Windwardside Main House

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.

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! We prefer to cook at home and enjoy quiet meals -- the kitchen has everything we need. The whole facility is every bit as lovely and well-appointed as it looks in the online photos. Everything is clean and good working condition when we arrive. If anything breaks or needs attention, the staff is quick to respond.

The drive up the mountainside from the main road is a bit daunting the first time -- you really do need a 4-wheel drive vehicle -- but you'll quickly acclimate to the roads. It's well-worth the drive! What we learned on this trip is that some rental companies send new guests to their residence with only directions. In contrast, a staff member from Calabash Cottages will meet first-time guests at the ferry, take them to the car rental pick up, then by the grocery if desired and finally lead them directly to the cottage and show them around. What a lovely welcome.

We couldn't recommend a place more highly!!

After first arriving in St. John for the first time we were blown away by the scenery. After meeting Brian at the ferry, who kindly greeted us, look us grocery shopping and to pick up our rental car. We followed Brian back to the house which at first we thought the road leading up was never going to get us there. Then, we arrived and it was the most beautiful place! We loved the privacy, the views and of course cooking dinner on the grill almost everynight. We would return to this house 100 times over again. It was not buggy and we loved using the hot tub at night after dinner with a rum punch in hand. The accommodations for daily beach lounging and snorkeling was just icing on the cake. Plenty of towels, snorkel gear options, coolers and chairs. We had the time of our lives visiting all the beaches and swimming with all the fish and sea turtles. We would wake up every morning to a beautiful sunrise shinning in through our bedroom screen doors. Most relaxing and mind soothing vacation we needed after a long winter in Maine. We can't wait to rent this house again. If you don't mind driving a mile or two up the half paved, half dirt road to get to your dream vacation destination, this is the place for you. Our pick up from the airport in St Thomas was arranged for us to and from and we never had to worry about planning our taxi service. Someone was always there to meet us with a welcome sign. I hope the next couple can enjoy this place as much as we did. If your looking for a laid back and relaxing tropical getaway, this is it!!!!

This villa is absolutely beautiful! The views from every window are outstanding and we especially loved the outdoor shower. The property is very clean and very private...a perfect spot. Susan & Diane are great and make sure everything goes smoothly from the pick up at the airport, car rental and meet and greet. I highly recommend this villa to anyone looking for a luxurious spot to relax. We will definitely rent here again and again.

My wife and I recently returned from a week at Windwardside Main House. Because of the reviews we had read we had very high expectations, but the property actually exceeded those high expectations. For starters, Susan's team was very professional and excellent to deal with. The property itself is private, clean and well maintained and has lovely furnishings and landscaping and wonderful views. In a word - romantic. We spent our days exploring the beautiful island of St. John, but at the end of each day we looked forward to returning to our retreat on the mountainside. I highly recommend this property.