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 06:20 am
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Guest Reviews for Windwardside Main House

Perfect Villa/ Exactly as Advertised
Jody H.
11-28-2012

If you love to drive around in a Jeep and spend your days in the water snorkeling and swimming, you will love St. John and Windwardside could not have been more perfect. The description is very accurate and it is even more spacious and has more amenities than we expected. The property was clean and has a nicely stocked kitchen. The hot tub is great for relaxing with a drink after a long day of swimming and it has a great view of Coral Bay. Also, there is a gas grill so you can cut back on restaurant expenses (typical price for dinner for two with 1-2 drinks easily exceeds 60 bucks). The owner's customer service was flawless and extremely quick with communication. The island intro with Brian was completely on-point and he provided great insight into how to get the most out of your stay for what type of vacation you are seeking. He probably chatted with us for an hour or more with a map and helped guide us to more casually local type restaurants and great snorkeling spots that aren't overhyped (instead of Trunk Bay, go to Jumbie). He also put us into contact with the boat Pirate's Penny for the obligatory boat trip to BVI and snorkeling (great trip and great crew... 10 person boat instead of the 50 person hoards on the booze cruise). Also, there were several great guidebooks in the living room for trails and snorkeling. We cannot wait to refer our friends and family to Windwardside and hopefully they will be bringing us back with them.

best beaches for snorkeling: Salt Pond Bay/ Waterlemon Key/ Brown's Bay/ Jumbie Beach

best beaches for swimming/ playing in water: Francis Bay/ Jumbie Beach

favorite hike: Ram's Head

favorite restaurants: Hercule's (Cruz Bay Carribbean/ Curried Chicken platter and pates are good... most affordable restaurant of the trip)

Pink Corner (Coral Bay Carribbean/ great local food)

Skinny Legs (Coral Bay Burgers/ yeah, it's burgers, but they are good ones and this is the place if you want to party in Coral Bay)

Donkey Diner (breakfast food is good/ never tried pizza)

Aqua Bistro (good food at reasonable (for St. John) prices

Miss Lucy's (Coral Bay... only had the conch fritters as meal, but they are easily the best on the island... we had them at several places that were not great)

Rhumb Lines in Cruz Bay if you're craving Thai

really, the food on most of the island is above average and there is no fast food, so at least you can see where restaurants are so expensive

wonderful
Daniel S.
11-06-2012

My wife and I spent two wonderful weeks at Winwardside, and were completely in love with the house and its landscape. Photos are quite accurate...I was sold on the beautiful brickwork of the patio...and this quality carries through the cottage's ceilings, finishes, and furnishings.

Spent many mornings and evenings in the hot tub and showered outside with the fantastic view. Breakfast on the porch, dinner on the patio...there are so many places to sit with a book that we only used lounge chairs on the patio in our second week!

St John is exquisite. Period. We can not recommend Coral Bay (and the east side) enough for its out-of-the-way, intimate feel, friendly locals, great beaches and snorkeling...Fresh fish for the grill directly from the fishermen, live music, killer BBQ. Driving to any other location on the island is no big deal.

Excellent customer service from initial booking, jeep rental, pickup, recommendations, follow-up calls to see if all was going well. We are considering renting again and including the guest cottage for a full-family trip on St John.

Our Response
We were very happy to read your review. Nice to know how much you enjoyed your stay. We look forward to hosting you and your family in the future. Thank you for writing!
Just As We Imagined
Bryan C.
10-09-2012

My girlfriend and I booked this trip several months in advance, knowing that come September, we'd be ready for a vacation. If we only knew how true this would be.

After a miserable travel experience from New York to St. Thomas, all of our frustration and contempt for a certain airline and rental car agency melted away once we were greeted by Bruce at the ferry dock on St. John. Upon arrival, Bruce arranged for a local (and reputable) car rental agency to open after they had closed for the day to rent us a car for the week. Since we arrived a little later in the evening than originally planned, Bruce suggested we stop at the market to do a quick provision to hold us over for the night. He guided us there, patiently waited as we scrambled to pick up some essentials, and showed us to the house. After giving us a quick tour, he answered all of our questions about the best places to snorkel, good restaurants to try, and beach suggestions. Words cannot express how grateful we were for this experience - certainly a welcomed and relaxed way to begin our vacation, and something that Bruce went out of his way to do for us. It was truly appreciated.

The house and grounds are just as pictured and described - absolutely lovely and perfect. Those unfamiliar with St. John (I had been several times before this trip) should note that the island is very hilly (as seen in the pictures). The road up to the house takes a relatively confident driver if you're used to driving on flat roads and highways as I am, but a few trips up and down and it becomes almost second nature (like driving on the left).

Some suggestions for those thinking about renting Windwardside:

1. A lot of people probably think a hot tub is useless in a tropical climate. Incorrect. We used the hot tub every night to watch the stars, drink some wine, and relax. It's definitely a perk.

2. Although you share a parking area with a nearby cottage, this place is absolutely private in every sense of the word. It was nice to be here and just be by ourselves.

