1BR Oceanview Vacation Rental St. John, Virgin Islands USA
About Susan Brierley
We are thirty year residents of Coral Bay. We travel frequently and our focus is always on finding beautiful spots to enjoy each others company. That is what we tried to do with each of our Calabash Cottages, My husband is a retired builder and we designed this home together. We built Windwardside in 1996 and have managed it as part of the Calabash Cottages group for over 20 years. Calabash Cottages offers charming and private cottages and villas in quiet secluded locations. Our main focus is to provide an assortment of options for couples in a tranquil setting.
Susan Brierley purchased this Villa in 1996
Why Susan Brierley chose Estate Calabash Boom
We love Coral Bay and wanted to design a home that did not tower over the hillside but fit into it's natural surroundings. The shape and orientation of this property allowed us to do just that while still offering fabulous views. We love quiet natural settings, tropical gardens and ocean views and we appeal to visitors who are looking for just that.
What makes this Villa unique
Windwardside Main House is a villa that invites lingering. You can hear waves gently falling collapsing in the distance. You'll be amused at the sugar birds darting about and you will find plenty of places to just read a good book. If you want to bring friends along it can be rented with Windwardside Guest Cottage and both groups will still have plenty of privacy. We hope to see you soon at one of our Calabash Cottages.
Pool / Spa
Canceled bookings will not receive a refund
Damage and incidentals
You will be responsible for any damage to the rental property caused by you or your party during your stay.
Children not allowed
Max guests: 2
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.
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!
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!
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.
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.
Batting 1000 for three years running
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!!
Thanks for staying with us again at Windwardside. When we built the Windwardside (Main House and Guest Cottage) we expected them to be used the way you do- by a group that travels together but also wants privacy. To our surprise most weeks the houses are rented by two separate parties. So it’s nice to hear your perspective on the Windwardside shared by the same group- enjoying the shared spaces to get together for a meal but having enough privacy to regroup. Thanks for telling guests about your stay. We look forward to hosting you again next year.
Remote and quiet setting, three quarters of a mile up dirt road with very little traffic. Beautiful view of Coral Bay and nearby islands. Near to beaches, shops restaurants, hiking trails and boating. Shares no facilities with other home on property except parking area.