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Fair Winds Cottages - Great for 2-4 people

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Outdoor dining area of the Main House
Relaxation and dining areas of the Main House
Welcome to Fair Winds Cottages
Coral Bay, the East End of St. John, Tortola and beyond from the Main House
The East End of St. John, part of the Virgin Islands National Park

Reviews

9.8 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 41000 sq ft

Popular amenities

  • Kitchen
  • Outdoor space
  • Parking available
  • Barbecue grill
  • Mountain view

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

2 bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen
Garden
Dining area

About this property

Fair Winds Cottages - Great for 2-4 people

Fair Winds Cottages is a colorful, well-appointed vacation property situated mountainside, overlooking Coral Bay. The villa offers truly spectacular views and offers privacy in its natural/garden setting. This delightful home is the perfect location for a honeymoon or romantic getaway. For couples vacationing together, the guest house provides a connected, yet private getaway with fully-equipped accommodations.

The main house, with its open floor plan, provides a living/dining area as well as a kitchen. It is connected to the master bedroom via a private deck with excellent views. A second building, connected to the main house by decks and a lighted tropical garden pathway, also offers full accommodations. It has a living/dining area, kitchen, bedroom and bathroom similar to the main house.

All rentals run from Saturday to Saturday. Requests with non-Saturday arrival dates will automatically be declined.

A 4 Wheel Drive Vehicle (Jeep or similar) is required to stay at this property. Nothing is within walking distance of the houses. It is your responsibility to book a vehicle. They do sell out during high season, so it's never too early to book one. If you are booking last minute please be sure you can secure a vehicle before confirming a booking.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 13–17
Guest house connected to main house by deck.
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking allowed: in designated areas

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is no carbon monoxide detector on the property, but there are gas appliances; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

We should mention

A car is required for transport to and from this property

About the area

St. John

Located in St. John, this holiday home is in the mountains and near the beach. While the natural beauty of Virgin Islands National Park and Trunk Bay can be enjoyed by anyone, those looking for an activity can explore Tortola Cruise Ship Port. Scuba diving and snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and hiking nearby.
View more Holiday homes in St. JohnOpens in a new window
Map
Coral Bay, USVI

What's nearby

  • Johnson Bay - 8 min walk - 0.7 km
  • Virgin Islands National Park - 3 min drive - 3.0 km
  • Cinnamon Bay Beach - 19 min drive - 10.5 km
  • Trunk Bay - 24 min drive - 11.3 km
  • Honeymoon Beach - 27 min drive - 14.9 km

Getting around

  • St. Thomas (SPB-St. Thomas Seaplane Base) - 98 min drive

Restaurants

  • Sebastian’s Seaside Grill
  • ‪Shambles - ‬22 min drive
  • ‪Maho Crossroads - ‬13 min drive
  • ‪Skinny Legs - ‬6 min drive
  • ‪Paddle-In Tiki Bar - ‬13 min drive

Frequently asked questions

Is Fair Winds Cottages - Great for 2-4 people pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Fair Winds Cottages - Great for 2-4 people?

As of 1 Apr, 2026, prices found for a 1-night stay for 2 adults at Fair Winds Cottages - Great for 2-4 people on 30 May, 2026 start from S$418, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Fair Winds Cottages - Great for 2-4 people?

On-site parking is available at the property.

What time is check-in at Fair Winds Cottages - Great for 2-4 people?

Check-in begins at 4:00 PM.

What time is check-out at Fair Winds Cottages - Great for 2-4 people?

Checkout is at 10:00 AM.

Where is Fair Winds Cottages - Great for 2-4 people located?

