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

Had a lovely week at this property. We are definitely

June 2026
5star rating
Had a lovely week at this property. We are definitely coming back next year.

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…

We had a lovely stay in this beautiful house. Lucas

November 2023
5star rating
We had a lovely stay in this beautiful house. Lucas was very responsive and the house had every amenity needed. Being able to walk to town is a great plus. We would happily stay in this house again. Rita

Had a great stay at Drew’s! The gardens were lovely

September 2025
5star rating
Had a great stay at Drew’s! The gardens were lovely and peaceful and the location was very walkable to whatever we needed. The home was cozy and comfortable.

房子在一栋老建筑中很漂亮,楼下有不错的餐厅,离地铁500米。一切都很好,唯一的问题是,新装修的味道还有,过一个月应该就会很好。汽车声音对需要安静的人来说可能会影响,我们睡的挺好。

July 2024
5star rating
房子在一栋老建筑中很漂亮,楼下有不错的餐厅,离地铁500米。一切都很好,唯一的问题是,新装修的味道还有,过一个月应该就会很好。 汽车声音对需要安静的人来说可能会影响,我们睡的挺好。

This place was exactly as advertised: new and updated re-model

August 2024
5star rating
This place was exactly as advertised: new and updated re-model with some of the original architecture and design. It was fresh, clean and roomy. The bed and linens were comfortable too. Will definitely book for next time.

The layout of this place is perfect for traveling with

August 2021
5star rating
The layout of this place is perfect for traveling with family – a big space to come together and ample bedrooms. The kitchen is nicely stocked with cookware, and a gas stove made cooking nice and easy. This was my first stay in Brewster and the …

Very nice place to stay in Boston.5-10mins Uber to midtown.

September 2017
5star rating
Very nice place to stay in Boston. 5-10mins Uber to midtown. The house is very large and things are very convenient.

If you like historic bldgs., high ceilings, huge windows and

July 2023
5star rating
If you like historic bldgs., high ceilings, huge windows and quirks and want location in middle of it all, this is for you. Edge of Back bay at Kenmore/BU neighborhood, Charles River, this is great launching pad for all that is Boston. Spacious st…

Fast response and very pleasant to communicate with. Would definitely

October 2025
5star rating
Fast response and very pleasant to communicate with. Would definitely recommend this place.