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Windwardside: Quiet, Great View, Hot Tub

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Courtyard and spa

Courtyard and spa Covered porch Bedroom with deck view from spa View from deck Dining Room Kitchen Hurricane Hole from porch Exterior dining table Detached bedroom overlooking courtyard Living area (left), courtyard and bedroom (right) Chair on covered porch living room view Layout showing Main House and neighboring cottage Dining/ seating area


Last updated: 04/21/2014
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:7 nights
  • Internet:Yes
  • Pets considered:No
  • Wheel chair accessible:No

Coral Bay villa description

This elegant, charming and romantic retreat (perfect for a honeymoon!) features lovely furnishings, a beautiful view and lush tropical gardens. The main house consists of two buildings that surround the large brick courtyard with spa. One of these buildings, the master bedroom, has a veranda overlooking the courtyard and is furnished with a four-poster mahogany bed, handcrafted on the island. The other building, the 'great house,' contains the dining room (situated in a cozy screened porch), the kitchen and the living room, as well as a covered porch from which the serene view of the Caribbean Sea can be enjoyed at leisure.

Property Type

      • Villa

      Accommodation Type

          • Vacation Rental


              • Guests Provide Their Own Meals


              • Wheelchair Inaccessible
              • Pets Not Allowed

              Bedrooms: 1 Bedroom, Sleeps 2

              Bathrooms: 2 Bathrooms


              • DVD Player
              • Radio
              • Stereo
              • CD Player
              • Books
              • Video Library


              • Away From It All
              • Adventure


                  • Necessary


                  • Restaurants
                  • Bay/Sound
                  • Rain Forests
                  • Reefs
                  • Ruins

                  Leisure Activities

                  • Horseback Riding
                  • Eco Tourism
                  • Paddle Boating
                  • Beachcombing
                  • Walking
                  • Photography

                  local services and businesses

                  • Groceries
                  • Medical Services
                  • Laundromat
                  • ATM/Bank
                  • Massage Therapist

                  Location Type

                  • Rural
                  • Mountain
                  • Near The Ocean

                  sports and adventure activities

                  • Swimming
                  • Wind-Surfing
                  • Fishing
                  • Tennis
                  • Scuba Diving Or Snorkeling
                  • Snorkeling
                  • Sailing
                  • Hiking

                  catering options

                      • Guests Provide Their Own Meals


                          • Dining Room


                          • Internet
                          • Wireless Internet
                          • Alarm Clock
                          • Ceiling Fans
                          • Filtered Water
                          • Hair Dryer
                          • Local Activities Guide
                          • Local Maps
                          • Paper Towels
                          • Local Restaurant Guide
                          • Basic Soaps
                          • Toilet Paper
                          • Telephone
                          • Linens Provided
                          • Parking Off Street
                          • Towels Provided
                          • Safe
                          • Iron & Board


                          • Freezer
                          • Coffee Maker
                          • Toaster
                          • Refrigerator
                          • Oven
                          • Microwave
                          • Blender
                          • Coffee Grinder
                          • Stove
                          • Cooking Utensils
                          • Pantry Items


                          • Beach Chairs
                          • Beach Towels
                          • Large Cooler
                          • Small Cooler
                          • Outdoor Grill Gas
                          • Wood Deck
                          • Lawn / Garden
                          • Porch / Veranda
                          • Terrace
                          • Balcony
                          • Patio
                          • Unscreened Porch / Veranda
                          • Screen Porch / Veranda
                          • Outdoor Grill
                          • Deck / Patio

                          Pool / Spa

                          • Hot Tub
                          • Outdoor Hot Tub


                          Write a review
                          • Windward Side

                            Windward Side

                            • Guest KC (tewksbury, ma)
                            • Date of stay 03/16/14
                            • Review Submitted 03/24/14
                            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.

                            Owner 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

                            Did you find this review helpful? Yes | No Helpful votes: 0/0

                          • Outstanding Property

                            Outstanding Property

                            • Guest Wayne J.
                            • Date of stay 02/10/14
                            • Review Submitted 02/21/14
                            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.

                            Owner 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

                            Did you find this review helpful? Yes | No Helpful votes: 0/0

                          • Even better second time around!

                            Even better second time around!

                            • Guest Deanna J.
                            • Date of stay 09/22/13
                            • Review Submitted 10/03/13
                            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!

                            Did you find this review helpful? Yes | No Helpful votes: 1/1

                          • Wonderful place to stay in St. John

                            Wonderful place to stay in St. John

                            • Guest Donna G. (Durham, NC)
                            • Date of stay 05/12/13
                            • Review Submitted 05/25/13
                            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

                            Owner 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

                            Did you find this review helpful? Yes | No Helpful votes: 3/3

                          • Perfect Villa/ Exactly as Advertised

                            Perfect Villa/ Exactly as Advertised

                            • Guest Jody H.
                            • Date of stay 11/18/12
                            • Review Submitted 11/28/12
                            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

                            Did you find this review helpful? Yes | No Helpful votes: 5/5

                          • wonderful


                            • Guest daniel s.
                            • Date of stay 10/22/12
                            • Review Submitted 11/06/12
                            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.

