About

Welcome to Friends of Friends Guesthouse, a charming retreat in the heart of Los Olivos, California. Just steps from the iconic town flagpole, our guesthouse offers the perfect blend of wine country charm and modern comfort.

The space features a thoughtfully designed one-bedroom layout with a comfortable living and dining area, a fully equipped kitchen, and a stylish bathroom complete with washer/dryer. Relax with a glass of local wine on-site before heading out to explore the dozens of world-class tasting rooms, restaurants, and boutiques right outside your door.

Whether you’re here for a romantic getaway, a weekend with friends, or a peaceful work-from-home retreat, our guesthouse provides a private, cozy escape surrounded by the best of Santa Ynez Valley living.

Meet Your Hosts

We’re Derek and Stefanie Boucher, longtime residents of Los Olivos. Since 2018, we’ve been proud to call this charming wine country town our home. We live in the main house on the property with our son and two lovable pugs, and we’re excited to share our guesthouse with friends and “friends of friends.”

Both of us work in marketing, but our true passion lies in creating memorable experiences and welcoming people to our community. When you stay with us, you’ll enjoy the privacy of your own space along with the comfort of knowing your hosts are nearby and happy to provide recommendations on the best local wineries, restaurants, and hidden gems.