A Winsome House

2 Bedroom, 2 Bath | Ajax Peak


Beds Baths Location Max Guests
2 2 Ajax Peak 4


Year In Season Off Season Holiday Additional Info
2024 $4,590/2

2024 In Season: January 7, 2024 - May 3, 2024
2024 Off Season: May 4, 2024 - December 17, 2024
2024 Holiday Weeks: December 18, 2024 – January 5, 2025 (10 night minimum stay over holidays)*
2025 In Season: January 6, 2025 - May 2, 2025
2025 Off Season: May 3, 2025 - December 17, 2025
2025 Holiday Weeks: December 18, 2025 – January 5, 2026 (10 night minimum stay over holidays)*

* Holiday rates MAY include Christmas/New Years, Thanksgiving, Easter, Presidents' Week and Carnival week

2025 $4,590/2

2024 In Season: January 7, 2024 - May 3, 2024
2024 Off Season: May 4, 2024 - December 17, 2024
2024 Holiday Weeks: December 18, 2024 – January 5, 2025 (10 night minimum stay over holidays)*
2025 In Season: January 6, 2025 - May 2, 2025
2025 Off Season: May 3, 2025 - December 17, 2025
2025 Holiday Weeks: December 18, 2025 – January 5, 2026 (10 night minimum stay over holidays)*

* Holiday rates MAY include Christmas/New Years, Thanksgiving, Easter, Presidents' Week and Carnival week

Additional Guests up to Max Guests, $250/week each.
Pool Net A/C Kids
View Availability Call Now
Be sure to call to check the very latest availability since bookings can change at any time.

About A Winsome House

Tucked into an emerald green hillside, lies a very special property. Winsome House is an escapist’s dream...a world away, yet convenient to everything. Only a quick 5 minute drive takes you to the world renowned beaches of St. John. Ram Head trail, Salt Pond beach and the solitude of the East End are reachable within fifteen minutes, as are some of the best hiking trails on St. John. Both casual and fine dining as well as provisions are close at hand in Coral Bay. Cruz Bay lies just a few minutes more away.

Winsome House, a no smoking villa, is nestled into the hillside 500 feet above sea level. Enjoying cool breezes and sweeping views of the Caribbean guests can relax in complete privacy and quietude.

This enchanting Caribbean home offers state of the art conveniences including air conditioning, cable television, high speed WiFi, 40 inch flat screen HDTV and BluRay player with iPod dock...but there is 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 custom mahogany doors to a beautiful covered gallery for savoring an al fresco meal while enjoying the incredible ocean views. Island ambiance is reflected throughout with designer furnishings, hand selected for both beauty and guest comfort.

Immediately adjacent to the Great House is the two story bedroom unit housing two equal and elegant bedrooms and baths,ensuring privacy and independence for all guests. The lower king bedroom opens onto the main deck and the pool area through two mahogany French doors. The large shower with view to the sea opens onto a private brick and native stone patio.

A wide stone staircase leads to the master bedroom above also furnished with king bed. The master bedroom has its own private, covered deck with peerless views of Bordeaux Mountain, Coral Bay and the valley below. The en suite bath offers a shower with exposure to the Caribbean and the tropical gardens to the East. Both bedrooms pamper the guests with high quality bedding a bath linens to delight and soothe after a long day at the beach.

Custom mahogany kitchen cabinetry stocked with Villeroy & Boch dinnerware and Calphalon cookware and cutlery will please even the most discriminating chef. A carved wooden table provides an elegant dining experience when weather dictates.

Step outside onto the large ipe teak deck and enjoy a cool dip in the pool which is furnished with a solar cover to keep the water temperature balmy year round. Colorful, professionally maintained tropical gardens surround Winsome House and watching hummingbirds dart from flower to flower could become a new pastime. Both sun and shade areas beckon for lounging, with unobstructed views of the turquoise Caribbean, Bordeaux Mountain, and the islands and bays below making it very, very hard to leave this magical spot.

