Family Caribbean Vacations

St. John is a perfect vacation spot for families with young – or not so young – kids.

The waters of St. John are pristine and the beaches have white, silky sand and gentle entrances so kids can stay at the water’s edge and watch little fish swimming by. What a perfect spot to introduce your kids (or anyone else) to the joys of swimming or snorkeling.

Floor Plan for Great Expectations villa

See detailed Floor Plans of the entire Villa compound

The villa was built with families in mind.

As you can see from the floor plans and photos,  Great Expectations was built on a land saddle between Hart Bay and Chocolate Hole Bay and special attention paid to making it friendly for young and young at heart.

  • 3 pairs of connecting bedrooms with lockout capability
  • Infinity pool plus 2 smaller pools – including a very shallow wading pool for the small ones.
  • Fenced in Tennis & Basketball court that can be also used for a safe place for kids to play games
  • Guest House is ‘down the path’ and can provide grandparent privacy or large extended family quarters (sleeping 6+)
  • Great Room has 60″ Flat Screen, games, books, puzzles and stereo
  • Highchairs & booster seats, portacribs, infant bathtub onsite, infant beach ‘cabana’ and lots of other amenities for babies and kids are available

Check out the complete list of our child friendly amenities.

Perfect for multiple generational family vacations

For a family vacation they'll never forget

Take a real island vacation AND bring the family along without any worries.

St. John = Family Friendly

If you are traveling with your kids (no matter the age) you will find St. John a fabulous destination for a family vacation with silky sand beaches of the Virgin Islands National Park, the pristine waters surrounding St John, and the family friendly island atmosphere of restaurant and shop owners all great reasons to choose St John as your vacation spot. As the owners of Great Expectations we realize that we cannot be totally objective about the St John villa that we designed and built, however, hopefully, the reviews by previous guests and the fact that we have an amazingly high repeat business, will convince you that Great Expectations can and will meet and exceed your expectations!

A Villa that was built for families with children

  • moms with childLots of safe, flat outdoor space to play with no steep cliffs prevalent at most St John villas
  • tennis court (fenced in) with tennis racquets and tennis balls
  • basketball hoop with basketballs
  • soccer and footballs
  • room to spread out - our St John villa consists of a Main Villa and Guest House, each with its own kitchen and dining area
  • numerous hammocks perfect for both the little ones and parents
  • 3 swimming pools (two at the Main Villa and one at the Guest House)
  • 2 hot tubs (one at the Main Villa and one at the Guest House)
  • wading pool perfect for the little ones
  • lots of shaded areas
  • lots of pretty flowers to delight children
  • indoor and outdoor dining
  • Complementary Netflix video-streaming so you can watch an unlimited number of movies
    lots of beach toys
  • Highchairs and booster seats, portacribs and infant bathtub
  • Children's DVDs, games, puzzles, books, and drawing paper and crayons
  • 5 minute walk to 2 beaches, Chocolate Hole with great snorkeling (some of the best anywhere around St John!) and Hart Bay that is great for shell collecting
  • No charge for children age 2 or younger who are staying in the same room as their parent.

Customizable Floor Plan

  • Each of the Main Villa bedrooms can connect directly to a neighboring bedroom
    • 3 sets of connecting bedrooms that can be configured in many different ways (e.g. with one King bed or two twins or a King bed with a foldaway bed or portacrib brought in for children)
  • Sun Room includes a trundle bed (and its own bathroom, TV/DVD player) and connects directly to the first floor bedroom in the Guest House and serves as a terrific choice for those parents who want a bedroom joining directly with their children's bedroom
  • Club Room includes a trundle bed (and its own bathroom, TV/DVD player) that often serves as a great 'teens get-away' room
mother child st john beach

Enjoying beach time

Kid-friendly beaches

St John beaches are very kid friendly. Frommer's, the well respected travel site, rates St John as one of the top 100 spots to take kids! And, no wonder, our waters and beaches are extremely 'kid' friendly. Water crystal clear. Clear enough for little kids to stand at the water's edge see their toes and watch as fish swim by. We have virtually no undertow and the National Park beaches are 'easy entry' beaches, no big or dangerous drop offs to worry about for those just learning to swim.

Family-friendly Restaurants on St. John

Many people ask if there are 'child friendly' restaurants on St John and the answer is a loud 'yes'! Almost every restaurant on St John will welcome kids, however, some are just more fun for kids (and therefore you as parents might also have a better time!). In Cruz Bay you will find a number of restaurants at Wharfside where kids can play on the beach while waiting for a meal at restaurants like High Tide, The Balcony at Cruz Bay, Cruz Bay Deli & Pizzeria, and the bit more upscale Waterfront Bistro. Other casual choices, although not on the beach, are Cafe Roma and Morgan's Mango.
On the east side of the island, Miss Lucy's and Vie's are both in the category of fun for kids. Kids can watch the chckens and kitty cats roam around under foot at Vie's Snack Shack and at Miss Lucy's they are quite apt to have a goat wander by as they wait for their meal. Miss Lucy's is also located right at the water's edge so playing on the beach while others sit and enjoy their meal is a nice option. Another casual restaurant in Coral Bay is Skinny Legs (great burgers) and Shipwreck Landing.

Island Babysitting

While it is great fun to bring your kids to St John, there might be times you will want an 'adult time' whether to go out for a nice quiet dinner, attend a celebration or just have some alone time. St John has a wonderful resource available in Kids Night In Babysitting Service. Contact Leslie directly to find out about her services and credentials.

Rental equipment

We also have a number of outfits that carry equipment for infants and toddlers. If you are looking for a stroller or full crib you might want to contact Christy's of St John and Island Baby

We're Grandparents too! Contact Us

Read how families love Great Expectations

Actual testimonials from families who have stayed at Great Expectations


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!

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.

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!

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

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.

Bill H.

North Carolina

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.



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.


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 often do you see games, puzzles & books for your use?



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.


Easton, CT

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!


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!


Marblehead, MA

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.

Nita & Petros A.

Lexington, MA

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.

Elaine & Dave L

Annapolis, MD

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.

Grandma K

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

Liz & Allan J.

Manhattan, NY

Our third stay for the 3 generation J. family at this wonderful 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

The C Group

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

Phyllis F

Nyack, NY

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?) wonderful this place really is...a fully-equipped kitchen, multiple card decks, videos, beautiful gardens, sunsets, sunrises

Paul & Ginnie

North Carolina

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...



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!

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!

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.

Bill O'C

It was an awesome week with kids and grandkids! We all made memories for a lifetime. Great Expectations was a perfect choice for us.

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

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.

St. John = Family Friendly

If you are traveling with your kids (no matter the age) you will find St. John a fabulous destination for a family vacation with silky sand beaches of the Virgin Islands National Park, the pristine waters surrounding St John, and the family friendly island atmosphere of restaurant and shop owners all great reasons to choose St John as your vacation spot. As the owners of Great Expectations we realize that we cannot be totally objective so you might want to take the word of our guests who have posted reviews (making us the #1 St John villa on Trip Advisor!).