Great Expectations

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Hillside, Estate Chocolate Hole, St. John
8 Bedrooms 8 Bathrooms 1 Half Bathrooms
Maximum Occupancy: 16

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Great Expectations

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Perfect for families and groups, Great Expectations features spectacular sunrises and sunsets, short-walk access to swimming and snorkeling at beautiful Hart Bay, and unparalleled vistas of the Caribbean Sea. For tennis enthusiasts, Great Expectations is one of the few villas that boasts its own private court. 

Great Expectations is comprised of several structures joined by a common patio and pool area. The main building contains the main living/dining area Great Room. The Great Room has a complete entertainment system, washer/dryer and half bath. 

The fully equipped kitchen has all of the amenities guests could expect...including a convection oven, refrigerator and dishwasher. Sliding glass doors in the Great Room open onto the patio/pool area. 

This beautifully landscaped area has a wading pool for younger guests, a refreshing swimming pool, a hot tub and a gas grill for casual dining or Caribbean style poolside entertaining. 

The other two buildings, each conveniently attached to the patio/pool area, offer privacy and breathtaking views to both east and west. Each building has two large air conditioned king bedrooms and there is a guest house with 3 more bedrooms and club room for the 8th bedroom see details of all below. The villa will accommodate 14 people in 8 air-conditioned bedrooms: 4 equal Master bedrooms all on the same level each with: - King-size bed or 2 Twin-size beds (the bedrooms are connecting and large enough also to accommodate a port-a-crib or foldaway bed for children) - private bathroom with double-sink vanity and large indoor-outdoor shower - private patios with spectacular views of the Caribbean Sea. These 4 equal Master bedrooms are located in two buildings separated by the Great Room. 3 spacious bedrooms in the two-story Guest House with: -Owners Suite (twice the size of one of the Main Villa bedrooms) on the top floor offering phenomenal views of the Caribbean Sea with a Queen-size bed (plus a futon for additional sleeping capacity), living and dining areas, kitchen and laundry, and private bathroom with double-sink vanity and a large indoor-outdoor shower - Guest bedroom (same size as one of the Main Villa bedrooms) on the 1st floor with a Queen-size bed (plus 2 futons for additional sleeping capacity) and private bathroom with a large indoor-outdoor shower - The Sun Room, also on the 1st floor, with 2 Twin-size beds which can be set-up as a King-size bed and private bathroom with a beautiful coral shower The 2 bedrooms on the 1st floor are ideal for parents who wish to have their children in a connecting bedroom. -The Club Room, located between the Main Villa and the Guest House, serves as a fitness room which, while smaller than the other rooms, can be used as a 8th bedroom for a couple of teenagers with a Trundle bed (2 Twin-size beds one of which stores under the other when not used) and a private bathroom with a gym-sized shower For your cooking and dining pleasure: »Stainless steel side-by-side 48" Sub-Zero refrigerator »Stainless steel professional Scotsman commercial icemaker »Stainless steel super quiet dishwasher »Stainless steel microwave oven »Halogen electric cooktop range with self-cleaning convection oven »Stainless steel outdoor gas barbecue grill »EPA-recommended ultraviolet 3 stage water filtering system »Cuisinart coffeemaker with filters, coffee bean grinder, and toaster »Electric blender and waffle maker »Professional Calphalon and Cuisinart cookware »Plenty of dishes and glassware and serving platters and bowls »Indoor and outdoor dining including a picnic table with awning »Gourmet spices including jerk, Cajun blackening, mustard seed, fine herbs, coriander, marjoram, sesame seed, cumin, Spanish paprika, cinnamon sticks, garlic, nutmeg, turmeric, curry, and, yes, salt and pepper yes, salt and pepper

Bedroom Specs

  • Queen( 2 )
  • Trundle Bed( 1 )
  • Twins - Convertible to King(s)( 1 )
  • Futon( 3 )
  • King can be split to twins( 4 )

Bathroom Specs

  • 8 Bathrooms


  • Maid Service ( 1 Days A Week )


  • Children : Children are welcome
  • Pets : Please inquire
  • Smoking : Not permitted


  • Air Conditioning ( Bedrooms )
  • Gym ( Elliptical Machine & mat )
  • Pool ( 2 pools - 1 at main house, 1 at guest house - plus wading pool )
  • Hot Tub ( 8- person spa at Villa + Hot tub at Guest cottage )
  • Television
  • Stereo/Hi-Fi System
  • CD Player ( with AM FM Radio )
  • iPod Dock/Stereo Hook-up
  • Beach Chairs
  • Beach Towels
  • Beach Cooler
  • Telephone ( All bedrooms, Living Room )
  • BBQ / Grill ( Gas )
  • Washer
  • Books
  • Games / Puzzles
  • Movie Collection
  • Safe ( Each Bedroom )
  • Hammock
  • Tennis Court
  • Pack 'n Play
  • High Chair
  • Children / Baby Toys
  • Bathrobes
  • Outdoor Shower
  • Ceiling Fans
  • Cable TV Service ( Netflix video streaming on a 60 inch Sharp LED HDTV )
  • Iron
  • Gourmet Kitchen ( dishwasher, ice maker, microwave )
  • Parking
  • Outdoor Sound System
  • Ironing Board
  • DVD Player ( blue Ray )
  • Wireless Internet

Rate Notes

  • Security Deposit: $500
  • 10% tax
  • Additional cleaning fee may apply for stays of less than 7 nights.
  • additional cleaning service available during your stay for $35 per hour per maid
  • Rates in U.S. dollars.
  • Rates based on double occupancy per bedroom.
  • Weekly rate is equal to seven times the nightly rate unless noted above.
  • Rates subject to change without notice.
  • Holiday rates and date periods may vary. Holidays may include Christmas, New Year's, Thanksgiving, Easter, President's Day, etc.
  • Additional fees may apply. Call for details.

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