Experience the tropical paradise of Five O'Clock on the Hill, where every bedroom offers a front-row seat to breathtaking Caribbean Sea views. Enjoy private balconies, outdoor lounging areas, and a six-foot-deep swimming pool surrounded by stone walls that maintain scenery while providing seclusion.
Reviews
1010 out of 10
Exceptional
Entire home
5 bedrooms6 bathroomsSleeps 12279 sq m
Popular amenities
Ocean view
Kitchen
Washing machine
Dryer
Free Wi-Fi
Add dates for prices
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!
Property amenities
Beach
Beach nearby
Beach loungers
Beach towels
Pool/Spa
Massage
Outdoor pool
Private pool
Internet
Available in the villa: Free WiFi
Parking and transport
Limo/town car service
Car recommended
Parking on site
Kitchen
Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Hob
Microwave
Oven
Paper towels
Refrigerator
Spices
Toaster
Dining
Chef service
Bedrooms
5 bedrooms
Bedsheets provided
Sofa bed
Bathroom
5.5 bathrooms
Bathtub or shower
Hair dryer
Shower
Toilet paper
Towels provided
Living spaces
Living room
Entertainment
Books
Games
Smart TV with cable/satellite channels
Outdoor areas
Balcony
Barbecue grill
Outdoor furniture
Laundry
Laundry facilities
Washing machine
Work spaces
Computer monitor
Desk
Desk chair
Printer
Comfort
Air conditioning
Pets
No pets allowed
Suitability/Accessibility
Smoke-free property
Services and conveniences
Concierge services
Housekeeping on request
Iron/ironing board
Location highlights
Near a health/beauty spa
Near a hospital
Near the bay
Near the marina
Near the ocean
Things to do
Golf
Optional golf privileges
Basketball nearby
Birdwatching nearby
Casino nearby
Ecotours nearby
Fishing nearby
Golfing nearby
Hiking/biking trails nearby
Horseback riding nearby
Jet skiing nearby
Kayaking nearby
Motor boating nearby
Mountain biking nearby
Parasailing nearby
Sailing nearby
Scuba diving nearby
Snorkelling nearby
Surfing/bodyboarding nearby
Swimming nearby
Wildlife walks nearby
Windsurfing nearby
Safety features
No carbon monoxide detector or gas appliances (host has indicated there are no carbon monoxide detectors or gas appliances on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
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.
Pets
Pets not allowed
Children and extra beds
This property does not allow children
Note from host: Not ideal for kids but will consider your needs.
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
We should mention
A car is recommended for transport to and from this property
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.
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).
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Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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.
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 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!
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.
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!!
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.
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!
Exactly the place my wife and I had envisioned for our family of 8 to relax and recharge and make memories. Five o’clock on the hill was beautiful and very well set up for a family getaway. There are several areas on the property for all 8 of us to hang out together, play cards, enjoy wine and drinks. The large covered patio with several tables was perfect for our gatherings. We could listen to the waves and enjoy the breeze flowing through the hill side. During the day the view was gorgeous and breath taking.
The bed rooms were designed to give each couple their privacy when they needed it. The biggest suite in the place only had a queen size bed while the other large suites had a king size bed. Suggestion to put a king bed in the main house bedroom.
Kitchen was very well stocked and had everything in it to cook dinner most nights during our stay. Grocery store located within 10 miles yo get groceries.
Pool was refreshing and was awesome to float in at night to watch the many stars in the sky. Just amazing. The hot tub and water fall were not working at the time, but it was okay.
Having laundry on site was also very convenient.
Overall, very satisfied with the beautiful property. Roy, John and Sam were perfect hosts. I highly recommend Five o’clock on the Hill for your next gathering. Perfect for spending quality time together, as well as having privacy when you want it.
Highly recommend having a rental car when staying at the property.
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!
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.
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!
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!
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.
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
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!
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.
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
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!
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
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.
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!!