Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
5 bedrooms5+ bathroomsSleeps 10
Popular amenities
Ocean view
Kitchen
Washing machine
Dryer
Free Wi-Fi
Explore the area
Christiansted, St. Croix Island
Grape Tree Beach
Place, Grape Tree Beach
6 min walk
Divi Carina Bay Casino
Place, Divi Carina Bay Casino
3 min drive
Reef Beach
Place, Reef Beach
4 min drive
Christiansted (STX-Henry E. Rohlsen)
Airport, Christiansted (STX-Henry E. Rohlsen)
45 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Coral Reef Suite
1 King Bed
Living Room
1 Double Futon
Master Bedroom
1 Queen Bed
Palms Suite
1 King Bed
Sea Fan Suite
2 Single Beds
Sea Mist Suite
2 Single Beds
5 bathrooms, 1 half bathroom
Coral Reef Bathroom
Toilet · Shower only
Main House Bathroom
Toilet
Master Bathroom
Bathtub or shower · Toilet
Palms Bathroom
Toilet · Shower only
Sea Fan Bathroom
Toilet · Shower only
Sea Mist Bathroom
Toilet · Shower only
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
Dining area
About this property
Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family!
Are you looking for ocean views, rolling hills and incredible tropical breezes? How about a home where every bedroom has a front row seat to the Caribbean Sea?
Book our home with confidence... with over 780 nights booked and more than 525 guests at Five O'Clock on the Hill, you can be sure that we know how to help our guests get the most out of their St. Croix vacations.
If you are looking for a Caribbean adventure for your family or a group of friends, Five O'Clock on the Hill offers plenty of space to gather everyone for breakfast, lunch, and dinner yet still offers room and privacy when you want to get away. Private balconies and a variety of other outdoor lounging areas won't cramp your style.
Destination weddings can be held on the neighborhood beach or right on our covered patio. If a wedding is in your future, we can assist you with arrangements.
With five bedrooms including en suite bathrooms spread over three terraced levels and two buildings, your companions will all enjoy the gorgeous sea views and spectacular starry nights from their rooms as well as their balconies. You can hear the sound of the waves throughout the villa – adding to your relaxation.
The Main House has one bedroom and and can accommodate 2-4 guests and the Guest House has four bedrooms and can accommodate up to 8 guests.
Two separate kitchen areas make it easy for large groups to cook and dine individually or together.
The six foot deep swimming pool and an adjacent waterfall feature are a perfect complement to this tropical home. Surrounded by stone walls the pool area is both beautiful and private… without blocking the scenery. Floating on your back at night will reveal some magnificent views on beautiful starry nights. The ambient light is minimal in the neighborhood making star gazing a wonderful pastime.
Five O’Clock on the Hill is located in the South Grapetree Bay neighborhood, adjacent to Jack’s Bay and Isaac’s Bay Beaches which are protected and maintained by the Nature Conservancy.
Grapetree Bay Beach is a short walk away and you will often find yourself alone on this beautiful private beach. Sea Turtles enjoy nesting in the solitude of this beach and can be seen hatching in the fall.
The property covers 1.6 acres and offers several private areas for outside lounging and dining. There is ample paved parking… enough to park five vehicles without blocking anyone in. Cable/Smart, TV, and WiFi internet are also included. A separate laundry room with outside access is near the pool area. Air Conditioning is available if you don't think our breezes are strong enough to keep your cool.
If you have eight or fewer guests in your group, please contact us before you book your reservation and save by renting the guest house only. (The guest house is the two story building closer to the ocean.)
Plenty of room and privacy for everybody GREAT VIEWS! - Five O'Clock on the Hill
Relax and Enjoy our spectacular views of the Caribbean Sea!
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Maximum of 12 people on the property at any given time.
Only registered guests allowed on the property after 9:00pm.
Air Conditioning must be turned off when leaving the property. Additional house rules can be found on the Rental Agreement.
Rental Agreement must be signed and returned to Homeowner within ten days of booking reservation, subject to cancellation.
