Guest House available June & July 2020. Villa is available the rest of the year.
About Roy Chilson
We have been visiting St. Croix together since 1977 and have always dreamed of one day sharing a vacation home with guests from all around the world. In 2014 we purchased our dream vacation home and we’re ready to welcome you to beautiful St. Croix. A real dream come true story! Over the years we have enjoyed our travels but always come back to St. Croix as our number one travel destination. Beautiful weather, friendly people, snorkeling, scuba diving, sailing, kayaking, hiking, kiteboarding, paddleboarding, great dining, celebrations... the list goes on.
Roy Chilson purchased this Villa in 2014
Why Roy Chilson chose Grapetree
Five O'Clock on the Hill is a special home located in a private neighborhood facing the sparkling waters of the south shore. Five O'Clock on the Hill was designed and built with larger groups in mind. The main house has one bedroom with a private bathroom, a living room to accommodate all of our guests, and a kitchen with enough space to prepare meals for all. The attached 26 x 26 covered patio (with adjacent space that is comparable in size but uncovered) is the perfect place for the entire group to gather for meals, lounging, presentations, and other social events. Sitting on the side of a hill, the multi-tiered property offers gorgeous views from every level, every room, and every patio. The two level guest house sits in front of and below the main house. This arrangement and layout add to the privacy of each of our guests. The upper level of the guest house consists of two large bedrooms with private bathrooms and a large eat-in kitchen between them that can be shared or restricted to either room. Each room has a private entrance on the north side with doors on the south side leading to the private balcony overlooking the ocean. The lower level also consists of two bedrooms with private bathrooms and a shared galley between them. Each of these rooms has a private entrance from the lower balcony which is even closer to the ocean. The separate kitchen areas provide our guests with the ability to enjoy an early morning cup of coffee, a late-night snack, or a full-blown dinner... in the privacy of their own space.
What makes this Villa unique
• Our multi-tiered home with outside entrances for each bedroom allows for individual privacy on all levels • Lots of communal space for large groups to gather • Unobstructed sea view from every bedroom • Every bedroom has a private bath • Southeast orientation provides a constant sea breeze • Small community in a quiet location • Every bedroom has its own balcony • Air Conditioning is available in each bedroom and the living room in the main house
Check-in: 3:00 PM
Check-out: 11:00 AM
Children not allowed
With the multi-level nature of the property, Five
Max guests:12 (sleeps up to 12 adults)
100% refund if canceled at least 60 days before arrival date. 50% refund if canceled at least 30 days before arrival date.
Five O’clock On the hill was absolutely spectacular! We were had the honor of staying there for 7 days, there were 6 adults (3 couples) in our party, and we all had our own private bedrooms & bathrooms, which all had their own digital locks. We shared a kitchen which allowed us the opportunity to have breakfast/lunches together and there was amazing patio space. As well as the front of all rooms had their own entryways to a bacony, which had the most spectacular 🌅� sunrises every morning ❤️, but, if you choose not to watch the sunrise from the balcony, you still had an amazing view from your king size bed. Did I mention this view was all ocean view?? Yes, it’s all ocean view from the balcony or from ur bed!! How spectacular is that. There was always a nice ocean breeze & sound that you heard no matter where you were at on the property. This was very relaxing, especially at night. The pool was very beautiful, clean & plenty of lounge chairs for everyone. While you were enjoying the poolside, you still had the opportunity to hear, and see the ocean and enjoy the warm tropical breeze.
We cannot thank Janet & Roy enough for all of their support & help during our stay.. not only did they meet us at the airport, but they helped guide us around the island 🌴�, provided helpful hints & showed us many hiking trails and beaches which helped to fulfill our ability to get in as many sites as possible. They definitely went above and beyond and deserve recognition. Thank you both for what you do! 🤗�
PS: Janet, Rich would like to thank you personally for all your assistance with ordering the ships 🚢� 🛳� and the lunar eclipse that we were able to view during our stay 😁�
I would recommend Five O’clock on the hill to anyone, we will definitely be back!!
Perfect for an intimate wedding ceremony & 5 day vacation with family
Five O'Clock on the Hill is a great choice for any small group event or wedding ceremony. Roy's professionalism, response time, and attentiveness are second to none. We planned our destination wedding to St. Croix entirely online before the hurricane, and Roy kept us up to date the whole time. When he met us at the airport, led us to the East End of the island, and helped us check in, we were so happy. Every door has a keypad with it's own code, so each couple (4 couples) got ultimate privacy. As the wedding couple we chose the upper level queen bedroom (not next to anyone else- the right window top balcony if you're looking at the house photo), and our family got private bedrooms with a king, queen, and 2 twins that they pushed together. The pool is clean and deep; Roy provides noodles so you can float. Be sure to purchase everything you need for your first meal, including condiments, before you check in as the East End is quite a drive from any shopping centers and hours at local places are limited. There is a full kitchen with dishwasher, which was great for us because our families love to make breakfast together! The patio provided a perfect backdrop for our ceremony, and although there is no air conditioning everyone slept well due to the cool breezes and the many open windows at the villa. If you enjoy privacy, an ocean view, and cool sweet breezes, then Five O'Clock on the Hill is for you! By the way, the clock in the entry isn't broken, its always 5 O'Clock!
