All properties in St. John, U.S. Virgin Islands

Stunning views! Infinity pool. 5* South Shore home.

Family-friendly Rendezvous & Ditleff villa with private pool and kitchen

Restrictions related to your trip

This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local and health advisories for this destination before you book.

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St. John, St John, U.S. Virgin Islands
  • The pictures do not do justice to how beautiful Leeward is! Sunrise and Sunset views…

    Jan. 9, 2022

  • What a great place to spend a week with family! The pool and outdoor space are fabulous…

    Jan. 2, 2022

See all 64 reviews
  • 10 guests
  • 4 bedrooms
  • 6 beds
  • 5 bathrooms
  • Parking available
  • Pool
  • Kitchen
  • Non-smoking
  • Air Conditioning

Property highlights

Main amenities

  • WiFi
  • Onsite parking
  • Near the beach
  • Non-smoking
  • Air conditioning
  • Hair dryer

What’s around

  • In Rendezvous & Ditleff
  • Rendezvous Bay - 6 min walk
  • Chocolate Hole - 30 min walk
  • Great Cruz Bay - 35 min walk
  • Sunset Beach - 36 min walk
  • Virgin Islands National Park - 2.6 mi / 4.2 km

Sleeping arrangements

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Twin Beds and 1 King Bed

Bedroom 4

1 King Bed

Book this property and collect stamps after your stay

Remember, collect 10 stamps, get 1 reward* night

Enter dates for 2 guests


About this villa

- Southerly aspect

- Full AC throughout

- Internet

- Secluded neighborhood

- 8 minute drive to Cruz Bay

- 47 ft infinity pool

- Outdoor pavilion and bar

- Four king sized beds + Twin daybed and twin trundle + playpen/crib

- All bedrooms are ensuite

- On-island property manager

- Long history of repeat guests

- Spacious gourmet kitchen

- Outstanding views of Rendezvous Bay

- Beautifully maintained tropical gardens

- 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. There is a twin daybed with twin trundle in one of the downstairs bedrooms as well as the king sized bed.

There is a crib/playpen with bedding, a high chair.

Rollaway beds can be rented if needed.

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 solar driven 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 many years, and with the recent remodelling we are extremely confident that it will continue to provide premium accommodation for those visiting St. John.

What’s around


  • In Rendezvous & Ditleff
  • Rendezvous Bay - 6 min walk
  • Chocolate Hole - 30 min walk
  • Great Cruz Bay - 35 min walk
  • Sunset Beach - 36 min walk
  • Virgin Islands National Park - 2.6 mi / 4.2 km
  • St. John Spice - 2.5 mi / 4.1 km
  • Cruz Bay Beach - 2.6 mi / 4.1 km
  • Battery - 2.6 mi / 4.2 km
  • Mongoose Junction - 2.6 mi / 4.3 km
  • Caneel Bay Beach - 4.1 mi / 6.7 km

Getting around

  • Cyril E. King Airport (STT) - 76 min drive
  • St. Thomas (SPB-St. Thomas Seaplane Base) - 68 min drive
See on map
St. John, St John, U.S. Virgin Islands

The manager

David Yellin

Speaks: English

The villa

Key facts

  • Villa (3300 sq ft)
  • Onsite parking
  • WiFi
  • Car recommended
  • Near the beach
  • Non-smoking
  • Air conditioning
  • Washing machine


  • 4 bedrooms
  • Bedroom one - 1 king bed
  • Bedroom two - 1 king bed and 2 twin/single beds
  • Bedroom three -1 king bed
  • Bedroom four - 1 king bed
  • Bed sheets provided


  • 5 bathrooms
  • Full bathroom one - 1 shower and 1 toilet
  • Full bathroom two - 1 shower and 1 toilet
  • Full bathroom three - 1 shower and 1 toilet
  • Half bathroom - 1 toilet
  • Hair dryer
  • Towels provided
  • Shampoo
  • Soap
  • Toilet paper


  • Refrigerator
  • Microwave
  • Dishwasher
  • Oven
  • Stovetop
  • Coffee/tea maker
  • Electric kettle
  • Toaster
  • Highchair
  • Cookware/dishes/utensils


