Rated by travelers the best St. John villa vacation rental

Great Expectations St. John vacation rental villa

Our villa is an 8-bedroom vacation rental villa on St. John, each with a private bathroom, and indoor/outdoor showers.

Great Expectations 4 buildings sit on a 1 acre saddle of land on Chocolate Hole East with 3 swimming pools, 2 hot tubs, a private basketball and tennis court, daily sunrise & sunset views, cool Caribbean breezes plus all the amenities you would expect of a first-class private villa. Perfect for vacationing couples, multi-generational families, and St. John beach wedding parties – Great Expectations exceeds guests’ expectations.

The numbers on St. John add up to paradise

When you look at the math, you can't deny that a vacation in St. John equals happiness.

US National Park


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Typical Happy Hour

Check out this great video from recent guests >

The Johnson family spent a week at Great Expectations in January of 2015 and put together a nice little video montage of their trip highlights.

See all of our St. John Videos >

Don't just take our word for it

Read real, unedited Testimonials from past guests of Great Expectations
  • Rich
  • birthday party celebration
    We stayed at Great Expectations last week to celebrate my husband's 50th birthday. There were a total of 19 of us, including grandparents, adult siblings and children. We planned the trip about a year in advance and I spent many hours reading reviews, looking at the website and every picture I could find. I am pleased to say that the villa is exactly as it looks - which is amazing! Everything was just so beautiful and our large group had plenty of space. What a treat to have every family have their own bedrooms (total of 8) with their own individual bathrooms! The pool was super clean, warm and with a breathtaking view. We spent every morning at the beaches and all afternoons & evenings in the pool. We had such a nice time. Every person said how wonderful the trip was and the villa provided the perfect home base for everyone. It was a very special trip for all of us and we will cherish the memories and time there.
  • Bill H
    Our multi-generational family group loved our stay at Great Expectations! The location is terrific: 5 minutes to Cruz Bay and a short drive to the Center Line Road to head over to Coral Bay. The set up of the home is ideal for large groups. Everyone has their own space, but can come together in a great room that has everything you need, and then some. It is the perfect layout for a large family reunion or multiple families travelling together. We had several teens in our group, who loved being able to use the tennis court and basketball hoop in the evenings. The house is clean, organized, and well stocked with everything you might need (great kitchen for cooking and making drinks). Chuck and Kristin (the owners) are extremely responsive and were very helpful with answering any questions we had. Patti, the property manager, also was fantastic, and responded within minutes (if not seconds) when we needed something or had a question. We've stayed in quite a few villas on the island and Great Expectations was the best! We will be back!
    Bill H
  • ★ ★ ★ ★ ★ 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.
  • robbins kids in pool
    Our family of 19, ranging in age from 2-72 recently spent 10 days at Great Expectations and it met all of our expectations and then some. The space was great for all of us to spread out. We really appreciated the multitude of patio areas and hammocks tucked away around the grounds where we could relax with a good book or just enjoy the views which were spectacular! Our grandchildren spent a lot of time in the 3 pools. We are a family that likes to cook so the very well equipped kitchen was much appreciated! We would stay here again in a heartbeat!
  • Robbins group
    We had an awesome time, visited 6 different beaches where kids and grandkids really got into snorkeling seeing lots of fish, turtles, and even a nurse shark in close to shore at Maho Bay. If the grandkids weren't at beach, they lived in the pools at GE! Not a lot of hiking as the heat and humidity was challenging...we really appreciated the air conditioned bedrooms! One odd incident...we had a good sized iguana (whom the kids named Otis) that hung around the grounds a lot. We never fed him or went near him but he actually lunged at 2 yr old Henry who was sitting in a patio chair outside the great room and grabbed his big toe! No blood drawn and Henry didn't seem fazed but it really freaked out his parents! Have you ever had any incidents like that? [our answer was 'no, and it is a good thing that iguanas are vegetarians!]. The villa was perfect, Chuck. We couldn't have asked for anything more. The whole family have had a vacation of a lifetime! August 2016
  • pool with kids
    After visiting ST John for at least 20 - 25 times since 1985 my husband & I could not think of a more perfect location to celebrate our 50th wedding anniversary with our family. Thanks to your wonderful villa - compound the 15 of us were all able to be together in one location. We had 8 adults and 7 children ranging in age from 7 to 15 - the swimming pools, hot tubs, & tennis court/basketball court are a big plus in keeping everyone entertained. The villa had everything anyone could ever hope or dream of in a rental - including Coby who is the best. Our family loved exploring all the beaches, snorkeling and hiking. We loved the fact that the great room was a separate building from all bedrooms. We were concerned about the weather as we have always visited ST John in February in prior years, but we should not have given it a second thought - it was warm, but not as bad as FL can be in the summer. Thank you Kristin & Chuck for providing a superb location to make wonderful family memories. The grandchildren are already asking when we can return. We would highly recommend ST John & Great Expectations to anyone.