3. Coral Bay is far less busy than Cruz Bay. We found many of the restaurants and shops closed while we were there. This was fine with us, as we had to get adventurous and creative a few times for meals. One night, we stopped at a local fish stand and bought some filets and conch that was pulled out of the ocean earlier that day and grilled it back at the house. It was delicious!

Thank you Susan, Diane, and Bruce! We hope to be back soon!

Our Response
Thank you so much for your detailed review. I am so glad to hear that you enjoyed your stay. I will pass on your comments to Bruce. I am sure he will be happy to hear them. September is a mixed bag on St. John. Half of the restaurants are closed but it is an even more relaxed time on the island when we all get a chance to slow down and talk to each other and the visitors. The beaches are quieter than ay other time of the year. We hope to see you again soon- Susan
Loved Windwarside Cottage
Allen K.
02-03-2012

My wife and I stayed at the Windwardside Cottage for two weeks. We had a fabulous time. The cottage was almost exactly as depicted in the pictures. Everything was spotless and freshly made up for us. The cottage was very spacious which we greatly appreciated. The separate bedroom/bathroom was a bit odd at first, but we easily got used to it and actually liked it. The main house has everything you could possibly want and was so relaxing. We enjoyed the hot tub on a daily basis just after we came back from the beach for the day. Having not one but two outdoor showers available was luxurious. We made our breakfast each morning and ate it in the roomy and airy dining room and sat on the outside patio each night talking and star gazing. The views from almost anywhere on the property were gorgeous. Susan and Diane were wonderful to deal with before we arrived and were in contact with us during our stay to see if we needed anything. They had someone waiting for us when we got off the ferry in Cruz Bay who escorted us to pick up our rental car, go to the supermarket for a quick shopping, and then take us to the cottage. Simply great service. BTW, the folks at Courtesy Car Rental are wonderful to deal with and the discount that Susan arranges with them is not trivial. The road up to the cottage was a bit challenging at first - perhaps because we arrived at night. But by the light of day it became just part of the fun of staying at the cottage. Staying in Coral Bay was divine. There are more than enough very good restaurants to keep you happy for several days. The cottage is just a short drive to all of them, as well as to Salt Pond Bay which is a wonderful beach to visit and has some good snorkeling. The cottage is also a 10-15 minute drive to several other East End beaches, Hanover, Haulover, Vies that are wonderful, not crowded and also have good snorkeling. Staying close to Coral Bay is absolutely the best decision we made. Driving to the famous North Shore beaches, such as Maho and Trunk was easy and not too far away. Susan also helped arrange our pick-up at and return to the St. Thomas airport by Dynamic Tours. It went very smoothly. All in all I cannot recommend the Windwardside Cottage highly enough. We have a place to return to on St. John.

Our Response
Dear Allen and Helen, I am so glad that you enjoyed your stay at Windwardside Main House. We appreciate the detail in the review. It means a lot for guests to hear about the experiences of past visitors. Enjoy your safai next year and we know we will see you in the future. Warm regards, Susan PS: For those reading this review the guests refer to Windwardside Cottage. The actually stayed at Windwardside Main House which is the neighboring home to Windwardside guest Cottage.
Wonderful last-minute getaway
Heather Y.
02-13-2011

We rented Windwardside cottage with five days notice after finding their discounted rate on Home Away. Diane did everything possible to help us get to the house. We were met by Bruce who gave us a thorough introduction to the island and escorted us to this great house atop a rough but fun dirt road.

If you're confused about the "two house" thing, don't be. This is just like renting a two-story house -- with bedroom/bath upstairs and livingroom/bath/kitchen/dining room downstairs. It's just that the stairs are open and the floors aren't directly on top of each other.

The house has everything one could think of - we cooked in breakfast and dinner and packed lunch to take as we explored the island in our 4x4. The kitchen lacked for nothing and the dining room was stacked with a great library of books and DVDs. Reading years of guest comments and perusing the St. John books helped us decide what to do each day.

The views from the porch and hot-tub are as described. The place is extremely private - we could occasionally hear but not see the couple staying at the guest house next door.

I would recommend following the owner's recommendations regarding transportation to the island and auto-rental on-island. We were picked up by a Warren of the transport company (holding our name when we got off the plane) and within 45 minutes of landing we were on the Red Hook Ferry. 20 minutes later, we were met in St. John by Bruce, who took us the car rental place, explained the three-road town, took us to the grocery store, and led us across island to the house. He gave detailed 4x4 instructions and made sure we knew the "must see" places on the island map. Really amazing service! The couple staying that the guest cottage next door went their own way, using taxis, renting on St. Thomas and taking the car ferry -- all were mistakes and, though they landed on St. Thomas at the same time as us, they arrived at the house seven hours later.

We didn't eat much food on the restaurant, but do recommend Coral Bay standby's The Tourist Trap (lobster rolls) and Vie's (conch fritters).

For beaches, we recommend Little Lameshur (gorgeous and private), Salt Pond (hike the Ram's Head trail and snorkel) and Maho - shallow, and easy for learning to snorkel. We swam with sea turtles there.

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