Welcome to Villa Calypso

The #1 Luxury Vacation Rental on St. John

Patio Arches with Ocean View
Patio Arches with Ocean View

This stunning private luxury villa in St. John overlooking Klein Bay with a private beach is the perfect place to enjoy a vacation with friends and family. Snorkel with the sea turtles and manta rays, or relax with a cool drink on a chaise lounge by the infinity pool or spa overlooking the deep blue sea. Explore the unspoiled beauty of St. John with some of the most magnificent, pristine beaches in the world, then return “home” to Villa Calypso for luxurious relaxation.

Old World Style With New World Comfort…

As you enter Villa Calypso’s custom brick and stone pathway, you will be greeted by arched, custom mahogany doors that will transport you to an Old World villa set back in time, with all the modern conveniences you would desire and expect in a luxury resort. From the luxurious and plush furnishings to the lighted lanterns that surround the villa, to the infinity pool overlooking the beautiful sparkling turquoise ocean beneath you, Villa Calypso will bring you to a place of happiness and peace.

Newly built in 2014, Villa Calypso offers 4 Master Suites (one with a 5th “kids suite” adjoining bedroom), each with its own beautiful private outdoor terrace with sweeping views of the crystal blue Caribbean. High-end window treatments, luxurious bedding, and custom furnishings accompany the exquisite rooms. Each private terrace has seating and tables to enjoy the magnificent beauty of the turquoise Caribbean water below.

Villa Calypso Rooftops

Fall Under Calypso’s Spell With Beautiful Ocean Views

Everywhere at Villa Calypso, you will hear the tranquil sound of the ocean waves breaking on the beach below, and feel the trade winds that cool you. Relax and enjoy the peaceful and upscale neighborhood of Klein Bay after a memorable day exploring the wonderful islands of St. John and the surrounding US & British Virgin Islands. Staying at Villa Calypso is a dream, for families or for couples.

Villa Calypso, with its incredible beauty and privacy, has been a vacation destination to country stars, entertainment and television personalities, and everyday folks from around the globe who want to experience decadent luxury yet still have all of the comforts of home.

Our gorgeous villa features tall columns and sweeping arches to highlight the jaw-dropping ocean views. It’s those views and the amazing ocean life that keep guests returning year after year to St. John.

Adventures In Klein Bay Are Only A Minute Away

Villa Calypso enjoys a private beach where you have direct water access to Klein Bay, directly below our villa! We have 2 double kayaks and water toys for all ages. We have built a private custom stone and brick walkway path that leads directly to the street below Villa Calypso, and to our private beach access. The beach is a pebble beach with areas of shade and sun. Please bring our beach chairs for some fun while you snorkel Klein Bay. We are also snorkeling distance to Ditleff Point and Monte Bay. Jump on our kayaks for an adventure in the morning, visiting all the small bays around us! Villa Calypso is a hidden gem!

Patio Lounge Chair with Lantern

Relaxation Starts the Moment You Arrive at Our Luxury Villa Rental on St. John

You’ll be met by our Villa Manager who will transport you to Villa Calypso. If you’ve rented a car, no worries, you can just follow him. Once you arrive at Villa Calypso, we’re happy to offer drinks and appetizers with a Welcome Dinner on your arrival day, so you can settle in comfortably from your long trip to St. John.

Located just a few minutes from Cruz Bay Village, Villa Calypso’s location makes shopping and dining easy!

Indulge in the Best Amenities For Your Comfort and Enjoyment

Great Room Gathering Area
Patio Dining Area At Night
Chaise Lounges, Umbrellas And Pool
Hot Tub And Ocean View
  • Villa Manager will meet you at the St. John dock and escort you to Villa Calypso. The villa manager will take care of you and your guests during your stay with us.
  • Full Central A/C in all bedrooms and indoor common areas.
  • 27×12 Heated Infinity Edge pool, Hot Tub that seats 10 comfortably, and lots of seating and places to safely put your drink while relaxing.
  • High-Speed Wireless Internet throughout
  • Dish/Satellite flat screen SMART TVs
  • Apple desktop computer
  • Rohl faucets and fixtures throughout, TOTO toilets, and all high-end fixtures for the discerning client.
  • Luxury Turkish bathrobes, white noise machines for privacy in bedrooms.
  • 4 Master Suites (all with King Sized, Luxurious ‘W Hotel’ Mattresses)
  • Kid’s bedroom with two twins off of one of the lower master suites. Doors to provide privacy between the rooms.
  • Private balconies for each master suite with plush outdoor seating.
  • Bathroom vanities all have double sinks, both indoor AND outdoor showers in each bedroom.
  • One Master has a connecting bedroom for children, which we call our Family Suite. This connecting room has 2 twin beds with a flat-screen TV. The bedroom does not have outdoor access for parents’ peace of mind. Both bedrooms have doors for privacy.
  • Gourmet kitchen with custom mahogany cabinets, large 9 foot Belgium Elm dining table that comfortably seats 10, Margaritaville Frozen Concoction Maker, Espresso/Cappuccino, popcorn maker, gourmet pots and pans, slow cooker, Bonjour French Press Coffee/tea maker, Belgian waffle maker, VITAMIX, CUTCO knives, and many more items that the gourmet chef in you will love!
  • Large great room has plush-comfortable, yet up-scale furnishings. One 9-foot and two 6-foot custom slipcovered Taylor Scott sofas. Perfect to comfortably seat ten guests.
  • SONOS Music Entertainment System.
  • A Large 55′ 3-D flat-screen TV with Satellite connection, 3-D Blue-Ray player, 3-D Glasses.
  • Blu-Ray DVD library, Books for Adults and Children.
  • Toys and baby items for young families – High-chair, pack and play, booster seats, bed rails, baby blanket, baby monitor.
  • Lots of Board Games for adults and for kids.
  • Elegant Powder Room under entry close to the great room, veranda, and pool/spa area.
  • Laundry room. We have a separate entrance for the Housekeeping staff.
  • LL Bean Beach Totes for every bedroom.
  • 1-minute walk on custom private stone and brick walkway path from the pool area to the beach.
  • Tommy Bahama Deluxe Backpack Beach Chairs are available for your use.
  • Both hard and soft-sided coolers are provided for your convenience for day trips.
  • Washer and dryer
  • Snorkel fins for adults and children
  • 2 double Kayaks
  • Villa Calypso has large veranda areas, all around the villa, for dining and relaxing in the shade.
  • Enjoy the Leeward Terrace for alfresco dining, with a large professional grill for cooking local fish, steaks, or whatever else you desire. Cafe string lights and lanterns create a tranquil and romantic setting.
  • Our large driveway can accommodate 3-4 vehicles.
  • Automatic Generator to power the entire villa, in the event of a power outage.

What People Are Saying About Villa Calypso