  • bad kitty
    Brought the whole family (14) here to St John to celebrate our 45th wedding anniversary. Visited many beaches, the ones on the North Shore including Cinnamon Bay. We had stayed there in the 70's and 80's. We also visited Maho Bay and Francis Bay (great!). We drove over to the East End beaches and took an Eco Kayak and snorkeling tour from Haulover. We also went down to Laneshur Bay - tough drive but BEAUTIFUL beach. Our trip on Bad Kitty to the BVI was really, really good. The Baths were breathtaking! Cruz Bay shopping and restaurants are always fun. This villa has EVERYTHING you could want or need and Coby is so helpful. What a wonderful place to celebrate with a large family. Perfect sunrises and amazing sunsets.
    Bill H.
    North Carolina
  • reading on pool float
    We had a wonderful time swimming, snorkeling, watching beautiful sunrises and sunsets. The location of the villa is perfect. The owners provided everything we needed - the kitchen was completely stocked with all the utensils you would need, gas grills, washing machine/dryer, water sports equipment, beach towels, tennis rackets and balls, etc., etc. They thought of everything! This was our second stay at Great Expectations and I would certainly recommend it.
  • great room tv and games
    I couldn't believe how well stocked the home was - even down to the beach towels & laundry detergent. I've never seen such a well-stocked kitchen at any of the homes we've rented...how often do you see games, puzzles & books for your use?
  • 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.
  • tennis
    Hi! We had an awesome vacation and your villa was the perfect place for us to stay (we loved it)! My nephew loved the "bachelor pad" with his own fridge. Actually, the weather was really pretty good -it only rained a few times on St John and wasn't a problem when it did. We played tennis 4 days! All of your recommendations were spot on - we used Christie's, Mathayom, Courtesy Car Rental, the taxi service in St John and Dream Weaver sailboat (and got discounts at all of them). Captain Jini and her first mate did an awesome job with the sailing and snorkeling - my 71 year old Dad had trouble when he got in the water and they worked with him and got him back in the water snorkeling which ended up being a highlight for him. We do hope to stay at your Villa again in the future... Thanks for the wonderful vacation house!
    Easton, CT
  • sunrise
    Our stay at Great Expectations was wonderful! We had two families including several children with us, and it accommodated our group perfectly. We enjoyed beautiful scenery with a very island-like ambiance throughout the property. We have stayed there twice now, and expect to return in the future. I would recommend it to anyone!
  • 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
  • maho bay rainbow
    The last of our children and families have flown off and the house is again empty and quiet. The unanimous decision was that all had had a wonderful time at Great Expectations. The house was spacious, allowing people to spread out, and very comfortable and well appointed. The views were spectacular! Every morning was spent at a beach. Our favorite was Maho with its sandy shore, shallow water and protected bay. The surprise was the intensity of the sun! We quickly moved to a siesta during the heat of the day...We all waited for so long for this week and now it is over and just a wonderful memory. We all enjoyed the use of your wonderful home and your help in making a plan a reality.
    Nita & Petros A.
    Lexington, MA
  • great room tv
    This is our third trip to Great Expectations and as always we had a glorious week...we brought the family, 9 adults and 2 granddaughters (ages 2-1/2 and 5). They enjoyed every minute. The house is set up perfectly for families.
    Elaine & Dave L
    Annapolis, MD
  • iguana
    I can hardly find the words to say how fantastic Great Expectations is! Beautiful, fabulous, relaxing, spectacular...I am so overjoyed my husband tried so hard to find this wonderful home for our 14 member family...We ll have loved the views, pools, tennis court, basketball courts, views, lizards, crabs, views, shopping, sightseeing, views trips to St. Thomas, snorkeling, scuba diving, views
    Grandma K
  • moon
    Our third stay for the 3 generation J. family at this wonderful home...one cannot imagine many places that have such a beautiful sunset, moonrise and magnificent sunrise all at the same location!...We've looked at LOTS of places to stay and even stayed at 2 others until we found ourselves here. There is no place better. We want a kid friendly and safe house, good views, convenient access and friendly, solid support from the hosts. All here...The pool here is safe too - no steep cliffs with inadequate railings. tennis kidsAnd the tennis court - ball play area is a unique gem....Its really nice to be in a comfortable home in Paradise. We are all looking forward to being here again and again and again
    Liz & Allan J.
    Manhattan, NY
  • tennis kids
    This was our first stay at great expectations for 15 of us and it was nothing short of paradise. We enjoyed the space of GE, or as we like to call it 'the compound.' We never heard each other at night when we were in our separate quarters. The DVDs, games, music, and available reading providing some nice entertainment when retreating form the sun. The pools, tennis court and jacuzzis got their share of use as well..There is no question we will be back
    The C Group
  • table couples
