Stunning views! Infinity pool. 5* South Shore home.
Villa in Cruz Bay
10 guests · 4 bedrooms · 5 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceOne of the higher cost properties in the area
Includes essentialsGarden, Pool, Kitchen or Kitchenette and more
About this villa rental
- 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.
Amenities
Pool
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Garden
Family friendly
Map of Cruz Bay
$$$$
Ratings and reviews
Summary of reviews
Leeward offers breathtaking ocean views, magnificent pool, luxurious bedrooms, well-equipped kitchen, and attentive property management. A perfect retreat!
10.0 / 10.0
Wonderful property!
10.0 / 10.0
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.
10.0 / 10.0
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!
10.0 / 10.0
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!
10.0 / 10.0
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.
10.0 / 10.0
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.
8.0 / 10.0
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.
10.0 / 10.0
Any complaints would be nitpicking an amazing stay.
10.0 / 10.0
Great location
10.0 / 10.0
Great property great view everything as listed
10.0 / 10.0
Everything about this place is 1st class!
10.0 / 10.0
Beautiful property. Perfect for our family. Each bedroom has a beautiful private bath and the kitchen and common areas are top notch! Great pool and the view is spectacular.
10.0 / 10.0
7 family members 21-85 years enjoyed the beautiful setting, home and accommodations for a week. It was hard to say goodbye to the early morning poolside coffees, mid day hors d’oeuvers & cocktails, and wonderful dinners in the spacious dining area. Also having a car available was a time saver and super convenient to explore the island. Thank you to our hosts who made the process easy and the experience so enjoyable!
10.0 / 10.0
The house is gorgeous and the views are stunning! We were two families of 4, each with teenage children, sharing this house and it provided a gracious amount of space. It was an easy trip to town and to the north shore beaches. We cooked in every evening and had every kitchen tool needed to prepare our meals. We started and ended every day on the back patio, gazing in awe at the beauty before us. It was our second trip to St. John and this was definitely our favorite location!
10.0 / 10.0
This is a fantastic property with unbelievable views. It is located just a short drive to Cruz Bay, but also far enough away from everything for some privacy. Very clean, nice layout and magnificent views from the infinity pool. Morning coffee views are second to none. The staff was great to work with. We had an issue with a tire ( my fault) and they were there within an hour. Took the tire and went to St John the next morning. Got a new tire and had it installed by 10 the next morning. Great service and very willing to help. I would highly recommend this place. We had a group of five and there was plenty of space. Never felt like we were on top of each other. We had a great experience
10.0 / 10.0
We have made 24 visits to St. John, #1 villa.
Tremendous 180* vistas and warm tropical breezes.
10.0 / 10.0
Our third stay there and it never disappoints! The best pace to enjoy peaceful luxury!
10.0 / 10.0
This was my first VRBO booking, and it was truly a spectacular experience in all ways. Great communication, super clean and it felt like home...views were out of a travel magazine cover page. Thanks for everything!
10.0 / 10.0
Tremendous views, well appointed and didn’t need a thing. Thanks for making our family vacation a success!
10.0 / 10.0
This is a lovely property. The ensuite set up for 4 couples was grand. The place is huge. We used all the lovely spaces. The beds were super comfortable. The pillows were a little too fluffy for my neck….so I subbed a sofa pillow in one of the pillow cases. The landscaping is wonderful. The pool is gorgeous, but ambient temp. So this early in season a few degrees cool.we still enjoyed the pool and the pool deck. The kitchen is large and lovely and well stocked. We always bring our own nonstick fry pans and sharp kitchen knives. We were glad we did here. Not deducting points for that. There is no way for property owners to keep up on those items. There was a good stock of essentials like TP, paper towels, laundry and dish soap. Taylor was outstandingly responsive. The location was quiet and safe. The view was straight south overlooking a bay with a peninsula on both sides. The view was amazing. The spaces are air conditioned or you can turn in your ceiling fan and listen to the surf roll in at night.
This was a 50th anniversary trip for us. The villa was fantastic. Sad to leave, Thank you Mr. Yellin for sharing your home with our family.
10.0 / 10.0
This property was stunning, clean, well stocked, and provided us with everything we needed for our family vacation. The pool and view made it difficult for us to leave the property to enjoy the beautiful beaches of St. John. We will definitely be back to this property.
10.0 / 10.0
Property and view were absolutely beautiful and the house is in a great location.
