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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

Great house. Very well equipped with all the crockery and…

June 2023
5star rating
Great house. Very well equipped with all the crockery and cutlery. Beach is a quick 8-10 mins walk. Very convenient. We had a great time.

⭐️⭐️⭐️⭐️⭐️ Wonderful stay! The house was spotless, cozy, and had everything we needed. Great location and an excellent host—highly recommend!

August 2025
5star rating
⭐️⭐️⭐️⭐️⭐️ Wonderful stay! The house was spotless, cozy, and had everything we needed. Great location and an excellent host—highly recommend!

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!

Great place and Drew made everything easy! Communication was prompt…

July 2025
5star rating
Great place and Drew made everything easy! Communication was prompt and efficient, would definitely recommend!!

The house is really nice and the pool was wonderful…

April 2021
5star rating
The house is really nice and the pool was wonderful and a great comfortable temperature. The location of the home is awesome since it is very close to the beach as well as groceries. Great home for families. We were able to grill and eat in the encl…

House has great location with easy access to rte 6,…

August 2023
5star rating
House has great location with easy access to rte 6, a lovely cape pond and the rail trail House has all needed amenities and is clean and very comfortable We had an awesome week and would easily book again😊

The photos don’t do this place justice, it is beautiful!…

July 2025
5star rating
The photos don’t do this place justice, it is beautiful! This was the perfect place for our stay to enjoy all that the Cape has to offer. We made a few day trips to explore the different areas and only had to travel 30-45 mins each time. The house w…

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…

House was exactly as described and depicted in the listing

September 2025
5star rating
House was exactly as described and depicted in the listing. It’s right in the border between Orleans and Eastham. Good location in the sense that it’s relatively easy to walk into Orleans or drive to nearby beaches. The house is tucked behind some r…