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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

Great venue

April 2019
5star rating
Great venue

6 of us stayed comfortably and enjoyed this space very

October 2023
5star rating
6 of us stayed comfortably and enjoyed this space very much.

A hidden gem in Boston!This place is in a beautiful,

May 2025
5star rating
A hidden gem in Boston! This place is in a beautiful, quiet neighborhood and located in a historic building full of charm. The interior is not only tasteful and stylish, but also incredibly high quality — especially the bed, which was super comfor…

Beach relaxation

June 2025
5star rating
Very comfortable stay. Enjoyed walking to the beach several times a day. House had everything we needed.

Lucas’ listing in Great Barrington was perfect for our group

February 2026
5star rating
Lucas’ listing in Great Barrington was perfect for our group of 8 (two families of 4). It was a short drive to Butternut Ski area and very close to the downtown area with shops and restaurants. Our kids loved the games available in the house as we…

Great location and super close to grocery store Whole Foods

May 2019
5star rating
Great location and super close to grocery store Whole Foods and the train. Highly recommend staying at this location. Super easy location to find and convenient.

Great place, location was perfect. Nice coffee shop in walking

July 2026
5star rating
Great place, location was perfect. Nice coffee shop in walking distance. Hosts were very friendly. Highly recommended

The place was as advertised, and good for our purpose

July 2024
5star rating
The place was as advertised, and good for our purpose (event at Fenway). The parking lot is a little sketchy but my car was safe and we had no incidents. The upstairs guests were terrible neighbors but certainly no fault of the host.

A great trip at a great house! Definitely recommend!

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

Drew’s place was perfect. Clean, awesome game room for kids,

August 2026
5star rating
Drew’s place was perfect. Clean, awesome game room for kids, easy to get in and out.