St John House Rentals

Windwardside Main House

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Windwardside Main Cottage

1 Bedroom | 2 Bath | Hot Tub | WiFi | Ocean View
(Guest cottage available as additional bedroom)

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 brick courtyard.

This traditional West Indian style home consists of multiple buildings with a large central courtyard. The main house 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.

Living and Dining

There is a full kitchen and living room, an adjoining bath, plus an inviting covered porch overlooking the sea.

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.

Windwardside Main House  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

Windwardside Main House Rates

$2065 Low Season (Apr 16-Dec 14)
$2835 High Season (Dec 15-Apr 15)

Availability Calendar

Inquiries & Reservations

Larger groups can rent Windwardside guest cottage as an additional bedroom. You will find a floor plan further below for reference.


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.

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.

We have stayed at Windwardside Cottage for a week every year for three years now. We just got back home and are already planning our next week there. Each year, the cottage has provided a comfortable and convenient home base from which to explore the wonderful island of St. John. We travel with another couple and there is plenty of privacy for everyone as well as delightful common space for meals and relaxing in the hot tub or on the porch. The views of Coral Bay are great! If you’ve never been, you can’t imagine how delightful it is to wake up and see such beautiful ocean, sky and flowers right from your bed!
Deb & Dave

Floor Plan

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.

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.

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 – ferry rates).

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.

St John House Rentals, Villas, Cottages and Vacation Homes

Please send an email inquiry from the page of each vacation home of interest. At St John House Rentals our homes are owned or run by a number of individuals and management companies and they all do their own booking. The email link on each home’s page will get you directly to the person who can help! We at St John House Rentals do not do bookings.