Fabulous house, fabulous host!
Five O’Clock on the hill is a wonderful, secluded spot overlooking the water. Our family of nine had plenty of room and Roy even provided a crib for our grandson. The rooms are spacious and the terrace which adjoins the main house is the perfect gathering place with spectacular views of the ocean. Roy was the consummate host. He met us at the airport, took us to the grocery store and gave us a detailed tour of the property and explanation of all of the systems. He also responded quickly to the small number of questions we had during our stay. An uncrowded beach and nature trial are a short walk from the house. When we didn’t feel like going to the beach, we greatly enjoyed the pool. The property is peaceful and quiet and the landscape is beautiful. We would return in a heartbeat.
Roy literally went out of his way to make a last minute booking seamless. Two days before our arrival the home we originally booked notified us that there was a major change. This being a trip celebrating my wife's 50th Birthday with a group of friends, it was so important to have what we had anticipated for months of planning.
The views are just amazing. It was a peaceful neighborhood, with the most traffic being ships miles out barely visible.
The house is well equipped to cook whatever you might want. Plenty of dishes, cups etc. Bedding and beds were comfortable. The gas grill was a little dated but we were able to cook burgers and dogs with no problem.
The Pool and Patio areas make gathering perfection.
The reason I am only giving 4 stars is because there were a few minor things that were unavailable due to the hurricane. Out of Roy's control. The island has done very well recovering in just a few months.
We are so looking forward to going back.
This house was perfect and met all of our family's needs...and we were alot of family!!!
First of all, we would like to thank Roy and Janet for going over and beyond our expectations of what a rental host encompasses. Not only did they offer to meet us at the airport and show us the way to "Five o'clock" but since we landed late in the day, offered and did do our grocery shopping so we would have a nice breakfast and COFFEE when we woke up in paradise!!! That is who Roy and Janet are! Thank you!
Now, about the house. We are a blended family of 10 adults and 3 babies. The home worked out perfect for our needs. Babies miraculously had cribs and high chairs....so, the top floor of the separate pod worked out for the 2 couples with kids. Having the kitchen in between was a bonus so that Bjorn and Elke, the parents/grandparents, who had the main house quarters, were not awakened and Elke got her beauty sleep.
Bjorn jumped in the pool every morning to wake up...the Swedes like that! (Elke is German)
The lower level of the pod was perfect for the unmarried couples since they are not used to kids and enjoy their peace and quiet. The view from both levels was sea and sky! AAAH!!!
The walk to the beach was close, although with babies maybe a car works better since we need to haul all the equipment to keep them happy.
P.S. Everyone was so excited to have their own on-suite bathrooms!!! Major bonus!!!
Thank you Roy and Janet! We will be back!
Thank you for the kind words Bjorn and Elke. You and your family were delightful and it was really obvious that you were all here for some great family time. We are quite happy that you enjoyed our home so much and look forward to your return visit.
Roy & Janet
YOU WILL FALL IN LOVE WITH 5 O'CLOCK ON THE HILL (AND ST CROIX)
For two weeks, four couples enjoyed privacy AND camaraderie - we each had our own BR and BA but the common area was perfect for shared dinners and game nights. We loved the access to the trailhead to Jack's and Issac's beaches and even hiked Goat Hill to view the glorious colors of the Caribbean on both sides of Point Udall. The pool was refreshing and we had unlimited seating areas. Having a vehicle provided the opportunity to explore all this laid- back island offers. While we enjoyed the fully equipped kitchen(s) and shared many meals "at home", we also must recommend Blue Terrace Restaurant, Duggans, and Chenay Beach Bar on the East End. Sandy Point is an incredible beach open just on weekends. While on the West End, you will love the menu at Sand Castle, dinner at C I Bone, and Rhythms at Rainbow Beach for lunch. Of course, no trip is complete without visiting Christiansted. So many restaurants and bars, all delicious. A sail at sunset was a true highlight. The same crew took us all out to Buck Island where we loved the snorkeling and can attest to the beauty of Turtle Island. Lunch at Buccaneers, a visit to Shoy's Beach, a visit to Frederiksted when the cruise ship was in, and an opportunity to watch the St. Patrick's Day parade in Christiansted were all highlights. We've been home only a week and all of us cannot stop sharing stories and pictures of our wonderful visit. In closing, the most memorable part of our visit is the awesomeness of our host, Roy Chilson. We cannot say enough about this amazing man. He went far above and beyond to assure our vacation was as special as this villa. Thank you from all of us. We loved every minute of our St Croix vacation!
Thank you for the kind words Nancy and for sharing your experiences on island. It was a pleasure having you and your crew at Five O'Clock on the Hill and we hope to see you again one day.