Important information
You need to know
Property # 733326vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the area
Christiansted
Located near the beach, this villa is in Grapetree, a neighbourhood in Christiansted. Apothecary Museum and Steeple Museum are cultural highlights, and some of the area's activities can be experienced at The Reef Golf Course and Reef Golf Course. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and horse riding nearby.
Christiansted (SSB-St. Croix Seaplane Base) - 31 min drive
Restaurants
Cheeseburgers in America's Paradise - 14 min drive
The Sausage Shack - 9 min drive
The Terrace At The Buccaneer - 19 min drive
Deep End Bar - 17 min drive
Castaways - 10 min drive
Frequently asked questions
Does Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family!
have a pool?
Yes, this property has an outdoor pool.
How much does it cost to stay at Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family!
?
As of 11 May, 2026, prices found for a 1-night stay for 2 adults at Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family!
on 16 Feb, 2027 start from S$988, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family!
pet-friendly?
No, pets are not allowed at this property.
How much is parking at Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family!
?
On-site parking is available at the property.
What time is check-in at Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family!
?
Check-in begins at 3:00 PM.
What time is check-out at Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family!
?
Checkout is at 11:00 AM.
Where is Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family!
located?
Located in Grapetree, this villa is within 1 mile (2 km) of Grape Tree Beach and Knight Bay. Isaacs Bay Beach and Teague Bay are also within 2 miles (3 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We loved the private location. The personal touch of having our groceries at the house and meeting us at the airport was above and beyond. We would definately return.
St. Croix was beautiful and an awesome place to visit. Local beaches and snorkeling at Isaac's and Jacks Bay were amazing. The house had plenty of room for our family of 8 and amazing views. Very glad we went!
Verified traveller
Stayed 7 nights in Mar 2023
Response from VrboOwner on 9 Apr, 2023
Thank you for your review Adam. It was a pleasure hosting your family. We love to snorkel at Jacks Bay too and also spend a lot of time hiking the trails throughout the 300 acres within Jack and Isaac Bay Preserve.
The views from this property are fantastic! The property was clean and spacious for our large group. Communication with Roy was hassle free and very quick. I will look to stay here on my next trip.
Bernard C.
Stayed 7 nights in Dec 2021
Response from VrboOwner on 23 May, 2022
Thank you for your review Bernard. We look forward to hosting your friends and family upon your return to St. Croix.
We loved our stay! It is very convenient for hiking and the beach. The pool was also very nice. It was clean. The owner Roy was very helpful. We stayed with our family for two weeks. The Christmas winds were blowing and cause some WiFi problems, but Roy worked to get them resolved.
We had a great time at Five O’Clock on the Hill. There is plenty of space to spread out and come back together. Everything is about 20 minutes away. The neighborhood was quiet with great views!
Christina S.
Stayed 6 nights in Aug 2022
Response from VrboOwner on 12 Oct, 2022
Thank you for your review Christina, it was our pleasure.
My wife and I stayed for a week, and it was perfect! Great views, great location for some R&R, Roy was very informative and a breeze to correspond with. Just an overall great escape to Saint Croix. Highly recommend.
Thanks Roy for letting us enjoy your Goldilocks!
Tony A.
Stayed 7 nights in Feb 2020
Response from VrboOwner on 27 Apr, 2020
LOL... Thank you for your review Tony, we appreciate your support and I enjoyed our conversations. I had to laugh when I read you last statement about Goldilocks... for the uninitiated the reference to Goldilocks is my perspective of the US Virgin Islands. The three islands, like the three bears, each have their differences and like Goldilocks and the three bears, I think that St. Croix is "just right".
We traveled with 11 adults and had plenty of space for all. The location was perfectly quiet with great views of the ocean during the day and stars at night. We ventured to framers park and smugglers cove several times to snorkel as they were just a short 5 minute drive. We also enjoyed the ability to walk to the Grapetree resort to have dinner and drinks. Roy and Janet were great hosts and ensured we had everything needed.
Derrick H.
