Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family!
4.9
Outstanding(60 Reviews)Villa in St. Croix
10 guests · 6 bedrooms · 6 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Free cancellationFull refund if you change your mind
Great for petsBring all your friends and family, even the furry ones
About this villa rental
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!
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!
Amenities
Pool
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Family friendly
Map of St. Croix
Reviews
4.9
Outstanding(60 Reviews)4.9
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!
4.9
The home has the most beautiful views of the ocean which can be viewed from a large veranda attached to the house .
4.9
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!
4.9
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.
4.9
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.
4.9
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.
4.9
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.
4.9
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!!
4.9
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!
4.9
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!!
4.9
Great place! Beds were comfy and the kitchen was fully stocked. Plenty of room and great and fun trails to explore close to the house.
4.9
Great place! Beds were comfy and the kitchen was fully stocked. Plenty of room and great and fun trails to explore close to the house.
4.9
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!
4.9
This is a lovely, well-appointed property. More of a villa than a house. 2 separate buildings that have separate kitchens. It has spacious group areas inside and out. Roy and Janet were delightful hosts. They provided lots of information before and during our stay and were available for information and to address any issues. I highly recommend this property and these owners.
4.9
Good time had by all. We enjoyed our stay. Quite and relaxing.
4.9
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!
4.9
Great place with awesome views
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.
4.9
Our time at 5 oclock on the hill will never be forgotten. From hanging out at the pool, playing games on the patio or just laying back at night stargazing. We've been home a few days now and all everyone keeps asking is when are we going back?
4.9
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!!
4.9
AMAZING
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!!
4.9
Our family couples retreat
Our time at 5 oclock on the hill will never be forgotten. From hanging out at the pool, playing games on the patio or just laying back at night stargazing. We've been home a few days now and all everyone keeps asking is when are we going back?
4.9
Location and Views are AMAZING.
Roy and Janet are great people, we had a few hiccups (one time things) and Roy was unbelievably quick to fix things. As far as the Villa goes there is a lot of room and the views are awesome. The setup is 1 main house with the big bedroom, Kitchen and living room. The 2nd house has the other 4 bedrooms with separate entrances and a smaller kitchen. All the rooms have great views and comfortable beds. The pool is super refreshing and the HUGE patio is a natural hangout spot right off the kitchen with ocean views.
The location is great as long as you have a car. Their local beaches (walkable) Grapetree and Jack's are beautiful. Jack's is basically 20 min hike and you will have it to yourself (make sure you think about shade before you go its limited).
Overall the Villa is great, St Criox is awesome and you will for sure have an awesome time.
4.9
Beautiful View
Hosts were very helpful and quick to respond. Great week at the main house.
4.9
Paradise
What a beautiful property! Comfy bedrooms, fantastic outdoor living space, well appointed kitchen. Everything you need to relax and unwind in the perfect Caribbean weather. Close proximity to great beaches and abundant hiking. Five o’clock on the Hill does not disappoint. Roy was a great host, from preparing the arrival to making sure that all was as stated for an uneventful stay.
4.9
Five o’clock on the hill is paradise!
The house is laid out perfectly and the views are absolutely stunning! The pool is fantastic and there are several amazing beaches within walking distance! The hosts were so gracious and kind who helped us along every step of the way! Would return to this house every single year without question! Thank you to Roy and Janet for sharing your slice of paradise with us. A perfect way to spend my 50th birthday!!
4.9
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.
4.9
Fantastic experience and views all around!
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.
4.9
The house is lovely! Situated in Grapetree Bay, at the east end of the island. The house is in a more quiet area, which is exactly what our family was looking for.
There was plenty of space for our party of six adults to spread out. Each couple had their own room and bathroom, with a kitchen on the main house floor and another kitchen connecting of two of the rooms on the second lower level.
Check-in and details were very thorough, Roy & Janet have thought of everything. Any questions we had were answered clearly in the instructions they provided. Our hosts were very responsive and quick to text us or call us back if we had any questions. Check in through key codes worked flawlessly.
The wonderful sea breeze and the way the window louvers worked in the rooms, combined with the fans, made it so we didn’t have to turn on the AC at all while we were there, even in June. AC is available in each of the rooms for folks who would like it, but honestly, you won’t need it.
The pool was so refreshing and it was a treat to float and stargaze on clear nights!
We spent a lot of time grilling on the patio area near the kitchen enjoying each other’s company, some good homemade cooking, and the gorgeous ocean views.