Situated by the sea, this holiday home is 0.6 mi (0.9 km) from Johnson Bay and 2.2 mi (3.5 km) from Virgin Islands National Park. Emmaus Moravian Church and Lameshure Beach are also within 3 miles (5 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 23 out of 26 reviews
Rating 8 - Good. 3 out of 26 reviews
Rating 6 - Okay. 0 out of 26 reviews
Rating 4 - Poor. 0 out of 26 reviews
Rating 2 - Terrible. 0 out of 26 reviews

9.8/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.6/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Lois S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was awesome! She was easy to communicate with and very accommodating. Answered any questions we had in a timely and kind manner.
Stayed 7 nights in Feb 2026
Verified

10/10 Excellent

Pat H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Margaret was wonderful! She answered all our questions promptly. The house was lovely and spotless! Everything you need for a relaxing vacation. AND a million dollar view!
Stayed 14 nights in Jan 2026
Verified

10/10 Excellent

Steven R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to stay on St John

Great views greet you each morning with the sunrise and tuck you in bed at night. Well appointed and maintained. Would definitely recommend.
Stayed 7 nights in Dec 2023
Verified

10/10 Excellent

Julie F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Island Vacation

We stayed at Fair Winds 12 years ago and were delighted to recently stay again. It’s a perfect setup for 2 couples and the views cannot be beat. The home is well maintained and very clean and the host is very responsive. It’s a quick drive to north or south shore beaches and there are several restaurant and grocery options nearby. We highly recommend!
Stayed 7 nights in Feb 2025
Verified

10/10 Excellent

Colleen T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Breathtaking views

Sunrise watch from bedrooms and star gazing at night and seeing birds eat the sugar from the coconut was blissful!
Stayed 28 nights in Mar 2023
Verified

10/10 Excellent

Rob W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pure Paradise

Property Offers Awesome Views. enjoyed the sunrise over the ocean right from our bed. Not too far from Coral Bay and surrounding Beaches. We will be back
Stayed 7 nights in Jan 2023
Verified

8/10 Good

Whitney M.

Liked: Cleanliness, communication, location, listing accuracy
The stay at Fair Winds was enjoyable. The view is absolutely stunning and worth the treacherous drive up to the property. Be sure to know that the drive up/down is partially on a very rutted out and rough road. It takes about 5-7 minutes to drive up and down the drive to get to the property and leave. The home was nice and comfortable. You get to see the sunrise every morning from bed. The location in Coral Bay is very quiet and not close to all the action in Cruz Bay. The kitchen was well equipped with dishes to cook with and glass containers to store food. The host was helpful and accomodating.
Stayed 9 nights in Sep 2025
Verified

10/10 Excellent

Will K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing sweet spot on the island

Fabulous views, a great deck, a quiet place on the east side of the island. We were a family of four (two older children 16+) who stayed for a week in April. The place was pretty perfect for us and we made extensive use of the gas grill and had great drinks and dinners on the deck while looking out at the hard to believe views. The place is cute, clean, and well equipped - we definitely took advantage of the beach towels and chairs. We would highly recommend to anyone looking for a private quiet spot near Coral Bay.
Stayed 7 nights in Apr 2023
Archival

10/10 Excellent

lisa and David k.

Great Getaway!

This cottage was perfect for our family of 4. We have 2 teen daughters who were able to enjoy their own personal space which included all the amenities of an efficiency apartment and their own hot tub! The main cottage was just a few steps away. The view of coral bay and the surrounding islands from the wrap around porch was like no other. We enjoyed the full sunrise every morning. The breezes, surrounding horticulture, tree frog symphony, and starry nights were both peaceful and invigorating. There is an amazing climb up a windy dirt road....4 wheel is a must!! We landed in St. John, rented a Jeep, did a grocery run, and took the car ferry to St. John. Margaret and Bryan were extremely helpful in getting us to the house and answering any questions we had during the week. The hiking, beaches, sailing, relaxing and tranquility can not be beat at St. John and Fairwinds Cottage is a phenomenal place to vacate!
Verified

10/10 Excellent

Kim W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

SPECTACULAR - THE VIEW!!!

