check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters


Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!
  • 1 - 4 of 4
Additional fees apply. Taxes may be added.
    • 4 BR
    • 4 BA
    • 1 HF BA
    • Sleeps 10
      • 6 BR
      • 8 BA
      • 1 HF BA
      • Sleeps 20
        • 3 BR
        • 3 BA
        • Sleeps 8
          • 5 BR
          • 5 BA
          • Sleeps 16
          • 1 - 4 of 4

          Recent Chocolate Hole Reviews

          Amazing place, amazing views, fantastic vacation!

          5 of 5
          The Kamabesu Villa was the perfect place for our 10 person family vacation. Having three separate quarters provided just the right configuration for our needs. The property was very well maintained and the customer service was great. The on-site caretaker was invisible unless needed and was then on the spot. Great amenities, pool, beds, cooking supplies and AC! I would highly recommend the Kamabesu Villa to anyone and everyone. We will be back!
          • Submitted: Aug 31, 2016
          • Stayed: Jul 2016

          Beach Hole Rental St John's

          4 of 5
          we were escorted to the house in our rented Jeep. The House was clean and well stocked with items required for a beach stay. Steve and Lisa toured the house with us an explained all the important items. The driveway requires a skilled driver. The driveway patch appears to not be a legal rode. Driving on the Island can present challenges with driving on the left, hairpin turns and impatient St. John drivers. All in all we had a wonderful time despite this. There were an excessive amount of lights and it was a challenge to commit so many to memory. The cable/wifi/phone worked intermittently. Many of the doors had fingerprints. The ceiling fans were long over due for cleaning.
          • Submitted: Jul 11, 2016
          • Stayed: Jun 2016

          Spectacular: Everything we were told and MORE!

          5 of 5
          This was a spectacular first trip to Great Expectations! We have heard glowing reports from family members who had stayed there before and we were not disappointed. The Great Expectations complex sits high on the ridge (saddle) of a small peninsula between Hart Bay to the east and Chocolate Hole Bay to the west just a couple of minutes south of Cruz Bay where the ferry comes in. It is convenient, yet very private. The private outdoor showers with a view of sunrise is matched only by the views of sunset (with a refreshment) by the infinity pool above Chocolate Hole at the front of the compound. Six of us stayed for the week. We all had our own rooms with private bathrooms and the outdoor showers. Each room is well appointed with screen doors on either end allowing a really pleasant tropical breeze; it never felt muggy and we never used the AC. The rooms afforded privacy, yet you were only steps from the central building with the great room and the pools and lounging area. The center piece of Great Expectations is the great room and the kiddie pool and infinity pool to the west with plenty of space to do yoga or just lie around in the many lounges or hammocks (you can also slip into the hot tub if you get worn out playing at the beach and snorkeling). Inside the great room is a very well appointed kitchen with good pots, pans and dishes, dishwasher, large fridge, plenty of counter space and good bar supplies. There’s an island with bar stools so it’s easy to migrate from cocktails, to dinner prep, to feasting, to the sitting area for dessert with movies on the flat screen. We could easily have accommodated several other couples in the space (as well as kids). The great room has a size XXL ceiling fan (literally: it’s about 8 feet across!) as well as many screen doors on the east and west sides so lots of breeze. There’s also an excellent stainless steel gas grill right outside the kitchen. On top of the great layout are all the extras including camp chairs to bring to the beach, a tennis court, kids water toys and coolers for the beach. It is hard to believe there could be better views, breezes, or accommodations anywhere on St. John (and we looked). We can’t recommend Great Expectations enough and look forward to our next trip back.
          • Submitted: Feb 22, 2016
          • Stayed: Jan 2016