    Three vacationing families for the past ten years...first trip to St. John and Great Expectations; 14 in total - kids ranging from 5 to almost 20. The setup of the house was great...the [chaise lounge] chairs are outrageous (are they sold stateside?)...how wonderful this place really is...a fully-equipped kitchen, multiple card decks, videos, beautiful gardens, sunsets, sunrises
    Phyllis F
    Nyack, NY
  • tennis view
    We are 3 families who vacation somewhere different each summer...what was great: the tennis court, our kids loved the pool...the outdoor showers were really neat...
    Paul & Ginnie
    North Carolina
  • cinnamon bay beach
    The Best - 8 grandkids, 8 adults - a week of great weather and super beaches - coupled with our fantastic accommodations at Great Expectations. Fully equipped with everything we needed for the beaches and cooking. Enjoyed the pools, tennis court and basketball - wonderful views. Can't say enough - just great!
  • Outdoor shower overlooking Caribbean
    We got married on island of St. John and we and our friends/family stayed here and a few other villas on the island. Everyone congregated at this villa b/c it was the nicest. Good balance of view, breeze, good stereo, decoration, private and shared space. Loved the outdoor showers!! The pool is nice and the kids all loved it. You'll need a car to get to the beach but we didn't mind. The house managers are great - very well organized and considerate
    Chicago, IL
  • pool at dusk
    Great Expectations exceeded my expectations. The property is in a great location - unbelievable views and very convenient to town. Rooms are well appointed and very comfortable. Decor is relaxed with a sophisticated Caribbean flair. Outdoor pools and porches were wonderful, lots of places to sit and enjoy the views and the company. Outdoor showers adjoining each room were a treat. The kitchen had everything we needed. Guest services were amazing, we had an issue with the satellite and it was promptly and professionally resolved by friendly staff. Working with the owner, Charles, over email was fantastic, and he went out of the way to make sure we had everything we needed and were prepared for our trip. I would highly recommend Great Expectations. We stayed here surrounding my sister's wedding, and I can't imagine a better choice for a large family to stay together in an intimate, private setting.
    Walland, TN
  • wedding table
    We had a great time at the villa. We were so fortunate to be able to have our wedding in St. John and stay at Great Expectations. Kristin and Chuck were great at letting us know their thoughts on a caterer, flowers and ideas to make our special day great. Thanks so much for letting us come into your beautiful home. Hopefully we can come back next year.
    Michael & Deana C
    Montauk, NY
  • sunrise hart bay
    Great Expectations has wonderful views for watching the sun rise and set! We brought our families down to St. John for our wedding. There were 16 of us. We were married on Trunk Bay at sunset. Everything was perfect!...We re so glad we picked St. John as the place to start our life together!
    Kristina & Kevin L
    Bloomfield Heights, MI
  • Our villa great room looking over pools
    We had a fantastic trip to St. John and Great Expectations was spectacular. This was my fourth stay at the property and each time is better than the last...there were so many upgrades the best of which was all the new appliances!!! We enjoyed the amazing views, the pools, and the shared living space. The private bedrooms made the stay most enjoyable as everyone had the ability to go to their own space if needed. The care taker Coby, was wonderful. He came at our beck and call, he was professional, and great at his job. We loved the location - it was close to town and a short ride to all the beaches. We will be back for a fifth trip. We love Great Expectations!
  • Sunset over pools
    Words seem inadequate to tell you how much our family loved your beautiful home, Great Expectations! The views took our breath away, the pools offered many hours of fun and relaxation and the well equipped kitchen provided each of us an easy space to prepare wonderful meals together. Coby was very gracious and responsive to our questions or needs. We really enjoyed his warm and friendly manner touched with a great sense of humor. The wedding was held at Oppenheimer Beach. It was a joyous celebration of family and friends! The rain held off, thankfully, and everyone had a wonderful time. The consensus from our family that it was a perfect week. They all loved Great Expectations and would definitely like to come again.
  • 4 buildings, 4 pools, 2 hot tubs and a tennis court
    It was an awesome week with kids and grandkids! We all made memories for a lifetime. Great Expectations was a perfect choice for us.
    Bill O'C
  • 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.
  • trunk bay woman on wall
    The F-Z wedding at GE was fabulous!  We were married on Trunk [Bay] and then celebrated with our friends & family here at Great Expectations.  We had 11 people in total.  Everyone loved the villa!
    Bethany Z.
  • Infinity Pool with lots of comfortable seating
    Sixty-five people [not all stayed here, fortunately] came to St. John to celebrate the marriage of our son. We had a welcome dinner at La Tapa, Party at Coconut Coast, Rehearsal dinner at Isolate, the Wedding at Catholic Church, the Reception at Voyages and a Beach party at Trunk. Everything was perfect - especially "Great Expectations." The pool was the center of our activity...the views were awesome.  We'll all be back!
    Sherwood & Patty C
    Philadelphia, PA
  • kids on tennis court
    As grandparents, we liked to plan an annual trip for our grown children (now parents) and their children. We've typically gone to Florida or California to see some sun and sand, but decided to investigate the US Virgin Islands. Well, Great Expectations is amazingly special and
  • 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.