Windwardside: Great View, Hot Tub, elegant, lush gardens, private

  • Bedrooms
  • Bathrooms
  • Sleeps

Windwardside Main House 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 it’s beauty and charm.

IMPORTANT INFO ABOUT RATES AND POLICIES: We have two rates: Low season from April 16 to December 14 ($1785) and High season ($2555) from December 15 to April 15. The only additional charge is 12.5% hotel tax. We do not collect a damage deposit. Our 20 year relationship with guests has taught us that this is not necessary. We treat our guests with respect and we have found that they return the favor. We do not charge a reservation fee or a cleaning fee or a service fee. If you encounter any additional charges when requesting a detailed quote it would be from the advertising site where you found us. Calabash Cottages is an established company and we do take direct bookings.

Car Rentals: Since the purchase of Homeaway and VRBO by Expedia we have seen an attachment at the bottom of our ads with them encouraging guests to book car rentals through their site. Because of our unique location we strongly advise against that. You do need a 4 wheel drive vehicle. We have for over 20 years done business with a very reliable company, Courtesy Car Rental. We believe in them enough that we forgo the commission they would give us and to apply it as a discount to your car rental. Please discuss car rentals with us before reserving. Our most important interest is in satisfying our customers. But the recent take over of our advertising sites by large corporations is constructing communication barriers. We can always be contacted directly.

The covered porch seats four, two in wicker chairs and two in mahogany plantation chairs based on the same design used hundreds of years ago. Sugar birds will dart in an out as you sink into an afternoon or evening on the deck. All of our homes in Coral Bay are located high enough on the mountain to take advantage of the cooling trade winds. The unique orientation of this home makes it the only one of our houses where you can hear the soft lapping of the waves on the shore across the bay

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.

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 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.

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

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.

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!


Virgin Islands, US Virgin Islands, St. John

Address: Rte 107, St John 00830, USVI
Zip or Postal Code: 00830
Latitude/Longitude: 18.330343837271922 / -64.7090074368042
Nearest AirportSTT25 miles
Nearest BeachCoral Bay2.5 miles
Nearest FerryCruz Bay Dock9 miles
Nearest RestaurantShipwreck Landing1 miles


We met our guests and show them out to the villa


Coral Bay (Calabash Boom)


Property Type:
Guests provide meals
Floor Area:
1,100 sq. f.
Location Type:
1 Bedroom, Sleeps 2
Queen Beds: 1
2 Bathrooms
Baths: 2
Showers: 3
Sinks: 2
Toilets: 2
Off-road parking
Hot Tub
Activities guide
Beach chairs
Beach towels
Dining guide
Outdoor hot tub
Private location
Alarm clock
Bathroom tissue
CD player
Ceiling fans
Coffee grinder
Coffee maker
Cooking utensils
DVD player
Filtered water
Hair dryer
Iron and board
Paper towels
Deck furniture
Gas grill
Patio furniture
Screened porch
Pet Friendly: No
Smoking Allowed: No
Child Friendly: Yes
Long Term: No
Elderly Accessible: Yes
Wheelchair Accessible: No
Other Services:
Cleaning inclusive
Linens provided
Towels provided
Local Activities:
Horseback riding
Area Services & Attractions:
ATM / Bank (2 miles)
Duty free shops (9 miles)
Groceries (1 miles)
Laundromat (6 miles)
Rainforests (6 miles)
Reefs (2 miles)
Restaurants (1 miles)
Ruins (4 miles)
Scenic drives (1 miles)
While we are not wheel chair accessible we have many elderly guests. There are steps involved but we would not want to say that made it unsuitable for the elderly. I could be in big trouble with my mom.


June 2024
September 2024
November 2024
December 2024
February 2025
March 2025
April 2025
  • Available
  • Pending
  • Booked
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Rental Terms

 Check-in Time: 4:00 PM
 Check-out Time: 11:00 AM
  Payment Options: Checks
Rental Agreement:
50% of payment is due via personal check when reservation is made. The balance is due 30 days before your arrival. Payments are fully refundable if we are able to find another guest to fill your vacancy. We do not charge service fees, reservation fees or cleaning fees.

on Apr 06, 2016
Paradiso con vista su Coral Bay!!

