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Leeward St John - Premier accommodation

Bedrooms 4
Half Baths1
Space 3,300 sq ft
Property type villa
Minimum Stay 5 - 7 nights


About the property

4 bedroom, A/C throughout, enviable south shore location

- Recently remodeled

- Southerly aspect

- Full AC throughout

- Two fully operating internet services, including satellite

- Secluded neighborhood

- 8 minute drive to Cruz Bay

- 47 ft infinity pool

- Outdoor pavilion and bar

- Four 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

- Environmentally conscious solar field

LEEWARD ST JOHN is a luxury modern villa beautifully situated on the South shore of St. John. Overlooking the tranquil Rendezvous Bay, the house is only an 8 minute drive from Cruz Bay town centre making this the perfect location for your stay in St. John.

Leeward is positioned to capture some of the best views on the island, with all rooms and the deck enjoying fantastic vistas of the south shore of St. John, the Caribbean Sea and St. Croix 40 miles away.

An arched entranceway with an impressive 9 ft solid mahogany door leads you to the spacious kitchen and indoor dining area, with vaulted ceilings and full height windows allowing you to drink in the breathtaking Rendezvous Bay below. With Thermador appliances, breakfast bar and Subzero wine fridge, the kitchen is fully equipped for even the most discerning chef's needs.

The views continue from the vaulted Great Room, which with comfortable seating and 60 inch TV provides the perfect space for relaxing indoors. From here, French doors open onto the expansive coral stone deck. Within the outdoor Pavilion is a shaded seating area as well as a bar and grill, whilst the deck has space for plenty of sun loungers. The south facing aspect ensures you can enjoy the Caribbean sun long into the late afternoon.

The best vistas are perhaps enjoyed from within the inviting 47 ft infinity edge pool, which steps from 4ft to 6 ft in depth, and appears to join the ocean below.

Leeward's four bedrooms are furnished with king sized beds and 42 inch TVs. All are ensuite, which are beautifully tiled and fitted with rain shower heads. The two upper floor bedrooms have covered balconies which create the perfect spot for your morning coffee or a moment of solitude looking out over the bay.

The house has A/C throughout with numerous ceiling fans ensuring comfortable temperatures.

We are environmentally conscious at Leeward, and a large array of solar panels are fitted out of sight beneath the house. Rain water and grey water is captured and used to water the luscious garden, in which we take pride. Power outages do occasionally occur in the USVI, so the house is equipped with state of the art battery back up power.

In summary, Leeward is a beautiful family house with well crafted details and upscale furnishings to ensure your vacation is a memorable one. We and numerous returning guests have enjoyed Leeward for 16 years, and with the recent remodelling we are extremely confident that it will continue to provide premium accommodation for those visiting St. John.

More Details

Property Manager
Howard and Lee Ann Jones
Member since: 2012
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
September 14, 2018

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 23+ 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 14 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 Bayern 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


Rendezvous & Ditleff Villa Accommodation and Amenities

Property Type:
  • villa
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 3300 sq ft
House Rules:
  • Check-in: Flexible
  • /
  • Check-out: Flexible
  • Max. occupancy: 10
  • Max. adults: 8
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
  • If St John is declared a national disaster area, or Leeward is damaged, we will return all deposits in full. Escrow account held at JPMorgan Chase.
  • Most St John pools are not fenced off. Please let us know if children under 8 will be in your party
Location Type:
  • Near The Ocean
  • Ocean View
  • Oceanfront
  • Adventure
  • Away From It All
  • Family
  • Romantic
  • Sports & Activities
  • Air Conditioning ...
  • Clothes Dryer
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Parking Off Street
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Freezer
  • Ice Maker
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
  • Dining
  • Dining Area
  • seating for 8 people
  • 4 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - toilet , shower
    Bathroom 2 - toilet , shower
    Bathroom 3 - toilet , shower
    Bathroom 4 - toilet , shower
    Bathroom 1 - toilet , Off of living room
  • 4.5
  • 4 Bedrooms, Sleeps 10
  • Bedroom 1 - 1 king , Master bed and ensuite bathroom. Balcony.
    Bedroom 2 - 1 king , Upstairs guest bedroom with ensuite bathroom. Balcony
    Bedroom 3 - 1 king , Downstairs bedroom and ensuite bathroom
    Bedroom 4 - 1 king , Downstairs bedroom and ensuite bathroom.
  • King size beds (4), all ensuite
  • Books ...
  • DVD Player
  • Games ...
  • Satellite / Cable
  • Stereo
  • Television ...
  • Balcony
  • Deck / Patio
  • Golf ...
  • Kayak / Canoe ...
  • Lanai / Gazebo
  • Lawn / Garden
  • Outdoor Grill
  • Tennis ...
Pool / Spa:
  • Private Pool
  • churches
  • duty free shops
  • health/beauty spa
  • marina
  • restaurants
  • ruins
Leisure Activities:
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • paddle boating
  • photography
  • scenic drives
  • shelling
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • groceries
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • fishing
  • golf
  • hiking
  • jet skiing
  • kayaking
  • parasailing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • surfing
  • swimming
  • tennis
  • wind-surfing


Exceptional! 5/5 -
(23 traveler reviews)

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Leeward St John - Premier accommodation
average rating of 5.0 based on 23 reviews

Pictures don't do this amazing home justice!

