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Book Online or call HomeAway Booking Assistance 888-640-7927

rated by travelers the best vacation villa on St. John -- Great Expectations

Bedrooms 6
Half Baths1
Space 4,650 sq. ft.
Property type villa
Minimum Stay 7 nights


About the property

6 a/c bedroom suites with private bathrooms, spectacular views, walk to beaches

Great Expectations can accommodate as many as 15 adults plus children in 4 equal Master bedrooms, 2 spacious bedroom Suites, and 2 additional rooms which can also be used as bedrooms for larger groups (we charge only for the bedrooms used). Each of these 8 rooms is air-conditioned and has its own (ensuite) private bathroom.

Great Expectations has spectacular views over the Caribbean (both the sunrise and sunset) and is within walking distance to 2 beaches. We offer wedding specials and discounts for grandparents and multiple couples.

Note that the rates we are able to show on the "Rates" page of this Website are for 2 people using 1 bedroom. PLEASE SEE BELOW FOR OUR RATES FOR MORE PEOPLE/BEDROOMS (we do not charge for children age 2 or under staying in the same room with their parents so let us know the ages of any children and, to inquire about our discounts, if there are any grandparents, brides, grooms, active military or other good and deserving people in your party!).

With 3 swimming/wading pools, 2 hot tubs, and even a private basketball/tennis court, Great Expectations is ideal for special celebrations and family gatherings. The Villa is also perfect for multiple couples vacationing together offering 4 equal Master bedrooms with private patios overlooking the Caribbean Sea. Each Master bedroom has a large bathroom with indoor/outdoor shower, a walk-in closet with wall safe and floor-to-ceiling mirror, soaring cathedral ceiling with skylight and transoms, and custom-made teak furniture from Bali with a King-size bed which can be set-up as 2 extra-long (California) Twin-size beds. All 4 Master bedrooms are on the same level along with -- to provide privacy for those staying up late or rising early -- a separate Great Room with a large living room, gourmet kitchen, and indoor and outdoor dining areas around the pool and hot tub patios and outdoor barbecue.

A nearby two-story Guest House offers 2 spacious bedroom Suites each about twice the size of one of the 4 Master bedrooms. Each Suite has a Queen-size bed and futons for additional sleeping accommodations if needed as well as a private bathroom with indoor/outdoor shower. Upstairs in the Guest House is the Owners Suite with its own kitchen, dining and living areas as well as laundry. It has spectacular views overlooking the Caribbean Sea. The Guest Suite on the first floor of the Guest House has an adjacent sitting area, The Sun Room, with yet another private bathroom, this one with a coral shower. The Sun Room can also be used as a separate, 7th bedroom with Twin beds or a King for larger groups or parents who would like their children in a connecting bedroom.

The Club Room has a trundle bed (2 Twins) with its own private bathroom and can be used as a separate bedroom for one adult or a couple of teenagers bringing the total number of bedrooms at Great Expectations to 8 (all air-conditioned and each with a private bathrooms) providing comfortable sleeping accommodations for as many as 15 adults plus kids. We charge only for the number of bedrooms used assuming double occupancy; we have had as few as one couple rent the entire villa and as many as 21 people (there were a lot of kids!).

All the openings (sliding doors, windows and transoms) are fully-screened. Italian tile adorns the floors. The Great Room has a gourmet kitchen with granite counters. Native stone work laced with local coral and shells frames the villa entrance and is used around the site to highlight the lush landscaping of beautiful, colored bougainvillea, hibiscus, croton, wild orchids and, and our favorite, frangipani. A number of significant palm trees as well as banana trees complement the beauty of the site.

Great Expectations offers extraordinary 'double' east/west views with both the sunrise and the sunset. The villa is located in Estate Chocolate Hole on the south shore of St. John, less than a 5 minute drive on paved roads to town (Cruz Bay) and 10 minutes to the famous, white sand beaches of the U.S. National Park. There are also two beaches within walking distance of the Villa.