Villa Photos

Location Map

Posted: Oct 15, 2023
Five star view! The luxurious and cool bedrooms! The pool! Oh and that view! We loved the privacy of this villa. The bedrooms smelled so good! Made me smile every time I walked in. We appreciated the nice linens, the cloth napkins, and well-appointed kitchen as well. The home was sparkling clean when we arrived!Thank you for a magical vacation!
Posted: Jul 1, 2023
Based on the reviews, I was expecting Winsome House to be fabulous. But it even exceeded my expectations!! The location is truly amazing. First of all, it's so private. Absolutely peaceful with only the birds' sweet songs for background noise. And the view is truly beyond description. Of course the view of the bay was incredible, but I think my favorite view was off to the right of the balcony - the green mountains with the brilliant sky. I took about a thousand pics! Aside from the view, the accommodations themselves were wonderful. I loved my upper floor bedroom. I called it my Rapunzel room. I couldn't get over the view from the shower! Both rooms were so beautiful and comfortable. One of my favorite days of the vacation was when I spent the morning reading on my bed in front of the wide open balcony doors. It was magical. The living/dining quarters were awesome. I loved the many patio doors! We enjoyed some nice dinners out, but my favorite meals were the ones we had on the patio. We watched movies on the iPad with that incredible view in the background. The convenience store just down the road was great for ice, groceries, etc. Colombo's just down the hill had the best breakfast - acai bowls! Beaches were close by. To me, this place is truly paradise. We absolutely will be back!!!!
C Young
Posted: Apr 13, 2023
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.
Spring Break in Paradise
D Connor
Posted: Mar 4, 2023
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.
Posted: Dec 10, 2022
Great location, very private. The house is clean and well kept. Also has everything you need for cooking- just bring your own food! The "goodie" welcome bag was much appreciated & was good! We hope to come back!
Tony L
Posted: Aug 29, 2022
Great location. Clean, spectacular view. Our second time staying here. Destination St. John is wonderful to work with.
Posted: Jun 7, 2022
Our family has greatly appreciated all our visits to A Winsome House over the past years. We always feel comfortable from the moment we walk in the door. View of Coral Bay is outstanding!
Amazing View
Heather B
Posted: Apr 2, 2022
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!
Therapeutic Spot
Meredith M
Posted: Mar 26, 2022
Gorgeous view with a beautiful house stocked with everything needed!
Reid L
Posted: Jan 5, 2022
Our stay in at "A Winsome House" was absolutely wonderful. This was our 10th visit to St John, and one our top two favorite houses. Very private, quiet, peaceful. Stunning views. Great layout, clean, lovely decor, comfortable beds. The house had everything we needed. Destination St John was fantastic to work with. all around great vacation. We hope to stay at A Winsome House again soon!
Posted: Nov 10, 2021
We loved staying at A Winsome House. The views, which are very important to us are some of the best we've seen on island. The location was perfect for enjoying both sides of the island & the north shore beaches. The beds were very comfortable. Washer & dryer worked great, as did all kitchen appliances. It had everything we needed. Destination St. John was great to work with, quickly answered emails prior to trip. Gift basket upon arrival was fantastic and so appreciated after our long day of travel. It was all delicious by the way. We ended up going to North Shore Deli to let them know & get more! Also thanks to Eric for staying late and showing us the house. Can't wait to come back! Thank you for an amazing time!
Linda F
Posted: Jul 24, 2021
Great house every thing we needed. I keep dreaming of the view.
Posted: Jun 17, 2021
We loved the privacy of this villa. Perfect million dollar view. Really made us feel at home. We appreciate all of the supplies already at the villa. We would definitely stay here again in the near future. Please keep our name in your files. We will definitely keep Destination St. John in our files.
Stephen L
Posted: Aug 6, 2020
This villa was actually better in person than the photos suggested. It was a beautiful quiet villa with beautiful expansive views. Had everything we needed and was just a quick drive to the north shore beaches. After driving around the island, I was even more satisfied with the location; I would certainly stay here again.
Winsome House
Myron Pozniak
Posted: Apr 9, 2019
This is where rubber bands get unwound.
Posted: Feb 5, 2017
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!
Posted: Jul 26, 2016
We very much enjoyed our stay at A Winsome House. The furnishings were nice and the layout of the property is great. We enjoyed the pool, deck areas, the view and the constant breeze. The location on the island was great with easy access to North Shore beaches and also Coral Bay. Thank you for a wonderful place to stay on the beautiful island!
Posted: May 12, 2016
We LOVED our stay at A Winsome House. The 35 steps and all...LOL. We cannot imagine staying at a more tranquil, welcoming and beautiful place. Our daughter LOVED her bed, as we did, as well. Don't know what you have for mattresses...but these were awesome!!
Posted: Mar 6, 2016
We had a great time on St. John. We loved the house and landscaping. The pool was used a lot also. The view was just beautiful! Fun time and good places to eat. The smoothies were tempting being so close to Ajax Peak Rd. and of course the donkeys were fun to see, also the deer and other free roaming animals. The locals were very cordial and visits to the BVI were great!
Posted: May 30, 2015
This was our second stay in this home and it was excellent again! The house is set up so well! With the bedrooms being seperate from the main house you can be up when ever you want and not disturb those trying to sleep. We love to cook and everything we needed was there for us. And everything for the beach too (chairs, coolers, towels). The view is amazing! We would sit and just get lost in it. You never get tired of it that's for sure. We will be back for that view for sure!
Posted: May 16, 2015
