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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

What a beautiful stay. 🙂 Drew was easy to communicate

January 2025
5star rating
What a beautiful stay. 🙂 Drew was easy to communicate with and space was exactly as described. Truly stunning!

This is a signature Boston stay experience. Perfect location, exquisite,

September 2019
5star rating
This is a signature Boston stay experience. Perfect location, exquisite, historic home, great amenities, seamless start to finish. Drew’s communication was timely, thoughtful, and super-clear. Highly recommend this booking.

Very nice stay and room

July 2026
5star rating
Very nice stay and room

Amazing location and enough space to fit our family. We

October 2025
5star rating
Amazing location and enough space to fit our family. We had a great stay. Everything was as described and clean. Thank you!

Amazing home. Beautiful place for our group. Parking space was

June 2018
5star rating
Amazing home. Beautiful place for our group. Parking space was great and the terrasse on the roof was very enjoyable.

Great location. Super comfortable and cozy cottage. 5mns walk to

November 2022
5star rating
Great location. Super comfortable and cozy cottage. 5mns walk to the beach.

Beautiful area of New Seabury, very quiet and amazing deck

May 2023
5star rating
Beautiful area of New Seabury, very quiet and amazing deck with flowering landscape. Lots of quiet time listening to birds in the morning. Beds were comfortable which is always a plus for us.

Nice cozy place. Missing a few necessities(which the host was

October 2023
5star rating
Nice cozy place. Missing a few necessities(which the host was responsive to),but overall a great place.

I love the place. Everything is clean. A lot of

December 2025
5star rating
I love the place. Everything is clean. A lot of nice restaurant near by. The host is very nice, and response to my question fast. Highly recommonded

Wonderful accommodations!

July 2020
5star rating
Exactly like the pictures…beautifully decorated