Windwardside Main House

1 Bedroom, 2 Bath, Hot Tub
Sleeps 2
(Guest cottage available as additional bedroom)
$1925 Low Season (Apr 16-Dec 14)
$2695 High Season (Dec 15-Apr 15)

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Windwardside Main House Deck, Hot Tub and View

Welcome to Windwardside, an elegant retreat with lovely furnishings, a beautiful view and lush tropical gardens. It is the most intimate and traditional of all of our homes In Coral Bay. The design is reminiscent of a bygone era in the caribbean but the amenities are modern and designed for comfort. My husband (a retired builder on the island) and I designed this home. We have years of experience of offering visitors to the island an unusual experience that brings them outside of their day to day life but is a comfortable and welcoming home away from home. Recent renovations to the house have added much to its beauty and charm.

Windwardside Main House Deck, Hot Tub and Bedroom

This traditional West Indian style home consists of multiple buildings with a large central courtyard. The mainhouse consists of two buildings: the first is a detached bedroom / bathroom with a veranda that looks over the courtyard, gardens and sea; the second is the “great house”. The great house is entered though a roomy screened-in porch which holds a beautifully furnished dining room and a cushioned window seating area. There is a full kitchen and living room, an adjoining bath, plus an inviting covered porch overlooking the sea. Larger groups can rent Windwardside guest cottage as an additional bedroom. You will find a floor plan further below for reference.

View from covered porch at Windwardside

Living and Dining Area

Our guests love the separation of the bedroom from the living area. It is a uniquely caribbean experience that allows you to end your day by admiring the night sky. Our skies are devoid of light pollution so we have a brilliant display of stars during the dark of the moon. During the days when the moon is full view from the hot tub is unbelievably romantic.

Living Room

Our kitchen is small but extremely well appointed. Windwardside (in conjunction with the neighboring Guest Cottage) has always been my choice when we have had family visiting so it is well set up for any meals you wish to enjoy in the comfort of the villa. You will find all the equipment you need to prepare your meals at home including a high quality gas grill. For those who prefer to take a break from cooking on their vacations there are numerous restaurant within a few miles from the villa. Our staff will be happy to tell you about the offerings both in Coral Bay and Cruz Bay.


Deck and view

Deck and chairs


The charming detached bedroom has a four poster bed and opens onto a relaxing verandah. Fill the coffee pot the night before and surprise your partner with coffee on the verandah as a romantic way to start the day. The master bedroom has a full bath with a shower located in an enclosed shower garden that is open to the sky but totally private. If the weather doesn’t allow for that (a rarity on St. John) there is also an indoor shower and full bath located off the living room.

Covered porch

Brick courtyard

Windwardside shares the property with the neighboring Guest Cottage. They share no amenities except the parking area and are visually obscured from one another by thick tropical foliage. Please be sure to read our reviews from former guests who can assure you that your vacation will be a private one.

Read Reviews

View from villa

Windwardside makes every attempt to protect the beautiful environment that makes it such a special place. The majority of our power is from discretely placed solar panels. Gray water from our showers is recycled to water our beautiful tropical gardens. Whenever possible we use natural cleaning products including laundry soap. As more options open we will continue to add to our green environment efforts.

Courtyard and chairs

Our staff are long time members of the Calabash Cottages team and will do their best to help you plan your perfect vacation from start to finish. We hope to see you soon!

Location: Coral Bay, St. John, U.S. Virgin Islands. Windwardside is located in quiet seclusion with mesmerizing views of Coral Bay, nearby islands and the Caribbean Sea. The house is situated two thirds of a mile up a little used road in Coral Bay. Surrounded by tropical plantings and marvelous vistas, you are still just a short drive to a cool splash in Salt Pond Bay or other equally inviting white sand beaches. Restaurants, shops and watersports are all available within two miles in Coral Bay. The main town on the island, Cruz Bay, is located 8 miles away. The airport is in St. Thomas which is reached via a twenty minute ferry ride. (Ferries leave every hour on the hour and cost $7 each way).

Windwardside was created to meet the desire to travel in groups with friends and loved ones yet still maintain a sense of privacy while doing so. This focus on privacy also makes it a wonderful retreat for couples. The whole complex – the Great House (master bedroom, two baths) and the guesthouse (one bedroom, one bath) can be rented as one by larger groups. Smaller groups or couples can choose from either the main house or the guest house. When rented individually privacy is assured by the orientation of the buildings and the heavy plantings screening them from one another.


Garden area

Lush garden

Additional Images

Nearby Beaches & Sights


  • Hot Tub
  • Snorkel Gear
  • Beach Chairs
  • Cooler
  • Beach Umbrella
  • BBQ
  • CD & VCR Player
  • Phone
  • Fresh Flowers
  • Robes, All Linens & Towels
  • Safe for Valuables
  • Wi-Fi Internet


We are happy to make suggestions for activities that suit your interests.  When you arrive at your cottage we will go over a map of the island and point out the best beaches, hiking trails, snorkel spots, etc.  Most activities can be arranged once you are on island but if you are planning a day on the water you may want to arrange that in advance. Consider Busy Bee Charters “Lap of St. John” on Wednesday for a really fun trip that departs right from Coral Bay.


Windwardside is managed by on island owners. We will meet your ferry on arrival, arrange for discounted car rentals and provide the personal attention you need to make your stay with us as pleasant and relaxing as possible. We can also arrange for a driver to meet your flight for the 50 minute ride to the Red Hook ferry dock.

For details about our our policies, reservations and travel suggestions please read our FAQ.