The closest beach for swimming and fabulous snorkeling is Chocolate Hole, just a short walk (or you can drive and park right next to the beach) -- a sandy beach with calm, protected water on the west side of the villa with some of the best snorkeling on the island thanks to a 'salt pond' (formed during hurricanes when the storm drives the ocean inland and the water then gets trapped). The second beach accessible from a path directly from the Villa on the east side is Hart Bay with great beach combing thanks to the coral reef just offshore

The Villa is furnished with custom-made teak furniture and carvings from Bali and, we think, very tastefully decorated with original paintings, sconces and even a native mural which was written-up in the local papers. Great Expectations does not pretend to be fancy, just very, very special as attested to by the reviews of past guests and our rating by travelers on Trip Advisor as the #1 vacation rental villa on St. John!


January 2, 2018 - April 14, 2018

1-2 persons....$8,000 per week

3-4 persons....$9,000 per week

5-6 persons....$10,000 per week

7-8 persons....$11,000 per week

9-10 persons....$12,000 per week

11-12 persons...$13,000 per week

13-14 persons....$14,000 per week

15 - 16 persons....$15,000 per week


April 15, 2018 - December 22, 2018

1- 2 persons....$4,750 per week

3 - 4 persons.....$5,750 per week

5 - 6 persons.....$6,750 per week

7 - 8 persons.....$7,750 per week

9 - 10 persons....$8,750 per week

11 - 12 persons...$9,750 per week

13 - 14 persons...$10,750 per week

15 - 16 persons..$11,750 per week

Prices are based on the number of bedrooms used assuming double occupancy. There are a total of 8 bedrooms available: 4 Master bedrooms in the Main Villa, 2 bedroom Suites in the Guest House. The Sun Room and the Club Room. More than 16 people may be accommodated for $500 per person per week. No charge for children age 2 or younger who are staying in the same room as their parent.

Rates do not include 12.5% Government Tax and $500 Refundable Security Deposit. Rates do include: meet and greet upon arrival on St John, concierge services, 24 hour emergency property management, cleaning prior to arrival and upon departure, and assistance with pre-trip planning and discounts for airport transfers, vehicle rental, boat trips, taxi tours, chef, catering and (grocery and beverage) provisioning, baby equipment rental, additional maid service, photographers, massages, and anything else (within reason) we can do to assist our guests to have a wonderful vacation.

Christmas and New Years weeks are a flat rate for up to 16 people; contact us for pricing and details. The 8 bedrooms available are: 4 Master bedrooms in the Main Villa, 2 bedroom Suites in the Guest House, The Sun Room and the Club Room.

More Details

Kristin and Chuck
Member since: 2001
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
October 18, 2017

About Kristin and Chuck

Kristin and Chuck live in California and Massachusetts when we are not on St. John!

Kristin and Chuck purchased this villa in 1998

Why Kristin and Chuck chose Cruz Bay

The dual sunrise and sunset views plus the constant easterly Tradewinds on a flat site (there are few tennis courts on St. John!) about 100 above the Caribbean Sea! Rated the #1 St. John vacation rental villa by travelers.

What makes this villa unique

3 swimming pools, 2 hot tubs and 1 basketball/tennis court!

Guestbook comments from the owner

Our vacation was wonderful. The stay at Great Expectations was the "best". Coby was very helpful with his suggestions of places to go and to eat. When the ice machine wasn't working and we called he came right over to check it. Having the sleeping areas separated from the main house works wonderful. Those wanting to stay up later didn't bother those that wanted to go to bed earlier. We all loved the outdoor showers...We all would come back in a heartbeat! Views were awesome and drive to town wasn't bad. (Missed the turn once.) Loved the big pool. The villa felt very welcoming as soon as we came thru the gate.

We all were wishing we had extended our stay at GE instead of moving over to Tortola. The villa there was large with a beautiful view (high up), but not as clean, bright, or as welcoming as GE. It also lacked several things, such as decor, decent supplies in the kitchen (no teaspoons, four tablespoons), or phone or computer as listed on sight. Many spider webs along ceiling. It was listed as luxury but was more rustic cabin. Would not return there.

