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Leeward St John - Premier accommodation.

Bedrooms 4
Separate WC's1
Property type villa
Minimum Stay 5 - 8 nights


About the property

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

Post Irma. We are ready to go.Huge progress is being made on island. We have just spend November on St John. Leeward house and gardens are looking good.

We will be accepting booking for available dates in 2018.

Southerly aspect

- Secluded neighborhood

- 8 minute drive to Cruz Bay

- Recently remodeled

- 47 ft infinity pool

- Outdoor pavilion and bar

- A/C throughout

- Wi-Fi throughout

- 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
Speaks English
Response time:
Within 12 hours
Response rate:
Calendar last updated:
21 January, 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. Leeward St John was completed in 1999.

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 20+ 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 12 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

Post Irma.

A traumatic time for St John and the island is still recovering ( Nov 2017) . Leeward is in good shape and ready for guests.

Internet connectivity Is patchy at this time, and there is no cable.

However progress is being made island wide and for those booking in 2018 you can expect a full resumption of services.

After Irma all deposits for cancelled trips were repaid in full.

We have a strong following of guests at Leeward and we believe that you treat people as you would expect / like to be treated yourself.

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


Accommodation and facilities for this holiday villa in Rendezvous & Ditleff in Estate Rendezvous and Ditlef

Property Type:
  • villa
  • Self-catering
  • Housekeeper Optional
House Rules:
  • Check-in: Flexible
  • /
  • Check-out: Flexible
  • Max. occupancy: 10
  • Max. adults: 8
  • 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.
Location Type:
  • 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
  • Hob
  • Toaster
  • Dining
  • Dining Area
  • seating for 8 people
  • 4 Bathrooms
  • 1 Separate WC
  • Bathroom 1 - Toilet , Shower Enclosure
    Bathroom 2 - Toilet , Shower Enclosure
    Bathroom 3 - Toilet , Shower Enclosure
    Bathroom 4 - Toilet , Shower Enclosure
    Bathroom 1 - Toilet , Off of living room
  • 4.5
  • 4 Bedrooms, Sleeps 10
  • Bedroom 1 - 1 Extra Lg. Double Bed , Master bed and ensuite bathroom. Balcony.
    Bedroom 2 - 1 Extra Lg. Double Bed , Upstairs guest bedroom with ensuite bathroom. Balcony
    Bedroom 3 - 1 Extra Lg. Double Bed , Downstairs bedroom and ensuite bathroom
    Bedroom 4 - 1 Extra Lg. Double Bed , Downstairs bedroom and ensuite bathroom.
  • King size beds (4), all ensuite
  • Books ...
  • DVD Player
  • Games ...
  • Satellite / Cable
  • Stereo
  • Television ...
  • Balcony
  • Terrace
  • Golf ...
  • Kayak / Canoe ...
  • Lanai / Gazebo
  • Garden
  • Barbecue
  • Tennis ...
Pool / Spa:
  • Private Pool
Leisure Activities:
  • beachcombing
  • bird watching
  • scenic drives
  • Shelling
  • sight seeing
  • walking
  • Wildlife Viewing
Sports & Adventure Activities:
  • fishing
  • hiking
  • Kayaking
  • Parasailing
  • sailing
  • diving
  • snorkelling
  • Snorkeling/Diving
  • swimming


Exceptional! 5/5 -
(16 traveller reviews)

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Leeward St John - Premier accommodation.
average rating of 5.0 based on 16 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.

  • Review Submitted: 28-Jul-2017
  • Date of Stay: 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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First Class Experience!

  • 5 of 5

Fantastic Villa. Amazing amenities and an experience fit for a king (or queen)!

  • Review Submitted: 03-Jun-2017
  • Date of Stay: May 2017
  • Source: HomeAway
Owner's Response: Very good! Thank you.
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Louisville, KY

Perfection in every way. The view of Klein Bay and the infinity pool was phenomenal.

  • 5 of 5

We had a memorable stay at Leeward. The home is gorgeous and decorated so well. It had all the comforts of home and was large enough that you could always find a quiet spot for yourself. The gorgeous planked vaulted ceilings added to the spaciousness of the home. The house was renovated in 2014 and the bathrooms are very nice. The kitchen is well-equipped with high-end appliances and was simply stunning (loved the view of the lanai/bay as I cooked!). We would highly recommend Leeward to anyone visiting St John. The only minor drawback was the inability to see the sunset from the lanai as it faces south. You can glimpse a "bit" of it from the lanai but you will need to visit Cruz bay (maybe with a drink in hand at the Beach Bar or Rum Hut) to see the beautiful St John sunset in all its glory. This is a very minor issue with this lovely home. We can't express how much we loved waking up to gorgeous views from every window. Leeward is simply stunning and became one of our favorite "happy places".

  • Review Submitted: 27-May-2017
  • Date of Stay: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you very much for taking the time to post a review. It is greatly appreciated. We re delighted you enjoyed Leeward. Our property managers were effusive about your party. It is always a pleasure to have such guests stay. You will,be very welcome to return.
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Amityville, NY USA

Fantastic Villa, we had great presidents week vacation!

