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Gather & Unwind in Style at Our St. Croix Getaway for Friends and Family!
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Reviews
10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
5 bedrooms5+ bathroomsSleeps 103000 sq ft
Popular amenities
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!
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!
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
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
Children
Adults only
Not ideal for kids but will consider your needs.
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
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.

Christiansted, St. Croix Island
What's nearby
- Grape Tree Beach - 6 min walk - 0.5 km
- Knight Bay - 2 min drive - 1.5 km
- Divi Carina Bay Casino - 3 min drive - 2.2 km
- Reef Beach - 3 min drive - 2.4 km
- Cramer Park Beach - 5 min drive - 2.8 km
Getting around
Restaurants
- Cheeseburgers in America's Paradise - 14 min drive
- The Terrace At The Buccaneer - 19 min drive
- Deep End Bar - 17 min drive
- The Sausage Shack - 9 min drive
- Sea Terrace Restaurant - 2 min walk
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
9.8/10
Location
10/10
Listing accuracy
Reviews
Verified
5 Jan, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 6 nights in Dec 2025
Verified
10/10 Excellent
andrea j.
29 Dec, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
family christmas vacation
andrea j.
Stayed 7 nights in Dec 2024
Verified
10/10 Excellent
William J.
30 Mar, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay at five o' clock on the hill
William J.
Stayed 31 nights in Feb 2024
Verified
10/10 Excellent
Verified traveller
18 Feb, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Good times
Verified traveller
Stayed 7 nights in Feb 2023
Verified
10/10 Excellent
Emily P.
1 Feb, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great vacation
Emily P.
Stayed 14 nights in Jan 2025
Verified
10/10 Excellent
Denise M.
23 Jul, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and spacious accommodations
Denise M.
Stayed 9 nights in Jul 2023
Verified
10/10 Excellent
Verified traveller
4 Apr, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Island Vacatoin
Verified traveller
Stayed 7 nights in Mar 2023
Verified
10/10 Excellent
Bernard C.
30 Dec, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic experience and views all around!
Bernard C.
Stayed 7 nights in Dec 2021
Verified
10/10 Excellent
Christina S.
15 Aug, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay at Five O’clock on the Hill
Christina S.
Stayed 6 nights in Aug 2022
Verified
10/10 Excellent
Tony A.
6 Mar, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Five on The Hill
Tony A.
Stayed 7 nights in Feb 2020
Verified
10/10 Excellent
Derrick H.
30 Jul, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place with awesome views
Derrick H.
Stayed 7 nights in Jul 2022
Verified
10/10 Excellent
Scott H.
16 Apr, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home and gracious hosts!
Scott H.
Stayed 7 nights in Mar 2024
Verified
10/10 Excellent
Derik B.
9 Feb, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise Island
Derik B.
Stayed 8 nights in Jan 2023
Verified
10/10 Excellent
Barbara M.
6 Dec, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Visit a niece who recently moved to St. Croix
Barbara M.
Stayed 7 nights in Nov 2023
Archival
10/10 Excellent
Stacey S.
13 Dec, 2016
Beautiful location for a retreat
Stacey S.
Verified
10/10 Excellent
Shirley R.
31 Jan, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Ideal for couples!
Shirley R.
Stayed 7 nights in Jan 2020
Verified
10/10 Excellent
Martha P.
30 Apr, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous Vacation & Celebration
Martha P.
Stayed 6 nights in Apr 2023
Verified
10/10 Excellent
MONICA I.
21 May, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
AMAZING
MONICA I.
Stayed 7 nights in May 2022
Verified
10/10 Excellent
Marc & Linda J.
14 Jun, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Grapetree Escape
Marc & Linda J.
Stayed 7 nights in Jun 2023
Archival
10/10 Excellent
Eli H.
29 Aug, 2015
Tropical Perfection
Eli H.
Verified
10/10 Excellent
Kellie B.
17 Apr, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place 🏠 Roy / Janet amazing host’s!
Kellie B.
Stayed 7 nights in Mar 2021
Archival
10/10 Excellent
17 Jul, 2015
Tropical paradise
Verified
10/10 Excellent
Heid K.
5 Mar, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great spacious property
Heid K.
Stayed 9 nights in Feb 2023
Archival
10/10 Excellent
Marilyn C.
20 Sept, 2016
A week in paradise
Marilyn C.
Verified
10/10 Excellent
Jill C.
5 Feb, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for families
Jill C.
Stayed 7 nights in Jan 2024
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.
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.
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.
• 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
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