Skip to main content

About Us

Reach Out to Get Started!

This field is for validation purposes and should be left unchanged.

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 adorable, well kept and clean. I would…

August 2024
5star rating
The house was adorable, well kept and clean. I would highly recommend.

굿

September 2025
5star rating
굿

Great host and very responsive

August 2025
5star rating
Great host and very responsive! We loved the location as we were able to take a short walk to the beach.

Our group felt welcomed even before we arrived

August 2025
5star rating
Our group felt welcomed even before we arrived. Drew was a great, professional, and responsive host throughout our stay. A truly beautiful property and great location. We highly recommend booking with Drew!

Great location. We had an incredible week. The home was…

September 2022
5star rating
Great location. We had an incredible week. The home was clean with tons of space and the pool and hot tub were fantastic!!

Drew’s home was perfect for our six family members attending…

September 2024
5star rating
Drew’s home was perfect for our six family members attending a local wedding. Having the two bathrooms was key! The super modern refrigerator was a nice surprise. The two indoor spaces to relax and watch TV we’re great and offered quiet in the fron…

Our stay went very well. We had 1 or 2…

August 2023
5star rating
Our stay went very well. We had 1 or 2 problems but they were minor considering they were sorted very quickly.

great homebase while in Cape Cod! will be staying here…

September 2023
5star rating
great homebase while in Cape Cod! will be staying here again in the future for sure! excellent spot if you have a dog with the fenced in yard