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Calypso del Sol (3BR/3BA) Special place, great location! Open as of 3/1/2018!

Bedrooms 3
Space 3,000 sq ft
Property type house
Minimum Stay 1 - 7 nights


About the property

House, 3 Bedrooms, 3 Baths (Sleeps 6)

Beautiful Calypso del Sol was only slightly damaged -- almost all cosmetic -- by Hurricanes Irma and Maria, and repairs are underway. While waiting for electricity, we used the time to upgrade and beautify our pool and other parts of the villa! We are now ready to offer you a glorious vacation as of March 1. Y'all soon come, as we say on island! John Strong! Love City Strong!

Calypso del Sol has glorious water views from the pool deck and from both large, covered porches, with inviting views of Chocolate Hole and Pillsbury Sound. You can relax around the unusually large pool or take a short walk to Chocolate Hole Beach or over the hill to Hart Bay. The house is fully and beautifully appointed to offer every comfort in a close-in but very private location, while making absolutely the most of its beautiful Caribbean setting. It is air conditioned and offers free WiFi.

The living room is furnished with traditional Caribbean furniture. With vaulted ceilings, ceiling fans, tiled floors, Caribbean art, and white walls, Calypso del Sol has a relaxing and inviting interior. For your entertainment, a TV/VCR/DVD, cable, and a stereo with a CD player are provided. The wicker sofas are covered in a colorful island print fabric. The great room is fully air-conditioned. And the views never stop.

The gourmet kitchen has cherry cabinets, a new dishwasher and stainless steel appliances, microwave, and a center island to allow collaborative meal preparation. The plates, glasses, serving utensils, etc., are also new and evocative of the tropics. The kitchen is fully equipped with almost every kitchen appliance or tool one could want. Although many wonderful restaurants can be found close by in Cruz Bay, you will probably find yourselves drawn to this efficient, fabulous kitchen to prepare a few meals featuring local food available from nearby grocery stores.

Among the most charming features of Calypso del Sol are its porches. Sliding glass doors toward the Bay open to the 500 square foot porch from the upstairs living/dining room with a fabulous view of Chocolate Hole Bay through the arched overhang. The same porch design on the lower level has comfortable rocking chairs, providing another attractive space outside the two downstairs bedrooms for reading or other activities. These porches are comfortably furnished to ensure maximum enjoyment and ease.

Just outside the living/dining room on the top level toward the pool is a screened porch with a table that seats 6 for al fresco dining – or you can eat in the inside dining room which also comfortably seats 6. A sofa and chairs make the screened porch an outdoor living or dining room, cooled by breezes from the ceiling fans.

Calypso del Sol sleeps 6 comfortably in its three equally-spacious bedrooms. One bedroom is off the living room, and has a king-sized bed; this bedroom – as the others – has a sliding glass door out to the porch and has wonderful views of Chocolate Hole Bay. Air conditioned and with ceiling fans, this room provides a tranquil, romantic island getaway. The large bath has a full, island style, walk-in tiled shower, and comfortable privacy.

The second and third equally-spacious bedrooms are on the lower level and open out to the large covered deck on that level. Each features king-sized beds that can also be configured as twin beds. Both bedrooms have sliding glass doors onto the porch and gorgeous views of Chocolate Hole Bay. Both are fully air conditioned. The porch has comfortable rocking chairs for easy reading or just watching the boats go by. The linens and décor for these bedrooms are tropical and cheerful, and “black out” curtains are provided for those who want to sleep in.

St. John’s gorgeous beaches may lure you into the Caribbean, but you may not be able to tear yourself away from Calypso del Sol’s azure blue, unusually large pool. The crystal clear pool is perfect for floating or swimming under St. John’s sun. Chaises make this a truly comfortable place to while away the day, reading or tanning or napping; floats are provided for enjoying the pool. Later, under the twinkling evening stars, you can enjoy the 6-person hot tub located right on the pool deck.

Calypso del Sol is the very definition of a charming, romantic, Caribbean-styled Villa. This Villa has it all. The landscaping consists of lush topical trees and flowers, including banana palms, guava, and many other local fruit trees. Because of its quietness, fine appointments, perfect location, and Caribbean style, Calypso del Sol is one of the most sought after homes on St. John for friends and families looking for adventure or for a quiet retreat.

Keywords: villa

More Details

Sally Jaggar
Member since: 2009
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
April 18, 2018

About Sally Jaggar

Three couples jointly own Calypso del Sol. We all live in Northern Virginia and have known each other for years. St. John has been the scene of many special events for of the couples even got married on St. John!

Sally Jaggar purchased this house in 2005

Why Sally Jaggar chose Estate Chocolate Hole and Great Cruz Bay

We all LOVE St. John and purchased Calypso to have a wonderful villa to share with others as well as a great place to stay ourselves. We're convinced that St. John is the best island in the Caribbean because it is so beautiful, the people who live there are wonderful, and the island is 2/3 National Park and therefore protected from over-development.

