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

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Enjoy breathtaking ocean views from the comfort of your balcony.
Enjoy a night swim under the starry sky, surrounded by a tranquil pool and modern architecture.
Enjoy meals with a view of the ocean from this dining area, featuring a round table for four and comfortable seating.
Relax in a shaded outdoor space with ocean views, featuring comfortable seating and dining areas.
Two detached houses with ocean views, set amidst lush greenery on a hillside.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms6 bathroomsSleeps 12279 sq m

Popular amenities

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

Explore the area

View in a 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 (STX-Henry E. Rohlsen)
    ‪45 min drive‬

Room options

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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!

During your stay at this villa, you're just a quick walk from Grape Tree Beach. You'll find features like an outdoor pool, concierge services, and laundry facilities. The villa offers free WiFi and a private pool.
  • Air-conditioned villa with private pool, kitchen, and washing machine
  • Free WiFi
  • Take a swim in the outdoor pool
  • Services include a concierge and limo or town car service
  • 6 minutes by foot from Grape Tree Beach and a 3-minute drive from Knight Bay
This villa offers its guests an outdoor pool, barbecue grills, and concierge services. The business-friendly villa also features laundry facilities and limo service. The front desk is open around the clock.

This Christiansted villa is smoke free.

Property manager

Roy Chilson

Languages

English

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)
  • First aid kit
  • Fire extinguisher

General

  • At least 80% lighting from LEDs
  • Energy-saving switches in guestrooms
  • Housekeeping (on request)
  • Property does not allow children
  • Unit size: 3,000 square feet
  • Water-efficient showers
  • Water-efficient toilets

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 28

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • No pets allowed

Children and extra beds

  • This property does not allow children.
  • Note from host: Not ideal for kids but will consider your needs.

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
Onsite parties or group events are strictly prohibited
Host has indicated there are no carbon monoxide detectors or gas appliances on the property
Host has indicated 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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.

Property is also known as

Please Read our Policy in the Description
Please Read our Covid 19 Policy in the Description.

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

Reviews

10

Exceptional

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

Reviews

10/10 Excellent

Emily P.

Liked: Cleanliness

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

andrea j.

Liked: Cleanliness

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

Scott H., Frederick, md

Liked: Cleanliness

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

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

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

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

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

Denise M.

Liked: Cleanliness

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

Marc & Linda J.

Liked: Cleanliness

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

10/10 Excellent

Martha P.

Liked: Cleanliness

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

Verified traveller

Liked: Cleanliness

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

Heid K., Bemidji, MN

Liked: Cleanliness

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

10/10 Excellent

Verified traveller

Liked: Cleanliness

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

Derik B.

Liked: Cleanliness

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

10/10 Excellent

JAMES L., Santa Fe

Liked: Cleanliness

Great Place for a Group

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.
Stayed 6 nights in Dec 2022

10/10 Excellent

Alice R.

Liked: Cleanliness

Five o’clock on the hill

Good time had by all. We enjoyed our stay. Quite and relaxing.
Stayed 5 nights in Oct 2022

10/10 Excellent

Christina S.

Liked: Cleanliness

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

Derrick H., Goshen Ohio

Liked: Cleanliness

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

MONICA I.

Liked: Cleanliness

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

Kristopher F.

Liked: Cleanliness

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?
Stayed 4 nights in May 2022

10/10 Excellent

Philip H.

Liked: Cleanliness

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.
Stayed 7 nights in Apr 2022

10/10 Excellent

Anthony F.

Liked: Cleanliness

Beautiful View

Hosts were very helpful and quick to respond. Great week at the main house.
Stayed 7 nights in Apr 2022

10/10 Excellent

James F., Bowerston Oh

Liked: Cleanliness

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.
Stayed 29 nights in Feb 2022

10/10 Excellent

Nicole E.

Liked: Cleanliness

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!!
Stayed 7 nights in Jan 2022

10/10 Excellent

Bernard C.

Liked: Cleanliness

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