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Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family!

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Five O'Clock on the Hill overlooking Grapetree Bay. Plenty of room for you!
Nighttime swimming at is an experience that you will always remember.
Looking southwest from the covered patio. Great place for family gathering.
Looking east from the upper patio with plenty of room for dining and dancing.
The living room in the main house is about 300 sq. ft.

Reviews

10 out of 10
Exceptional
5 bedrooms5+ bathroomsSleeps 10278.7 sq m

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen
  • Barbecue grill

Explore the area

Map
Christiansted, St. Croix Island
  • Grape Tree Beach
    ‪6 min walk‬
  • Casino at the Divi Carina Bay
    ‪3 min drive‬
  • St. Croix Point Udall
    ‪9 min drive‬
  • Christiansted (SSB-St. Croix Seaplane Base)
    ‪31 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!

Property manager

Roy Chilson
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 3:00 PM
Minimum age to rent: 28
Check out before 11:00 AM
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Children

Adults only
Not ideal for kids but will consider your needs.
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
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

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

We should mention

A car is recommended for transport to and from this property

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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Christiansted, St. Croix Island

What's nearby

  • Grape Tree Beach - 6 min walk - 0.5 km
  • Casino at the Divi Carina Bay - 3 min drive - 2.2 km
  • The Reef Golf Course - 5 min drive - 3.7 km
  • Cramer Park Beach - 7 min drive - 2.7 km
  • St. Croix Point Udall - 9 min drive - 5.0 km

Getting around

  • Christiansted (SSB-St. Croix Seaplane Base) - 31 min drive

Restaurants

  • ‪Cheeseburgers in America's Paradise - ‬14 min drive
  • ‪The Terrace At The Buccaneer - ‬19 min drive
  • ‪The Mermaid At The Buccaneer Hotel - ‬20 min drive
  • ‪Duggan's Reef - ‬5 min drive
  • ‪Salt Great Pond - ‬13 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.

Is Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family! pet-friendly?

No, pets are not allowed at this 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 60 out of 63 reviews
Rating 8 - Good. 3 out of 63 reviews
Rating 6 - Okay. 0 out of 63 reviews
Rating 4 - Poor. 0 out of 63 reviews
Rating 2 - Terrible. 0 out of 63 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

andrea j.

Liked: Cleanliness, check-in, communication, location, listing accuracy
family christmas vacation
this property was fantastic for our xmas holiday had a ton of area and everyone had their own space as well
Stayed 7 nights in Dec 2024

10/10 Excellent

Emily P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great vacation
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.
Stayed 14 nights in Jan 2025

10/10 Excellent

William J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay at five o' clock on the hill
The home has the most beautiful views of the ocean which can be viewed from a large veranda attached to the house .
Stayed 31 nights in Feb 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
Good times
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.
Stayed 7 nights in Feb 2023

10/10 Excellent

Denise M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and spacious accommodations
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.
Stayed 9 nights in Jul 2023

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
Island Vacatoin
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!
Stayed 7 nights in Mar 2023

10/10 Excellent

Bernard C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Dec 2021

10/10 Excellent

Scott H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home and gracious hosts!
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!
Stayed 7 nights in Mar 2024

10/10 Excellent

Christina S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay at Five O’clock on the Hill
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!
Stayed 6 nights in Aug 2022

10/10 Excellent

Tony A., Lino Lakes

Liked: Cleanliness, check-in, communication, location, listing accuracy
Five on The Hill
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!
Stayed 7 nights in Feb 2020

10/10 Excellent

Barbara M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Visit a niece who recently moved to St. Croix
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.
Stayed 7 nights in Nov 2023

10/10 Excellent

Derrick H., Goshen Ohio

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Jul 2022

10/10 Excellent

Derik B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise Island
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!
Stayed 8 nights in Jan 2023
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Stacey S.

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!

10/10 Excellent

Martha P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous Vacation & Celebration
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!!
Stayed 6 nights in Apr 2023

10/10 Excellent

Shirley R., Lowell, USA

Liked: Cleanliness, check-in, communication, location, listing accuracy
Ideal for couples!
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.
Stayed 7 nights in Jan 2020

10/10 Excellent

MONICA I.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!!
Stayed 7 nights in May 2022

10/10 Excellent

Marc & Linda J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Grapetree Escape
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.
Stayed 7 nights in Jun 2023
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Eli H.

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!

10/10 Excellent

Kellie B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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. ❤️
Stayed 7 nights in Mar 2021

10/10 Excellent

Heid K., Bemidji, MN

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great spacious property
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!!
Stayed 9 nights in Feb 2023
This review was submitted before 2018 and has not been verified.

10/10 Excellent

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.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Marilyn C.

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.

10/10 Excellent

Jill C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for families
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!
Stayed 7 nights in Jan 2024

8/10 Good

Kevin S., Winchendon

Seriously Super
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.
Stayed 8 nights in Jan 2018

About the host

Hosted by Roy Chilson

Host profile image
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.

Languages:

English

Premier Host

They consistently provide great experiences for their guests