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Leeward St John - Newly remodelled premier accommodation.

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


Minimum Stay
5 - 7 nights

About the property

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

- 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:
20 February, 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 Cruz Bay

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


Accommodation and facilities for this holiday villa in Rendezvous & Ditleff in St John

Property Type:
  • villa
  • Self-catering
  • Housekeeper Optional
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 ...
  • Events Allowed
  • non smoking only
  • pets not allowed
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 -
(11 traveller reviews)

Leeward St John - Newly remodelled premier accommodation.
average rating of 5.0 based on 11 reviews

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: Jan 29, 2017
  • Date of Stay: Aug 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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0 0

Our most memorable family vacation!

  • 5 of 5

THE VIEW! THAT POOL! Everything about this Villa is absolutely amazing, but its the view and the pool that takes you away any time of the day. The house is modern, beautifully appointed and has all high end appliances and more cooking supplies than you will ever need! We were a group of 6 adults and 3 young children and the house accommodated everyone with plenty of space and more than enough outdoor seating. Our day trips to the beaches were made easy with beach chairs, beach towels, coolers and ice provided by the villa.

The location of this Villa is perfect! Set up on a hill in private residential neighborhood, our time spent at the Villa and by the pool were peaceful and relaxing. Leeward is a quick drive to Cruz Bay and all its action! Not too far from the gorgeous beaches of St. John, which we visited daily, but all roads lead us back to that amazing infinity pool! Relaxing on the floats, drinking while sitting on the in-pool bench or looking out over the infinity edge....blue water for miles disappears into the blue sky! The kids swam for hours, and even danced thanks to the incredible sound system outdoors! In the evenings we'd sip cocktails in the warm air while taking in the view of passing cruise ships! Where else can you see the sun rise and set for the same spot...just perfect!

The property management company were a pleasure to work with! They were very helpful and responsive to our questions during our planning stage and even more so once we arrived to the island. I even had several conversations with the home owner leading up to our trip and he was just as helpful! In our conversations you could tell he took such pride in the Leeward Villa! And from the moment we first stepped into the home I could see why!

We hope to be back soon and highly recommend this villa for your next vacation!

  • Review Submitted: Jan 29, 2017
  • Date of Stay: Nov 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for such a delightful review. Leeward is in an enviable location, and we do try to ensure that all guests have a memorable stay. We have many repeat guests and understandably they don't post reviews, so it is very kind for first time visitors to do so. Of course, you will be very welcome to return .
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0 0
Wichita, Kansas

Great stay for our family vacation!

  • 5 of 5

We stayed at this Villa for our spring break vacation and had an incredible stay. Our group of 6 included my parents, my wife and 2 kids (teens) and I. The layout of this home was perfect for us with 4 bedrooms stacked 2 and 2, each with their own bathroom. The views out of the top floor rooms are absolutely amazing! The property management group, Carefree Getaways, were easy to work with and very helpful for us first time St. John visitors. They helped us choose a car rental company and gave us advice on things to do during our stay. The Villa is exactly what the pictures show and more. I never would have thought the pool was as big as it was and 8 ft. deep. The outdoor living area is perfect and a great place to spend time. The kitchen was equipped for all our needs and we fixed numerous meals both indoors and out using the grill. We are already planning another trip in the future with 3 other couples and can't wait to spend more time here. St. John was exactly what we wanted, its just too bad you have to land on St. Thomas to get there!

  • Review Submitted: Mar 23, 2015
  • Date of Stay: Mar 2015
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for posting a review, it's very kind of you to do so. We remember our first trip to St John many years ago, and how mesmerised we were by the beauty of the island. That first trip will long remain in the memory banks! We're very pleased you enjoyed staying at Leeward. Pictures just never seem to do justice to the views out over Rendezvous Bay, and having a morning coffee on the deck just looking out is a pretty good way to start the day... It's great to have a responsive, reliable and totally dedicated management team on island. As owners we know things will run smoothly, and guests can be assured that they will be taken care of. You'll be very welcome to return.
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0 0

A Thanksgiving Trip to Remember

  • 5 of 5

My family of six rented this gorgeous villa the week of Thanksgiving. The management company, Carefree Getaways, were incredibly responsive and helpful with our questions leading up to the trip. They provided thorough and helpful information and there were no surprises. Well…the only surprise was that the villa is even more lovely than the pictures! Each bedroom and bath is beautifully appointed. Our kids are older (25, 25, 17 & 14) and the layout of the four bedrooms gave each of us privacy and no one felt like they "got the bad bedroom." The kitchen is fantastic and fully equipped. I even cooked a full Thanksgiving dinner -- and it was easy! The location is perfect. Just far enough way from the congestion of Cruz Bay, but very convenient for dining, beaches, etc. The views are breathtaking -- morning sunrise AND evening sunset from the privacy of the beautiful deck. We would HIGHLY recommend this villa and would choose to stay there again if we're lucky enough to make it back to St. John!

