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About Us

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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

A beautiful home in a nice quiet area

April 2021
5star rating
A beautiful home in a nice quiet area

The house is perfect it was really great to stay…

July 2022
5star rating
The house is perfect it was really great to stay there and we wish to come back.

We really enjoyed our stay. The house was well kept,…

August 2023
5star rating
We really enjoyed our stay. The house was well kept, clean, and everything was in perfect working order. The game room and large selection of board games was really fun for the kids. We also enjoyed the fire pit and the peaceful, quiet backyard…

Had a fun time with family at Drew’s place. It…

July 2023
5star rating
Had a fun time with family at Drew’s place. It was very warm so we appreciated the well working air conditioners in all the rooms. Being able to walk to nearby Long Pond that has a nice beach was great with small kids. And the game room was a big …

Sparkling clean. Virtually everything is brand new including all appliances.…

June 2022
5star rating
Sparkling clean. Virtually everything is brand new including all appliances. Weill equipped kitchen. Great location to the largest fresh water lake on Cape Cod. The beach and boat ramp is a 5 minute walk. Close to the rail trail for biking and/or…

Drew was an awesome host! Always helpful and the recommendations…

July 2023
5star rating
Drew was an awesome host! Always helpful and the recommendations he gave us were great! The house was beautiful, our kids and family loved it! Especially the big garden they had for playing. We’ll definitely come back!

Very comfortable house in a beautiful spot. Lots of well…

July 2023
5star rating
Very comfortable house in a beautiful spot. Lots of well thought out amenities.

Drew is an excellent host providing a relaxing atmosphere for…

July 2021
5star rating
Drew is an excellent host providing a relaxing atmosphere for this wonderful home. The location is perfect for enjoying a cup of coffee on the quite porch away from it all while still being within walking distance of a couple of great restaurants….