Great Expectations - Chocolate Hole

8 Bedrooms | 8.5 Baths | 16 Max. Guests

Beds Baths Location High Season
1/2/24 - 4/17/24
Low Season
4/18/24 - 12/18/24
Max Guests
8 8.5 Chocolate Hole 16

Call for rates and availability.

Request a Reservation for Great Expectations

A/C Internet - WiFi IPod Base Station Kids allowed
Yes - 3 pools! Yes Yes - 2 hot tubs! Audio Sound System
Cable TVs Washer/Dryer Ocean view

Great Expectations is the perfect villa for families or large groups. This villa features 8 A/C bedrooms, 8 ½ baths, 4 pools, hot tubs and Jacuzzis, tennis court and gym. 

Prices are based on the number of bedrooms used assuming double occupancy. There are a total of 8 bedrooms available: 4 bedrooms in the Main Villa, The Club Room, the first floor bedroom and connecting Sun Room in the Guest House, and the Owner's Suite on the top floor of the Guest House. More than 16 people may be accommodated only with the express consent of the owners. The additional weekly cost for more than 16 people is $250 per person.

This villa is centrally located between two bays, Rendezvous and Chocolate Hole, and is a 9 minute drive from Cruz Bay.

Great Expectations st john usvi villa

  Great Expectations is made up of 4 separate buildings to provide lots of flexibilty and privacy.


Renovated the Villa Great Room -- We have installed a recycled glass countertop (custom-made at Maho) and mounted above it a 60 inch Sharp LED High Definition TV with (complimentary) Netflix video streaming. Blu-Ray DVD player, iPod/iPhone/MP3 connection to indoor and outdoor speakers, complimentary WiFi, SubZero stainless steel refrigerator, commercial Scotsman ice maker, new seating, and a gigantic Big Ass (truly, that is what the Company is named!) ceiling fan.

great room

The Main Complex of Great Expectations features four private and equal-sized air-conditioned master bedroom suites in two pavilions on either side of the Great Room, which comprises living and dining areas and the gourmet kitchen.

villa living area and kitchen

New swimming pool and patio: In addition to our popular wading pool for the little ones and our dip pool, we now have a wonderful new swimming pool (20' x 30') overlooking Chocolate Hole harbor and, a spacious new patio (also overlooking Chocolate Hole harbor) which provides lots seating and lots of shade.


Your 5th A/C bedroom doubles as a gym. All three pavilions open onto the garden courtyard with outdoor dining, pool, hot tub, and built-in grill area overlooking sailboats moored just below in Chocolate Hole.

pool and exterior of villa

A short flight of stairs takes you down past the exercise room to the regulation size tennis and basketball court below. Along a lighted palm tree path, through gardens of tropical fruits and flowers, is the two-story Guest House with two more air-conditioned bedrooms suites and its own Jacuzzi swimming pool for the couples that want that “Carefree Get-Away”!

tennis and basketball court

Great Expectations has one of the only private tennis courts on St John.  Not only is it a regulation doubles court with the same surface as used in the US Open but the view can't be beat!  Great Expectations has become one of the most popular villas for large groups.  With the Main Villa and the Guest House,  swimming pools,  hot tubs, and numerous hammocks and private patios, there is plenty of room to gather together yet people are able to spread out and enjoy their own piece of paradise.

tennis court

Tennis court

Tennis court

New pool.

new pool

New bedroom and bathroom in the Guest House.  The Sun Room, named for the multiple skylight, clearstory windows providing lots of light, can serve as a sitting room for the first floor bedroom, a connecting bedroom for parents with young children, or a completely separate 8th bedroom for larger groups. We have furnished the room with a trundle bed which can be configured as a Daybed (1 Twin), two Twin beds, or a King bed.  The adjoining, large 9' x 9' bathroom has a coral shower, recycled glass counter, and skylights. Both the bathroom and bedroom have air-conditioning. 

Great Expectations is a non-smoking villa.

Guest house

Additional Images
living area st john villa pool pool
st john villa bedroom view st john usvi villa bedroom
virgin islands villa bedroom bedroom bedroom and gym
bedroom exterior of villa villa bedroom
Floor Plan Building 1 - Sunrise Building 2 - Great Room
Building 3 - Sunset Building 4 - Guest House Building 4 - Guest House
Beds Baths Location High Season
1/2/24 - 4/17/24
Low Season
4/18/24 - 12/18/24
Max Guests
8 8.5 Chocolate Hole 16

Call for rates and availability.

Call for Holiday Rates

*Rates shown are weekly.

2024 Dates
High Season: January 2, 2024 - April 17, 2024
Low Season: April 18, 2024 - December 18, 2024
Thanksgiving Week: November 21 - November 28, 2024
Holiday Season: December 19, 2024 - January 2, 2025

2025 Dates
High Season: January 2, 2025 - April 20, 2025
Low Season: April 20, 2025 - November 23, 2025
Thanksgiving Week: November 23 - November 30, 2025
Low Season: November 30, 2025 - December 19, 2025
Holiday Season: December 19, 2025 - January 2, 2026

All rates subject to 12.5% USVI Hotel Tax. A $35 non-refundable security deposit and $35 reservation fee are required.
Rates are subject to change without notice.

Request a Reservation for Great Expectations

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