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Leeward St John - Newly remodelled premier accommodation.

Bedrooms 4
Separate WC's1
Property type villa
Minimum Stay 5 - 7 nights


About the property

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

Update October 25

We will be on St John from Nov 12 for an indefinite period.

Thank you to so many guests for showing both their concern and commitment to Leeward.

It is very gratifying to receive messages of support and new bookings!

All deposits for cancellations have been repaid.

VRBO reservations were so much easier to process.

We suffered tile damage to the Great Room roof and one cracked rafter. Whilst addressing this we decided to renew and upgrade the original roofing. This roof was not changed during the remodelling in 2015/16.

We await roofing tiles.

The new pagoda has been designed. The last one was built to withstand 160mph winds. At 200mph it stood little chance and disappeared over the main roof. The new structure will be reinforced concrete, like the main house.

The pool has been drained, cleaned and refilled.

Solar power keeps the house ticking over.

We will provide objective input whilst on St John.


Saturday 30

A quick update.

Solar field at Leeward is providing power to the house except for AC.

A team of 6 has been working all week to restore the gardens.

Minor roof repairs to the Great Room start on Monday.

We have decided to rebuild the pergola and that will occur in the next few weeks.

We have received some cancellations and all those deposits have been repaid in full, with just a few administrative hold ups for those that didn't go via VRBO.

Progress is being made on St John, so please be patient before altering travel plans.

Anyone who wishes to roll forward their stay at Leeward are very welcome to do so.

Thursday 14.

Relief efforts on St John are moving up a gear, which is gratifying.

This is not a blog, but an attempt to keep those with bookings at Leeward up to date.

We have had numerous messages of support and we are very appreciative . Thank you all.

On a practical note, we will refund any deposits for those that wish to cancel on the back of Irma.

I am not putting any time limit on that, so please do not feel you have to rush to make that decision.

No one with reservations at Leeward has to adhere to a cancellation policy.

All cancellation policy requirements are voided.

This means we can all wait for as long as possible before deciding whether to travel,or not.

Automated requests for second payments that usually occur 60 days out, should be ignored.

Those additional payments can be made when you arrive.

We will look at discounting those additional payments as a way to stimulate the local economy.

At the moment we don't have access to bank accounts on St John but we will refund from our personal accounts in the meantime.

Tuesday 12

Leeward is home to 6 people on St John at the moment who have had to vacate their own badly damaged homes.

We suffered some tile damage, and lost the pool pavilion roof.

Otherwise the house held up well.

All reservations through October are cancelled.

We will make a call on November when we can assess progress being made on island.

Please be assured that we are doing all we can to assist the aid effort on St John.

Leeward's largely superficial repairs will occur in due time.

To be honest there are more pressing concerns at this time.

As most observers will know, power is the crucial element. Solar and back up generators need to be supported by the grid, and that may take time.

I have asked people to be patient whilst St John is nursed back to health. It will recover, the only question is the length of time.

All rental deposits are covered, so please do not fret about that.

We will honour all such payments.


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 a few hours
Response rate:
Calendar last updated:
27 October, 2017

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

The South shore of St John is a popular destination for visitors. Rendezvous Bay is the most beautiful of the residential areas on the south shore, and Klein Bay is a charming and picturesque community within Rendezvous.

We were fortunate to buy this plot long before the real estate boom. It is a choice lot, high enough to benefit from the gentle trade breeze, but low enough to feel as if you can step off the deck in to the ocean. The house faces due south making the pool and deck a favoured place. Enjoying an early morning coffee on the deck overlooking Ditleff Point, lounging on the pool side furniture soaking up the sun shine, laying on a pool float listening to music from the outdoor speakers, or having a late afternoon cocktail are all options you'll want to consider. And the night sky is a a joy to behold.

The house itself benefits from high quality finishings. Yet it is not pretentious. Maintenance and cleanliness are high on the agenda, so you can relax in comfort. A/C and copious ceiling fans throughout the property keep it cool. There are stunning views from every aspect.

We're a pretty active family, and after a day out on the latest adventure, nothing beats coming back to Leeward, firing up the BBQ, and sipping a cold beer or a rum cocktail whilst looking out over the ocean.

No Caribbean property is complete without a garden and we take pride in the gardens at Leeward. It can be challenging at times, but there is a good array of mature palms and shrubs, fruit trees including mango, banana, coconut, star fruit and lime. I like to rise early and wander about the garden watching the humming birds feed and marvel at the colours of the foliage and tropical flowers.

Leeward is a well maintained upmarket, family house with beautiful furnishings. Its views are unsurpassed, with many guests enjoying fabulous memories of the house. I feel confident you will too.

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


Car: recommended


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

Property Type:
  • villa
  • Self-catering
  • Housekeeper Optional
House Rules:
  • Max. occupancy: 8
  • Events Allowed
  • pets not allowed
  • non smoking only
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 8
  • 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 - Newly remodelled 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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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
Thanksgiving Week
18 Nov 2017 - 24 Nov 2017
7 night minimum stay
Holiday Season
23 Dec 2017 - 2 Jan 2018
7 night minimum stay
for 7 nights
High Season
3 Jan 2018 - 14 Apr 2018
5 night minimum stay
for 5 nights
Notes: Rates are based on 4 guests; add £128 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 £60 per night, per additional guest
My Standard Rate
5 night minimum stay
for 5 nights
Notes: Rates are based on 4 guests; add £64 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

Please ask the manager or check their rental agreement when booking the property.
Ask Manager a Question

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