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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

Good place to stay, super convenient and walkable

May 2025
5star rating
Good place to stay, super convenient and walkable

We had a large group come up to Boston and

March 2018
5star rating
We had a large group come up to Boston and this house had everything needed. The photos do not do it justice for how big and nice it is. Would recommend for any large group going up to boston.

Amazing apartment! The place is clean, well equipped, and has

October 2017
5star rating
Amazing apartment! The place is clean, well equipped, and has adequate space, good decoration, convenient location! Strongly recommend!

We truly enjoyed our time at this home. This is

July 2020
5star rating
We truly enjoyed our time at this home. This is a great place to stay.

Drew’s place is absolutely amazing. One of the best places

February 2026
5star rating
Drew’s place is absolutely amazing. One of the best places I’ve stayed in Massachussets. Highly recommend!

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

Cannot beat the location! Convenient to everything via foot or

July 2018
5star rating
Cannot beat the location! Convenient to everything via foot or T. Hosts responsive and helpful! Perfect for two families. The bottom front bedroom w the two doubles would not be a good spot for light sleepers due to the food trucks making very ear…

This was a very charming place – clean and tastefully

October 2024
5star rating
This was a very charming place – clean and tastefully decorated. The bed was very comfortable. If you can’t handle climbing steep stairs with luggage, this isn’t the right choice. Unfortunately, when we arrived, there was a questionable characte…

This home is perfect for your next costal vacation or

April 2023
5star rating
This home is perfect for your next costal vacation or trip! It is quaint, homey, clean, and beautiful!!! Drew is an attentive host and helped answer any questions in a timely manner. We will be back!

We stayed 3 nights and I chose this place due

July 2025
5star rating
We stayed 3 nights and I chose this place due to the positive reviews. The place was very clean, comfortable, close to everything, and it had everything we needed. We had to go looking for some cooking oil and a few basic amenities, but there were…