Greetings From The Owners

Thank you for your interest in staying with us at Villa Calypso! My name is Gail and my husband Darryl and I are the new owners of Villa Calypso (formerly known as Casa La Famiglia), as of mid-May 2021.

You are in good hands, as management is my profession and we take your vacation very seriously. I have been a Certified Property Manager (CPM) since 1986 and have managed more than 6400 units at one time. We have owned and managed vacation rental properties for the last 10 years in Montana, and have been sailing in the crystal clear waters and dreaming of spending more time in the Caribbean for the last 30 years. Finally, we’ve acquired our first island property! (Yes, there will be more to come!)

As you might know, Villa Calypso was formerly called Casa La Famiglia. We changed the name for several reasons but primarily because no one could pronounce it, spell it, or remember it. We also wanted to add a splash of color, music and fun to an already beautiful villa.

Why Villa Calypso?

Calypso goddess graphic Villa Calypso's brandmark (the goddess Calypso) with a left-to-right color gradient spanning from ocean blue to turquoise to aquamarine.

According to mythology, Calypso was a beautiful goddess/sea nymph who used her powers to enchant, making one not want to ever leave to return home. Those under her spell fall in love and don’t make much of an effort to leave on their own.

We chose the name Calypso because of the dazzling beauty of this villa, the Mediterannean mythological architecture, and like the spell of the goddess herself, the desire that just being at Villa Calypso creates in our guests to stay here forever. It is our hope that if and when you do depart, you will carry the spirit of Calypso back home with you, and retain a longing to return to Calypso again soon.

We look forward to helping you create a wonderful vacation in St. John, and like all of the guests before you, fall in love with Villa Calypso.

Until then, if you are interested in checking out our other properties and learning more about us, you can visit the website for Glacier Bear Retreat, the only luxury vacation rental INSIDE the boundaries of Glacier National Park in Northwestern Montana, or Snow Bear Chalets, the world’s 1st ski-in/ski-out treehouses, located slopeside at Whitefish Mountain Resort. Snow Bear Chalets actually made the cover of TIME Magazine selected as one of the 100 World’s Greatest Places 2018! You can also learn more about me as your host, at InspireMeToday where we’ve been providing free inspiration to millions of people each day all over the world since 2008.

Should you have any questions or wish to chat with me, you can reach me at 844-SJVilla (844-758-4552).

Thank you and we look forward to helping you create a magical holiday for you and your family!