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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

Stunning property. Amazing private lake with free access to kayaks.…

June 2022
5star rating
Stunning property. Amazing private lake with free access to kayaks. Beautiful, clean house with great amenities. Lucas was very friendly and easy to communicate with.

Great house with exceptional location. Smooth process throughout.

September 2022
5star rating
Great house with exceptional location. Smooth process throughout.

We had a very enjoyable stay in this cabin. It’s…

August 2022
5star rating
We had a very enjoyable stay in this cabin. It’s very nice and was exactly as the posted pictures. A well stocked and clean house. The hot tub was delightful at the end of the day. The location is great and close to all the different towns yet…

Drew was super responsive and helpful. We had a wonderful…

September 2024
5star rating
Drew was super responsive and helpful. We had a wonderful stay!

Beautifully kept and located space to spend a few days.…

September 2024
5star rating
Beautifully kept and located space to spend a few days. Super convenient walking to many coffee shops, bakeries, and restaurants. Quaint part of town. Bed and linens very comfortable. Bathroom clean and spacious for a studio. Kitchenette has eve…

Place is beautiful inside. The deck and fire pit were…

July 2023
5star rating
Place is beautiful inside. The deck and fire pit were so much fun for our family. Sorry we only get to experience a couple of days of Falmouth. I would highly recommend Drew’s place.

This home is perfect for your next costal vacation or…

May 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!

Can’t say enough great things about Charlesgate Suites. Fantastic place…

March 2024
5star rating
Can’t say enough great things about Charlesgate Suites. Fantastic place in a great location. Check-in was super easy. We had everything we needed in this extremely clean air bnb. Bed was so much comfortable and the kitchen was well equipped. We de…