                            Owner response: We were very happy to read your review. Nice to know how much you enjoyed your stay. We look forward to hosting you and your family in the future. Thank you for writing!

                            Did you find this review helpful? Yes | No Helpful votes: 2/2

                          • Just As We Imagined

                            Just As We Imagined

                            • Guest Bryan C.
                            • Date of stay 09/02/12
                            • Review Submitted 10/09/12
                            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!

                            Owner response: Thank you so much for your detailed review. I am so glad to hear that you enjoyed your stay. I will pass on your comments to Bruce. I am sure he will be happy to hear them. September is a mixed bag on St. John. Half of the restaurants are closed but it is an even more relaxed time on the island when we all get a chance to slow down and talk to each other and the visitors. The beaches are quieter than ay other time of the year. We hope to see you again soon- Susan

                            Did you find this review helpful? Yes | No Helpful votes: 4/4

                          • Loved Windwarside Cottage

                            Loved Windwarside Cottage

                            • Guest Allen K. (Brooklyn, New York USA )
                            • Date of stay 01/15/12
                            • Review Submitted 02/03/12
                            My wife and I stayed at the Windwardside Cottage for two weeks. We had a fabulous time. The cottage 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 the Windwardside Cottage highly enough. We have a place to return to on St. John.

                            Owner response: Dear Allen and Helen, I am so glad that you enjoyed your stay at Windwardside Main House. We appreciate the detail in the review. It means a lot for guests to hear about the experiences of past visitors. Enjoy your safai next year and we know we will see you in the future. Warm regards, Susan PS: For those reading this review the guests refer to Windwardside Cottage. The actually stayed at Windwardside Main House which is the neighboring home to Windwardside guest Cottage.

                            Did you find this review helpful? Yes | No Helpful votes: 3/3

                          • Wonderful last-minute getaway

                            Wonderful last-minute getaway

                            • Guest Heather Y. (Washington DC)
                            • Date of stay 01/23/11
                            • Review Submitted 02/13/11
                            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 4x4. 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 4x4 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.

                            Recommended for: Romantic getaway, adventure seekers.

                            Did you find this review helpful? Yes | No Helpful votes: 5/5

                          • We had a wonderful Honeymoon!

                            We had a wonderful Honeymoon!

                            • Guest Steve (Boston, MA.)
                            • Date of stay 01/02/11
                            • Review Submitted 01/11/11
                            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.

                            Recommended for: Romantic getaway, adventure seekers, sightseeing.

                            Did you find this review helpful? Yes | No Helpful votes: 1/1

                          Rental basis: Per property
                          Dates Nightly Weekend Night Weekly Monthly * Event
                          Low seaon
                          Apr 16 - Dec 14, 2014
                          7 night min stay


                          Changeover Day: Sunday

                          High Season
                          Dec 15 - Apr 15, 2015
                          7 night min stay


                          Changeover Day: Sunday

                          Low Season
                          Apr 16 - Dec 14, 2015
                          7 night min stay


                          Changeover Day: Sunday

                          Additional information about rental rates


                          • Tax Rate 10%



                          12/15 to 4/15 $2555/week (2 Guests)

                          4/16 to 12/14 $1785/week (2 Guests)

                          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.

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                          Last updated: 04/21/2014
                          Check availability
                          23 Available
                          21 Unavailable
                          22 Today
                          23 Selected dates


                          • Nearest Airport: St. Thomas at 20 Miles
                          • Nearest Beach: Salt Pond Bay at 2 Miles
                          • Nearest Restaurant: Shipwreck Landing at 1 Miles

                          Owner info

                          Contact us

                          Speaks: english



                          • Courtyard and spa

                            Courtyard and spa

                          • Covered porch

                            Covered porch

                          • Bedroom with deck

                            Bedroom with deck

                          • view from spa

                            view from spa

                          • View from deck

                            View from deck

                          • Dining Room

                            Dining Room

                          • Exterior dining table

                            Exterior dining table

                          • Living area (left), courtyard and bedroom (right)

                            Living area (left), courtyard and bedroom (right)

                          • living room view

                            living room view

                          • Dining/ seating area

                            Dining/ seating area

                          • Kitchen


                          • Hurricane Hole from porch

                            Hurricane Hole from porch

                          • Detached bedroom overlooking courtyard

                            Detached bedroom overlooking courtyard

                          • Chair on covered porch

                            Chair on covered porch

                          • Layout showing Main House and neighboring cottage

                            Layout showing Main House and neighboring cottage

                          $1,785 - $2,555 per week (USD)

                          1 Bedroom / 2 Bathroom
                          Sleeps 2

                          View calendar: Updated 04/21/14
                          Minimum stay: 7 nights
                          Dates are unavailable
                          Please stay a bit longer. A stay of nights or more is required for these dates.
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                          +1 340 776-6368

                          Speaks: english
                          Always make sure to call the number on the listing to confirm payment details. Only pay using credit card, PayPal, check, or direct bank transfer. Learn More
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