  • 5 of 5

We loved our stay at Leeward. Kids first beach trip, intimate island wedding and mom's Bday all celebrated here. We even honored the 1yr anniversary our of dad passing. The views are amazing, the pool is perfect and the kitchen a chefs dream! The home is beautifully designed like something out of a magazine but also extremely comfortable and cozy. We hope to come again and just so appreciate the owners sharing their beautiful home.

  • Submitted: Jul 28, 2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you Kristen . We re delighted that your visit to St John and Leeward was so memorable. What a wonderful place for your children to have their first becah vacation! You ll find it hard to beat so you ll have to come back😊. Thank you for taking the time to post a review , and for being such wonderful guests.
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Arlington, TX

Gorgeous view, beautiful home...

  • 5 of 5

This home is really well built, and has all the creature comforts of home. The view from the back porch and most of the rooms are amazing. The property owners and the property managers were easy to work with and were super responsive. We had an absolutely blast with our group and would definitely consider staying here again.

  • Submitted: Sep 5, 2018
  • Stayed: August 2018
  • Source: VRBO, from HomeAway
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Amazing Family vacation

  • 5 of 5

Truly a Home Away from home, Leeward had everything one would need for a relaxing enjoyable stay. Morning coffee on the patio, late afternoon pool time were just a few relaxing times to mention. St John’s has done well to bounce back from Hurricanes. Heard some very heart breaking stories from some very greatful residents. My family and I were glad to give back to the island that has given us so much with its beauty.

Thank you Howard and Lee Ann for our stay in your lovely home.

  • Submitted: Aug 7, 2018
  • Stayed: July 2018
  • Source: HomeAway
Owner's Response: Thank you Lorraine. We are approaching the one year anniversary of Hurricanes Irma and Maria, and it is certainly a date etched in the memory of all who live or have property there. As you say the island has bounced back well, and a lot of that is due to people like yourself who come to visit. Thank you for your faith in St John, and for choosing to stay at Leeward.
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Breathtakingly beautiful

  • 5 of 5

This was hands down my favorite home I have ever vacationed in. The views are absolutely amazing, I didn’t want to leave the house the whole time we were there! The pool was perfect and the home had everything we needed. The furnishings were beautiful, from the actual furniture in the house to the bed linens and bath linens. The kitchen had everything we needed even the chefs that came and cooked for us said that it was a wonderful kitchen to cook in. I can’t wait to go back!

  • Submitted: Jun 3, 2018
  • Stayed: May 2018
  • Source: VRBO, from HomeAway
Owner's Response: Thank you Glyn for a wonderful review. It can be hard to take yourself away from the house. We always find a morning at the beach and a few hours poolside in the afternoon make a pretty perfect day! We appreciate you taking the time to post a review, and you lol be very welcome to return.
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Special Place!

  • 5 of 5

I liken Leeward to a fishing hole. It’s something you don’t want to share because you want all the fish for yourself. That said, I owe it to the owners to let anyone and everyone know what a very special place it is. A group of us enjoyed our stay there in May of this year. The island was doing amazingly well for having suffered through two category five hurricanes. Most everything was open. The roads were clear. The beaches were pristine. We could not have had a better time. I can’t wait to get back. Next year seems like too long a time to wait . I may have to return in the fall. In my opinion, there is no better view than with your arms resting on the edge of Leeward’s infinity pool with a cocktail in hand. Leeward is my favorite place on the island and I have been going there for almost a decade.

  • Submitted: May 13, 2018
  • Stayed: April 2018
  • Source: VRBO, from HomeAway
Owner's Response: What a wonderful review. Thank you for your endorsement Michael. It is a fabulous view, and it sounds like you enjoyed it in real style. Good job!
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It was Perfect!

  • 5 of 5

Everything we needed for a relaxing week. (4) couples had plenty of room in the (4) master bedrooms. Loved the new appliances and cleanliness of the home. Cant beat the view!! Would definitely recommend to anyone.

  • Submitted: Apr 30, 2018
  • Stayed: April 2018
  • Source: HomeAway
Owner's Response: Thank you Carl. Always reassuring for people to know that Leeward can handle 4 couples with ease. Glad you all had a good time.
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Car: recommended


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

The quoted rates are based on 1-4 people. For each additional person the rates are as follows:
- High Season $150 per night pp
- Low Season $75 per night pp
- Off Season $70 per night pp.

If using the instant booking facility , please ask before booking more than 12 months in advance, or if dates fall outside of a Saturday to Saturday stay.

Infinity edge and open pool, please ask about children under 8 years of age.

Manager's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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