  • 5 of 5

Hello, we stayed at Leeward from Feb 19-27, 2017. It is a beautiful, very well maintained house! So clean and bright, perfect for our group. The kitchen was huge and amazing as we like to cook home many nights. The outdoor and pool area were absolutely stunning, so large and comfortable. The bedrooms and bathrooms were also bright, clean, up to date and spacious. We love the location also, so easy to get to town. The owner spent great time with me on the phone and was very knowledgeable when we were initially looking at the house. The management group on island was very pleasant and easy to work with. This was our 12 vacation on St John and we would absolutely stayed at Leeward again!

  • Review Submitted: 08-Mar-2017
  • Date of Stay: February 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you. It is always gratifying to get positive feedback from St John 'veterans' ! For those people who know the island well an endorsement is especially valued. We do appreciate the time and effort in submitting a review. Of course, you will be very welcome to return on your next trip to St John.
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Shaftsbury, Vermont

Perfect stay in Paradise!

  • 5 of 5

My husband and I, together with another couple, had an absolutely perfect stay at Leeward St. John Villa. It surpassed our high expectations - in fact, the glorious photos of this property do not adequately capture the allure and tranquility of the location and view. The home is luxuriously outfitted - our every need was met beautifully. From the huge chef's kitchen to the four king bedrooms with beautiful ensuite baths, to the most perfect infinity pool overlooking the spectacular south facing vista of Rendezvous Bay (and St. Croix beyond), we couldn't have found a more perfect spot to "leave the world behind". Every room has a beautiful ocean view. Thank you, Howard and Lee Ann, for outfitting your home with everything we could possibly have needed - beach towels, beach chairs, gas grill, floats, tasty treats upon arrival, and the list goes on and on. We so enjoyed reading the many journal entries of previous guests who have had the privilege of staying in this beautiful home over the years. The tips on beaches, restaurants, suggested boat trips to neighboring islands - all helped to make our own stay perfect! This was our second visit to St. John, and our first to Leeward. But it most certainly will not be our last! This home gets our very highest recommendation!

  • Review Submitted: 07-Mar-2017
  • Date of Stay: February 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for submitting your review of Leeward, and thank you again for such a wonderful endorsement. We do make every effort to ensure each and every guest at Leeward has a memorable week, and we do encourage everyone to leave suggestions and comments for other guests that follow. There is quite a wealth of St John experience in all the guest books at Leeward. You will be very welcome to return when the allure of St John becomes overwhelming!
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Amazing Villa, amazing family vacation!

  • 5 of 5

What an amazing villa Leeward is! I can honestly say, and I speak for my entire family; that our first trip to St John was without a doubt our best vacation ever! The property is absolutely gorgeous and the view from the beautiful infinity pool is breathtaking! After long day trips to the many beaches it was very refreshing to relax with a drink in the pool and watch the sunsets. Everything is provided for outings to the beach...chairs, beach towels and coolers.

The villa is beautifully appointed yet has a very "homey" feel. The kitchen is well equipped with high end appliances and all the modern amenities you could ask for! Leeward is conveniently located to Cruz Bays shops, bars and restaurants. The property managers at Carefree Getaways were extremely helpful in guiding us to the villa and making sure we knew where everything was and answering any questions we may have!

Our family is looking forward to another trip to St John and another stay at Leeward Villa. I highly recommend staying at Leeward...you will be glad you did!

Thanks Howard and Lee Ann for sharing your beautiful villa!!

  • Review Submitted: 29-Jan-2017
  • Date of Stay: August 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you Vicky for such a kind review. A beautiful island, a lovely house and a good attitude guarantees a successful vacation! Sounds like you nailed it!
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Car: recommended


Prices & Availability

Prices for this holiday villa in Rendezvous & Ditleff, St John

Rental Basis:
per property
Manager accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
High Season
3 Jan 2018 - 14 Apr 2018
5 night minimum stay
for 5 nights
Notes: Rates are based on 4 guests; add £122 per night, per additional guest
Low Season
15 Apr 2018 - 31 Aug 2018
5 night minimum stay
for 5 nights
Notes: Rates are based on 4 guests; add £61 per night, per additional guest
Off Season
1 Sep 2018 - 28 Oct 2018
5 night minimum stay
for 5 nights
Notes: Rates are based on 4 guests; add £57 per night, per additional guest
Thanksgiving Week
15 Nov 2018 - 22 Nov 2018
8 night minimum stay
Holiday Season
19 Dec 2018 - 2 Jan 2019
7 night minimum stay
for 7 nights
My Standard Rate
5 night minimum stay
for 5 nights
Notes: Rates are based on 4 guests; add £61 per night, per additional guest

Additional pricing information

Tax Rate 12.5%

The quoted rates are based on 1-4 people. For each additional person the rates are as follows:
- High Season $150 per night pp
Refundable deposit is required by first time visitors to Leeward. I hope you understand the reasoning behind this. Everyone has always received a full refund.

Manager's Cancellation Policy

  • 100% refund for cancellations more than 60 days before check-in date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.
Ask Manager a Question

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