4 bedroom, A/C throughout, enviable south shore location
Howard and Lee Ann Jones
About Howard and Lee Ann Jones
We first traveled to St. John in 1994, with two very young children in tow, desperate to escape the London winter blues. Earlier in our marriage we'd travelled to a number of Caribbean islands, but the beauty of St. John was just awe inspiring. On that very first visit we purchased land, beginning a long and wonderful association with the Island of St. John. As our family grew and aged, the one constant in all our lives was Leeward. In their early years, the children spent time in the shallows of Maho Bay, playing and learning to snorkel, but also accompanied us on hikes and more adventurous outings as their confidence grew. Now we do all that, but can also throw in an hour at the Beach Bar or Woodys! Leeward has provided countless memories as the family has grown up. The London winters are still dreary, and we escape frequently to St. John. The lure of the island is strong, and even after 25+ years there is a rush of anticipation as we prepare for another visit. In 2015 we decided that it was time to extensively upgrade the house. We sought the expertise of well respected local architect Michael Milne, which has resulted in the breathtaking incarnation of Leeward you see today. It is a gorgeous island, and a beautiful house from which to enjoy it. Our family has done so, and judging by the number of repeat guests at Leeward, some stretching back over 16 years, many others have done so to. We prefer to call guests 'Friends of Leeward' as opposed to 'Visitors'. We do hope you'll find time to visit St. John, and if your travel plans incorporate another villa, that is fine too. Enjoy the natural beauty of St. John. We know you'll be back.
Why Howard and Lee Ann Jones chose Rendezvous & Ditleff
This was a choice lot which we were fortunate to buy long before the property boom on St John. The southerly aspect and views out over Rendezvous Bay are simply gorgeous. The extensive remodelling in 2016 has enhanced the views and has made Leeward a stylish, but family friendly home.
What makes this Villa unique
- Southerly aspect - Secluded neighborhood - 8 minute drive to Cruz Bay - Recently remodeled - Infinity pool - A/C throughout - Wi-Fi throughout - All king sized beds - All bedrooms are ensuite - On-island property manager - Long history of repeat guests - Spacious modern kitchen - Outstanding views of Rendezvous Bay - Access to private neighborhood beach
Check-in: 1:00 PM
Check-out: 10:30 AM
check with owner
check with owner
Please tell us if children under 8.
Max guests:8 (sleeps up to 8 adults)
Cancellations for Thanksgiving, Xmas and New Year weeks are subject to 20% fee. 100% fee if within 60 days of arrival. Trip cancel insur. recomended.
Most St John pools are not fenced off. Please let us know if children under 8 will be in your party. The pool rules are signposted in the pergola.
No drones to be used at Leeward.
100% refund if canceled at least 60 days before arrival date.
Photos don’t do it justice
The view when you first enter the house will take your breath away! The owners have thought of everything for your comfort. Our family had a fabulous week here and can’t wait to return. Taylor (the property manager) is fabulous. He recommended a place for dinner the first night (La Tapas) and gave us the phone number to call for reservations. Don’t miss out on a meal at this place! Later in the week, when one of our party came down with a sore throat and fever, he not only gave us directions to the clinic, but also sent us screenshots of a step by step map. It was great to come “home” to Leeward each day, after visiting the amazing beaches of St. John. I can’t say enough about what a gorgeous property this is. You will definitely not be disappointed!
Thank you Laura. We are so glad that you enjoyed your vacation on St John and your stay at Leeward. It is truly a special place. We are very lucky to have such a great on island manager in Taylor and we're pleased to hear that he was able to help out.
Perfect in every sense
Our family had a wonderful time spending a week in Leeward the week before last. Pre trip communication with Howard and Lee Ann was flawless as was coordination with Taylor upon arrival on the island. We had a slight snafu with a car rental and Taylor came back to the property the following morning to take as back to town to rent our vehicles. The online description and photos of the property are 100% accurate. They cannot however capture the 3 dimensional beauty of the home and surrounding spaces. The pool and deck are stunning. The kitchen, common areas, bathrooms, and bedrooms are spotless and in perfect condition. This was our 5th trip to St John but the 1st time overlooking Rendezvous Bay. Based on the beauty, serenity, and convenience, this will be our 1st choice for future visits. I shared pictures on social media and received many requests from friends for the link. Don't hesitate to book Leeward if planning a trip to St. John. Thank you Howard and Lee Ann for opening your home to us.
Thank you Paul for such a wonderful review and thank you for sharing our vrbo link. Please do get in touch whenever you want to come back. You will be most welcome!
Howard and LeeAnn
This was one of the most beautiful homes in which I’ve ever had the pleasure of staying. The home is gorgeous, the view is amazing and the management was fantastic. Cannot wait to make another visit. Highly recommended!!
Thank you Philip. We're glad that you and your friends had a lovely time while at Leeward. Please come back and see us again soon.
LeeAnn and Howard
60th birthday with four couples
This is an excellent home with an incredible view. Nice outdoor area with infinity pool. Four nice bedrooms, beautiful well equipped kitchen and terrific sound system . I would give this property six stars if I could.
Thank you Michael. It was a pleasure to have you at Leeward. We hope your future plans will bring you back to stay with us again.
LeeAnn and Howard
Gorgeous Home with Stunning Views
My husband and I spent a lovely week at Leeward Villa with our daughters and their families. The villa's layout, amenities, and decor were amazing as were the views from the vanishing edge pool. Interior access to all of the bedrooms was an added bonus as we had young children in our group. The property manager and owners were highly responsive to any questions/needs that we had before and during our stay. In conclusion, I would highly recommend Leeward and look forward to revisiting her in the near future.
Thank you Clara! We are so glad that you and your family enjoyed your stay on St John and at Leeward. We are pleased that the house allows for the flexibility to enable your extended family of 11 to stay comfortably. We look forward to welcoming you back again soon.
Lee Ann and Howard
Absolutely , positively fabulous house. Do not hesitate to book. You will not be disappointed. The only thing you need to bring is your swimsuit and flip-flops. The house has every amenity you will need for your stay.
Thank you for this lovely review. We are so glad you enjoyed your stay and hope to see you again soon at Leeward. Let us know your size and we can even have your flip flops ready next time.😎