Thank you for providing such a wonderful vacation home for others to experience in the Caribbean. When first planning this trip we said it would be a "once in a lifetime trip"; we are hoping that isn't the case and that we will be able to return again some time.
May 2014
  • 1 of 5


Estate Chocolate Hole and Great Cruz Bay Villa Accommodation and Amenities

Property Type:
  • villa
  • Catering available
  • Breakfast - Booking Possible
  • Lunch - Booking Possible
  • Dinner - Booking Possible
  • Housekeeper Optional
Floor Area:
  • 4650 sq. ft.
House Rules:
  • Max. occupancy: 20
  • pets considered
  • children welcome ...
  • non smoking only
Location Type:
  • Beach
  • Near The Ocean
  • Ocean View ...
  • Family
  • Activities Guide
  • Air Conditioning ...
  • Alarm Clock
  • Basic Soaps
  • Broadband Access ...
  • Ceiling Fans
  • Clothes Dryer ...
  • Filtered Water
  • Fitness Room / Equipment
  • Hair Dryer
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided ...
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking Off Street
  • Safe
  • Telephone ...
  • Toilet Paper
  • Towels Provided
  • Washing Machine ...
  • Wireless Internet ...
  • fax
  • 4 Ring Stove
  • Blender
  • Catering Available ...
  • Coffee Grinder
  • Coffee Maker
  • Cooking Utensils
  • Dishwasher ...
  • Freezer
  • Ice Maker
  • Kitchen ...
  • Microwave ...
  • Oven
  • Pantry Items
  • Refrigerator ...
  • Toaster
  • Child's Highchair
  • Dining Area
  • seating for 15 people
  • 8 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - toilet , shower , Main Villa bedroom
    Bathroom 2 - toilet , shower , Main Villa bedroom
    Bathroom 3 - toilet , shower , Main Villa bedroom
    Bathroom 4 - toilet , shower , Main Villa bedroom
    Bathroom 5 - toilet , shower , bidet , Owners Suite
    Bathroom 6 - toilet , tub , shower , Guest House
    Bathroom 7 - toilet , shower , The Club Room
    Bathroom 8 - toilet , shower , The Sun Room
    Bathroom 9 - toilet , The Great Room
  • 6 Bedrooms, Sleeps 20
  • Main Villa Master Bedroom 1 - 1 king , air-conditioned, ensuite bathroom, ocean views
    Main Villa Master Bedroom 2 - 1 king , air-conditioned, ensuite bathroom, ocean views.
    Main Villa Bedroom 3 - 1 king , air-conditioned, ensuite bathroom, ocean views
    Main Villa Bedroom 4 - 1 king , air-conditioned, ensuite bathroom, ocean views
    Guest Suite - 1 king , 1 queen , 2 twin/ single , 2 sleep sofa /futon , air-conditioned, 2 ensuite bathrooms
    Owners Suite - 1 queen , 1 sleep sofa /futon , air-conditioned, ensuite bathroom, ocean views
  • 4 Main Villa Master bedrooms each have a California (extra long) King-size bed which can be converted into 2 California (extra long) Twin-size beds and are spacious enough to accommodate a foldaway bed and portacribs for children. The 4 guest bedrooms offer 2 bedrooms with Queen-size beds and futons plus 2 bedrooms each with a Twin-size Trundle bed (when not needed, one bed stores under the other to provider more space in the room). All 8 bedrooms are air-conditioned and have ceiling fans, wall safes, and, of course, private bathrooms with spacious showers.
  • Books
  • CD Player
  • DVD Player
  • Games
  • Games for Kids
  • Music Library ...
  • Radio
  • Satellite / Cable ...
  • Stereo
  • Television
  • Video Library ...
  • Balcony ...
  • Barbecue
  • Beach Chairs
  • Beach Towels
  • Binoculars
  • Deck / Patio ...
  • Large Cooler
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Patio
  • Tennis Court
  • Terrace
  • Walkway to Water
  • suitable for elderly or infirm
Pool / Spa:
  • Hot Tub ...
  • Outdoor Hot Tub
  • Outdoor Pool
  • Private Pool ...
Onsite Services:
  • Concierge
  • bay/sound
  • duty free shops
  • health/beauty spa
  • reefs
  • restaurants
Leisure Activities:
  • beachcombing
  • bird watching
  • boating
  • horseback riding
  • shelling
  • shopping
  • sight seeing
  • walking
Local Services & Businesses:
  • Babysitter
  • fitness center
  • groceries
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • fishing
  • hiking
  • jet skiing
  • parasailing
  • sailing
  • scuba diving or snorkeling
  • skiing
  • snorkeling
  • snorkeling/diving
  • snowmobiling
  • surfing
  • swimming
  • tennis
  • wind-surfing
Weddings, birthdays and anniversary celebrations welcome!


