Winsome House

Click Image To View Gallery

Check Availability & Book Now

Interested in renting this Villa? Contact Us! We respond promptly - including on weekends and evenings.

Hillside, Ajax Peak, St. John
2 Bedrooms 2 Bathrooms
Maximum Occupancy: 4

Call For Pricing

guest testimonials for

Winsome House

May 2013 Hi Debbie. First off just wanted to say thank you so much for the impeccable service, especially Rachel, from day 1. Your response time was like nothing we have encountered with our trips to the Carribean so far. We will def utilize in the years to come. We are pretty low maintenance people so not much to make a complaint about. Villa was beautiful and one of the cleanest we stayed at. Everything we needed was provided. Only a couple minor things. Know people would prob lose but some snorkeling equip provided would be great. Just include in deposit. Secondly, and the only aesthetic thing, can they please paint the bottom of the pool? Not sure if vac even working. The view, service,and villa itself were absolutely fantastic. You will be hearing from us again to visit this beautiful island. All was fantastic. Tx so much for all your help. Have a great day
Submit A Testimonial


Perched high on the slope of Ajax Peak, Winsome House looks out over Coral Bay, Hurricane Hole, and the British Virgin Islands. Nestled into the hillside 800 feet above sea level, Winsome House offers sweeping views of the Caribbean and complete privacy and quietude.
Winsome House provides an enchanting Caribbean experience for two couples or a small family. Built in 2004 in the style of the old plantation houses, a Great House provides the dining and entertainment spaces and a separate, two-story building houses the equal-sized bedrooms and baths. 1300 square feet of deck unites both buildings into one indoor/outdoor living space.

Glimpsed through five mahogany French doors, the sea is never far from view. The ambiance of the tropics is reflected in the Tommy Bahama and Indonesian furnishings throughout the house.

Mahogany kitchen cabinetry stocked with Villeroy & Boch dinnerware and Calphalon cookwear and cutlery will please the most discriminating guest. A beautiful carved wooden table provides an elegant dining experience when weather dictates. On a 30-foot, covered terrace, alfresco dining is possible in all but the most inclement weather. 

An unobstructed view of the sea from the pool and the deck beckons for lazy days at home. Spacious decks, both covered and uncovered, accommodate all degrees of sun worshipping. 

Separation of the bedrooms from the Great House and from one another assures privacy and independence for all guests. On the same level as the Great House, the lower 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 brick and native stone patio. 

Up a wide, brick staircase separating the bedrooms from the Great House is the upper-story bedroom with king bed. The bedroom opens onto a private, covered deck with just possibly the best view in the house. The shower too with its sea view is sure to delight. 

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 is close at hand in Coral Bay or a mere 20 minutes away in Cruz Bay.

Bedroom Specs

  • King( 1 )
  • set of full beds( 2 )

Bathroom Specs

  • 2 Bathrooms



  • Pets : Please inquire
  • Smoking : Not permitted


  • Air Conditioning ( bedrooms )
  • Pool
  • Television ( 40 inch flat screen HDTV and BluRay player )
  • iPod Dock/Stereo Hook-up
  • Beach Chairs
  • Beach Towels
  • BBQ / Grill ( Gas )
  • Ceiling Fans
  • Fully Equipped Kitchen
  • Washer & Dryer
  • Wireless Internet

Rate Notes

  • Security Deposit: $
  • Extra Person; $250/week
  • 12.5% Government Hotel Tax.
  • $50 damage deposit waiver fee
  • Rates in U.S. dollars.
  • Rates based on double occupancy per bedroom.
  • Weekly rate is equal to seven times the nightly rate unless noted above.
  • Rates subject to change without notice.
  • Holiday rates and date periods may vary. Holidays may include Christmas, New Year's, Thanksgiving, Easter, President's Day, etc.
  • Additional fees may apply. Call for details.

Similar Villa Listings

Check Availability

Website Design & Development by Ironistic

Contact a Villa Specialist

Not sure where to start your search for a Caribbean villa rental?

Contact a CaribbeanDays villa specialist today! Having visited each and every Caribbean island many times, our specialist can guide you in choosing the right island and villa for your getaway. Fill out the form below to contact a specialist and get started.

  • This field is for validation purposes and should be left unchanged.

Call Now