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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

We had 16 people at the cabin and it was…

October 2024
5star rating
We had 16 people at the cabin and it was a very comfortable stay for everyone. The outdoor porch was very nice!

Drew’s house was very clean, well organized and spacious. We…

October 2024
5star rating
Drew’s house was very clean, well organized and spacious. We had everything we needed and felt right at home. The location is ideal. We could not have asked for a better host. If you’re planning a visit to Cape Cod, I highly recommend staying here…

We had an amazing stay! Drew was very easy to…

August 2022
5star rating
We had an amazing stay! Drew was very easy to communicate with and very responsive. The house was great, close proximity to the private beach, as well as to shops and town. The house was in great condition with a beautiful backyard.

Plenty of room for our 8 people.Everyone really enjoyed pool…

July 2024
5star rating
Plenty of room for our 8 people.Everyone really enjoyed pool area. beds quite comfy,plenty of nice clean towels and linens. Overall a very nice experience! Thank You

Large home with lots of space located in a very…

October 2024
5star rating
Large home with lots of space located in a very nice community. Would book again!

The house is very spacious and and clean. It is…

June 2022
5star rating
The house is very spacious and and clean. It is located in a wood and you really get privacy. It is beautifully maintained and the kitchen is well equipped. We just loved our stay at the house!

It’s hard to put into words how beautiful and charming…

June 2023
5star rating
It’s hard to put into words how beautiful and charming this place was to stay. The perfect cape cod house. Incredibly beautiful surroundings and details of the house and yard. Incredible hosting, spotlessly clean, fantastic area. It was a stressful…

Great space with a lot of activities and room to…

August 2022
5star rating
Great space with a lot of activities and room to spread out and enjoy family time.

House was spacious and very clean. The lot is large…

May 2024
5star rating
House was spacious and very clean. The lot is large and off road. Would definitely rent again