Stayed 7 nights in Jul 2022
Response from VrboOwner on 12 Oct, 2022
Thank you for your response Derrick. I enjoyed the conversations and look forward to your next visit.
We had a family reunion here in March 2024, Roy met us at the airport to personally welcome us, guide us to the grocery store, guide us to the house and give a personal tour of the home. Wow! It’s amazing! Comfortable, gorgeous views, perfect layout for large groups and the house had everything we needed for a relaxing vacation. Home is in a great location for beach access and getting to Christened. We would love to stay there again!
Everything was communicated so well! Amazing views, no issues, spent a lot of time researching this before I made a decision. For the price we paid, it was way worth it! Super appreciative of the house and amenities. Location was perfect for my family. Lot of hiking, 30 minutes to town, quiet at nights. Beautiful water!
Derik B.
Stayed 8 nights in Jan 2023
Response from VrboOwner on 21 Feb, 2023
Thank you for your review Derek. We like to hear when our guests have thoroughly researched the many properties comparable to Five O’Clock on the Hill and chose ours for their vacation. Thank you for the pictures… we will be updating our website soon and will post a couple of the drone shots.
Property was perfect for our group. We were visiting a niece who recently moved to St. Croix. The house is very well equipped if you wanted to cook meals. We enjoyed our breakfast everyday on the patio with a gorgeous view of the ocean. We were 4 couples that had plenty of room to enjoy time together or separate. The pool is very relaxing. The owner was extremely helping with any question or request we had.
Overall, we would not hesitant to book this home again.
Barbara M.
Stayed 7 nights in Nov 2023
Response from VrboOwner on 2 Jan, 2024
Thank you for your review Barbara. It was a pleasure hosting your crew and thank you for the pictures. We hope to see you again.
Archival
10/10 Excellent
Stacey S.
13 Dec, 2016
Beautiful location for a retreat
This private villa provided an excellent location for our Rejuvenation & Restoration Retreat. In their free time, participants were able to enjoy the ample space around the property and still feel like they had privacy. The villas close proximity to hiking trails & beaches provided the perfect opportunity to get outside and enjoy nature. In addition the porches were perfect for a yoga class under the stars and a sunrise yoga class. Roy was great to work with as we coordinated this event- he was very accommodating! I would definitely host another retreat here in the future!
Stacey S.
Response from VrboOwner on 6 Mar, 2020
Thank you Stacey. We are glad that our home worked so well for your retreat. Stacey is a resident of St. Croix and runs a full time business at Stone Bodyworks Wellness. Between her ELDOA, SUP Yoga, SUP Fitness, and Yin Yoga classes, she also does fitness coaching and personal training. Stacey has an incredible reputation for her knowledge and teaching skills. We look forward to hosting your next event Stacey
5 on the hill is a great property especially for couples. Privacy with separate entrances and wonderful common areas.
Chris met us at the airport stayed with us for shopping and then led us to the villa. Very helpful.
I can’t say enough good words about the responsiveness of Roy when we had some minor problems.
Only real issue was the cleanliness of the pool however I believe that has been remedied.
Shirley R.
Stayed 7 nights in Jan 2020
Response from VrboOwner on 24 Jun, 2020
Thank you for your review Shirley. I do apologize for pool and appreciate your understanding.
We were a party of 10 women celebrating my 60th birthday. Five O'Clock on the Hill was the PERFECT place to celebrate! Gorgeous views, wonderful accommodations, lots of room for us to spread out, and then come together for morning coffee, game playing, lady chat sessions, and more.
Roy was fantastic in communication, suggestions, and providing a lovely compound (I say compound because it's not just a house, it's a remote self-contained establishment) for all our needs and comfort.
THANK YOU, THANK YOU!!
Martha P.
Stayed 6 nights in Apr 2023
Response from VrboOwner on 5 Dec, 2023
Thank you for your review Martha,
It was a pleasure hosting you and your traveling companions. Your description of Five O'Clock on the Hill warms my heart as it is exactly how we felt when we first looked at the property. It took a couple of years to renovate the place but it was well worth the time. Have you made your reservation for your 65th (not to rush things).
