Who are we?

Welcome to My Dream Journey, where faith, family, and unforgettable vacations come together. We’re the Massingill family—a husband-and-wife team raising five wonderful children here along the beautiful Emerald Coast of Florida. What began as a dream to create memory-filled getaways for families like ours has grown into a vacation rental business rooted in trust, hospitality, and care.

We recently welcomed our fifth child into the world, and while our current family photo shows just four of our little ones, know that our newest addition is already part of the team—likely supervising pool setups or making sure the golf cart is ready to roll.

Every home we manage is designed with real families in mind—from heated pools and beach carts to bunk rooms and fenced-in yards. Whether you're staying with us or entrusting your home into our care, we’re here to serve with integrity, excellence, and the kind of personal touch only a family-run business can offer.

We believe your vacation should feel like coming home—only better. 

Let My Dream Journey be part of yours.