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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

This place was great. The pictures don’t do it justice.

March 2018
5star rating
This place was great. The pictures don’t do it justice. It was centrally located and we were able to use Lyft or Uber to get to downtown quickly. Lots of sleeping space and areas for hanging out. Would love to come back when the weather is better …

We had a great stay for a family get together.

October 2024
5star rating
We had a great stay for a family get together. The location is perfect for walking into town or exploring the Berkshires by car.

Wonderful

May 2025
5star rating
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The property was clean and comfortable, making it ideal for

February 2026
5star rating
The property was clean and comfortable, making it ideal for a long stay in Boston. The location was great and only a few minutes walk from the Green Line (Kenmore), which meant it was easy to explore Boston. The hosts were very friendly and very q…

The Chester is now my favorite place to stay in

November 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…

Great location and great beach nearby!

May 2026
5star rating
Great location and great beach nearby!

This homes prime location was ideal for our Cape Cod

October 2024
5star rating
This homes prime location was ideal for our Cape Cod adventures. Set on a tiny, quiet, dead end street we were able to enjoy beautiful walks to restaurants and stores. It was a short distance away from parks, the bay, and Nauset light. Inside was …

The house is beautiful – clean and the location is

November 2023
5star rating
The house is beautiful – clean and the location is perfect for walking into town or to the lake. There are great amenities. Highly recommend!

Great unit for a group of adults who can manage

June 2018
5star rating
Great unit for a group of adults who can manage the stairs. The unit is spacious and modern. Close to all of the Boston attractions. One convenient parking space

The house is great. Directions were spot on and house

December 2023
5star rating
The house is great. Directions were spot on and house was easy to find. They are not joking when they advise only 4 wheel or AWD. If your vehicle doesn’t have them don’t choose this house for the winter. We didn’t run into any issues but the hill/…