Roy
It was an amazing experience in St Croix. The house was absolutely wonderful and such a great experience!! Roy was very communicative and readily available for any needs. Jill was fantastic! Met us at the airport, took us to the grocery store, showed us the ins and outs of the house. She was also super-responsive with any needs. Absolutely 5-star service from Roy and Jill, hands down. If we or friends/family are ever in St Croix, 5 O'clock will definitely be our #1 choice!!
MONICA I.
Stayed 7 nights in May 2022
Response from VrboOwner on 12 Oct, 2022
Thank your for your response Monica, It was a pleasure hosting your group. Jill is a part of our wonderful support team. While I am always available for out guests, Janet and I are not always on island and having a great support team is is very important to us. We do hope that you come back to St. Croix.
Nice location near the Grapetree Bay Hotel that has 2 nice restaurants and a nice bar. Only downsides were things out of the owner's control: 1) neighbor up on top of hill has 3 humongous floodlights that illuminate the whole valley obscuring the SE sky (terrible for stargazers like our group); 2) lots of sargassum pushed ashore by northerly winds which made it hard to fish or snorkle; and 3) lots of noise from construction of house nearby. But just went to Point Undall to stargaze and to nearby Cramer Park (5 min away by car) and it's beaches. Otherwise it was great and owner was quick to respond to our questions.
Marc & Linda J.
Stayed 7 nights in Jun 2023
Response from VrboOwner on 5 Dec, 2023
Thank you for your review Marc,
We are glad that you enjoyed your stay at Five O’Clock on the Hill in St. Croix. I wish that you had mentioned the lights during your stay… for stargazing, we reposition the lounge chairs on the lower patio or move to the upper patio when they are on.
Regarding the sargassum… Grapetree Bay has been quite fortunate not to suffer from the sargassum. Being on the southeast shore the sargassum is far offshore as it passes by Grapetree Bay.
We are happy to report that the home you mentioned has been completed and our neighborhood is once again, a peaceful one.
Roy
Archival
10/10 Excellent
Eli H.
29 Aug, 2015
Tropical Perfection
Five O' Clock on the Hill went above and beyond what I expected during my 3 plus week stay on St. Croix. East Grapetree was the perfect location for anyone who wants to have the secluded island feel, along with being able to take a short, very scenic drive to Christainsted to enjoy some great food and nightlife. The home is beautiful and fully equipped to meet any need. We enjoyed how close an convenient the basically private beach was, along with all the hiking trails. Roy was there to great us when we arrived, he was very accommodating and a treasure chest full of local knowledge and great recommendations. Because of the great experience we had, and the shear natural beauty that the property and island have to offer, I have already planned my business retreat to take place here. I cannot wait to return!
Eli H.
Response from VrboOwner on 6 Mar, 2020
Thank you for your comments Eli and we look forward to your next visit.
Great experience!!! Roy and Janet are amazing people. Before we left Roy made sure we had everything taken care of from renting a car or taxi, getting groceries... He just made sure we had a smooth process ☺️ The house is a perfect set up with beautiful views and an amazing breeze from the ocean. Roy makes sure you know if need any assistance with the house you can call or text him. We would definitely recommend this house!! Make sure to book because it won’t last long!! Thank you Roy and Janet for opening your house to us for a memorable experience. ❤️
Kellie B.
Stayed 7 nights in Mar 2021
Response from VrboOwner on 22 Apr, 2021
You are quite welcome Kellie and thank you for your reviews. It was a pleasure having you and your family as our guests and we look forward to your next visit. Hopefully we will be on island when you return.
