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A Winsome House

Photo gallery for A Winsome House

Pool
Pool
Living area
Interior
Private kitchen

Reviews

10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 4

Popular amenities

  • Ocean view
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning

Explore the area

View map
Saint John, VI
  • Place, Virgin Islands National Park
    ‪1 min walk‬
  • Place, Ajax Peak
    ‪1 min walk‬
  • Place, Emmaus Moravian Church
    ‪3 min drive‬
  • Airport, St. Thomas (STT-Cyril E. King)
    ‪70 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Deck or patio
Kitchen
Balcony

About this property

A Winsome House

Tucked into an emerald green hillside, lies a very special property. Winsome House is an escapists dream.. a world away, yet convenient to everything. In fact, only a quick, 5 minute downhill drive brings you to the world renowned North Shore beaches. The home is nestled into the hillside 800 feet above sea level, offering sweeping views of the Caribbean and complete privacy and quietude.

This enchanting Caribbean home offers state of the art conveniences including air conditioning, wifi and flat screen TV.....but Winsome House provides so much more! Built in the elegant style of historic plantation homes, this villa is as beautiful as it is functional. The inviting Great House provides interior dining and entertainment spaces, which open through handcrafted mahagony doors to a wonderful covered gallery for savoring that incredible ocean view while enjoying an al fresco meal. Island ambiance is reflected throughout with designer furnishings, hand selected for beauty as well as guest comfort.

A separate, two-story building sits just steps away, housing two equal and elegant bedrooms and baths, and ensuring privacy and independence for all guests. This home is perfect for couples and families alike. The lower king bedroom opens onto the main deck and the pool through two mahogany French doors. The large shower, from which the sea can be viewed, opens onto a private brick and native stone patio. Just up a wide, brick staircase is the master bedroom, also with king bed. This bedroom opens onto a private, covered deck with yet another incredible view. The ensuite bath also offers a shower with an incredible sea view that is sure to delight. Both bedrooms pamper guests with high count bed and bath linens to delight and soothe after a day at the beach..

Custom Mahogany kitchen cabinetry stocked with Villeroy & Boch dinnerware and Calphalon cookwear and cutlery will please the most discriminating . A beautiful carved wooden table provides an elegant dining experience when weather dictates.
Step outside onto the large epei wood deck, and enjoy a cool dip in the pool, which is equipped with a solar cover, to keep the water temperature balmy year round. Colorful gardens surround you and watching the hummingbirds dart from flower to flower will become a new pastime. Both sun and shade areas are provided for lounging, and an unobstructed view of the turquoise sea and islands beyond will beckon.. making it hard to leave this magical spot!

Situated ideally at mid-island, Maho Bay and the string of North Shore beaches are but a five-minute drive away. Ram Head, Salt Pond and the solitude of the East End are reachable within fifteen minutes, as are many of the island's best hiking trails. Casual to fine dining and provisions are close at hand in Coral Bay or a few more minutes away in Cruz Bay.
Winsome House is a non-smoking villa.



Keywords: Villa, home, house, rental home, vacation home, holiday home, rental villa, vacation villa, rental cottage, vacation cottage

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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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

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 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

About the area

St. John

Upper Carolina, a neighbourhood in St. John, is home to this villa. While the natural beauty of Virgin Islands National Park and Trunk Bay can be enjoyed by anyone, those looking for an activity can explore Tortola Cruise Ship Port. Jet skiing, kayaking and snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking nearby.
View more Villas in St. JohnOpens in a new window
Map
Saint John, VI

What's nearby

  • Virgin Islands National Park - 1 min walk - 0.0 km
  • Ajax Peak - 1 min walk - 0.0 km
  • Mamey Peak - 2 min drive - 1.7 km
  • Reef Bay Trailhead - 2 min drive - 2.0 km
  • Emmaus Moravian Church - 3 min drive - 3.1 km

Getting around

  • St. Thomas (SPB-St. Thomas Seaplane Base) - 76 min drive

Restaurants

  • Sebastian’s Seaside Grill
  • ‪Skinny Legs - ‬6 min drive
  • ‪Shambles - ‬16 min drive
  • ‪Trunk Bay Beach Bar - ‬20 min drive
  • ‪Maho Crossroads - ‬7 min drive

Frequently asked questions

Does A Winsome House have a pool?

Yes, this property has a pool.

How much does it cost to stay at A Winsome House ?

As of 15 April 2026, prices found for a 1-night stay for 2 adults at A Winsome House on 14 December 2024 start from NZ$1,061, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is A Winsome House pet-friendly?

No, pets are not allowed at this property.

How much is parking at A Winsome House ?

On-site parking is available at the property.

What time is check-in at A Winsome House ?

Check-in begins at 3:00 PM.

What time is check-out at A Winsome House ?

Checkout is at 10:00 AM.

Where is A Winsome House located?

Located in Upper Carolina, this villa is within 1 mi (2 km) of Ajax Peak and Virgin Islands National Park. Maho Beach and Annaberg Plantation are also within 3 miles (5 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. 10 out of 10 reviews
Rating 8 - Good. 0 out of 10 reviews
Rating 6 - Okay. 0 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Steve B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spring Break in Paradise

Wonderful property, third time to St. John, first at this location, a wonderful stay. Stunning views from every window, all amenities first-rate, kitchen well-stocked, furnishings lovely and comfortable, easy access to beaches; deck, and pool just what was needed at the end of a long day at the beach. The check-in process is easy, appreciated a parking pad for the car, and loved the architecture of the home, arched screened doors throughout created a wonderful breezy island stay, and especially enjoyed having the bedrooms in a separate building just next to the main house with the balcony on the second floor for the amazing view. The paved road to the house is very helpful when navigating the hills to be expected as part of any trip to STJ. Couldn't have asked for a better location or accommodations.
Stayed 7 nights in Mar 2023
Verified

10/10 Excellent

Cecily Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely House with Beautiful Views, Perfect Location for visiting all parts of St John.

