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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 an amazing stay at this charming house in…

May 2024
5star rating
We had an amazing stay at this charming house in Eastham! The natural light and water views were beautiful and peaceful. The house is in a great location for enjoying the area’s beaches, biking on the rail trail, shopping, and dining. We had ever…

Clean, nicely appointed, great location driving distance to everything you…

June 2022
5star rating
Clean, nicely appointed, great location driving distance to everything you need (beach, seafood, stores). We’d definitely rent here again! We stayed here with 6 adults and two kids (it’s cozy, but we fit). Drew was a great host, very easy to comm…

Great stay. We had some minor issue with some basic…

August 2024
5star rating
Great stay. We had some minor issue with some basic items being in short supply (trash bags, toilet paper), but Drew was very responsive and followed up with the cleaning service to replenish them and reimbursing us the cost of supplies when that …

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July 2024
5star rating
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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

Great place, amazing area, and overall fun time in nature.…

October 2021
5star rating
Great place, amazing area, and overall fun time in nature. Will definitely be back!

This was the perfect place for a mini work from…

September 2023
5star rating
This was the perfect place for a mini work from home getaway – the space was comfortable and clean, the yard was perfect for our dog (who made sure to maximize her time outside), and the location was close to fun activities/restaurants

Wonderfuel and place !!

September 2024
5star rating
Wonderfuel and place !!

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….

Tranquil view has a lovely large screened porch for morning…

October 2024
5star rating
Tranquil view has a lovely large screened porch for morning coffee and to enjoy the view. We had sunny fall days which were perfect to enjoy our trip. We walked to the beach a few times. I sat out there with a book a few afternoons. Golfed nearb…