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Calypso del Sol (3BR/3BA) Perfect location, pool, amenities, views for 2 to 6!

Bedrooms 3
Space 3,000 sq. ft.
Property type house
Minimum Stay 5 - 7 nights


About the property

House, 3 Bedrooms, 3 Baths (Sleeps 6)

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 12 hours
Response rate:
Calendar last updated:
March 26, 2017

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 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
  • non smoking only
  • pets not allowed
  • children welcome
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
  • 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 -
(10 traveler reviews)

Calypso del Sol (3BR/3BA) Perfect location, pool, amenities, views for 2 to 6!
average rating of 5.0 based on 52 reviews

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: Nov 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: Apr 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: Jan 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: Aug 2013
  • Source: VRBO, from HomeAway
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Beautiful home for a wonderful week!

  • 5 of 5

Our entire experience with Calypso Del Sol was amazing! From the 1st email from the very lovely owner, Sally,who answered every question and was so knowledgable of the island to when we returned home and received some clothes we left behind! The location was wonderful, a few minutes past the Westin (where we stayed 5 years ago). Our jeep rental was perfect for exploring the island. We rented a dingy for the day from Noah's Ark by the Beach Bar and it was the best day of week, my 2 & 4 yr old wanted to do it again the next day. Don't miss dinner at the Ocean Grill for some fresh seafood and amazing house made desserts. Vie's Snack Shack (I believe on the east side) has some delicious chicken and possibly the best coach fritters on the island, definitely worth the $ for her private beach. We shared this home with another family- 4 adults, and 3 kids under the age of 5. We aren't sure who enjoyed the pool more, the kids or adults! The 2 bedrooms downstairs did not connect to each other or to the rest of the house from inside (we had to walk past the pool and up the stairs) which was confusing at first but wasn't really a big deal in the end. Perfect for 3 couples sharing the home. Everything was VERY clean and the property management were more than helpful in fixing the problem right away when one of the air conditioners wasn't working properly. We hope to stay here again on our next visit to St. John!

  • Submitted: Jun 4, 2013
  • Stayed: Apr 2013
  • Source: VRBO, from HomeAway
Owner's Response: We're so happy when Calypso works well for folks staying there! And one reason we have an on-island villa manager is to make sure that guests can get answers to questions or virtually immediate assistance if anything seems to "go on the fritz" at the villa. Everyone loves Nancy and Ernie, who take care of Calypso and keep it in tip top order.
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Perfect Location on beautiful St John

  • 5 of 5

Calypso was wonderful for our family of 5, great location overlooking chocolate hole and proximity to Cruz Bay make this an excellent choice for travelers looking to explore St John as well as go into town. The owners were beyond helpful with any questions I had before and during our stay. Highly recommend!

  • Submitted: Apr 3, 2013
  • Stayed: Mar 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

Estate Chocolate Hole and Great Cruz Bay House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Winter/Spring '17
Jan 7 2017 - Apr 21 2017
5 night minimum stay
Apr 22 2017 - Nov 17 2017
5 night minimum stay
Thanksgiving '17
Nov 18 2017 - Nov 24 2017
5 night minimum stay
Fall '17
Nov 25 2017 - Dec 20 2017
5 night minimum stay
Christmas '17/New Years '18
Dec 21 2017 - Jan 5 2018
7 night minimum stay
Winter '18
Jan 6 2018 - Apr 6 2018
5 night minimum stay
Summer/Fall '18
Apr 7 2018 - Nov 16 2018
5 night minimum stay
Thanksgiving '18
Nov 17 2018 - Nov 23 2018
5 night minimum stay
Fall '18
Nov 24 2018 - Dec 21 2018
5 night minimum stay
Christmas'18/New Years '19
Dec 22 2018 - Jan 4 2019
5 night minimum stay

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.
Enter dates for accurate pricing
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