My husband and I enjoyed every minute of our stay at Fair Winds. Accommodations are very clean and comfortable, well equipped kitchen, plenty of towels, beach chairs, etc... pretty much everything you need! I've seen some talk about the road up, but we didn't think it was terrible. The view is spectacular! We were a little worried about it being warm, but with the constant breeze, fans, windows, and sliding glass doors, the temperatures stayed very comfortable. This is a perfect set up for 2 couples or a family with older children, offering plenty of privacy and space. Treat yourself to a day on the water with Busy Bee Charters! We did and loved it! Justin W. was our captain and he was excellent! He is very knowledgeable about the history of the Virgin Islands, and took us to some great snorkeling spots! Margaret, the manager, was awesome! She always responded promptly and made sure we had everything we needed. Even provided recommendations of places to go and what to see on St. John! If you're looking for a great place to stay with a great view in Coral Bay, then this is the place!
Stayed 7 nights in May 2021
Response from VrboOwner on 17 May, 2021
Thank you so much for the great review! It was a pleasure to host you and I'm so glad you enjoyed the house.
Verified

10/10 Excellent

kevin b.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome views and perfect layout.

The morning views from anywhere on site are the perfect start to your morning and the layout is great for teenagers to have their separate space. The kitchen was well stocked with all necessities plenty of bath and beach towels, beach chairs and cooler for daily adventures. Everybody enjoyed the outdoor shower over the indoor one and the water filtration makes the tap water just as good as bottled water which was great, one less thing to worry about. The drive up the hill with a jeep is no factor and gives you an opportunity to say hello to the chickens, deer and donkeys, overall great trip and would definitely stay at Fair Winds again. Thank Y'all.
Stayed 7 nights in Apr 2022
Verified

10/10 Excellent

Hollie D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best view on the island!

We were blown away by the view of Coral Bay, along with the well groomed gardens around the villa. Loved hearing all the birds and frogs. Exceptional! The driveway is an adventure, but just makes it that much sweeter!
Stayed 7 nights in Jan 2022
Verified

10/10 Excellent

Bernard Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Stunning views and very comfortable

Very peaceful and relaxing place to stay with killer views and wonderful indoor and outdoor space. Hot tubs were great. Really nice breezes throughout the day. A little bit of a trek to get up to the house but worth it for what you get.
Stayed 7 nights in Jan 2022
Verified

10/10 Excellent

Ann S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Incredible

I can not say enough about this property, and Margaret, the property manager. We had such a special trip. The property is ideal for a pair of couples traveling together to share a space and also have a lot of privacy. We really enjoyed the hot tubs after a day of hiking and snorkeling, the view made this such an incredible experience. We will absolutely rent this property again.
Stayed 12 nights in Dec 2021
Verified

8/10 Good

Yuri P.

Liked: Cleanliness, check-in, communication, listing accuracy

Beauty of st John

The property have very nice view But getting up there is not fun the road is bumpy and steep Inside we found scorpion in the bathroom and lizard and spider in the bedroom Mosquito were bad
Stayed 7 nights in Dec 2021
Verified

10/10 Excellent

Michael L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for Teens

The property was perfect for us traveling with two teens. Kids had there own space for privacy and the main house and deck area was big enough and great for family time. The views from the cottage were the best we saw during our entire stay. It is near the top of the mountain and the road is a little steep at parts. It made my wife a little nervous, but we had absolutely no problems getting up there with our jeep. We were there in July and we were concerned that it would be uncomfortable with no AC. The breezes up there are incredible and kept us cool with just ceiling fans. We will definitely return to this cottage.
Stayed 8 nights in Jul 2021
Verified

10/10 Excellent

Karen S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gorgeous sunrise views

We thoroughly enjoyed our stay at Fair Winds. The separate cottages allowed our grown children to have their own space and privacy. The place was immaculate and well-stocked when we arrived. Margaret, the manager, was available to assist with any questions and gave great advice about the area. Every morning I awoke to a gorgeous sunrise and each evening fell asleep to a cooling breeze. We had a fantastic vacation and I would highly recommend staying at Fair Winds Cottages to any couple or family with grown children visiting St. John.
Stayed 7 nights in Jun 2021
Verified

