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Plenty of room and privacy for everybody GREAT VIEWS! - Five O'Clock on the Hill

Plenty of room and privacy for everybody GREAT VIEWS! - Five O'Clock on the Hill

Photo gallery for Plenty of room and privacy for everybody GREAT VIEWS! - Five O'Clock on the Hill

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.

Overview of Plenty of room and privacy for everybody GREAT VIEWS! - Five O'Clock on the Hill

Reviews
10 out of 10 Exceptional
5 bedrooms5+ bathroomsSleeps 12279 sq m

Popular amenities

  • PoolPoolPool
  • Pet-friendlyPet-friendlyPet-friendly
  • KitchenKitchenKitchen
  • Barbecue grillBarbecue grillBarbecue grill
  • Free WiFiFree WiFiFree WiFi
  • WasherWasherWasher

Explore the area

Map
Christiansted, St. Croix Island
  • Popular LocationGrape Tree Beach6 min walk
  • Popular LocationCasino at the Divi Carina Bay3 min drive
  • Popular LocationSt. Croix Point Udall9 min drive
  • AirportChristiansted (STX-Henry E. Rohlsen)38 min drive

Rooms & beds

5 bedrooms (sleeps 12)

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

Plenty of room and privacy for everybody GREAT VIEWS! - Five O'Clock on the Hill

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.)

Relax and Enjoy our spectacular views of the Caribbean Sea!

Property manager

Roy Chilson
Premier Host
Premier Host

Amenities

Pool
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi

House Rules

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

Children

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

Events

No events allowed
With homeowner's written approval prior to booking

Pets

Pets allowed: dogs and cats less than 20 lb per pet (limit one pet total)
With homeowner's written approval prior to booking

Smoking

Smoking is not permitted
No indoor smoking allowed.
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.

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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
Note from host: With homeowner's written approval prior to booking
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
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
  • Casino at the Divi Carina Bay - 3 min drive
  • The Reef Golf Course - 5 min drive
  • St. Croix Point Udall - 9 min drive
  • Chenay Bay Beach - 14 min drive

Getting around

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

Restaurants

  • The Mermaid At The Buccaneer Hotel - 20 min drive
  • The Terrace At The Buccaneer - 19 min drive
  • Salt Great Pond - 13 min drive
  • Deep End Bar - 17 min drive
  • Goat - 11 min drive

Frequently asked questions

Does Plenty of room and privacy for everybody GREAT VIEWS! - Five O'Clock on the Hill have a pool?

Yes, this property has an outdoor pool.

Is Plenty of room and privacy for everybody GREAT VIEWS! - Five O'Clock on the Hill pet-friendly?

Yes, this property allows cats and dogs (limit 1 total) with a maximum weight of up to 20 lb per pet.

What time is check-in at Plenty of room and privacy for everybody GREAT VIEWS! - Five O'Clock on the Hill?

Check-in begins at 3:00 PM.

What time is check-out at Plenty of room and privacy for everybody GREAT VIEWS! - Five O'Clock on the Hill?

Checkout is at 11:00 AM.

Where is Plenty of room and privacy for everybody GREAT VIEWS! - Five O'Clock on the Hill 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.
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Rating 10 - Excellent. 58 out of 61 reviews" "
Rating 8 - Good. 3 out of 61 reviews" "
Rating 6 - Okay. 0 out of 61 reviews" "
Rating 4 - Poor. 0 out of 61 reviews" "
Rating 2 - Terrible. 0 out of 61 reviews" "

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

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

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

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

10/10 Excellent

Ethel C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Five O’clock Family Vacation
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.
Stayed 7 nights in Jan 2024

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

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.

Premier Host

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