What makes this house unique

At Calypso, we especially love the fabulous sunsets, the big pool, the screened porch, and the perfect location – close enough to Cruz Bay but way quiet. Oh yes, and the birds and iguanas.

Guestbook comments from the owner

Sadly, we are back home in Tennessee. We had an absolutely wonderful time in Saint John! Your house was perfect for us 3 couples! Thank you!
Sep 2016
  • 1 of 42


Estate Chocolate Hole and Great Cruz Bay House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 3000 sq ft
House Rules:
  • Max. occupancy: 6
  • children welcome
  • pets not allowed
  • non smoking only
Location Type:
  • Near The Ocean
  • Ocean View
  • Water View
  • Waterfront
  • Family
  • Romantic
  • Activities Guide
  • Air Conditioning
  • Alarm Clock
  • Basic Soaps
  • Broadband Access
  • Ceiling Fans
  • Clothes Dryer
  • Hair Dryer
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking
  • Parking Off Street
  • Safe
  • Telephone
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Free Wifi
  • 4 Ring Stove
  • Blender
  • Catering Available
  • Coffee Maker
  • Cooking Utensils
  • Dishwasher
  • Freezer
  • Grill
  • Ice Maker
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
  • Child's Highchair
  • Dining Area
  • 3 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
  • 3 Bedrooms, Sleeps 6
  • King size beds (1), Twin or Single Beds (1)
  • Books
  • CD Player
  • DVD Player
  • Games for Kids
  • Music Library
  • Satellite / Cable
  • Stereo
  • Television
  • VCR
  • Video Library
  • Balcony
  • Barbecue
  • Beach Chairs
  • Beach Towels
  • Deck / Patio
  • Large Cooler
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Raft
  • Screen Porch / Veranda
  • Small Cooler
  • Wood Deck
  • limited accessibility
  • suitable for elderly or infirm
Pool / Spa:
  • Hot Tub
  • Outdoor Hot Tub
  • Outdoor Pool
  • Private Pool
  • bay/sound
  • health/beauty spa
  • library
  • marina
  • playground
  • pond
  • rain forests
  • reefs
  • restaurants
  • ruins
Leisure Activities:
  • beachcombing
  • boating
  • eco tourism
  • gambling casinos
  • horseback riding
  • miniature golf
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • water sports
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • deepsea fishing
  • fishing
  • fly fishing
  • hiking
  • parasailing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • swimming
  • tennis
Screened porch, easy access into house (no steps), beach chairs and coolers provided, black out drapes in each bedroom, safe for valuables, books and guides about St. John and its beaches


Exceptional! 5/5 -
(12 traveler reviews)

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Calypso del Sol (3BR/3BA) Special place, great location! Open as of 3/1/2018!
average rating of 5.0 based on 54 reviews

Loved our family vacay villa; quiet and with an unforgettable view including the iguanas!

  • 5 of 5

Well don't let my delay in posting a review undermine the terrific time my family had in St. John in July. A large part of the trip's success was staying at Calypso del Sol. In booking the villa, Sally was super easy to work with and quick to respond to questions. Once the villa was booked, Sally supplemented our trip planning with helpful information about the area. We contacted the property manager on the island on the ferry ride over and she met us at our car rental. We followed her to the villa, which was a blessing since we needed some initial help navigating the left side of the road! Sally ensured that the house was set up for our family (12 your old twins and our 17 year old niece). The villa is lovely, clean, quiet, and comfortable. The views from either deck or the pool are unforgettable. The pool was so nice after a day at the beach. The villa's location provided easy access to the beaches and to the grocery and restaurants. The kitchen is well equipped so we ate in a few nights and tried out the excellent restaurants the other nights. The ability to make our own lunches allowed us to spend the day at the amazing beaches or relax and enjoy the view at the villa. And we all were captivated by the iguanas that live in the nearby tree! We hope to return to St. John and stay at Calypso del Sol.

  • Submitted: Sep 5, 2017
  • Stayed: July 2017
  • Source: Vacation Rentals, from HomeAway
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Amazing views

  • 5 of 5

Wonderful: had everything we needed. Loved that the other 2 bedrooms were down stairs and the master upstairs. Great house, close enough to everything, wish I had more time to stay

I guess that means I need to return,, Thanks for a great vacation.

  • Submitted: Aug 3, 2017
  • Stayed: July 2017
  • Source: HomeAway
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Trip of a Lifetime

  • 5 of 5

Myself, my fiancee, and two friends recently traveled to St. John for a wedding and stayed at Calypso. We found the house to be absolutely perfect for our vacation. The place is clean, well kept, and a very accommodating host. It is in a very good location, not too far from town, but also not too close. You can spend all day lounging by the pool and taking in the views of Chocolate Hole, then be more than comfortable sitting on the deck to watch the sunset. All utilities worked well & the amenities made our stay that much more enjoyable. I can not say enough good things about Calypso, and highly recommend it as an option for anyone traveling to St. John.

