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)

Please note: We never advertise on Craigslist. We will never request guests to wire money directly to our bank accounts.
If you should encounter either of these please contact us directly to avoid fraud.

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.

Kitchen

Deck and view

Deck and chairs

Bedroom

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

Garden area

Lush garden

Additional Images

Nearby Beaches & Sights

Amenities

  • 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

Activities

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.

Arrival

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

Calendar Updated on December 16, 2018 at 07:21 am
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Guest Reviews for Windwardside Main House

We had a wonderful Honeymoon!
Steve
01-11-2011

We LOVED our stay at the Windwardside main house. The pictures are very accurate and it is a wonderful place to get away from it all. The location on the east side of the island by Coral Bay is great for those who want to get away from the more "tourist" focused scene in Cruz Bay. We found the people in Coral Bay to be extremely friendly and the restaurants were the best on the island. Plus, the proximity to Salt Pond and Little Lameshur beaches was great since we like less of a crowd. I highly recommend this villa and hope to stay there again in the future. We're hoping to rent both the main house and guest cottage sometime in the future with friends. It's a perfect set up for two couples to share.

Great House!
Amy W.
10-13-2010

We have rented this house in St John 3 times and have had a great

time every single time. The house is well appointed with everything one would need and more! The birds are amazing and so are the plants.

Nice and private but close to beaches and restaurants.

The owners are nice, have good info. and will help you make reservations for your rent-a-car.

PARADISE!!!
Sarah
08-11-2010

Windwardside was BEYOND amazing!! My husband and I couldn't have enjoyed out stay any more than we did. The staff was more than accommodating and quick to answer any questions we had, and even brought some groceries for us so we would have something to eat after a long day of traveling. The pictures are very accurate, and the house and view of coral bay are absolutely beautiful!!! We could not have asked for a better place to spend our honeymoon and hope to return someday soon!

Windwardside = AMAZING
Kat G.
07-06-2009

Stay at Windwardside!!!

My husband and I stayed there for our honeymoon and we could not have picked a better spot! The views are breath-taking and the cottage/house is just perfect - comfortable, clean, very nicely decorated.

Our rental car was set up for us and we were even taken to the grocery store to get some basic necessities.

I would recommend this place 100% - my husband and I are already planning a trip back!

Windwardside Main House
Ann R.
06-10-2009

There can't be a more lovely location than Coral Bay, or a prettier property than Windwardside. If anything, the pictures don't come close to capturing the serenity and comfort we felt staying there (but go ahead and enjoy the photos too!) Our vacation time in this well-furnished villa allowed us to re-charge our batteries and escape the pressures of everyday life. Think open-air showers, never-ending flowers, and gentle tradewinds... If necessary for extra visitors, there is a guest house also available.

The best part about this get away is turning over all the arrangements to the owners.From transport from the airport to the ferry, to car rental (4 WD is essential), to helpful local greeters who answer every question, make restaurant, shopping, and beach recommendations, all we had to do was relax. Just remember to set your watches for "island time" as you pause to take in all the breath-taking views!

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