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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

Beautiful house with great views of the lake and plenty…

October 2022
5star rating
Beautiful house with great views of the lake and plenty of decks with seating areas by the lake.

Nice, modern, clean.

October 2022
5star rating
Nice, modern, clean.

Very nice home. Recommended!!

June 2022
5star rating
Very nice home. Recommended!!

The house was a perfect getaway in a great location.…

July 2021
5star rating
The house was a perfect getaway in a great location. It’s only minutes from Red River Beach and not too far from downtown Chatham. We had a wonderful stay and definitely recommend this property.

This was my second stay. Everything was spotless, bedding looked…

October 2024
5star rating
This was my second stay. Everything was spotless, bedding looked fresh. The temps were a little cooler so I loved snuggling under the down comforter. It was fun being so close to Kittansett and the water. Easy walk to the beach access or to the…

Our family of 11 had a fantastic time here. Loved…

January 2023
5star rating
Our family of 11 had a fantastic time here. Loved the house, artwork on the walls and the well furnished kitchen. Would definitely stay here again!!

Our stay was wonderful. Beautiful apartment in a great location.…

October 2023
5star rating
Our stay was wonderful. Beautiful apartment in a great location. Owner was quick with responses. Would definitely recommend for your stay!

Lucas was very responsive and provided clear and easy instructions…

November 2023
5star rating
Lucas was very responsive and provided clear and easy instructions throughout our stay. The unit was clean and as described. Definitely recommend!

Great location. Easy access to everything.

June 2021
5star rating
Great location. Easy access to everything.

Great nine days in Becket. House had EVERYTHING we needed.…

July 2023
5star rating
Great nine days in Becket. House had EVERYTHING we needed. pond was great for fishing, kayaking, saw beavers, geese, and more. Lots of games and great screened, covered porch for the rainy days. Our family had a terrific visit.