  • Submitted: Dec 20, 2016
  • Stayed: November 2016
  • Source: VRBO, from HomeAway
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Loved everything about it!

  • 5 of 5

Photos don't do it justice! Everything about it was clean and maintained. Owner and manager provide excellent service. I would highly recommend and would plan to return if I get the chance. We came for the beaches and had a fantastic time. Really enjoyed starting our day and coming home to the pool and hot tub.

  • Submitted: May 1, 2016
  • Stayed: April 2016
  • Source: HomeAway
Owner's Response: Thanks for your kind words! We work hard to help you have a great time on wonderful St John. So glad you enjoyed it. We'll look forward to seeing you at Calypso again -- soon!
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Wonderful Villa, Great Location, Kid Friendly

  • 5 of 5

My wife and I have been to St. John three times (staying once in the owner's other villa) and each time it is of course fantastic. Calypso was a great home away from home with everything you need from kitchen supplies, coolers, beach stuff (and for kids!) and cards for the late night games. We brought our two kids aged 5 and 3 and the villa manager set up one room for them as we stayed next door. We also brought my wives parents and all four of the adults agreed that Calypso was the nicest villa we have stayed in so far. The hot tub is a great plus even though the weather is always perfect. The porches are great to relax outside and even in a 3BR you have so much space sometimes it is hard to find each other! The pool is awesome with great views and really what else can you ask for. The location is right next to the supermarkets and Cruz Bay for the late nights or early dinners and drinks.

We would highly recommend, though it seems many agree as it is ALWAYS booked!

Thanks to the owners for a wonderful time and we will be back again next year!

  • Submitted: Feb 12, 2015
  • Stayed: January 2015
  • Source: VRBO, from HomeAway
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Reston, Virginia

A Wonderful Stay, One of Many at Calypso Del Sol

  • 5 of 5

My wife and I have stayed at Calypso Del Sol a few times now, we love it there and we suspect you will too. We just returned from beautiful St. John after a late season two week stay in September.

Calypso is a great villa, whether it’s just for the two of us or if we bring family or guests. You’ll love the comfort and scenic views from the well appointed living room and kitchen and each bedroom. We particularly enjoyed the patio’s -- watching the sunset with a refreshing drink and good company or the view over the bay with a cup of coffee in the morning.

Whether you just want some down-time reading your favorite novel ( I read Grisham’s “ The Racketeer) by the pool or you want to enjoy a day at any number of beautiful beaches, anyplace you want to go is just a short drive from Calypso’s front door. I also was able to stay connected online ( yes, I had to work—a little) with the WiFi available. Our thanks to Nancy and Ernie who were available instantly if we had any problems with anything.

We’ve been to many popular vacation spots in the Caribbean, but because of St. John’s proximity within the USVI’s -- from your beach chair on many of St. John's pristine beaches, you’ll have an almost surreal view of near-by islands, many of which are a short dingy-ride away, other’s you can visit by any number of easily available sailing charters. Calypso Del Sol would be a great choice for experiencing all that St. John has to offer.

  • Submitted: Sep 25, 2013
  • Stayed: August 2013
  • Source: VRBO, from HomeAway
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Nearest Airport
15 Miles
on St Thomas -- a ferry ride away
Nearest Barpub
1.5 Miles
try Woody's or The Beach Bar in Cruz Bay
Nearest Ferry
1.5 Miles
in Cruz Bay
Nearest Restaurant
0.5 Miles
at the Westin Hotel, or in Cruz Bay
Nearest Beach
0.25 Miles
Chocolate Hole Bay and Hart Bay, plus many others
Car: necessary

Chocolate Hole Bay is quiet but glorious, with wonderful views out to the Sound toward St Thomas. The Bay typically has a few dozen small boats -- mostly sail boats -- anchored in it, making for a beautiful scene. You can walk about 10 minutes down to the beach for some gentle swimming and snorkeling off this sandy but 'unimproved' beach. Happily, this quiet area does not attract crowds like the famous North Shore beaches. One advantage of the Chocolate Hole location is that it is about 7 minutes to town, but the area is a quiet, safe neighborhood.

Other Activities: Sunning, reading, exploring, hiking, snoozing -- trying island drinks!


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $350
Tax Rate 12.5%

IMPORTANT: Our rates vary by the number of people staying used: basically, the additional weekly rate for each additional two people is $300.
NOTE: the rates presented here are FOR 3 OR 4 PEOPLE. Thus, low season rates are $3000 for 1 or 2 people, $3300 for 3 or 4 people, or $3600 for 5 or 6 people. PLUS tax.
No cleaning costs for guests staying 8 days or less; for 9 days or more, we require a mid-stay cleaning which costs $175.

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.

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