Virgin Island Vacations

Vacation Paradise for Couples

Whether stealing away with just two of you or bringing a group of people Great Expectations is a great setting. With 270 degree views of the surrounding sea and islands and close enough to Hart Bay to hear the waves break on the shore below the villa, you will find this St John villa an amazingly relaxing setting for your Caribbean vacation.

Our villa is a terrific setting for a bunch of couples vacationing together or a group of single friends.  Each of the villa bedrooms has a king bed which can be separated into two twin beds. With the ability to rent all or part of the villa, you can come with as few as 1 person or up to 14.  We have had groups of single people who wanted all twin beds and were able to easily accommodate their needs. More often though, we have groups consisting of several couples and several people needing single bed accommodations, that too, is easy for us to accommodate.  This flexibility in our sleeping accommodations makes Great Expectations an ideal villa for large gatherings.  Take a look at the floor plan for detail of the bedroom configurations.

You will also find plenty of spaces to gather with your friends. The large pool patio has lots of lounge and comfortable outside seating, including a large outside table for dining, and hammocks. Adjacent to the swimming pool is a wading pool which has been as popular with adults as it has been for the little ones.  If you are more energetic than those lounging in the pools, you might find yourself bouncing a ball around on our tennis court which also has a basketball hoop on one end.

What is as much fun as the larger spaces are the smaller spots to have a private conversation with a friend or just have that private spot for yourself! You will find that this St John villa has plenty of those private spots spread throughout the compound.

