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

Cruz Bay, Saint John
$1408 avg/night Minimum Stay 5 Nights
Bed 4

Bed

Bath 4

Bath

Home Villa

Property Type

Sleep 10

Max Sleeps

Night 5 nights

Min Stay



- 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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers Beach Towels Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 3300 Sq Ft (307 Sq M)
  • KITCHEN

    Blender Dishwasher Electric Kettle Ice Maker Kitchen Island Microwave Oven Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Recommended Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Garden Outdoor Furniture
  • POOL/SPA

    Massages Outdoor Pool Private Pool
  • BATHROOMS

    4.5 Bathrooms Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Ecotours Nearby Fishing Nearby Fitness Facilities Nearby Hiking Nearby Horse Riding Nearby Kayaking Nearby Parasailing Nearby Power Boating Nearby Swimming Nearby Tennis On Site Water Sports Equipment Windsurfing Nearby
  • ENTERTAINMENT

    Books DVD Player Games Stereo Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • FAMILY FRIENDLY

    Children's Games Highchair
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Chef Housekeeping (on Request) Iron/ironing Board Phone Safe
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Rates & Availability

Review Review

  • Maggie U.

    Submitted Feb 19, 2026

    Stayed Feb 5, 2026

    We had a wonderful stay at Leeward. The house is beautiful and we're convinced you won't find a better view elsewhere. We also appreciated the owner asking personally how our stay was and what improvements could be made in the future.The only issue we had during our stay was an island wide power outage, which was out of anyone's control. The issue we had with this was the solar panels did not work the way they should have and left us with no power for over 24 hours which was upsetting, especially for the price you're paying for the home. We also felt it would have been extremely helpful to have the property manager meet us at the home at our check in time to go over the workings of the home. Staying on St. John is not your usual Vrbo stay and it would have been helpful to know how to conserve energy or how the solar panel system works.This was not our first time on St. John, but this was our first time at Leeward and we will definitely be back!

  • David D.

    Submitted Jan 15, 2026

    Stayed Dec 27, 2025

    Fantastic house and fantastic host!

  • Tina M.

    Submitted Jan 10, 2026

    Stayed Jan 3, 2026

    A piece of paradise, with fabulous views. The bedrooms/bathrooms were all stocked with everything you needed. The outdoor pool area was wonderful & pool/beach towels were provided. The pool lounge chairs and outdoor sitting area were very comfy. Beat family vacation!

  • Scott G.

    Submitted Oct 11, 2025

    Stayed Oct 4, 2025

    Very beautiful house. Met our needs and exceeded our expectations.

  • Debra I.

    Submitted Oct 8, 2025

    Stayed Sep 27, 2025

    Wonderful home with an absolutely amazing view! This property was perfect for me and my family!

  • kris a.

    Submitted Sep 16, 2025

    Stayed Sep 9, 2025

    It was 6 ladies for my 60th birthday! The house was perfect. I can’t wait to come back to St.John. Great kitchen ,living area for games and the views are the best on the island .

  • Pat S.

    Submitted Sep 2, 2025

    Stayed Aug 10, 2025

    Awesome house! We had a great time.

  • Angie H.

    Submitted Jul 20, 2025

    Stayed Jun 18, 2025

    Beautiful house! We enjoyed our stay and will definitely be back!

  • Submitted Apr 13, 2025

    Stayed Apr 5, 2025

    We had an amazing stay at Leeward. Two families with young children. The owner, property manager, and valet were

  • Gloria B.

    Submitted Mar 22, 2025

    Stayed Mar 14, 2025

    Epic views and the infinity pool was amazing!!

  • sharon g.

    Submitted Jan 11, 2025

    Stayed Jan 4, 2025

    4 fairly equal bedrooms with 4 en suite bathrooms. Great view

  • Tara H.

    Submitted Jan 4, 2025

    Stayed Dec 28, 2024

    Nice kitchen

  • Jenny R.

    Submitted Dec 27, 2024

    Stayed Dec 20, 2024

    Stunning, well-appointed home with exceptional views, infinity pool, and patio, including pergola for shade. We enjoyed everything about our week in this gorgeous home and location, close to beaches, hiking, and ready access to town. Our host alas arranged for car rental, and for a driver to meet us at the ferry the first day with the car so starve could easily find the home, and yo pick up the car and keys on the last day. We hope to be back again!

  • Jennifer J.

    Submitted Sep 24, 2024

    Stayed Sep 18, 2024

    Loved the property. Great view and convenient location (12 min from Cruz Bay). 4 great master suites, gorgeous pool and wonderful kitchen. Friendly and helpful property manager. Thank you!

  • Lorre H.

    Submitted Aug 11, 2024

    Stayed Aug 3, 2024

    Wonderful property!

  • Denise M.

    Submitted Jul 27, 2024

    Stayed Jul 21, 2024

    Photos don’t do the view from the pool deck of this home justice. The house and location are phenomenal. We took our family (adult children) and enjoyed every minute. The house has so much space and was well furnished. Check in was simple. The property manager was incredibly responsive. The only challenge of the week was the first trip down the driveway (backing in is definitely the way to go), but once you do it the first time, it feels routine. St. John has so much to offer and if you want a top notch experience with your own little piece of paradise while you stay, book this house.

  • Susan N.

    Submitted Jul 21, 2024

    Stayed Jul 13, 2024

    We spent a week at Leeward with kids, adults, and a couple of seniors/grandparents. It was absolute perfection! The pool is gorgeous, large, and perfect for the three kids while the adults enjoyed the covered seating area. The view is simply incredible as well! The beds were all very comfortable and the house was stocked with everything you could possibly need. This was my fourth time to St. John and I appreciated the driveway on the home being easy to get in and out of. The distance to town was perfect as well - far enough away but only a 10 minute drive. We loved it so much and hope to return one day!

  • Amy F.

    Submitted Jul 13, 2024

    Stayed Jul 4, 2024

    Our family stayed at Leeward February 2019. We loved the house and setting so much we came back with our friends. Everyone loved the property and had a wonderful time!

  • Beth C.

    Submitted Jul 7, 2024

    Stayed Jun 15, 2024

    This is the second time we have stayed at this property and we have stayed in about 8 villas on St. John. I believe this has one of the best views and an amazing infinity pool. The one weak point of the place was communication. I didn't receive replies back to e-mails and there was basically no help with checking in- thankfully we had been to the villa before but if we were new to the island it would be nerve wracking to navigate there on our own. Last time we came someone met us and guided us there and then gave a tour/instructions of the house but impersonal this time- maybe a leftover COVID response! Overall, however, recommend this location highly.

  • Sherida B.

    Submitted Jun 21, 2024

    Stayed Jun 8, 2024

    The villa is wonderful, but the real star is the view of the bay and its crystal clear turquoise water. We never tired of looking at it. The pool was spectacular. We had beautiful, sunny days the entire week. It was a vacation we will always remember.

  • Karen G.

    Submitted Jun 3, 2024

    Stayed May 25, 2024

    Our family of 6 adults and 2 toddlers and an infant enjoyed our stay at Leeward. The view was the money shot! On a clear day, you could see all the way to St. Croix. The downstairs bedroom with the trundle bed was great for a toddler. The pack and play was used for the infant and was in great condition. The kitchen was well appointed with everything you could possibly need. The great room was a large space if you wanted to watch a movie in the evening. Very comfortable furniture. The beds were also comfortable. Taylor, the property manager was very as well as the owner. Would definitely recommend.

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Total

Includes taxes and fees
$1,408+
View details