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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 location! Walking distance to shops and restaurants. We had

June 2022
5star rating
Great location! Walking distance to shops and restaurants. We had a great trip!

The place looked just like the pictures. Drew was a

February 2026
5star rating
The place looked just like the pictures. Drew was a fantastic host and very friendly. It was great to have the restaurant Mida right next door. I highly recommend their espresso martini.

Awesome

July 2024
5star rating
Perfect home clean newly updated and so close to the beach

Awesome place. Great location. Great hospitality. Would stay here again.

December 2017
5star rating
Awesome place. Great location. Great hospitality. Would stay here again.

Wonderful

December 2025
5star rating
The location was great for our needs and the property was very clean.

We had a wonderful time in Boston, your place is

October 2025
5star rating
We had a wonderful time in Boston, your place is beautiful, spacious, clean and quiet, just as we expected. Thank you for being a great & responsive host. We hope to come back in the future

Can’t recommend this place enough for a small family looking

May 2023
5star rating
Can’t recommend this place enough for a small family looking to explore all that Berkshires have to offer, while also being walking distance to food, shopping, etc

Cape cod family trip

August 2024
5star rating
We all enjoyed our stay. The only problem. The beds upstairs were to low to the floor. The older people had a hard time getting out of bed.

The train was a bit loud at night.

October 2023
5star rating
The train was a bit loud at night.

Such a great place, would definitely recommend. Very clean and

January 2024
5star rating
Such a great place, would definitely recommend. Very clean and spacious. Lucas is highly responsive!