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

Christiansted, Saint Croix Island
$924 avg/night Minimum Stay 5 Nights
Bed 5

Bed

Bath 5

Bath

Home Villa

Property Type

Sleep 10

Max Sleeps

Night 5 nights

Min Stay

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!

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers Beach Towels Near The Beach
  • SAFETY

    Fire Extinguisher First Aid Kit No Carbon Monoxide Detector (host Has Indicated There Is No Carbon Monoxide Detector Or Gas Appliances On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Energy-saving Switches Property Does Not Allow Children Unit Size: 3000 Sq Ft (279 Sq M) Uses Some LED Lighting Water-efficient Showers Only Water-efficient Toilets Only
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Electric Kettle Microwave Oven Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Recommended Limo/town Car Service Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Outdoor Furniture
  • POOL/SPA

    Fence Around The Pool Massages Outdoor Pool Private Pool
  • BATHROOMS

    5.5 Bathrooms Bathtub Or Shower Hair Dryer Toilet Paper Towels Provided
  • WORKSPACES

    Computer Monitor Desk Desk Chair Printer
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Birdwatching Nearby Casino Nearby Ecotours Nearby Fitness Facilities Nearby Golf Privileges Golfing On Site Hiking/biking Trails Nearby Power Boating Nearby Sailing Nearby Scuba Diving Nearby Windsurfing Nearby
  • ENTERTAINMENT

    Books Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa Near A Hospital Near The Bay Near The Ocean Near The Sea
  • SERVICES AND CONVENIENCES

    Chef Concierge Services Housekeeping (on Request) Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Rates & Availability

Review Review

  • Jen E.

    Submitted Jan 5, 2026

    Stayed Dec 25, 2025

    Host was so easy to work with and welcoming. Place was private and beautiful views!

  • Emily P.

    Submitted Feb 1, 2025

    Stayed Jan 18, 2025

    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.

  • andrea j.

    Submitted Dec 29, 2024

    Stayed Dec 20, 2024

    this property was fantastic for our xmas holiday had a ton of area and everyone had their own space as well

  • Scott H.

    Submitted Apr 16, 2024

    Stayed Mar 30, 2024

    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!

  • William J.

    Submitted Mar 30, 2024

    Stayed Feb 11, 2024

    The home has the most beautiful views of the ocean which can be viewed from a large veranda attached to the house .

  • Jill C.

    Submitted Feb 5, 2024

    Stayed Jan 27, 2024

    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!

  • Ethel C.

    Submitted Jan 24, 2024

    Stayed Jan 2, 2024

    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.

  • Barbara M.

    Submitted Dec 6, 2023

    Stayed Nov 29, 2023

    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.

  • Denise M.

    Submitted Jul 23, 2023

    Stayed Jul 11, 2023

    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.

  • Marc & Linda J.

    Submitted Jun 14, 2023

    Stayed Jun 3, 2023

    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.

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Total

Includes taxes and fees
$924+
View details