10.0 / 10.0
Wonderful
10.0 / 10.0
Excellent. Friendly and attentive property manager.
10.0 / 10.0
St John - 8 Friends & Wedding
8 long time friends spent the week together in St. John for the wedding of one of our mutual childhood friends. The house was perfect for us! Overall the pictures do not really do the actual property justice... It's much better in person! The view/pool deck/patio was amazing. The 8 of us in the house spent a majority of our time outside or in the large kitchen. Everything that we needed was there. Taylor the house manager was great as well; checking in with us to make sure we had everything we needed. All 8 of us in the house had an amazing time and the house really was a large part of that.
10.0 / 10.0
Perfect St John House
The pictures do not do justice to how beautiful Leeward is! Sunrise and Sunset views everyday. Can not wait to come back
10.0 / 10.0
Fantastic !
What a great place to spend a week with family! The pool and outdoor space are fabulous for hanging at the house and sitting outdoors for dinner. Morning views of the water from the main floor bedrooms cannot be beat!
The property owners and manager were very responsive to our questions during the stay.
Thank you for making the start of 2022 so special !
10.0 / 10.0
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!
10.0 / 10.0
Stunning home on St John
Everything from booking to arriving went smoothly…the home is incredible with beautiful views
10.0 / 10.0
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!
10.0 / 10.0
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.
10.0 / 10.0
Bliss!
Our second time here and already can’t wait to return. A perfect place and a perfect host!
10.0 / 10.0
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!
10.0 / 10.0
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.
10.0 / 10.0
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.
10.0 / 10.0
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!
10.0 / 10.0
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.
10.0 / 10.0
Great place to stay.
Great!
10.0 / 10.0
Paradise is not Lost!!
We loved Leeward!! This property was just magnificent. The photos are accurate but really no photo can truly capture the beauty of the view. The bedrooms were beautifully appointed with comfortable beds, sheets and pillows. The bathrooms were spacious and the towels were honestly just like being home. The family room TV worked well and couches were cozy year the island in the kitchen served us for many snacks drinks and laughter. The kitchen stocked like hone as well. The deck with many seating options and a beautiful pool was a perfect spot for morning yoga. We traveled with our 18& 22y old and explored St John’s beautiful beaches daily but a day at the house and pool was just as serene. Taylor the property manager was awesome and attentive but we hardly had a question or need!! Thank you to the owners Leeann and Howard for sharing your priceless home. We will be back!!
10.0 / 10.0
Spectacular Villa --Absolute Perfection ❤
Words cannot adequately describe this spectacular villa and the amazing views from the pool deck.. My husband and I enjoyed our morning coffee out on the veranda every morning.. We concluded our evenings with a glass of wine, enjoying the ocean views and breezes. The landscaping is beautiful and fully hides the neighboring villas. My 14 year old son loved exploring the yard and watching the hermit crabs. I loved looking at the exotic flowes and vegetation. 🌺 My 17 year old daughter and 19 year old boyfriend loved sunbathing on the huge pool deck. The villa comes fully equipped and we were able to use Bluetooth to play our beach Playlist by the pool.
Taylor, the on island manager, was extremely helpful and always available if we needed something. Lee Ann and Howard, the owners, were amazing to work with. We would love to meet them in person someday!
For restaurants. we highly recommend Extra Virgin Bistro and Lime Inn. Make reservations well in advance!
We also recommend booking a private catamaran tour with either Big Blue Exercursions and Soulshine. It"s the best way to experience St. John.
My only complaint is that we did not book additional days!
Thank you, Lee Ann and Howard for an unforgettable trip in paradise!
FAQs
How much does this villa cost compared to others in Cruz Bay?
The average price for a rental in Cruz Bay is $850 per night. This rental is $659 above the average.
Is parking included with this villa?
Yes, parking is listed as an amenity at Stunning views! Infinity pool. 5* South Shore home.. For more information, we encourage you to contact the property about where to park.
Is there a pool at this villa?
Yes, a swimming pool is available for use at Stunning views! Infinity pool. 5* South Shore home.. Enjoy the water!
Is Stunning views! Infinity pool. 5* South Shore home. pet friendly?
Unfortunately, this villa is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Stunning views! Infinity pool. 5* South Shore home.?
We found 11 amenities for this rental. This includes pool, air conditioner, kitchen or kitchenette, internet / wifi, and parking.
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