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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

It’s exactly as advertised, great space and great location. It’s

October 2021
5star rating
It’s exactly as advertised, great space and great location. It’s a no brainer for anyone looking for a place to stay in Boston.

The house and property were beautiful. Our group consisting of

July 2024
5star rating
The house and property were beautiful. Our group consisting of 3 couples were very comfortable. The location to town and Lake Mansfield was excellent. We enjoyed a day of exploring the shops and restaurants in town and walking our dogs to the lak…

Absolutely beautiful home! My husband, myself and two kids stayed

July 2024
5star rating
Absolutely beautiful home! My husband, myself and two kids stayed at Drew’s place for our family cape vacation. The home was spotless and had everything we needed! Great location close to the beach, marketplace, mashpee commons etc! Overall had a …

Drew’s place was perfect for my time in Boston. The

July 2025
5star rating
Drew’s place was perfect for my time in Boston. The location couldn’t be better—with easy access to public transport, restaurants, and everything you’d want to explore around the area. The space was clean, comfortable, and had everything I needed …

This was a lovely large home. The kitchen had lots

August 2022
5star rating
This was a lovely large home. The kitchen had lots of nice equipment and some spare seasonings, etc. It was stocked with plenty of trash bags, paper towels and TP. The beds are comfortable and have lovely sheets. Lots of TVs (all working) and pl…

We had a little trouble finding the correct lane down

July 2023
5star rating
We had a little trouble finding the correct lane down to the house, but once there it was just perfect for the four of us. Had everything we needed, was close to town center, lovely view – great spot!

We felt that it was overpriced for 500$/night

September 2025
5star rating
We felt that it was overpriced for 500$/night

Great House for Butternut Ski Trip

January 2024
5star rating
We had a great time at the house. Clean, warm, cozy. Matched the VRBO description. Would definitely recommend.

This place FAR exceeded our expectations and it looks even

February 2018
5star rating
This place FAR exceeded our expectations and it looks even better in person than the pictures. It was slightly hard to find at first, but the host had provided clear instructions at first which helped ensure we didn’t have any issues. The place is…

Exceptional

August 2024
5star rating
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