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 will be back, thank you for a hidden gem in Boston.

April 2024
5star rating
The check in was flawless, all done by an electronic key pad. The entrance is beautiful, well lit, with the charm of old Boston with its hand painted wallpaper and winding staircase. Our suite on the second floor was easy to get to and had more th…

Nice Modern Place. Bed was comfy and nice big bathroom.

July 2024
5star rating
Nice Modern Place. Bed was comfy and nice big bathroom. Drew was very responsive and was a great host

We had a great stay at Lucus’s cabin in great

October 2023
5star rating
We had a great stay at Lucus’s cabin in great Barrington. Easy check in, walkable to the main strip, clean. We would definitely come back!

Drew was extremely responsive and I had a really great

April 2026
5star rating
Drew was extremely responsive and I had a really great experience. The place was obviously extremely beautiful, but what stood out to me is that my check in was 4pm, but I arrived in Boston at 12. He allowed me to leave the luggages in the room wh…

Great location. We had a ten person family gathering ages

August 2021
5star rating
Great location. We had a ten person family gathering ages 5 to 85 for four nights. It provided the common space to gather and individual space to relax. Whole Foods is almost next to it, plus great bakery and restaurants within 3 minutes walkin…

As described in posting. I stayed here with 2 co-workers

October 2025
5star rating
As described in posting. I stayed here with 2 co-workers for a couple nights and there was plenty of room for everyone. A little tricky to find, but the directions/instructions made it very easy.

Gran opción para visitas de mas de 2 días

May 2024
5star rating
lo amplio y bien cuidado los detalles , muy bien decorado y amplios espacios todo bien

We loved this clean, bright and spacey apartment in Back

May 2025
5star rating
We loved this clean, bright and spacey apartment in Back Bay/near Fenway. We walked to different neighborhoods like Fenway, Beacon Hill, Back Bay and Boston Commons from there- easy access to everything. The bed was comfortable and the space was g…

Great place in great location with all the amenities. Would

October 2021
5star rating
Great place in great location with all the amenities. Would definitely return. Thanks for everything.

An excellent home in an excellent location! Everything went smoothly

August 2025
5star rating
An excellent home in an excellent location! Everything went smoothly from checking in to checking out. The home was clean, Drew and Tyler responded promptly to questions, and everything overall was great.