CALISTO & CO.
Our Brand
Everything we do is built on trust, service, and seamless living — across real estate, rentals, and full-service property care. Calisto is where luxury, technology, and hospitality come together to create effortless ownership and unforgettable stays.
Meet our Founder
Ryan Vandegrift, Founder & CEO
After careers in law, commercial real estate, and historic home restoration, Ryan Matthew Vandegrift turned his passion for real estate, interior design, and global travel into what is now Calisto. What began as a personal investment project in the Dominican Republic has grown into a multi-service brand serving homeowners, travelers, and property investors across the Caribbean and Spain.
Our Story
Calisto began with a simple mission: to make real estate ownership and travel more seamless, beautiful, and rewarding. What started as a solution for managing a few personal properties has grown into a multi-service company trusted by clients around the world.
The Calisto Difference
Calisto isn’t just a real estate company, a rental brand, or a property management service — it’s all of those things, seamlessly connected through one trusted partner.
What sets us apart is the way we bring it all together. Whether you're buying, managing, renovating, or renting your home, Calisto offers a fully integrated experience — supported by local experts, 24/7 concierge care, and a tech-enabled platform that keeps everything organized and accessible.
From our custom portals to our streamlined booking and service systems, we use innovative technology to remove friction and create a seamless, elevated experience for both homeowners and guests. It's not just full service — it's smart service, built for how people live, travel, and invest today.
The Meaning Behind Our Logo
The palm tree reflects our passion for vacation destinations and the relaxed, elevated lifestyle that Calisto helps our clients enjoy. The color pink is a tribute to the vibrant Danish brand our founder helped expand into Miami — the very brand that supported the launch of Calisto by helping raise the company’s initial funding.
We chose this symbol and color because they set us apart. Calisto isn’t traditional, and we’re proud of that. Our logo is a daily reminder of where we came from, what we believe in, and the kind of joyful, seamless experience we strive to deliver.
Our Brands
Calisto Realty – Real estate sales with 1% cashback and full post-sale support.
Calisto Stays – Curated vacation rentals in stunning destinations with 24/7 guest support.
Calisto Home Services – Comprehensive property care from cleaning to gardening.
Calisto Manage – Full-service property management for secondary homes.
Host with Calisto Stays – Rental management for holiday homes, from bookings to check-out.
Calisto Projects – Renovation and design management, from concept to completion.
Calisto Concierge – Personalized support for both owners and guests, available 24/7.
Our Promise
Calisto exists to make homeownership and travel not just easier — but better. With expert teams, seamless systems, and a personal approach, we deliver more than just services. We deliver peace of mind, lasting relationships, and elevated living, wherever life takes you.
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That’s why we proudly offer our Calisto Happiness Guarantee — a commitment to making things right if your experience doesn’t meet expectations. When you book and pay directly through Calisto, your satisfaction is guaranteed.