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

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January 2025

Photo gallery for Stunning views! Infinity pool. 5* South Shore home.

Outdoor pool
Beach nearby, sun-loungers, beach towels
Outdoor pool
Interior
Fridge, microwave, oven, stovetop

Reviews

10 out of 10

Exceptional

Entire home

4 bedrooms5 bathroomsSleeps 10307 sq m

Popular amenities

  • Parking available
    Parking available
  • Washer
    Washer
  • Pool
    Pool
  • Barbecue grill
    Barbecue grill
  • Kitchen
    Kitchen
  • Air conditioning
    Air conditioning

Explore the area

Map
Cruz Bay, St John
  • Chocolate Hole Beach
    4 min drive
  • Chocolate Hole
    4 min drive
  • Great Cruz Bay
    4 min drive
  • St. Thomas (STT-Cyril E. King)
    72 min drive

Room options

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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



- 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.
During your stay at this villa, you're just a quick walk from Klein Bay. Enjoy features like an outdoor pool. The villa offers free WiFi and a private pool.
  • Air-conditioned villa with private pool, kitchen, and washing machine
  • Free WiFi
  • Take a swim in the outdoor pool
  • Onsite recreation includes tennis courts
  • 6 minutes by foot from Klein Bay and a 4-minute drive from Chocolate Hole Beach
This villa offers its guests an outdoor pool, barbecue grills, and a garden. The front desk is open around the clock.

This St. John villa is smoke free.

Property manager

David Yellin

Languages

English

Property amenities

Beach

  • Near the beach
  • Beach sunloungers
  • Beach towels

Pool/Spa

  • Private pool
  • Outdoor pool
  • Massages

Internet

  • Free WiFi

Parking and transport

  • On-site parking
  • Car recommended

Kitchen

  • Fridge
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Coffee grinder
  • Blender
  • Toaster
  • Paper towels

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bed sheets provided

Bathrooms

  • 4.5 bathrooms
  • Shower
  • Toilet paper
  • Hairdryer
  • Towels provided
  • Shampoo
  • Soap

Living spaces

  • Living room

Entertainment

  • Smart TV with cable/satellite service
  • DVD player
  • Games
  • Books
  • Stereo

Outdoor areas

  • Balcony
  • Barbecue
  • Garden
  • Outdoor furniture

Laundry

  • Washing machine and dryer
  • Near a laundromat

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Safe
  • Housekeeping (on request)
  • Chef
  • Iron/ironing board
  • Phone

Location highlights

  • Near the sea
  • Near a health or beauty spa
  • Near a hospital

Things to do

  • Fitness facilities nearby
  • Water sports equipment
  • Tennis on site
  • Scuba diving nearby
  • Fishing nearby
  • Sailing nearby
  • Horse riding nearby
  • Wildlife and game walks nearby
  • Power boating nearby
  • Parasailing nearby
  • Kayaking nearby
  • Ecotours nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector installed (host has indicated that there is a smoke detector on the property)
  • Fire extinguisher
  • First aid kit
  • Deadbolt lock

General

  • Unit size: 3300 sq ft (307 sq m)

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 25

Check-out

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

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Note from host: Children under 8 require a waiver due to pool

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts cash
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
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.

Property is also known as

Leeward St John Premier Accommodation Villa Cruz Bay
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!!
Leeward St John Premier Accommodation

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

Reviews

10

Exceptional

Rating 10 - Excellent. 101 out of 102 reviews" "
Rating 8 - Good. 1 out of 102 reviews" "
Rating 6 - Okay. 0 out of 102 reviews" "
Rating 4 - Poor. 0 out of 102 reviews" "
Rating 2 - Terrible. 0 out of 102 reviews" "

10/10

Cleanliness

Reviews

10/10 Excellent

Jennifer J.

Liked: Cleanliness
Amazing property and great vacation!
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!
Stayed 5 nights in Sep 2024

10/10 Excellent

Lorre H.

Liked: Cleanliness
Magnificent views
Wonderful property!
Stayed 7 nights in Aug 2024

10/10 Excellent

Denise M., INDIANAPOLIS, IN

Liked: Cleanliness
Beyond Expectations
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.
Stayed 5 nights in Jul 2024

10/10 Excellent

Susan N.

Liked: Cleanliness
The most gorgeous views!
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!
Stayed 7 nights in Jul 2024

10/10 Excellent

Amy F.

Liked: Cleanliness
Lovely return visit
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!
Stayed 9 nights in Jul 2024

10/10 Excellent

Beth C.

Liked: Cleanliness
Beautiful View
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.
Stayed 7 nights in Jun 2024

10/10 Excellent

Sherida B.

Liked: Cleanliness
Breathtaking View
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.
Stayed 7 nights in Jun 2024

8/10 Good

Karen G.

Liked: Cleanliness
Beautiful view
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.
Stayed 7 nights in May 2024

10/10 Excellent

Michael M.

Liked: Cleanliness
Even Better than anticipated.
Any complaints would be nitpicking an amazing stay.
Stayed 7 nights in Apr 2024

10/10 Excellent

Martin G.

Liked: Cleanliness
Beautiful property
Great location
Stayed 7 nights in Mar 2024

10/10 Excellent

Corey W.

Liked: Cleanliness
Nice place
Great property great view everything as listed
Stayed 7 nights in Feb 2024

10/10 Excellent

Dean S.

Liked: Cleanliness
Great Villa!
Everything about this place is 1st class!
Stayed 7 nights in Jan 2024

10/10 Excellent

Christina B.

Liked: Cleanliness
Holiday in paradise
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.
Stayed 5 nights in Dec 2023

10/10 Excellent

Doug B.

Liked: Cleanliness
Peaceful getaway
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!
Stayed 6 nights in Dec 2023

10/10 Excellent

Tom W.

Stunning Views
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!
Stayed 6 nights in Jun 2023

10/10 Excellent

Aaron G.

Liked: Cleanliness
Great property
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
Stayed 7 nights in Jun 2023

10/10 Excellent

Martin G.

Liked: Cleanliness
Best villa we have ever stayed at on St. John
We have made 24 visits to St. John, #1 villa. Tremendous 180* vistas and warm tropical breezes.
Stayed 7 nights in Mar 2023

10/10 Excellent

Dan H.

Liked: Cleanliness
Perfection!
Our third stay there and it never disappoints! The best pace to enjoy peaceful luxury!
Stayed 7 nights in Feb 2023

10/10 Excellent

Peter S.

Liked: Cleanliness
Fantastic experience on St John!
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!
Stayed 7 nights in Feb 2023

10/10 Excellent

Nelson A.

Liked: Cleanliness
Beautiful Spot
Tremendous views, well appointed and didn’t need a thing. Thanks for making our family vacation a success!
Stayed 7 nights in Jan 2023

10/10 Excellent

Christine T.

Liked: Cleanliness
Watch the sunrise and the sunset!
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.
Stayed 7 nights in Jan 2023

10/10 Excellent

Sharon Z., North Royalton, OH

Liked: Cleanliness
Spectacular Home
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.
Stayed 7 nights in Dec 2022

10/10 Excellent

Tessa B.

Liked: Cleanliness
Stunning Property
Property and view were absolutely beautiful and the house is in a great location.
Stayed 5 nights in Nov 2022

10/10 Excellent

Dianne L.

Liked: Cleanliness
Relaxing
Wonderful
Stayed 6 nights in Sep 2022

10/10 Excellent

Laughton S.

Liked: Cleanliness
Great property, wonderful views, large kitchen, comfortable for our group of 6
Excellent. Friendly and attentive property manager.
Stayed 6 nights in Aug 2022