  • Dining table

Entertainment and recreation

  • Cable/satellite TV
  • DVD player
  • Stereo
  • Books
  • Games
  • Massages
  • Children's games
  • Jet skiing nearby
  • Horse riding nearby
  • Parasailing nearby
  • Ecotours nearby
  • Snorkeling nearby
  • Sailing nearby
  • Kayaking nearby
  • Swimming nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Hiking nearby
  • Powerboating nearby
  • Surfing/boogie boarding nearby
  • Windsurfing nearby
  • Health or beauty spa nearby
  • Scuba diving nearby
  • Tennis courts


  • Private pool


  • Barbecue grill
  • Garden
  • Patio
  • Outdoor furniture

Other amenities

  • Iron/ironing board
  • Safe
  • Beach towels
  • Housekeeping (on request)
  • Beach loungers
  • Telephone
  • Chef

Things to know

House rules

  • Pets not allowed
  • Events/parties not allowed
  • No smoking
  • Max. guests: 10
  • Minimum check-in age: 25

Check-in and check-out

  • Check-in after 3:00 PM
  • Check-out before 10:00 AM

Special check-in instructions

  • You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.

Fees & policies

Required at check-in

  • Government-issued photo ID may be required
  • Minimum guest age is 13
  • Minimum check-in age is 25

Travelling with others

  • Note from host: Children under 8 require a waiver due to pool
  • Pets not allowed


  • Onsite parties or group events are strictly prohibited.

    Guests can rest easy knowing there's a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock on site.

  • This property is licensed under an applicable law.Property registration number 440057

Also known as

  • Leeward St John Premier Accommodation Villa Cruz Bay
  • Leeward St John Premier Accommodation
  • Leeward St John Premier Accommodation Villa
  • Leeward St John Premier Accommodation Cruz Bay
  • Leeward St John Premier Accommodation
  • Leeward St John Premier Accommodation
  • Leeward St John December Dates Christmas Week now Available!!


  • Yes, there's an outdoor pool.
  • Sorry, pets aren't allowed.
  • You can check in starting at 3:00 PM. Check-out time is 10:00 AM.
  • Yes. Nearby restaurants include Sam & Jack's Deli (2.2 mi), Extra Virgin Bistro (2.4 mi), and Quiet Mon Pub (2.4 mi).
  • Practice your swing on the tennis courts. Additional recreation nearby includes wildlife walks, birdwatching, and ecotours. Enjoy a swim in the outdoor pool or use the villa's other amenities, which include private pools and a garden.
  • 10.0.Exceptional

    Perfect Christmas vacation!

    I can't recommend the property highly enough! We stayed for six nights right before Christmas and had an exceptional experience. The property is in excellent condition, very clean and maintained well. The views are better than the pictures. The rooms and common spaces are huge! We ate mostly home-cooked meals during our stay and the kitchen was perfect for everything from BBQ chicken to fresh-caught fish. Communication with the property manager was awesome and everything exceeded expectations. Highly recommended!

    David S., 6 night trip, Dec. 19, 2021

    Verified Vrbo guest review

  • 10.0.Exceptional

    Stunning home on St John

    Everything from booking to arriving went smoothly…the home is incredible with beautiful views

    Karen O., 14 night trip, Dec. 4, 2021

    Verified Vrbo guest review

  • 10.0.Exceptional

    Gorgeous Villa with Spectacular views.

    Great Villa. Every room with private bath. Gourmet kitchen. Infinity pool with breathtaking views of Rendezvous bay. Loved it!! Hope to come back soon!

    Stacey S., 7 night trip, Nov. 27, 2021

    Verified Vrbo guest review

  • 10.0.Exceptional

    Get away with close friends at the Leeward

    We visited St John 2 years ago and this year when we were looking for a place to celebrate our anniversary and recent birthdays, we decided on St John again. We wanted to try a different location on the island, so we checked out VRBO. Upon putting in our requirements for this vacation, they suggested Leeward. Upon our arrival, we were greeted by the property manager, Taylor. Taylor was very professional, offering his number if we had any questions. When we did, he answered knowledgably and quickly. We were greeted with a fruit tray and champagne, as they knew we were celebrating milestones. This property was perfect, with just enough space for our party, beautiful views, and perfect location. We fully enjoyed our time there, we ate most out meals there, preparing them in the well-appointed kitchen. The house was just perfect, being just a few miles from Cruz Bay, and beautiful beaches, where our party did some snorkeling and exploring during most days, and when we wanted to stay at the house, we made full use of the beautiful swimming pool. We didn’t want to leave, and I am sure we will be back, renting Leeward again in the near future.