Availability Calendar for Windwardside Main House

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Guest Reviews for Windwardside Main House

Benjamin Weil

This was our first time back at Windwardside in many years (having often stayed at another villa in the area based on Windwardside), and our first time back on St. John since the 2017 hurricanes. At this stunning and peaceful villa, you would never know there had been a hurricane. Everything is pristine and in perfect working order, and the captivating landscaping is as beautiful as ever. Like many guests, it was hard for us to leave Windwardside in the morning, and we usually chose to prepare our own dinner there in the well-equipped kitchen. To us, Windwardside is the true personification of luxury. It may not be the most expensive villa on St. John, or have the most bedrooms, or look like a Park Avenue apartment, but it has simple, tasteful, harmonious architecture, a serene and stunning setting, absolute privacy, and is extremely well managed. It's nice to know that it has become a home away from home for so many satisfied guests. We can't wait to return.

Absolutely Beautiful!!!

This was our first trip to St. John and the Windwardside Cottage was everything as advertised plus some. The villa was spotless and offered all the amenities of home. We spent most of our days at the beach (we actually visited 8 beaches in 7 days) soaking up the sun and snorkeling. We had originally planned not to cook much on this trip but we so looked forward to returning to the villa after an active day on the island that we prepared most of our meals there. When they say that you need 4 wheel drive to get to the cottage they are not kidding, but this all part of the allure of staying at Windwardside Cottage. I have to tell one experience I had. We lost power for a few hours Wednesday evening and I awoke because it got a little hot with no fans operating. I went down to the main cottage and laid down on couch in the screened room because it was a little cooler with the breeze coming off the ocean. Well, with the island being so dark, the stars were just amazing. I laid there gazing for an hour or better and saw 3 shooting stars!!! Susan and her staff made our vacation seamless and stress free from the time we stepped off the plane till we reluctantly had to return home. If you are considering St. John for a vacation then don't think twice about the Windwardside Cottage. I know this will become an annual stay for us.

Our Response
Thank you for your lovely review! I am glad the power outage on a hot night gave you a little bonus. Their is great stargazing on St. John on moonless nights. I'm happy to hear we will be seeing you again. For future guests this review mentions Windwrdside Cottage but was actually for Windwardside Main House.
Paradiso a St John

Sono stato per una settimana di vacanza con tre amici e non avremmo voluto andarcene più!!! La vista e' stupenda e la casa, suddivisa in tre edifici, quindi con la massima privacy, lo e' altrettanto! Ogni sera al rientro dal mare ( e che mare ) ci si rilassava nella Jacuzzy ( ce ne sono addirittura due!) con un drink! E non ci sono vicini o rumori se non quelli degli uccellini! Fantastica vacanza!!! Serve una jeep per raggiungerla, ma sull'isola tutti affittano Jeep!

Our Response
Thanks for your review, Andrea. I enjoyed meeting you. I have just enough Italian to understand most of it. So glad that after such a long trip Windardside did not disappoint!
Tropical Oasis

It truly was a tropical oasis in every way. So many times you are very disappointed but not at Windwardside Villa as it exceeded our expectations and more.We had traveled to St Thomas before but not St Johns...and there is clearly a huge difference between the two with St Johns overwhelmingly the superior experience. The villa was a great launch point for daily adventures but a welcome retreat at the end of the day. All the amenities of home in a beautiful, breath- taking setting. Susan and her team left nothing for chance and were attentive to every detail. We are booking our return trip to Windwardside villa / Coral Bay now and hope to make it an annual affair.

Our Response
Thank you for such a nice review. St. John and St. Thomas are indeed very different vacation spots and have a different appeal. I'm glad that you appreciated what St. John had to offer and enjoyed the time spent at Windwardside. It is a gorgeous setting. We hope to see you again. All the best- Susan
Everything we could have dreamed!

My husband and I just spent a week at Windwardside Cottage for our honeymoon. We decided on this villa because of the wonderful reviews, the detailed description and the wonderful things we had heard about the island of St. John. Additionally, we decided that the quiet Coral Bay side of the island would fit us better than Cruz Bay.

Well, I can say that it is absolutely a gem. The villa is everything you see in the pictures! The lush landscaping, the privacy, the lovely hot tub, all of the balcony and deck options. We started every day by having a cup of coffee on the balcony off the kitchen which has amazing views in the morning, and all day! Then, we would make our plan for the day.

We so enjoyed Salt Pond Bay that we spent 3 of our 7 days there. The Ram Head Trail hike that starts at the end of that beach has such beautiful views and is just long to feel like we got a little work out in and earned our beach time. We loved using all the of the supplies that the house had-- beach chairs, cooler, etc. We would then make our way back home, shower and either cook at the house and soak in the hot tub or meander to one of the restaurants around Coral Bay.

The food on that side of the island is VERY casual. Aqua Bistro has some nice fish options. But in order to get a fancier meal, you will need to make you way to Cruz Bay, which is not a big deal at all. We loved Morgan's Mango.

Besides Salt Pond Bay, the other beach we really loved was Cinnamon Bay. It has everything you could want to spend the day. We went for the little walk around the ruins before we went to the beach. You can rent kayaks or any other water equipment. There is also a small store and a restaurant with sandwiches burgers etc. It wasn't crowded, and the beach was spectacular.

There is nothing bad to say about Windwardside or St. John in general. We did have one maintenance issue, but it was addressed and fixed within the hour.

The only challenge is the drive up to the house. And it really is a challenge. Other reviews have described it as steep or bumpy. And that is an understatement. It is super bumpy! It is completely worth it, but I wish someone had described it more because we were kind of shocked the first time we did it.

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