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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 centrally located and easy to walk around. The place

September 2023
5star rating
Very centrally located and easy to walk around. The place was clean and very welcoming. The host was super responsive and available. So happy I booked this instead of a hotel.

Drew’s place was perfect for a work/play trip to Boston.

March 2026
5star rating
Drew’s place was perfect for a work/play trip to Boston. The apartment is close to a T station, and walking distance from all Boston attractions. There are 2 great restaurants within 50 feet, Mida and Ilona, and Toro is a 10 minute walk. Drew was …

The high windows provide so much natural light, and the

December 2020
5star rating
The high windows provide so much natural light, and the place was incredibly clean.

Drew’s place in Harwich was fantastic for my family! Location

July 2024
5star rating
Drew’s place in Harwich was fantastic for my family! Location is centrally located and made exploring the area easy and coming home to the game room, nice yard and fire pit at night was terrific! Great for families and would highly recommend!

We had a terrific stay at the house. The pool

August 2024
5star rating
We had a terrific stay at the house. The pool and yard were great for the kids and the house was excellent.

Lucas’s place was amazing! Everything was super clean and nice.

October 2020
5star rating
Lucas’s place was amazing! Everything was super clean and nice. The area is great if you like the outdoors. My friends were very impressed with the whole place! Good price for a great place.

Amazing view. Totally quiet and private and everything was like

October 2025
5star rating
Amazing view. Totally quiet and private and everything was like new with classy touches and upgrades everything.

Drew’s place was great for our family of six adults.

October 2022
5star rating
Drew’s place was great for our family of six adults. Lots of room to spread out, comfy beds and large kitchen for cooking. Also room for everyone to sit and watch TV. Nice, safe neighborhood, great for walking. Private yard. We would stay here ag…

excellent host. Highly recommand

May 2026
5star rating
excellent host. Highly recommand

Lucas’s home made our weekend in Boston complete! The home

December 2018
5star rating
Lucas’s home made our weekend in Boston complete! The home is well done with great architectural features!