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.
Posted: Aug 8, 2013
My husband and I recently celebrated our liberation from college payments by spending an enchanting week at Winsome House in St John. We were greeted at the ferry by an adorable young lady who got us on our way to our magical getaway. We never expected Winsome House to be so perfect. The house had everything we could have possibly dreamed of and more. The beds were extremely comfortable. The showers with french doors facing the breathtaking view were heavenly. If you are looking for total privacy Winsome House is for you. Area beaches are a few minutes away. We enjoyed going to different bays each day. Although the kitchen is first class we opted out of cooking and ate out each night. Coral Bay is also minutes away. We will definitely be back to paradise. Thank you for a relaxing and rejuvenating visit.
Posted: Jul 2, 2013
...And the management company, Destination St John's booking process, quick replies to all my questions and help with all our needs were excellent. We will be back!
Posted: May 16, 2013
...Greeter always helpful and Destination St. John staff is great to work with.
Posted: Nov 3, 2012
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!
Peacefull Warrior
Posted: Aug 26, 2011
The views from this property are spectacular, especially the sunrises… (sigh) This home is very thoughtfully decorated, clean and well-cared for. The landscaping is gorgeous. Even the showers have an open-air view of the bay. Even 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.
Posted: Apr 2, 2021
My wife and I have made many trips to St John over the last 20 years. We have used several different agencies and also booked directly from villa owners. One thing we have come to expect is the island moves at a different pace than the mainland. However, the team at Destination St John turned that expectation upside down on our most recent visit. We decided to use our grill one night but discovered it was out of gas. They delivered a full tank the next morning! This is just one example. All interaction with them was prompt and courteous from initial booking to checkout. We will definitely be using them for future visits.
Posted: Dec 5, 2020
Destination St. John was top notch at helping us out with needs, questions and concerns. Easy and fast communication and transactions. What a surprise to find a welcome basket with delicious snacks - great after a long travel day!
Posted: May 30, 2016
...Destination St. John was extremely helpful and quick to respond with all questions, excellent management company! We can't wait to book again for another vacation in paradise!!!!
Posted: May 26, 2016
...The management company (Destination St. John) is always a pleasure to work with.
Posted: May 8, 2016
...The property managers were great. Destination St. John rep met us at dock, and showed us around, and the office promptly answered a few questions we had. They even left a wonderful basket of goodies for us to enjoy on our arrival. We will be back! Thank you Destination St John!
Posted: May 1, 2016
...The folks at Destination St. John were helpful as always. Can't wait to go back!
Posted: Feb 29, 2016
...We also appreciated the Destination St. John staff welcoming us and being helpful. We hope to be back again next year!
Posted: Nov 2, 2015
...We've used Destination St. John many times to rent on St. John and cannot wait to do it again! -truly!
Posted: Aug 6, 2015
...My expectations were far exceeded by the incredibly generous hospitality of Leslie and the team at Destination St. John. There was a special hositality basket with delicious treats.
Posted: Jul 16, 2015
...Destination St. John was easy to work with and our greeter did a great job of getting us settled. We also enjoyed the basket of snacks left in the fridge. I wouldn't hesitate to recommend this property at all!
Posted: Jul 11, 2015
...We highly recommend using the management company Destination St. John to rent this Villa, we have used them for the past 8 years and they are simply the best!!!
Posted: May 28, 2015
...We rented through Destination St John both times and they are professional, friendly, curtious and a pleasure to work with. Thank you Kelly for making both of our stays amazing.
Posted: Mar 24, 2015
...The staff at Destination St. John were very nice, accommodating, and quick to respond to our (literally) last minute request. They had the villa cleaned & ready the next day, with a staff member ready to meet us & show us to the villa...they even put a very nice welcome basket of food/snacks in the refrigerator. Another villa rental company sent me a rude email saying they were too busy to schedule a cleaning service...I'm so glad we stayed with DSJ...Great service!...I plan to use them exclusively in the future.
Posted: Aug 4, 2014
...Destination St John was excellent to work with. We enjoyed the welcome basket after a very long day of travel.
Posted: May 29, 2014
...The Destination St. John website was very informative and well put together, we knew exactly what to expect and couldn't wait to get there.
Posted: May 16, 2014
...Hope to return someday and visit the beautiful island again. And we would contact Destination St. John for accomodations again.
Posted: Jul 13, 2013
...We've been using Destination St. John for the last 6 years for villas and couldn't be more pleased....This Company is the BEST and so are all their employees, they take care of any need/question you may have 24/7.
Posted: Jul 11, 2013
...Destinations St John took care of any problem we had immediately.
Posted: Jul 9, 2013
...Thanks to Destination St John for taking care of us.
Posted: Apr 20, 2013
...Destination St. John left a wonderful gift basket in the fridge which made us feel very welcome. We plan to return to St. John and would certainly book our trip through Destination St. John again!

Security/Cancellation Policy

A $1000 security deposit may be required. Cancellations 60 or more days prior to arrival are non-refundable unless property can be re-committed for reserved dates. If property is recommitted for your dates, a 15% service fee will apply. No refunds will be issued within 60 days of arrival, under any circumstances. We STRONGLY urge you to purchase travel insurance.

Reservation Payment


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Visa, Mastercard, Discover, Checks