HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag

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

23 Reviews
Bedrooms 1
Property type villa
Minimum Stay 7 nights


Minimum Stay
7 nights


Photos and Description of this 1 bedroom holiday villa in Calabash Boom - Windwardside Main House

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: Rentals run from Sunday to Sunday. We have two rates: Low season from April 16 to December 14 and High season from December 15 to April 15. The rates are as stated in the rates section. 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. There are no extra costs for reservations, cleaning or service. 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 information about our rentals is easily found.

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!

More Details
  • pets not allowed
  • wheelchair inaccessible

Property Manager
Susan Brierley
Member since: 1998
Speaks English
Response time:
Within an hour
Response rate:
Calendar last updated:
28 October, 2016
Call Manager

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 St John

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 allowed 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.


based on 23 holidaymaker reviews

Windwardside: Quiet, Great View, Hot Tub, elegantly appointed, lush gardens
average rating of 5.0 based on 23 reviews
Pasadena, CA USA

Tropical Oasis

  • 5 of 5

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.

  • Review Submitted: Jun 15, 2016
  • Date of Stay: Jan 2016
  • Source: VRBO, from HomeAway
Owner's Response: 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
Did you find this review helpful?
0 0
Tupper Lake, N.Y., USA

Absolutely Beautiful!!!

  • 5 of 5

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.

  • Review Submitted: May 11, 2016
  • Date of Stay: Apr 2016
  • Source: VRBO, from HomeAway
Owner's Response: 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.
Did you find this review helpful?
0 0
Bologna, Italy

Paradiso a St John

  • 5 of 5

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!

  • Review Submitted: Mar 29, 2016
  • Date of Stay: Mar 2016
  • Source: VRBO, from HomeAway
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!
Did you find this review helpful?
0 0
Bedminster NJ

Everything we could have dreamed!

  • 5 of 5

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.

  • Review Submitted: Feb 6, 2015
  • Date of Stay: Jan 2015
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0
Richmond, VA, USA

Batting 1000 for three years running

  • 5 of 5

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!!

  • Review Submitted: Dec 15, 2014
  • Date of Stay: Dec 2014
  • Source: VRBO, from HomeAway
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
Did you find this review helpful?
1 0

Vacation of a lifetime!

  • 5 of 5

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!!!!

  • Review Submitted: May 26, 2014
  • Date of Stay: May 2014
  • Source: HomeAway
Did you find this review helpful?
2 0


Nearest Airport
20 Miles
St. Thomas
Nearest Barpub
1 Miles
Shipwreck Landing
Nearest Ferry
8 Miles
Cruz Bay
Nearest Restaurant
1 Miles
Shipwreck Landing
Nearest Beach
2 Miles
Salt Pond Bay
Car: necessary

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.

Other Activities: Hiking, kayaking


Prices & Availability

Prices for this holiday villa in Calabash Boom, St John

Rental Basis:
per property
Manager accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
Low Season 2016
16 Apr 2016 - 14 Dec 2016
7 night minimum stay
for 7 nights
High Season
15 Dec 2016 - 15 Apr 2017
7 night minimum stay
for 7 nights
Low Season 2017
16 Apr 2017 - 14 Dec 2017
7 night minimum stay
for 7 nights

Additional pricing information

There is an additional 12.5% hotel tax that will be added to the weekly rate.
12/15 to 4/15 $2555/week (2 Guests)
4/16 to 12/14 $1785/week (2 Guests)

Hotel tax in the Virgin Islands is increasing to 12.5% as of January 1, 2016.
Windwardside can be rented with or without the guest cottage. This home was designed to offer lots of flexibility when rented along with the neighboring guest cottage. Two couples traveling together can share the living room, dining room and kitchen of the 'great house', yet each will have their own cottage.

Check or money order. 50% percent due at time of reservation. Balance due 30 days before arrival.

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.
Enter dates for accurate pricing
Enquire Now
Available arrival


Accommodation and facilities for this holiday villa in Calabash Boom, Virgin Islands (US)

Property Type:
  • villa
  • Self-catering
Location Type:
  • mountain
  • Mountain View
  • near the sea
  • Ocean View
  • rural
  • Water View
  • Adventure
  • Away From It All
  • Romantic
  • Alarm Clock
  • Basic Soaps
  • Ceiling Fans
  • Filtered Water
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking Off Street
  • Safe
  • Telephone
  • Toilet Paper
  • Towels Provided
  • Wireless Internet
  • Blender
  • Coffee Grinder
  • Coffee Maker
  • Cooking Utensils
  • Freezer
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Hob
  • Stove
  • Toaster
  • Dining Room
  • seating for 4 people
  • 2 Bathrooms
  • Outdoor - Outdoor Shower
    Bathroom 1 - Toilet , Shower Enclosure
    Bathroom 2 - Toilet , Shower Enclosure
  • Enclosed outdoor shower garden
  • 1 Bedroom, Sleeps 2
  • Bedroom - 1 Large Double Bed
  • Books
  • CD Player
  • DVD Player
  • Radio
  • Stereo
  • Video Library
  • Balcony
  • Deck Chairs
  • Beach Towels
  • Terrace
  • Large Cooler
  • Garden
  • Barbecue
  • Outdoor Grill Gas
  • Patio
  • Veranda
  • Conservatory
  • Small Cooler
  • Terrace
  • veranda
  • Water Sports Gear ...
  • Wood Decking
  • 2 garden chairs
  • 4 deck chairs
  • pets not allowed
  • wheelchair inaccessible
Pool / Spa:
  • Hot Tub
  • Outdoor Hot Tub
  • bay
  • rain forests
  • reefs
  • restaurants
  • ruins
Leisure Activities:
  • beachcombing
  • eco tourism
  • horse riding
  • paddle boating
  • photography
  • walking
Local Services & Businesses:
  • ATM/bank
  • groceries
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • fishing
  • hiking
  • sailing
  • diving
  • snorkelling
  • swimming
  • tennis
  • wind-surfing

Partner Offers

Portable wifi hotspot

You might like these similar properties