  • Review Submitted: Jan 8, 2015
  • Date of Stay: Nov 2014
  • Source: VRBO, from HomeAway
Owner's Response: We're very pleased that you all enjoyed a fabulous week on St John, and at Leeward. Having an on island management company is a big help. We've known Cindy, who runs Carefree, for over 20 years and we have complete faith in her and her team. We like the views from the deck as well. Hard to get a picture that truly shows it in it's glory. Many people who stay at Leeward say the same thing. Anyway, thank you so much for making the effort to post a review, and if the island lures you back, please do get in touch.
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0 0

Great Home with very nice amenities.

  • 5 of 5

My wife and I and our two boys 9 and 10 recently spent a week at Leeward. The house was just great. Well appointed kitchen for cooking. It's very nice to have a home stocked nicely with most of the essentials already there. (paper towels, trash bags, etc). The pictures are what you get and that view is spectacular. Location works well to get to town or all the beaches. Store is close for anything you need. We will be back! The Carefree management team is always there for answering a question or just offering tips. Thanks for a great trip.

  • Review Submitted: Jul 22, 2014
  • Date of Stay: Jul 2014
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for taking time to post a review. We're delighted you all had a good time. Leeward does have a beautiful aspect, and we make it a priority that the house is well maintained so that everyone can enjoy their vacation in comfort. Very glad to hear our property managers took good care of you. We think they're pretty special as well. You'll be very welcome to return.
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1 0

Paradise - a very special place!

  • 5 of 5

We arrived for our one week family stay at the enchanting Leeward Villa and instantly fell in love with the place. Set upon the private mountainside overlooking Klein Bay and Dittlif Point, the views are breathtaking. The villa is just a short ride to Cruz Bay and close enough to all of the beaches by car. We enjoyed walking to Klein Bay, set right below the villa. A bit of a walk, but worth it to snorkel amongst the many fish and starfish.

It was simply amazing to wake up every morning to the beautiful view from the bedroom balcony. We enjoyed many relaxing mornings just sitting outside taking in all of the views with our morning coffee. We often spent our evenings and dinner poolside. Turning off all of the villa lights, we were in awe by the glitter of the many stars above us. We knew we were in paradise - a very special place!

The villa's accomadations were perfect for our stay. Each of the 4 bedrooms were well appointed, clean and comfortable. The professionally equipped kitchen was perfect for preparing meals during our stay. We enjoyed barbecuing and eating every evening poolside at the huge outdoor dinning table. Evenings we would relax in the beautifully furnished living room.

The management team at CareFree Getaways were most professional. From the moment we stepped off the ferry they made sure our stay would be most relaxing and successful.

We highly recommend staying at the Leeward Villa. Don't think twice - while on St. John - this is truly the place to be!

  • Review Submitted: Aug 29, 2013
  • Date of Stay: Jul 2013
  • Source: HomeAway
Owner's Response: I think VRBO has a double posting here.
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2 0


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
Low Season
15 Apr 2017 - 1 Sep 2017
5 night minimum stay
for 5 nights
Notes: Rates are based on 4 guests; add £68 per night, per additional guest
Thanksgiving Week
18 Nov 2017 - 24 Nov 2017
7 night minimum stay
Holiday Season
20 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 £136 per night, per additional guest
Off Season
1 Sep 2018 - 26 Oct 2018
5 night minimum stay
for 5 nights
Notes: Rates are based on 4 guests; add £63 per night, per additional guest
My Standard Rate
5 night minimum stay
for 5 nights
Notes: Rates are based on 4 guests; add £68 per night, per additional guest

Additional pricing information

Refundable Damage Deposit £402
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.
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Partner Offers

Portable wifi hotspot

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