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!

Owner's Response:

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!

on Apr 06, 2016
Perfect Oasis

This was the 3rd time we stayed with Calabash Cottages, and this one certainly did not disappoint! All of the standards are high and constant! The personal service, quality of the villa, and obviously the views! It all comes down to location, location, location, and we love that the cottages are far from the hustle and bustle, you get a touch of nature with the birds, lizards, butterflies, and yes even the spiders! Some days we didn't even feel the need to leave our little oasis on the mountain. Thank you to Susan and her team!

Owner's Response:

Hi Christine,

Thanks for choosing to stay with us a third time. We're flattered anf happy that you are willing to trust your vacation to us. And thank you also for taking the time to write us a reveiw. We certainly hope to host you in the future.

on Apr 06, 2016
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.

Owner's Response:

Thank you for sending your honeymoon at Windwardside Guest Cottage. i am very happy to hear that you enjoyed your stay despite the road. We try to describe it but I guess the bumpiness is all relative. A lot of our guest laugh it off. Others wonder if they are going to need to have fillings replaced. Fortunately it is only 2/3 of mile. The road is a government road but we are raising private funds and even got a small grant to work on it. In fact yesterday we had a work day up there. Hopefully in the next six months or so it will be improved. Not expecting a super highway. though :)

I love to hear about guests enjoying spending part of their time enjoying the deck and the view. There's a lot to see on St. John but just relaxing on the covered decks is so peaceful and lovely. Glad to hear you took advantage.

Thank you for letting us know that your maintenance issue was handled promptly. Things can always go wrong but we make an extra effort to jump on them when they do.

Thank's for letting us (and future guests) know about your stay. Susan

on Apr 06, 2016
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!!

Owner's Response:

Hi Deborah, 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. Susan

on Apr 06, 2016
Stay here if ya wanna have an amazing adventure!

It has taken me a bit to get on here and leave my review..mainly because I miss this place so much. It is truly breath taking,gorgeous,romantic,adventurous,charming,convienent,
spaciousand almost perfection! My husband and I loved the drive up because it was just fun and felt like we were staying off the beaten path. I seriously miss how I would laugh going down the hill, and after the first day my husband was a pro driving up and down. Bottom line, if you want one of those high up gorgeous views, you have to stay up in the hill tops to get those amazing pictures! And trust me this is the place to stay! The grounds are just , wow. All the flowers and greenery made you feel like you were in the jungle. I loved waking up every morning and drinking coffee on the porch , staring at the rising sun and being in awe of the views. There are bugs here though, so be mindful...staying here is being closer to nature and if you are looking for a high end resort feel I would go blow your money at the hilton...but if you want a fantastic deal for what you get and to be surrounded by absolute nature with still outstanding natural luxury experience, then please stay here! It made our trip so much fun staying on the more private side of the island. Yes there is alot to do on the boat dock side, but this side of the island has so much more breathing can visit beaches that have nobody on them , seriously ! And there is a great conveince store right before you turn into the neighborhood, it just opened last year and the owner is a really great guy. He actually has an IOU when I forgot my money he let me take my groceries as long as I would pay him back before out trip ended ( I did duh lol ) ...cannot find that in Texas anywhere! And besides that there are some great resturants, but Aqua Bistro was our favorite. We ate there 4 times and loved it everytime. And the drive to the other side of the island is just absolutly first we would drive thru the middle but after a few days we switched to the right side of island, going along the beaches...get to know your maps and do it both ways, it really is a great drive across....and please plan your beach visits accordingly. I made a loose schedule for each day ( it may have been laminated ) and by doing so we were able to visit and enjoy SO many beaches...also I highly recommend going in off season...yes some resturants will be closed, but you will be on a island that feels almost empty and that is a really amazing feeling.... it made it more romantic, less stressful ...and easier driving cause there was almost no traffic! ...back to this property.... it is wonderful...tree frogs at nightime, the outdoor shower which is so beautiful , the huge courtyard, the hot tub we spent everynight in (we rigged our laptop and set it on chair and watched movies every night out there ) , the full sized kitchen was such a plus....and the absolute best part was the customer service from the managment team!! Please I urge you if you stay here ( you really should do this anywhere you stay) and have any issue contact them and I promise you these guys will be there to fix or help out in any way. We had one small issue and literally in an hour I recieved a phone call (in suite landline) and they were on it immediatly. Truly great group of managment and because of this place and their team my husband and I had an amazing wedding anniversary was just perfect in so many ways and I tear up thinking about it !! P.S I am adding pictures of not only the grounds but also some of the beaches, so that you can see what the beaches look like during off season...I will trade in every resturant being open for peopless beaches any day! Makes for much better pictures ; )

