk to Lake Mansfield for a dip. The house was exactly as described and easily accommodated 9 of us. Fun to grill and hang on the deck (bring your b…

Nous avons passé un merveilleux séjour chez Drew ! La

September 2024
5star rating
Nous avons passé un merveilleux séjour chez Drew ! La maison est spacieuse avec de chouettes extérieurs… nous avons apprécié le petit-déjeuner sur la terrasse et les s’mores au coin du feu. Les enfants ont adoré la salle de jeu. Parfait petit havr…

Beautiful, clean space! Lucas was quick to reply to any

November 2017
5star rating
Beautiful, clean space! Lucas was quick to reply to any questions. Would definitely recommend to others.

Great property manager with excellent communication

May 2022
5star rating
Great property manager with excellent communication

Super cute place in the best location!

November 2025
5star rating
Super cute place in the best location!

Convenient location, nice view, nice use of space inside. Would

December 2024
5star rating
Convenient location, nice view, nice use of space inside. Would stay again 👍🏼

Close to town, cozy, warm and comfortable.

January 2025
5star rating
The house was great! It is set back and high up, so that it overlooks the beautiful and quaint shops and restaurants of Great Barrington. The house has giant windows, high ceilings, a gas fireplace, and comfortable beds! It was a perfect place …

Spent a long weekend at this Back Bay brownstone with

July 2019
5star rating
Spent a long weekend at this Back Bay brownstone with ten people. The location is amazing…central to everything Boston has to offer. We were able to walk just about everywhere we went! The brownstone itself is five levels of historic details …