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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Incredible Island Home in the Perfect Location NO HURRICANE DAMAGE- READY TO GO

Bedrooms 2
Property type villa
Minimum Stay 7 nights


About the property

Villa, 2 Bedrooms, 2 Baths, (Sleeps 4-5)

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

More Details

Property Manager
Property Manager
Member since: 2010
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
March 5, 2018

Guestbook comments from the manager

Upon arrival you immediately see the amazing view Winsome House has to offer. Comfort and amenities of home, with a beautiful Caribbean fee. The photos online do not do justice to the beauty you experience, down to the routed edges of the wood beams. The home is perfectly located close to Coral Bay and all of the North Shore beaches. This was our 6th time in St. John but the first time renting a villa. Can't wait to return to Winsome House again. And the gift basket was so very appreciated and delicious!
May 2017
  • 1 of 7


Upper Carolina Villa Accommodation and Amenities

Property Type:
  • villa
House Rules:
  • Max. occupancy: 5
  • pets not allowed
  • non smoking only
Location Type:
  • Ocean View
  • Water View
  • Air Conditioning
  • Broadband Access
  • Clothes Dryer
  • Linens Provided
  • Parking Off Street
  • Telephone
  • Washing Machine
  • Wireless Internet
  • Cooking Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen
  • Microwave
  • Refrigerator
  • 2 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
  • 2 Bedrooms, Sleeps 5
  • King size beds (1), Baby Cribs (1)
  • CD Player
  • DVD Player
  • Satellite / Cable
  • Stereo
  • VCR
  • Balcony
  • Deck / Patio
  • Lanai / Gazebo
  • Outdoor Grill
Pool / Spa:
  • Private Pool
  • nude beach
  • restaurants
Leisure Activities:
  • boating
  • shopping
  • sight seeing
  • wildlife viewing
Sports & Adventure Activities:
  • fishing
  • hiking
  • jet skiing
  • kayaking
  • parasailing
  • sailing
  • snorkeling/diving
  • surfing
  • swimming
  • wind-surfing


5/5 -
(4 traveler reviews)

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Incredible Island Home in the Perfect Location NO HURRICANE DAMAGE- READY TO GO
average rating of 5.0 based on 11 reviews

Excellent again!

  • 5 of 5

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.

  • Submitted: May 30, 2015
  • Stayed: May 2015
  • Source: VRBO, from HomeAway
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Madison, WI

Beautiful home

  • 5 of 5

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!

  • Submitted: Nov 3, 2012
  • Stayed: October 2012
  • Source: VRBO, from HomeAway
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3 0

Paradise Found!!!!

  • 5 of 5

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

  • Submitted: Nov 20, 2011
  • Stayed: November 2011
  • Source: VRBO, from HomeAway
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4 1
Portland, Oregon

The Ideal Island Retreat!

  • 5 of 5

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.

  • Submitted: Aug 26, 2011
  • Stayed: December 2008
  • Source: VRBO, from HomeAway
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Additional information about rental rates

Extra person $250 + Tax
Tax Rate 12.5%

In and off season rates listed on this site are based on maximum number of guests not including tax. Call manager for complete pricing as your actual pricing may be lower. Holiday rates listed are based on full occupancy but not include local tax of 12.5%/ Holiday season requires a minimum 10 night stay. Confirm rates with manager to assure accuracy.

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.

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