Exceptional! 5/5 -
(12 traveler reviews)

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rated by travelers the best vacation villa on St. John -- Great Expectations
average rating of 5.0 based on 17 reviews

PERFECT! This place is pure tropic magic!

  • 5 of 5

I am beyond impressed with this magical property. Everything went beyond what we expected. The place was spacious, comfortable, clean, and with spectacular views all around. We stayed here with a group of 15 and everyone absolutely loved it. The owners were very helpful with any questions/concerns about booking, and Patti (property manager) was super sweet and helpful during our stay. Highly recommend this place!!!

  • Submitted: Jun 20, 2017
  • Stayed: Jun 2017
  • Source: HomeAway
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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
  • Source: HomeAway
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Third Times a Charm!

  • 5 of 5

Third Times a Charm

Of course the first two times were too. Great Expectations is truly spectacular - it's also comfortable. This time we were six adults for a week in January of hanging out and relaxing. And, as we expected, Great Expectations did not disappoint. The spaces are perfect for a medium to large sized group, and appropriate for all ages. Bedrooms are large, very comfortable and private. Each suite has fully screened sliding doors at each end with ocean views. This means that lovely breezes and air flow makes the use of air conditioning unnecessary. Each suite has their own private bathroom and totally private outdoor shower. Taking a shower while the sun sets or rises (you get both from this property) is really special.

The Great Room easily accommodates a large group for meals, and the kitchen is the best equipped we've ever seen in a rental property. Again, between the Big A** ceiling fan, screened sliding doors on both sides and the breeze, there's no need for air conditioning here either. The views from the dinning area are mesmerizing. This year the poolside barbecue area had been totally redone. New grill with lots of power for everything from fish to pizza. Plenty big enough to cook for a crowd. Lots of counter space for outdoor food preparation or serving and a beautiful new mural on the back splash.

The views never fail to delight. Sunsets, moon rise, double rainbows and dark skies for star gazing. We love being lulled to sleep by the sound of waves in Hart's Bay and waking to the birds.

Truly an amazing place. Well maintained and always looking for ways to enhance their guests stay. Both the owners and the property manager are very responsive and helpful.

We can't recommend Great Expectations enough and look forward to returning.

  • Submitted: Feb 11, 2016
  • Stayed: Jan 2016
  • Source: HomeAway
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Exquisite Location

  • 5 of 5

We had 13 Adults with us on the Wedding of a Lifetime. Every single guest said it was the best vacation they ever had. The Great Expectations Villa was more than we ever thought it could be. There was not ONE amenity that we were missing. They thought of everything! The set up of Great Rooms and Bedrooms is magnificent! The pool/hot tub area is breathtaking. You get to see Sunrises in the morning from your rooms and Sunsets in the evening from the pool area. Coby is a dream to have as a Property Manager. He can help you solve any problem you have whether it's a question about the Villa or just interested in the Island and all it has to offer. What a friendly man to have introduce you to the great Island of St. John. We had Aqua Blu as our car rental service and her father, Chico, as our taxi service. What a nice Duo they are. We also had a meal catered by St. John Catering. Every single person said it was the best meal they have ever eaten. There are so many things to see on the Island from hiking and beaches to Island city life..........but, why would you want to :) The Villa is amazing. Highly recommend this Villa to anyone that is inquiring. We had a private wedding on the property and it was amazing. There is a nice patio area for the wedding ceremony and dinner. A+++++ rating from this happy crew!!!! Thank you Chuck and Kristin for a superb place.

