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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

Thanks. Had a great time. Some Glitches with shutting the…

August 2025
5star rating
Thanks. Had a great time. Some Glitches with shutting the house but Lucas was always there to help.

Excellent location. Perfect for walking the city.

August 2025
5star rating
Excellent location. Perfect for walking the city.

The house was in an awesome private location. Everything was…

August 2022
5star rating
The house was in an awesome private location. Everything was accurately described in the listing. Beautiful home, well stocked with everything to make our stay very comfortable. Our host communicated very well with us, set expectations, was respon…

入住非常满意,空间比想像的更大,很温馨、很干净,地段市中心、地理位置优越,是一次非常满意的入住体验。明年期待再次入住

February 2023
5star rating
入住非常满意,空间比想像的更大,很温馨、很干净,地段市中心、地理位置优越,是一次非常满意的入住体验。明年期待再次入住

The place was very comfortable had the dogs stay with…

August 2024
5star rating
The place was very comfortable had the dogs stay with us as well! Only 30 mins away from P-town. Made great memories with family!

The Chester is now my favorite place to stay in…

December 2024
5star rating
The Chester is now my favorite place to stay in Boston! The location is fantastic: close to mass transit, shops, restaurants, NEC, Northeastern, the Pru, Newberry, Fenway. The unit is absolutely gorgeous (looks just like the photos)…we appreciated…

Super highly recommended – close to beach, and everything you…

August 2023
5star rating
Super highly recommended – close to beach, and everything you could want on Cape including the ferries – can’t go wrong – hope we can book this place next summer. Have fun!

Great place, close to the beach

July 2023
5star rating
Great place, close to the beach

Amazing location: Drew’s place made us feel so much at…

July 2022
5star rating
Amazing location: Drew’s place made us feel so much at home (genuinely felt like our own holiday getaway); personably decorated, the layout, lovely garden (including new BBQ and firepit) plus spacious area around including for parking, etc. ensure…