Vacationing with your kids and grandkids? Getting married? Traveling with 5 or more couples?

For reservations of 7 days or more with typically 7+ rooms, occasionally, we offer special discounts for reservations made directly with us so that rather than having to pay a rental agent fee, we are able to pass the savings on to you of up to $1,000 off our weekly rates for grandparents, brides, grooms, and LGBTQ+ weddings, 4 or more couples, and other good and deserving people!

One discount per reservation with a minimum stay of one week excluding the holiday weeks of Christmas, New Year’s, President’s Week, Easter, the 4th of July (St John Carnival) and Thanksgiving.

Check out our current availability and please come and enjoy the beauty and tranquiilty of St. John while helping others at the same time.


Return to Soggy Dollar

We visit Sandcastle Hotel on Jost Van Dyke annually like many others.  But, since Hurricanes Irma and Maria, we've found out that the 6 magical rooms on White Bay will not be rebuilt for 12-24+ months. We wanted to help Soggy 'families' who stay on that amazing stretch of sand by offering a Return to Soggy Dollar special with a stay at our villa.

Great Expectations will provide you and your Soggy family a great St. John vacation: sunrise and sunset views, multiple pools, and a Great Room to relax in, as well as your own private bedrooms. Use our Great Room and pool area is a short-term replacement for the dining room morning coffees and swims on White Bay. Plus, we'll make it easy for you to get back to Jost Van Dyke and enjoy White Bay. 

We've been back to White Bay multiple times throughout the rebuild process in October, November, and December. Soggy Dollar, Hendos, and the other beach businesses are coming along quite nicely. If you haven't noticed, the Soggy Cam is back online! While you can't stay overnight, you can still head over for a day to play.

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Soggy Family Special benefits

Missing Sandcastle Hotel and your yearly beach vacation?
Show us that you've stayed at Sandcastle Hotel in the past, Book a 7-night or more stay at Great Expectations for 6 or more people, and we'll include:

Winter 2019 (Jan 5 - Apr 13) | $1400+ value

Summer 2018 (Apr 14 - Dec 22) | $1600+ value


Black Fridayish Winter 2019

Black Fridayish Winter 2019

While many people spend Thanksgiving weekend shopping for the latest gadgets, we would like to offer you the experience of an amazing St. John vacation. We've only got a few weeks available this winter and decided to create a special for you and your family or group. Book any of our remaining winter weeks and receive: + 25% off any 2019 winter stay of 7 nights or more at Great Expectations* + Your choice of either (~$700 value): One 4 Door Jeep Wrangler (or equivalent) rental from St. John Car Rental or One Full Day Charter for up to 6 with PalmTreeCharters.com * Offer valid for 7 night or more available rental between January 5 - May 4, 2019. New reservations only. No other discounts may apply. Stays longer than 7 nights will be prorated at the discounted rate. Offer ends 11:59p EST Sunday Dec 2, 2018.
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Grandparents stay FREE

Grandparents stay FREE

We offer a free room to grandparents when accompanied by their kids and grandkids. One discount per reservation. One week minimum stay. Discount equal to the incremental cost of one bedroom, or $1,000 per week (pro-rated for longer stays).
Start your Family Vacation planning
6th Couple Stays Free

6th Couple Stays Free

For couples trips, we offer a free room to the 6th couple. One discount per reservation. One week minimum stay. Discount equal to the incremental cost of one bedroom, or $1,000 per week (pro-rated for longer stays).
Plan your Couples Trip
Bride & Groom stay FREE

Bride & Groom stay FREE

St John is one of the most wonderful places in the world to get married. Great Expectations is the perfect place to stay for a small or large wedding party, or maybe the family of the couple. Reserve our Villa for your St John wedding and the newlywed couple stays FREE. One discount per reservation. One week minimum stay. Discount equal to incremental cost of one bedroom, or $1,000 per week (pro-rated for longer stays).
Start planning your St. John Wedding