Check in after:

3:00 PM

Check out before:

11:00 AM

Great Expectations is an 8 bedroom villa located on a 1 acre saddle of land overlooking Chocolate Hole and Hart/Rendezvous Bays. Our location offers nearly constant Caribbean breezes, as well as sunrise and sunset views daily. Our St. John ‘compound’ is built around 4 concrete buildings, 3 pools, hot tub, a tennis / basketball court and multiple landscaped areas with hammocks for relaxing. It is perfect for multi-generational family vacations, island wedding groups, couples’ vacations, and other large vacation groups. Typically limited to 16 people, we have had groups (with smaller children) as large as 21. The villa has 4 Master bedrooms that can be configured with King or paired Twin XL beds, 2 additional guest suites with queen beds and additional sleeping options, and 2 smaller rooms with Twin trundles, one of which can be made into an additional King. The main villa has an extensive patio area with a small wading pool, larger dip pool and the primary infinity-type pool. The Great Room has a full kitchen & bar with Sub Zero refrigerator, ice maker, dining table, living room area, 65″ LED flat screen, Sonos music system w/ outdoor speaker and a half bath room. The main patio area includes a built in grill area, large hot tub, and multiple tiled areas with outdoor dining/seating, upright and chaise lounge lawn furniture and hammocks. The main six bedrooms have full baths with private outdoor showers. We have 100Mbps broadband internet with WiFi converting the entire property. We only rent to one group at a time and rates are based on the number of bedrooms used. There are a total of 8 bedrooms available: 4 Master bedrooms in the Main Villa, 2 bedroom Suites in the Guest House, plus our Denis and Jumbie rooms. More than 16 people may be accommodated at the rates of $500/person/week. We do not charge for children age 2 and under who are in the same room as their parents. Rates include the following travel services: meet and greet upon arrival on St John, 24 Hour Emergency Service Repair, travel & planning consultation prior to your stay from owners.



  • 🎉


  • 🎉




  • 📃
    Cancellation policy is a 24 hour period

    This home allows you to cancel your reservation and get a full refund as long as it is done within 24 hours from the time you made the booking.

  • 📃
    This is another rule that you have to follow

    When booking this property you will solely be responsible for all the people in your group. In the event that there is any type of mishaps you will be the one to blame.

  • 📃
    The last rule that you will ever have to follow.

    I, probably as much as you, absolutely hate rules! I am declaring that this will be the last rule that you will ever have to follow. In the event that someone tells you something that you do not like you will know what to tell the.