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Meet the Team

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.

Alicia

Alicia is a hospitality enthusiast who transitioned into the world of short-term vacation rentals back in 2017 and never looked back. With experience across various aspects of property management, she now focuses solely on owner acquisition and finds joy in engaging with new homeowners, illustrating the benefits of partnering with our team! When not in conversation with homeowners, Alicia can be found enjoying outdoor adventures with her family and their lively Chesapeake Bay Retriever, Shuba!

Andrew

Andrew is a seasoned vacation rental manager with a decade of experience in the industry. As the founder and owner of South End Hospitality, Andrew has established expertise in optimizing operations and delivering exceptional guest experiences. Prior to venturing into property management, Andrew managed restaurants, honing valuable skills in guest service and team leadership. With a solid background in both hospitality and property management, Andrew possesses a unique perspective and a knack for seamlessly merging the two industries. With a passion for creating memorable stays, Andrew is dedicated to ensuring guests have unforgettable vacation experiences. Andrew lives in Jamaica Plain with his two cats Olive & Saffron.

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.
Stay On The Cape is the newest office for South End Hospitality, a vacation rental management company located in Boston. Since 2015, South End Hospitality has been managing short-term vacation rentals and limited-service boutique hotels in Boston and throughout Massachusetts.

Currently, they have over 50 single-family vacation rentals, on the Cape, in the Berkshires, and in Boston and manage a portfolio of boutique limited-service hotels with around 150 doors and growing.

History of Stay On The Cape

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

The house was great and a perfect location for getting…

July 2021
5star rating
The house was great and a perfect location for getting to town. Plenty of room for our group and everything was impeccable. Would stay here again.

Drew was very communicative and the check in process was very easy

September 2025
5star rating
Drew was very communicative and the check in process was very easy! The house had everything we needed for our stay.

My wife and I really enjoyed our stay. The cottage…

June 2024
5star rating
My wife and I really enjoyed our stay. The cottage was exactly as described. It was quiet, peaceful and relaxing. For us it was just what the doctor ordered.

Lovely home & location! Accommodates plenty of guests too!

September 2023
5star rating
Lovely home & location! Accommodates plenty of guests too!

Great value, perfect for a group or a few couples….

August 2022
5star rating
Great value, perfect for a group or a few couples. Quiet neighborhood, well stocked kitchen and working grill! Lovely to have breakfast on the patio and AC in each room!

Nice secluded home in a beautiful neighborhood. Very close to…

July 2023
5star rating
Nice secluded home in a beautiful neighborhood. Very close to everything. We ended up walking to the beach which was a pleasant surprised. Wonderful stay!

We had a wonderful holiday in Cape Cod thanks to…

July 2025
5star rating
We had a wonderful holiday in Cape Cod thanks to our stay at Drew’s place! It was comfortable, clean, and convenient for our activities around town!

Beautiful quiet spot in the woods with an incredible heated…

April 2021
5star rating
Beautiful quiet spot in the woods with an incredible heated pool. Very near Jack Knife beach which has free parking. Loved the attached screened in dining space. Awesome cathedral ceilings and a great loft space. Plenty of sleeping space for the two…