Skip to main content

About Us

Reach Out to Get Started!

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

We had a great long weekend at Lucas’ house with

April 2026
5star rating
We had a great long weekend at Lucas’ house with our two kids (3 & 6). The walkability to town and proximity to cafes and restaurants was perfect and the house had everything our family needed to be comfortable. There were only four of us but the …

House has great location with easy access to rte 6,

August 2023
5star rating
House has great location with easy access to rte 6, a lovely cape pond and the rail trail House has all needed amenities and is clean and very comfortable We had an awesome week and would easily book again😊

Exceptional

September 2024
5star rating
Very nice stay. Clean and quiet.

Feel like a Bostonian in this beautiful brownstone.

June 2026
5star rating
Apartment is in a very nice neighborhood. Lots of space, beautiful design. We’ll equipped. Everything was great. Small details I was missing a tea towel in the kitchen. The hall in front of appt 102 is really dark. I could only guess the numbers o…

Great place in a great neighborhood.

February 2026
5star rating
Great place in a great neighborhood.

Everything about this house is beautiful my family and I

August 2024
5star rating
Everything about this house is beautiful my family and I enjoy this weekend ✅thanks

A great trip at a great house! Definitely recommend!

November 2020
5star rating
A great trip at a great house! Definitely recommend!

Beautiful house for our family’s vacation with a great kitchen

September 2021
5star rating
Beautiful house for our family’s vacation with a great kitchen and grill for staying in and cooking or short walk to downtown Great Barrington for dinner, shopping, or coffee! Hosts were extremely helpful and responsive.

Me encantó todo! Gracias chicos

March 2024
5star rating
Todo! Nada

Beautiful space—well-decorated, great ambiance, impeccably clean. Easy access to nearby

June 2023
5star rating
Beautiful space—well-decorated, great ambiance, impeccably clean. Easy access to nearby universities and very close to the T. Note that it has a lot of exposed stairs and wouldn’t be a suitable place to stay with toddlers.