We were stunned by the beauty of the views and the surrounding landscape of this lovely 2 BR house. The house is built in Caribbean style, and furnished in a warm and comfortable style. It is actually 2 buildings, one with great room, cooled by breezes and fans, and the other building having 2 BRs cooled by breezes and fans, or AC. But we didn't find AC necessary, at all. We preferred to hear the tree frogs and birds singing. We would often cool off in the pool after a hot day at the beach. Everything you need is included- there are beach chairs, coolers, ice packs, beach towels. Bathrooms included extra towels, hairdryers, and shampoo, etc. just as you would expect in a 5 star hotel. Located just 10 mins from Maho Beach or Coral Bay, everything felt close. A light and airy experience! You will need a 4 wheel drive car.
Stayed 10 nights in Apr 2023
Verified

10/10 Excellent

Heather B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing View!

My girls and I loved the villa! We spent days by the pool and the location is close to all the glorious beaches. The home had everything we could want or need. We would highly recommend this villa!
Stayed 7 nights in Apr 2022
Verified

10/10 Excellent

Meredith M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Therapeutic Spot

Gorgeous view with a beautiful house stocked with everything needed!
Stayed 7 nights in Mar 2022
Verified

10/10 Excellent

Linda F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house every thing we needed. I keep dreaming of the view.

Great
Stayed 10 nights in Jul 2021
Verified

10/10 Excellent

Evelyn A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Breathtaking views

Such a great property and the owners were so attentive. We had a wonderful time. Memories to last a lifetime. I posted pictures and already all of my friends are asking to book this amazing property!
Stayed 7 nights in Mar 2021
Archival

10/10 Excellent

Todd W.

Excellent again!

This is the second time we have stayed in this home and again it was excellent! The house is set up wonderfully. We love how the bedrooms are seperate from the main house so if someone gets up early they don't disturb the others. Or if you want to stay up late others won't be disturbed. We love being able to cook and everything we needed in the kitchen was there. Also what we needed for the beach (chairs, coolers, towels). The view is amazing! We would sit and just get lost in it. We will be back for sure.
Archival

10/10 Excellent

Beautiful home

This is the second year in a row that we have stayed at Winsome house and absolutely loved both stays. The views are breathtaking and the deck expansive. My favorite parts of each day were walking up and watching the sun rise from the deck and relaxing next to the pool at the end of the day after a long (but fun) day of snorkeling. The house is centrally located, making it easy to explore all of the different beaches St. John has to offer. I loved having two seperate yet equally sized master bedroom suites. I would highly recommend staying here, you will not be disappointed!
Archival

10/10 Excellent

Paradise Found!!!!

Just returned stateside from a 1 week stay on St John at Winsome House. It was my 4th trip to the island and by far the best. The owners and property managers of Winsome House have thought of EVERYTHING!! This stunning home lacks for nothing! The archtitecture is beautiful, the views are jaw dropping, and the management company wonderful to work with. The home is spotless! The driveway has some tough spots to navigate (rocky and bumpy) but 4 wheel drive comes in handy. It really needs to be graded and have some loose stone filled in. But a small price to pay for such a spectacular location with privacy!! Most of the local St Johnian resident's attitudes have not changed over the years. They are still a somewhat rude bunch with maybe 25% of them realizing that customer service and a smile are important. They mostly give the impression that you are an interruption of their work rather than the reason for it. "Island time" seems to be an excuse for "lazy". The management company excluded from this comment. Bernard was a pleasure, Thank you Bernard! If you choose Winsome House for your vacation, you will not be dissapointed in any way!!!!!!!! I cannot wait to re-book! R. Jensen
Archival

10/10 Excellent

The Ideal Island Retreat!

My husband and I stayed at Winsome House on two occasions: in spring 2007 and late fall 2009. We can’t wait to go back! The views from this property are spectacular, especially the sunrises… {sigh} I wish I was there now. This home is very thoughtfully decorated, clean and well-cared for. A lot of care has gone into the landscaping, which is gorgeous. Everything -- from the bed linens to the dishes – is high quality. Even the showers have an open-air view of the bay. The house is stocked with a diverse selection of music and movies, so if you do get a rainy day or two, there’s plenty to keep you occupied. But then, just watching the storms roll in from the covered deck is a great way to spend an afternoon. The house is convenient to several of the best beaches (Maho Bay; Francis Bay), and there’s plenty of tasty food options in and around Coral Bay-- we enjoyed Aqua Bistro and Miss Lucy's the best. My favorite memories of staying at Winsome House: the tree frogs singing me to sleep; waking up to the sunrise; drinking my coconut crème coffee (from St. John Spice) on the porch overlooking Coral Bay; cooling off with a cold beer and a dip in the pool; dinner at Miss Lucy’s followed by the heart-pumping drive up the steep driveway in the dark… so many great memories here! Highly recommended for couples or families.

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