Owner's Response:

Thank you for your review. I agree with you that there are definitely some advantages to being here during the off season. The quiet beaches are so incredibly peaceful. We always make sure guests know about our bumpy road but like you mentioned that's where the beautiful views are and it is all part of the adventure. Fortunately, it is only 2/3 of a mile but it can seem a bit longer. I am very fortunate to have such great support staff and I am happy that your maintenance issue was taken care of promptly. That's our goal. I hope that you make it back to Windwardside in the future. Thanks for trusting us with your vacation time. All the best- Susan

on Apr 06, 2016
Vacation of a lifetime!

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!!!!

on Apr 06, 2016
Windward Side

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.

Owner's Response:

Thank you so much for staying with us and also for taking the time to let potential guests that you enjoyed your stay. It’s a very good feeling to know that we have made you happy enough that you are already planning a future visit. We look forward to hosting you again! Susan

on Apr 06, 2016
Outstanding Property

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.

Owner's Response:

Thanks so much for staying at Windwardside. I am happy to hear that we exceeded your expectations. Our whole crew really tries to make sure that we give you the best possible vacation. Also, thank you for your review. Our guests experiences mean so much more than what we can tell potential renters. If you return to St. John we hope to see you again. Susan

on Apr 06, 2016
Even better second time around!

We stayed in the small guesthouse two years ago for our honeymoon, and couldn't wait to come back. This time we stayed in the main house and once again are counting the days until our return. Susan and her team leave nothing out...every detail is covered from the beautiful furnishings to providing us with all the information we needed for getting to and around the island. We loved it so much we recommended it to some friends who stayed there a few weeks before us. We went from there to Tortola, which was nice, but it wasn't the same because now we are spoiled!

on Apr 06, 2016
Wonderful place to stay in St. John

We can't say enough good things about our stay at Windwardside Main House. You always wonder when you rent a place to stay if it will look as good as the pictures. Well, this place was even better than we could have imagined from the pictures. The customer service provided by Diane and Fitz throughout this process (from making the reservation, through the day we left) was superb. Fitz met us at the ferry, took us to pick up our rental car, took us to the grocery store and then to the house (and was very patient while we gathered our goods at the store). Diane checked on us after a couple of days to ensure we didn't have any questions or need anything. I've never had quite an experience like that when renting a property on vacation. The house had all the necessities for cooking, had beach items (towels, chairs, coolers and snorkeling gear), was quiet, and had spectacular views. The grounds were beautifully planted, and we could sit on the porch in the morning with our coffee, taking in the view and watching all the birds. We were concerned about renting a place that didn't have air conditioning in the bedroom, but we quickly got use to it, and the ceiling fan and breezes through the screened doors and windows made it very pleasant (an added plus to having no glass windows was being able to listen to the beautiful symphony of the night was wonderful!). Some might think the drive up to the house is a bit daunting, but after a couple of times doing it, you become a pro. We were sad to leave such a beautiful place, but hope to be back very soon, and will definitely plan on staying here again.
--Donna & David

Owner's Response:

Dear Donna, Thanks for staying with us and for the lovely review. I'm so glad that you enjoyed the chorus of tree frogs and crickets. Even after thirty years on St. John I still love those sounds. I will pass your kind words on to Diane and Fitz. Susan


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