I loved our stay and recommend Five O’Clock on the Hill for anyone wanting a relaxing and welcoming experience!
4.9
Beautiful views, luscious sea breezes, and stargazing the on the pool patio!
The house is lovely! Situated in Grapetree Bay, at the east end of the island. The house is in a more quiet area, which is exactly what our family was looking for.
There was plenty of space for our party of six adults to spread out. Each couple had their own room and bathroom, with a kitchen on the main house floor and another kitchen connecting of two of the rooms on the second lower level.
Check-in and details were very thorough, Roy & Janet have thought of everything. Any questions we had were answered clearly in the instructions they provided. Our hosts were very responsive and quick to text us or call us back if we had any questions. Check in through key codes worked flawlessly.
The wonderful sea breeze and the way the window louvers worked in the rooms, combined with the fans, made it so we didn’t have to turn on the AC at all while we were there, even in June. AC is available in each of the rooms for folks who would like it, but honestly, you won’t need it.
The pool was so refreshing and it was a treat to float and stargaze on clear nights!
We spent a lot of time grilling on the patio area near the kitchen enjoying each other’s company, some good homemade cooking, and the gorgeous ocean views.
I loved our stay and recommend Five O’Clock on the Hill for anyone wanting a relaxing and welcoming experience!
4.9
Place was perfect
We really enjoyed it
4.9
We so enjoyed everything about our visit except leaving! Roy was great, the greeters were great, the amenities were great! Highly recommended! We will be back! Thank you!!!
4.9
Fabulous
We so enjoyed everything about our visit except leaving! Roy was great, the greeters were great, the amenities were great! Highly recommended! We will be back! Thank you!!!
4.9
St Croix was beautiful and the views from the home were breathe taking. I would 100% recommend the Island and home to my friends and family
4.9
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. ❤️
4.9
Great place 🏠 Roy / Janet amazing host’s!
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. ❤️
4.9
Roy was always super helpful and accommodating in answering my questions. The house was great! It is on the east end and away from any towns but that was ok as we spent a lot of time at the house. We were there with a group of 10 adults. Roy even helped facilitate a private chef to come in and cook dinner for us one night. It was amazing!!!!! Highly recommend the house and the chef.
4.9
Great week!! We all loved it.
Roy was always super helpful and accommodating in answering my questions. The house was great! It is on the east end and away from any towns but that was ok as we spent a lot of time at the house. We were there with a group of 10 adults. Roy even helped facilitate a private chef to come in and cook dinner for us one night. It was amazing!!!!! Highly recommend the house and the chef.
4.9
Beautiful Island Escape
Thank you Roy and Janet for a great experience on St Croix Island. We really enjoyed having the room for the whole family. We really loved the sound of the waves while relaxing and breezes flowing thru. We enjoyed the location being away from the hustle of town but not a far drive. The short walk to Jack's bay was great for swimming and snorkeling. Since there are no window coverings in the main house it is difficult to sleep when the moon is full or sleep in when the sun rises. Most of us are early risers so the sun rise was awesome but my older family members like to sleep in a little. Over all we had a great experience and would stay here again. Hopefully the jacuzzi parts come in soon and you get it fixed as we really missed that.
Thanks again Roy and Janet
4.9
Thank you Roy and Janet for a great experience on St Croix Island. We really enjoyed having the room for the whole family. We really loved the sound of the waves while relaxing and breezes flowing thru. We enjoyed the location being away from the hustle of town but not a far drive. The short walk to Jack's bay was great for swimming and snorkeling. Since there are no window coverings in the main house it is difficult to sleep when the moon is full or sleep in when the sun rises. Most of us are early risers so the sun rise was awesome but my older family members like to sleep in a little. Over all we had a great experience and would stay here again. Hopefully the jacuzzi parts come in soon and you get it fixed as we really missed that.Thanks again Roy and Janet
4.9
Fiveonthehill
St Croix was beautiful and the views from the home were breathe taking. I would 100% recommend the Island and home to my friends and family
FAQs
How much does this villa cost compared to others in St. Croix?
The average price for a rental in St. Croix is $425 per night. This rental is $795 above the average.
Is parking included with this villa?
Yes, parking is listed as an amenity at Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family! . For more information, we encourage you to contact the property about where to park.
Is there a pool at this villa?
Yes, a swimming pool is available for use at Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family! . Enjoy the water!
Is Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family! pet friendly?
Yes! This villa is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family! ?
We found 11 amenities for this rental. This includes pool, air conditioner, pets allowed, kitchen or kitchenette, and internet / wifi.
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