Archival
10/10 Excellent
17 Jul, 2015
Tropical paradise
Five O'Clock on the Hill is an island paradise, the location of the house is perfect the East End is a short drive to downtown Christiansted with all the nightlife and restaurants you could want, but also is removed enough to be quite and peaceful when you return. Our favorite times on the island were the beaches, which are a one minute walk from the house, also hiking to the top of Goat Hill and the trail head is a 30 second walk from the house. Fredricksted, on the West End, was very fun as well it's a little more touristy but great beaches and perfect place to pick up any souvenirs. The owner of the property Roy was extremely nice and very knowledgeable about all the opportunities on the island. I really want to travel more in my life and see other places but Five O'Clock on the Hill was so nice and refreshing I might just go there for every vacation. I honestly can't wait to go back.
Response from VrboOwner on 6 Mar, 2020
Thank you Ryan, your comments are appreciated and we look forward to your next visit. You should try the paddle boarding next time.
We had 4 couples staying here and the property gave us plenty of room to spread out when necessary yet plenty of outdoor space to gather when we wanted! Roy responded to each of our numerous questions, and was always super helpful with advice. The location is within walking distance of two fantastic beaches (15-20 minute walk) that are not heavily occupied. The snorkeling there was also fantastic! The kitchen was well appointed with everything we needed to cook various meals and the pool was nice to have available in the evening to cool off. They also have beach chairs and coolers for our use at the beach which was very helpful. It’s a well thought out rental and we could tell that they take pride in their home. The property is about 20 to 25 minutes away from Christiansted, for those who are looking for a more touristy town. We enjoyed our time at Five o’clock on the hill!!
Heid K.
Stayed 9 nights in Feb 2023
Response from VrboOwner on 15 Mar, 2023
Thank you for your review Heidi. It was a pleasure having you and your family. We always enjoy hearing from our guests.
Archival
10/10 Excellent
Marilyn C.
20 Sept, 2016
A week in paradise
From the time we arrived until our departure a week later, our visit to St Croix and 5 O'clock On The Hill was a delight. The owner Roy met us at the airport, waited while we stocked up on groceries, and led us to our home for the week. The accommodations served our party of 5 couples perfectly. Everyone had their own space, and there was plenty of room to spread out. We felt safe, and never worried about anything while we were away. Since we are all divers, this was important to us because our dive gear is expensive and we need room to dry things out. The island had some nice restaurants, and the towns provided great shopping and some historical places of interest to visit. All in all it was a great week. I would recommend these accommodations for large group or for families looking for a quiet island get away. Thanks Roy for a very enjoyable week.
Marilyn C.
Response from VrboOwner on 6 Mar, 2020
Thank you Marilyn. It is wonderful to read your comments and those of others that express exactly what Janet and I felt about this home when we bought it. We are quite happy and thankful that you and your group chose Five O'Clock on the Hill as your home away from home while you explored St. Croix and the many dive sites that surround us. We look forward to seeing you again and hope that St. Croix has left you yearning for more.
Absolutely loved our stay at Five O’clock on the Hill! Being met by John at the airport was so helpful and a nice touch. Roy was very nice and responsive with communication. By the second day, we felt completely at home. The house is very well stocked and we didn’t want for anything. It is on the quiet (East) end of the island which fits our style. The longest drive to the far west takes under an hour and you can’t beat the scenery. We hiked to Jack’s and Isaac’s beaches from the house to snorkel which was convenient. The star gazing was beyond excellent. Sunrise was a quick 10 min drive to Point Udall. We look forward to coming back with our adult children because there is plenty of space to spread out! (Cons which are not the owner’s fault: the previously mentioned spotlights on another house 6pm-midnight but we could still see the stars on the upper patio; lots of work on other houses but nothing too intrusive) Thank you, Roy and Janet!
Jill C.
Stayed 7 nights in Jan 2024
Response from VrboOwner on 7 Feb, 2024
Thank you for review Jill. We loved your comment, "By the second day, we felt completely at home." From the day we first looked at Five O'Clock on the Hill we felt that this was a vacation home that makes you feel comfortable.
Roy
About the host
Hosted by 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 here 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.
Why they chose this property
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. Each of these rooms has a private entrance from the lower balcony which is even closer to the ocean.
What makes this property 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 main house living room.