  • ★ ★ ★ ★ ★ 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!!!
  • sunset laurence
    What a special place! Yes, it's great to have a pool, a hot tub, and a tennis court, but what's really fantastic is the setting and the layout of the property. You can watch the sun come up over one bay and watch it go down over another. There are cross breezes in every room, and the bedrooms are in separate buildings from the great room, so when you're ready to let the Caribbean breezes lull you into blissful sleep, you can escape to your own private hideaway. And the main building is a great place to gather, make meals together in the well-stocked kitchen, and hang out during the evening or on the rare rainy afternoon with books, games, or a movie. The only downside is that we had to leave.
  • moon rising over rendezvous bay
    10 of us enjoyed an amazing vacation together. The house is big enough so that everyone has their own space yet intimate enough to feel like home. Kitchen is well equipped and we ate most meals at home. Jeep rental is a must therefore we missed walking down to town but the house was so nice we didn't want to leave it at night. Good luck with catching the amazing sunset...the clouds got in our way, but still spectacular.
  • wounded warrior dive
    The Villa was just perfect for the group of wounded warriors from Walter Reed Army Medical, we were able to accommodate everyone very comfortably. The views are spectacular and the great room and pool area is a great central meeting area. After a full day of diving the guys we were able to relax and enjoy every moment !! The support of the entire community of St John for our wounded warriors is outstanding and Great Expectations exceeded everyone's expectations. We hope to have this opportunity again and make it a yearly event for SUDS. Thank you so very much for your generosity for without it SUDS could not continue to support our men and women who have given do much to our country.
    Soldiers Undertaking Disables Scuba (SUDS)
  • tennis aw
    Our Stay at Great Expectations was great. We had 5 different families with a total of 15 people. Kids ages ranged from 13-21...the tennis court/basketball court are a big plus when you have to keep kids entertained. The layout of the villa works perfectly if you are traveling with a group. Bedrooms allow you to have your own space with your own private balcony area while the main room and pool area are perfect when you all want to be together. The only reason I did not rate the location as 5 star is because I prefer a bit more isolation from neighbors; you are in a residential area so houses are close and lots of them. That being said we heard very little noise all week and the landscaping around the houses provide privacy...I'm from the country...I prefer my neighbors a couple of miles away:). It was very convenient to town so that was a plus. I would recommend this villa to anyone and would stay again if traveling with a large group.
  • rainbow
    Our private getaway was perfection in paradise and the view was phenomenal! On a ridge between Chocolate Hole and Hart Bay, we got to see amazing vistas.  In the morning the sun rises over Hart Bay as I enjoyed my morning coffee to the sound of birds and waves. Ah!  During the day we explored the island and went to the various beaches.  As we snorkeled, we saw and octopus, squid, turtles and all kinds of fishes in the reefs.  On the way back to the villa, we shopped in Cruz Bay at Mongoose Junction and Starfish market.  We'd shower and get nice and tidy to watch the sunset over Chocolate Hole with rum cocktails.  The Great Room's kitchen had everything we needed to cook at the villa, when we didn't eat out in Cruz Bay.  There is a lot of room at Great Expectations, so much that when we wanted to be alone from the rest of the family, we could go to our room and sit on our private patio.  We didn't want to leave!  Thank you Kristin and Chuck, your villa truly is the best on St. John!
  • beach chair
    Great Expectations, the best villa on St. John! If you normally stay at the westin with other families on your vacation (as we do), you may consider treating yourself to Great Expectations. They have taken an incredible location (Great views of ocean and harbor), and created a mini resort, where they provide everything you could think of, to make your stay a dream vacation. You go to bed with a perfect temperature trade winds blowing thru your room, as the sun sets off your back deck. You get awoken to that same incredible breeze, lift your head slightly, to the sun coming up over the ocean. Due to the incredible thought out amenities and view, the group of 14 actually saved money, as we decide against hitting the restaurants, and made dinner after beach one of the most enjoyable parts (kids played in pool and tennis court as we cooked on the barbeque). Perfectly situated, it is a 2 minute drive to the food store and cruz bay, but you feel like your on an island. One of the best parts, is due to the design, you get the separation of having your own rooms and space (key if u have little kids), but still get the pleasure of sharing the day together, like you are in your own home.
    Marblehead, MA
  • rainbow over tennis court
    Amazing! There were 8 of us on this return visit to Great Expectations and though this place has always been a wonderful getaway, the renovations to the Great Room definitely added to our experience. The views from both sides of the house were, as always, breathtaking, and in addition to being able to see both amazing sunrises and sunsets, we were treated to 2 full rainbows during our week. We can't wait to return. [this was the 4th time she has stayed at Great Expectations]
    Charleston, SC
  • table couples
    Kristin and Chuck have thought of every need for a vacation of a livetime Nine couples from TN, MI, MA, FL,& VT just returned from a week together at Great Expectations to celebrate Steve and Carrie's 10th anniversary. (They stayed at G. E. for their wedding.) We enjoyed St. John - the restaurants, beaches, happy hours, etc. - BUT the best times were had in the great room and pool area at the villa. Several nights we chose to stay in and use the gourmet kitchen and grill area. We can not think of one suggestion to improve this perfect paradise and are planning for a return trip in early 2014!
    Paula N.
    Satellite Beach, FL
  • Butcher St John wedding 2002
    We invited 60 people to our beach wedding and ended up with 38 guests. Our close wedding party of 14 stayed at Great Expectations. You made everything so easy - all of our friends & family who stayed there with us just loved it.  There was never anything we lacked - you and Chuck have really equipped the villa very well.  From the kitchen supplies to books, island info to water toys, we were never in need.  And the layout of the property made everyone feel they had privacy, while we still had plenty of room to gather as a group both inside and out. We chartered Calypso for an all day snorkel, we had our rehearsal dinner at Duffy's (now Dog House Pub), were married on Gibney Beach and had a big reception/party after in the Oppenheimer house catered by Passion Fruit. The friends and family who attended still say to this day: best wedding & best vacation ever!
    Carrie B.
  • cooking
    This is the second year that we spend two fantastic weeks at Great Expectations with family and friends. As fantastic as our experience was last year, it was enhanced by the addition of the new property manager, Coby, who was incredibly responsive and proactive. Upgrades to the TV, the refrigerator, the dishwasher, storage containers, and beach chairs demonstrate that Chuck and Kristin care about their property and making sure that their guests are well taken care of. We have been vacationing in the Virgin Islands since 2000 and have rented 5 other properties on St. John and on Tortola (and stayed at the Westin). While the others were very nice -- and at least one of them much pricier -- none compares with the overall quality and value of Great Expectations. We would definitely stay there again and recommend it to anyone who wants a relaxed, yet quality, island vacation. - 10 friends (and family) who have been vacationing together forever.
  • 10 little indians in pool
    We have been going to St. John since 1996 and have always had a large group (20 or more). This time we have 10 and Great Expectations was a perfect villa to rent. It was so great to having the group in one villa. It was nice to have the bedrooms off to the sides away from the Great Room. You weren't bothered in the morning if someone wanted to be in the Great Room or kitchen or even by the pool. The views are breathtaking and there was always a nice breeze in the bedroom. The club room was perfect for our single person that wanted privacy. The location from town is perfect and also puts you closer to Coral Bay. In conclusion, if you have a group (and if it is mixed with adults and children), I would definitely recommend this house. The guest house (which we used last minute) was also nice. Great house for a great rental price!
    Downers Grove, IL
  • Morning coffee with WiFi
    My wife and I took 3 other couples to stay at Great Expectations in March of 2014 and felt like royalty in our very own St. John mansion. The eight of us stayed on the villa's main side (with 4 matching bedrooms, each with their own outdoor shower) and spent mornings sharing coffee, breakfast and stories in the great room. Most days we drove rented Jeeps to the beach and ended up at happy hour, followed by either dinner in Cruz Bay or Coral Bay or we ended back at the villa grilling some fresh fish while watching the sunset. All 8 of us could not have had a better vacation and especially loved the various pool areas, hot tubs and hammocks where we could be together or alone, depending on the mood.
    Steve B
  • wedding table pool great expectations
    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.