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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

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.

Loved this spot! Charming with great views. Walking distance to

September 2025
5star rating
Loved this spot! Charming with great views. Walking distance to some great coffee shops and restaurants. We had an awesome weekend here. Thanks Lucas!

Really nice stay

August 2024
5star rating
We really enjoyed our stay. The pros are you can easily walk to the great downtown. It’s a big hill but a very close walk. And you can walk to the lake which is great for kids. The property was very clean and works well if you need 3 bedrooms. I…

Excellent, thoroughly enjoyed our time

March 2025
5star rating
Excellent, thoroughly enjoyed our time

Loved the location of Drew’s cottage on the Cape! We

June 2023
5star rating
Loved the location of Drew’s cottage on the Cape! We enjoyed the location and coziness of the cottage!

Drew’s place in Harwich was wonderful and stocked with all

May 2022
5star rating
Drew’s place in Harwich was wonderful and stocked with all the essentials and more to make our stay comfortable. We also appreciate that it’s dog friendly. A nice surprise was that the house looked even better in person than in the pictures. The b…

It’s a gem. Yes, I will stay at the same

May 2023
5star rating
It’s a gem. Yes, I will stay at the same place again. Very private and I felt like home the moment I walked in. Super clean, a few lights weren’t working but overall this can be one of the best AirBnB experiences I have. There are houses rules, yo…

The house was stellar, beds/pillows super comfy, shared space perfect

August 2024
5star rating
The house was stellar, beds/pillows super comfy, shared space perfect for a big group, we had a toddler with us and he was very safe no big hazards for kids. Outdoor shower got tons of use with our fam! The yard is huge we played a lot of yard gam…

Awesome modern house to stay in! Great location and spacious!

August 2018
5star rating
Awesome modern house to stay in! Great location and spacious!

Experiencia satisfactoria.

December 2024
5star rating
Que tenía excelente privacidad, que es un apartamento estudio muy equipado, que es céntrico y que todo lo que se ve en la publicidad es lo que en realidad ofrece el lugar. Que no está claro en la publicidad si es un hotel o un arbnb, y la asistenc…