Skip to main content

About Us

Reach Out to Get Started!

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

As advertised.

January 2021
5star rating
Nice week in the Berkshires for my family. Would recommend to others.

Great stay in a perfect location near Fenway. We went

July 2025
5star rating
Great stay in a perfect location near Fenway. We went to a Red Sox game on Saturday and the location was ideal, just a short walk to the park. The place was clean, comfortable, and exactly as described. Overall a great experience and I would defin…

First and foremost, Lucas IS a super host. Down to

November 2020
5star rating
First and foremost, Lucas IS a super host. Down to every detail and no question was too trite. The house was immaculate, clean, and cozy. The beds were unusually comfortable which is so rare in rentals; the wifi was incredibly fast which was impor…

Great stay, perfectly clean, comfortable beds. Thanks!

July 2024
5star rating
Great stay, perfectly clean, comfortable beds. Thanks!

Lovely stay in Great Barrington at Lucas’s place. Exactly as

December 2023
5star rating
Lovely stay in Great Barrington at Lucas’s place. Exactly as described. Cute, stylish, family friendly, fantastic location for slopes and minutes from Main Street. Highly recommend.

Had a fun time with family at Drew’s place. It

July 2023
5star rating
Had a fun time with family at Drew’s place. It was very warm so we appreciated the well working air conditioners in all the rooms. Being able to walk to nearby Long Pond that has a nice beach was great with small kids. And the game room was a big …

The place was super clean and charming, a perfect space

September 2024
5star rating
The place was super clean and charming, a perfect space for me to unwind after busy days.

보스턴에서의 휴가 잘 보내고 갑니다. 체크인방법이나 주변 장보는 곳과의 거리

September 2025
5star rating
보스턴에서의 휴가 잘 보내고 갑니다. 체크인방법이나 주변 장보는 곳과의 거리 등이 좋았습니다. 식기세척기, 세탁기, 건조기, 음식물처리기 등이 다 구비되어있었습니다. 문제가 생기면 빠르게 대응해주기 위해 노력해주셔서 잘 지낼 수 있었습니다.

What a beautiful gem to find in June! We thought

June 2026
5star rating
What a beautiful gem to find in June! We thought the location was ideal, felt very safe, we walked almost everywhere we went, and was pleasantly surprised with the beach path! Drew was very easy to work with and he got back to us right away, a bi…

The house is in a great location and was as

June 2021
5star rating
The house is in a great location and was as described. The house was in a great condition, everything was clean and has ample parking. There was ample toiletries and linens. The pillows were great too! When something was missing, we reached out to…