  • Submitted: Dec 21, 2015
  • Stayed: Dec 2015
  • Source: VRBO, from HomeAway
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Better than a Martini After a Tough Day

  • 5 of 5

You know what I mean. You get home, exhausted, and all you want for dinner is a stiff one. It's shaken, not stirred. You take a sip, and all is well with the world. So that is exactly what each moment is like at Great Expectations. When you drive up the villa takes your breath away. The flora is responding to the rainy season, which seems to always happen at night so your day is not impacted. Bright pinks and oranges and sweeping palms sending out their tentacles greet you, as does Coby, the responsive, efficient, friendly face of the property manager. The infinity pool adjacent to the wading pool sparkles and we enjoyed many dinners prepared poolside at the handsome outdoor grill. The kitchen is well equipped with every appliance and spice you can think of. The sunset view might be topped by the sunrise view, which we enjoyed from the sexy outside but private shower. We loved the powerful fans and found we did not need the air conditioning. Internet was solid in the great room. Laundry, streaming movies, suntan lotion, paperbacks, beach towels and chairs are all on site.We love to shell, and took the hillside hike to Hart Bay, finding numerous small conch including a specimen quality hawkwing. Incredible! The Starfish Market is top notch and their gourmet deli/liquor store should not be missed, fill up a bottle of their balsamic and olive oil for your salads conjured up with Josephine's micro greens from their market. Yum. Miss them already. We shared the villa with one other couple, enjoying our privacy but thinking a load full of our other friends could easily share these accommodations with us the next time. Well maintained, the owners clearly want their villa to deserve the accolades it receives. Expect great things, you won't be disappointed.

  • Submitted: Nov 22, 2015
  • Stayed: Nov 2015
  • Source: HomeAway
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It really is the best

  • 5 of 5

I almost don't want to tell you how wonderful Great Expectations is because I want to keep it for myself. But since the secret is already out I will go ahead and say book now. The owners are amazing, the villa manager Coby goes above and beyond- and always with a smile. The views from every angle are breathtaking and the infinity pool and outside set up are perfect. The hammocks hanging everywhere are so comfy and great for relaxing and taking it all in. I really think I could use every superlative imaginable and it still wouldn't be enough to convey my feelings about the stay there. Just go. We are already talking about going back so I will try and re-book before you lol but I honestly want everyone I can reach to know that this is the place to stay at.

  • Submitted: May 28, 2015
  • Stayed: May 2015
  • Source: HomeAway
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Car: recommended

Other Activities: basketball


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $500
Tax Rate 12.5%

Please inquire about our rates for more people based on the number of bedrooms used (let us know the ages of kids and any grandparents, brides, grooms, active military for discounts). The Villa is rented to one group at a time (you will be the only guests no matter the size of your party). Deposit of 50% of room rate due at time of booking by check (credit card payment available through Paypal).

January 1, 2017 - April 22, 2017

1-2 persons....$7500 per week

3-4 persons....$8500 per week

5-6 persons....$9500 per week

7-8 persons....$10,500 per week

9-10 persons....$11,500 per week

11-12 persons...$12,500 per week

13-14 persons....$13,500 per week

15 - 16 persons....$14,500 per week

April 23, 2017 - December 16, 2017

1- 2 persons.....$4250 per week

3 - 4 persons.....$5250 per week

5 - 6 persons.....$6250 per week

7 - 8 persons....$7250 per week

9 - 10 persons....$8250 per week

11 - 12 persons...$9250 per week

13 - 14 persons...$10,250 per week

15 - 16 persons..$11,250 per week

For 2018 add $500 to above rates.

Prices are based on the number of bedrooms used assuming double occupancy. There are a total of 8 bedrooms available: 4 Master bedrooms in the Main Villa, 2 bedroom Suites in the Guest House. The Sun Room and the Club Room. More than 16 people may be accommodated for $500 per person per week. No charge for children age 2 or younger who are staying in the same room as their parent.

Rates do not include 10% Government Tax and $500 Refundable Security Deposit. Rates do include: meet and greet upon arrival on St John, concierge services, 24 hour emergency property management, cleaning prior to arrival and upon departure, and assistance with pre-trip planning and discounts for airport transfers, vehicle rental, boat trips, taxi tours, chef, catering and (grocery and beverage) provisioning, baby equipment rental, additional maid service, photographers, massages, etc.

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.