    Fletcher S., 7 night trip, Nov. 6, 2021

    Verified Vrbo guest review

  • 10.0.Exceptional


    Our second time here and already can’t wait to return. A perfect place and a perfect host!

    Dan H., 8 night trip, Oct. 23, 2021

    Verified Vrbo guest review

  • 10.0.Exceptional

    Perfect experience

    Leeward is a beautiful home in a great location. The views are breathtaking! The pool was lovely. The owners and manager were a pleasure to work with as well. Would love to return in future!

    Dawn B., 7 night trip, Oct. 16, 2021

    Verified Vrbo guest review

  • 10.0.Exceptional

    A slice of heaven

    This is my 4th time to St John as well as my 4th VRBO estate. This estate ranks # 1 or 2 overall and definitely # 1 with the incredible views overlooking Rendezvous Bay. Simply stunning. The estate is equally amazing and is built extremely well with no spared expense. The garden areas surrounding the property are impeccable. The owners and property manager are very responsive and ensured everything was taken care of prior to arrival as well as during our stay. Overall an amazing 10 days of vacation.

    Ronald F., 10 night trip, Sep. 10, 2021

    Verified Vrbo guest review

  • 10.0.Exceptional

    Incredible Stay and Great House for a Large Group

    As we walked into the property for the first time, the first thoughts that ran through many of our minds were, "The pictures do not do this justice." The views overlooking Rendezvous Bay are amazing. LeeAnn was great to work with. As we navigated Covid, LeeAnn was gracious enough to work through those challenges. She is quick to respond and works hard to ensure everyone has a win/win resolution. Kudos to LeeAnn. We generally do a group house every year (over the past 10 years), and this house is one of our favorites. We love to cook when on the islands and this house was not lacking any cooking utensils. Multiple coffee makers and toasters made breakfast very easy. I used a Vitamix for the first time and we made frozen painkillers that "almost" rival Longboard's in Cruz Bay. The living room was big enough for all of us to lounge and enjoy. The couches and wingback leather chairs were very comfortable to watch TV or the spontaneous dance party. Bedrooms were large with plenty of room to feel at home. The beds were luxurious and you did not feel guilty if you slept in. The infinity pool is a great way to spend a day or two when you don't want to hit the beach or other activities. Warning - most of the pool is pretty deep, so make sure you have floating devices. The neighborhood is fairly private and there was minimal noise. It made the morning coffee outside very tranquil. We stayed for 8 nights and on our last day, all of us remarked how the view never gets old. Truly, an enjoyable stay and when we decide on our dates to return in 2023, we will look to see if Leeward is available.

    Eric H., 8 night trip, Aug. 28, 2021

    Verified Vrbo guest review

  • 10.0.Exceptional

    Beautiful Property Amazing Views

    Had a wonderful time with my family of 7. The views were absolutely stunning! The home was gorgeous and had everything we needed! We love Leeward and hope to be back again soon! Thanks for everything it was paradise!

    christine B., 7 night trip, Aug. 20, 2021

    Verified Vrbo guest review

  • 10.0.Exceptional

    Beautiful getaway.

    Fantastic experience. Great connection with the owners and the property manager Taylor. We did grocery service through landlubbers and had in houses massages as well. Property was as expected, views from the pool are full, unobstructed and breathtaking. All the rooms were spacious and ample bathroom space. Nobody bothered us, whole time was very private and relaxed. We had taxis pick us up from the driveway to downtown. Beaches were not far either. Only downside to this trip was the amount of businesses in town closing down for summer and cancelling our reservations, which In no way was the hosts fault. Loved the island, we’ll be back.

    Robert P., 5 night trip, Aug. 8, 2021

    Verified Vrbo guest review

See all 64 reviews