10/10 Excellent

joanne m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful place to stay on St. John

We were very pleased with this house for our vacation. The views are amazing, the house is very clean and well-equipped, the property manager is very prompt to respond. I was glad we rented both cottages since the main house does not have an indoor shower - which it does mention in the description but I had missed. Also, other reviews mention the rugged road to the house - but it's so challenging that I think it should be included in the property description. Beyond the expected switchbacks, the road itself is in terrible condition and the steepness going up and down is not something that every driver would be comfortable with. We did fine with it - but our driver is very experienced. It won't stop us from returning but I think people should be warned and prepared for it. Other than that, the house was perfect!
Stayed 7 nights in Jan 2020
Verified

10/10 Excellent

William L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic view!!

Everything was great except the last mile of road getting to the house. It really needs some work.
Stayed 9 nights in May 2019
Archival

10/10 Excellent

cathy m.

All and more!

Remote, private, inspiring, beautiful, romantic...this place is everything as advertised and more. We will be back!
Archival

10/10 Excellent

Valerie C.

Fantastic views! Great house!

We rented the main house for a week. All of the photographs are accurate and don't do justice to how beautiful the views are. The house was well equipped. The separate bedroom was a nice retreat and the outside shower was very enjoyable. Keep the Bananaquits sugar feeder full and they will entertain you every day. This is just a few minutes drive to the restaurants and grocery stores in Coral Bay. Due to the steepness and ruggedness of the road, a Jeep or other 4-wheel drive vehicle is necessary.
Archival

10/10 Excellent

Toddi N.

Couldn't have been better

Fair Winds was my best booking yet on St. John, and we've stayed 7 times. We shared this spot with my bestie and her hubby from Los Angeles, cooked our own gourmet meals and ate on the deck when we weren't enjoying the island restaurants. The tree frogs noises were amazing to sleep with at night and house was super comfortable, fun, and the views, simply amazing. We took a private charter to the USVI and spent a couple of days with Captain Phil on his boat. What a great trip and the price was right. My friend's husband is not much of a vacation guy but he's been asking to go back! Brian and Margaret are great managers. For us, this was equal to the trip of a lifetime.
Archival

10/10 Excellent

Meredith R.

Once in a Lifetime view!

The Amazement and adventure of our drive to the top of Calabash Boom, was equally matched and exceeded by our view at the top! The pictures shown here, although beautiful, cannot adequately describe the wonder. This beautiful villa and accompanying guest house are perfectly appointed for relaxation, light entertaining and a soak in the jacuzzi after the beach. A quick trip to the market for easy breakfast foods,snacks and ice pretty much equipped us for our stay. This is the perfect getaway spot for a family of four or a getaway with a few friends. If you arrange to stay here they will be your best friends for life! MUST visit Trunk Bay and Waterlemon Cay (Swim out to island to snorkel!) Enjoy!
Archival

10/10 Excellent

Joy M.

gorgeous

The ideal place to be on St. John's for the view, the accomodations, the beaches, and snorkeling. Very desirable if you want to be on the quieter side, and we enjoyed the local feel of the restaurants. Managers Bryan and Margaret were helpful with travel arrangements.
Archival

10/10 Excellent

Wonderful Get Away

Property is excellent for a family with teens or two couples, as the sleeping units are separated by a common area. It allows for group socialization, but also individual retreat and privacy if desired. Beautiful panorama of Hurricane Hole and the BVI's beyond. Convenient to Coral Bay restaurants and hiking Ram's Head. 30 min. drive to Cruz Bay. Margaret and Bryan manage the property and are very helpful and nice. Great get away.

About the host

Hosted by Margaret

Host profile image

Languages:

English
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