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St. John villa expert

Know Before You Go...

Great Expectations has amazing views of Chocolate Hole and Hart Bay, but the sunrises and sunsets are the home’s main attraction. Everything you need in an island vacation is right here, including an on-site tennis court and three pools. Four of the bedrooms can be connected for families, and there’s tons of amenities for infants and children. Best of all, the beaches are just a short drive away!

Shawna , 214-350-6220 x9102

Fun for families!

Great Expectations is a warm, vibrant villa with a spacious floor plan and tropical views. Terra cotta tiles and original local stone combine with endless amenities, like property-wide WiFi, to create the perfect family vacation villa.

All three pools benefit from a chemical-free filtering system and lots of sunshine. There’s also an 18” deep wading pool for kids and two hot tubs with LED lights, a waterfall, and UV filtration. Open-air canopies provide shade to nearby loungers and seating. The stainless steel BBQ grill and several oversized hammocks make it easy to stay outside all day and all night. Activities and fun are within reach thanks to a regulation doubles tennis court with a basketball hoop and a fenced-in play area. Basketballs, tennis racquets, and tennis balls are all provided. Chocolate Hole and Hart Bay are only a 5-minute walk or drive from Great Expectations, and both offer great snorkeling spots. The villa has beach toys, coolers, towels, mats, chairs, and baby beach cabanas to take down to the sand. Great Expectations has many “green” features such as solar panels, a Tesla Powerwall battery bank, and a large water cistern.

Antique, Danish country armoires and local artwork decorate Great Expectation’s warm interior. A 65” LED TV with complimentary Netflix and SlingTV is mounted into the wall between the kitchen and living room, and cushioned seating provides plenty of room to enjoy movies. There’s also a large selection of books, games, puzzles, CDs, and DVDs. The kitchen is equipped with stainless steel appliances, a sub-zero fridge, and an ultraviolet three-stage water filtering system. It’s smaller appliances include a coffeemaker, toaster oven, blender, and waffle maker. Families will appreciate the highchairs, booster seats, children’s books, and art supplies. Guests can enjoy meals around the dining table or the kitchen’s breakfast bar.

Great Expectations was specifically designed for couples vacationing together and multi-generational families with young children. The villa has four master suites all on the same level, so everyone has the same size, views, and amenities. Each of these suites offer an ensuite bathroom, air-conditioning, a walk-in closet, a private patio, and extra long twin beds that can be converted into a California King. Each master suite connects to one other master suite, which is ideal for families. The fifth main house suite has a trundle bed with two twins, an ensuite bathroom, air-conditioning, and a DVD player. The guest house offers more space for teenagers, in-laws, or grandparents. It has two queen suites with futons, a living room, a sun room with a daybed, and a private bathroom. Great Expectations also offers foldaway beds and porta-cribs that can be placed in any bedroom.

Great Expectations is within a short drive from several restaurants, activities, and sights. St. John is home to golf, spas, shops, water sports, restaurants, and a national park. There’s something for every traveler at Great Expectations.

Quick Quote

Dates People Nightly
May 5, 2019 to Dec 20, 2019
7 Night Minimum
1-2 people $700 USD
3-4 people $843 USD
5-6 people $986 USD
7-8 people $1,129 USD
9-10 people $1,271 USD
11-12 people $1,414 USD
13-14 people $1,557 USD
15-16 people $1,700 USD
Dec 21, 2019 to Jan 5, 2020
7 Night Minimum
1-16 people $3,129 USD
Jan 6, 2020 to May 2, 2020
7 Night Minimum
1-2 people $1,257 USD
3-4 people $1,400 USD
5-6 people $1,543 USD
7-8 people $1,686 USD
9-10 people $1,829 USD
11-12 people $1,971 USD
13-14 people $2,114 USD
15-16 people $2,257 USD

Notes on Rates:

  • All rental rates are based on two persons per bedroom.
  • This property charges rates in US Dollars (USD).
  • Rates are subject to change.
Rates shown in

Choosing the right villa is just the first step in creating the perfect vacation experience. We help you plan every element of your villa vacation, from rental cars to spa treatments, completely personalized to you.

  • spa services
  • chef/cook services
  • butler service
  • car rental
  • restaurant reservations
  • activity and sightseeing
  • ferry/airport transfers
  • grocery provisioning
  • laundry service

    Beds & Baths

    Main House

    • Bedroom 1
      • 1 King, Air Conditioning
      • Ensuite Full Bath with Shower
    • Bedroom 2
      • 1 King, Air Conditioning
      • Ensuite Full Bath with Shower
    • Bedroom 3
      • 1 King, Air Conditioning
      • Ensuite Full Bath with Shower
    • Bedroom 4
      • 1 King, Air Conditioning
      • Ensuite Full Bath with Shower

    Guest House

    • Bedroom 5: Guest Suite
      • 1 Queen, Air Conditioning
      • Ensuite Full Bath with Shower
    • Bedroom 6: Guest Suite
      • 1 Queen, Air Conditioning
      • Ensuite Full Bath with Shower
    • Club Room: Trundle
      • 1 Trundle, Air Conditioning
    • Futon: Trundle Full/Twin
      • 1 Double, 1 Twin Sofa bed, Air Conditioning

    Other Bathrooms

    • Bathroom 7: Full bath


  • 1 Housekeeper: Weekly
  • 1 Gardener
  • 1 Concierge


  • Answering Machine
  • BBQ Outside (Gas)
  • Board Games
  • Book Library
  • Cable TV
  • CD Library
  • CD Player
  • Ceiling Fans
  • Dishwasher
  • DVD Player
  • Equal Bedrooms
  • Family
  • Fax
  • Gated Community
  • Guest House
  • Hair Dryers
  • Hammock
  • Hot Tub
  • Internet Access/WiFi
  • Microwave
  • On-Site Gym Equipment
  • Pool at Villa
  • Safe
  • Short Walk to Beach
  • Stereo System
  • Sunrise View
  • Sunset View
  • Telephone
  • Tennis On-site
  • Video Library
  • Washer/Dryer
Pool 20 x 20 x 2' - 5' deep
Air Conditioning A/C in bedrooms
Location Chocolate Hole/Hart Bay
Sq Ft. 4,800
Beach Hart Bay beach and Chocolate Hole are within walking distance from the villa, however walking is not advised. It's a very strenuous hike. The beaches are a couple minute drive from the villa.
Transfers Airport escort to your villas upon arrival. Departure transfers not included.
Notes Dining room seats 8
Included Tennis rackets and basketball for tennis/basketball court.
Children Welcome
Availability and usefulness of sports and outdoor equipment is not guaranteed because of heavy use and exposure to the elements.


Shopper Approved