Our Story
About STAYIN
The Foundation
20+ Years of Hospitality Expertise
STAYIN was born from a simple belief: vacation rentals should feel like staying with a friend who happens to have exceptional taste and 20 years of hotel management experience.
Our founder Lenny spent over two decades managing some of New York City's most demanding hospitality environments — learning that the difference between a good stay and an unforgettable one lives in the details. The perfectly stocked kitchen. The thoughtful welcome. The response that comes in minutes, not hours.
When Lenny and co-host Mairely launched STAYIN, they brought that same standard to short-term rentals — starting with the A-Frame on Pudding Hill in the Catskills, and growing to a curated portfolio spanning New York, Connecticut, Florida, and Punta Cana.
Today, STAYIN manages properties for owners who want more than a property manager — they want a partner who cares as much about their investment as they do.
20+
Years of Hospitality
What We Stand For
Our Values
Hospitality First
Every decision we make starts with the guest experience. From the thread count of the linens to the speed of our response — it all matters.
Radical Transparency
No hidden fees. No fine print surprises. We tell you exactly what you're paying and exactly what you're getting.
Owner Partnership
Your property is your investment. We treat it that way — with the same care and attention we'd give our own.
Continuous Improvement
We track performance, read every review, and constantly refine our approach to deliver better results for owners and guests alike.
Where We Operate
Our Markets
New York
Catskills & Hudson Valley
Connecticut
Hartford County
Florida
Central & South Florida
Dominican Republic
Punta Cana