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Windwardside: Quiet, Great View, Hot Tub, elegantly appointed, lush gardens

$ 385
| | 2 Guests | 1 Bedrooms| 2 Baths
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Property Description

1BR Oceanview Vacation Rental St. John, Virgin Islands USA

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!

Reviews From Past Guests
“Perfect Oasis” by Christine
Date of Stay: 1/31/16

“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!”

“Everything we could have dreamed!” by Jen
Date of Stay: 1/25/15

“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” by Deb and Dave
Date of Stay: 12/7/14

“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!!”

“Stay here if ya wanna have an amazing adventure!” by Shayla L
Date of Stay: 9/28/14

“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 room…you 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 system…so 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 week…it 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 ; )”

“Vacation of a lifetime!” by Cassandra J.
Date of Stay: 5/19/14

“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!!!!”

“Windward Side” by KC
Date of Stay: 3/16/14

“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.”

“Outstanding Property” by Wayne J.
Date of Stay: 2/10/14

“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.”

“Even better second time around!” by Deanna J.
Date of Stay: 9/22/13

“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!”

“Wonderful place to stay in St. John” by Donna G.
Date of Stay: 5/12/13

“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”

“Great View” by Milwaukee
Date of Stay: 4/21/13

“The Windwardise Main House owned by Susan Brierley was perfect for us. The view overlooked Johnson Bay and was spectacular from both the house and the separate bedroom. Even though a couple was staying at the smaller cottage on the property, it was separated enough that we hardly knew they were there. The absolute privacy was just what we wanted.

The property was clean and ready for us when we arrived and could not have provided a better venue for our vacation. Even the view from the hot tub was amazing!

We can’t wait to come back!”

“Perfect Villa/ Exactly as Advertised” by Jody H.
Date of Stay: 11/18/12

“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” by daniel s
Date of Stay 10/22/12

“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.”

“Just As We Imagined” by Bryan C
Date of Stay: 9/2/12

“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!”

“This is the real deal” by Betsy and Meade
Date of Stay: 2/5/12

“Windwardside Main House is a good example of truth in advertising. The beautiful pictures on the Calabash Cottages Website are accurate images of what you will see when you arrive. This is a peaceful spot, without road or neighbor noise, where you can read on the porch overlooking Coral Bay. The beauty of this place relieves you of any pressure to hurry off and do stuff. Not that there’s not plenty to do. But we found that we were content to spend part of every day right there.
The property has been landscaped beautifully with tropical plants, totally private, which broadens the options for hot tub attire. Incidentally, the hot tub is new and in perfect working condition, as are beach chairs and snorkle equipment. We found that the owners want to know immediately if something is not in working order so that they can replace it. Which leads us to what made us know that this place was legit. after our first contact with owner, Susan Brierley. You will quickly notice fastidious attention to detail, anticipation of what you want to know next, and her immediate response to every communication. We suggest you follow her advice, and you will be grateful. Susan will check with you frequently to know if everything is OK. This owner gets an a+ on communication.
We chose to eat in most of the time, buying what we needed for the first couple of days in Cruz Bay after we arrived by ferry, where we were met by David (the nicest guy in the world, who led us patiently to the rental car place, grocery, and then to the house at the other end of the island). During the week, we got whatever we needed at Lily’s Market in Coral Bay and also bought fresh fish at the roadside. The yellow-tail snapper was fantastic. Our favorite place to snorkel was South Haulover Bay, where you can park right at the beach and there is a good coral reef to the right and the left without a long swim.
We hope to return to Winwardside Main House next year.”

“Loved Windwarside” by Allen K.
Date of Stay: 1/15/12

“My wife and I stayed at the Windwardside e for two weeks. We had a fabulous time. The villa 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 Windwardside highly enough. We have a place to return to on St. John.”

“The Perfect Retreat!” by Greytdoggie
Date of Stay: 2/6/11

“My wife and I rented Windwardside Main House back in 2007 and enjoyed it so much that we went back again this year for a winter getaway! It is the perfect retreat with fantastic views and lots of privacy. The great house is perfect for dining and the covered porch is a wonderful place to sit, relax, watch the birds feeding, and enjoy the view of Coral Bay! The bedroom is perfect and the outdoor shower is a real treat! I particularly enjoyed the courtyard and hot tub to unwind after a day of hiking and snorkeling.

We highly recommend Windwardside for anyone looking to stay on the ‘quiet side’ of the island. Susan and Diane are great to work with and I am certain we will be back again in the near future!”

“Wonderful last-minute getaway” by Heather Y
Date of Stay: 1/23/11

“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 4×4. 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 4×4 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.”

“We had a wonderful Honeymoon!” by Steve
Date of Stay: 1/2/11

“We LOVED our stay at the Windwardside main house. The pictures are very accurate and it is a wonderful place to get away from it all. The location on the east side of the island by Coral Bay is great for those who want to get away from the more “tourist” focused scene in Cruz Bay. We found the people in Coral Bay to be extremely friendly and the restaurants were the best on the island. Plus, the proximity to Salt Pond and Little Lameshur beaches was great since we like less of a crowd. I highly recommend this villa and hope to stay there again in the future. We’re hoping to rent both the main house and guest cottage sometime in the future with friends. It’s a perfect set up for two couples to share.”

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Property Price
Price per night: $ 385.00
Price per night
Minimum Booking days
Extra price per guest
Price per night in weekends
Booking starts only on
Booking starts/ends only on
From 2017-02-01 To 2017-04-15
$ 385.00
From 2017-04-16 To 2017-12-15
$ 275.00
From 2017-12-16 To 2018-04-15
$ 385.00
Property Details
Property Status: normal
Property Size: 1,200 ft2
Bedrooms: 1
Bathrooms: 2
Check-In Hour: 4 PM
Check-Out Hour: 10 AM
Cancellation Policy: Refunds only if house is rented for the same time. In that case there is no cancellation fee
Property Features
Hot Tub
Non Smoking
Wireless Internet


March 2023
April 2023

Susan Brierley

My husband Paul and I are long term residents of St. John. We love to travel and our travel almost always focuses on finding beautiful natural surroundings. My husband (a retired builder on the island) and I designed Windwardside and Sago Cottage (Calabash Cottages) with the intention of providing that to like minded guests. We care very much about preserving the beauty of Coral Bay. An important part of our design process was to create homes that nestled into the hillside rather than towering over it. We are very proud of how that succeeded without sacrificing anything in terms of the view. We take a very personal interest in our guests and never want to have someone disappointed in their stay with us. We have a small and dedicated staff that shares this view. We like to have a personal conversation with all of our potential guests. if we do not feel like one of our homes is a good fit for you we will honestly let you know that. If you do decide to stay with us you can be sure we will do everything possible to make your vacation all that you hoped it would be.

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