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Fair Winds Cottages: Private villa with phenomenal views

Bedrooms 2
Space 1,000 sq. ft.
Property type house
Minimum Stay 7 nights


About the property

2 bedrooms, 2 bathrooms; sleeps 4.

Fair Winds Cottages is a cozy vacation property situated mountainside overlooking Coral Bay. The villa offers truly spectacular views as well as privacy. This delightful home is the perfect location for a honeymoon or romantic getaway. For couples vacationing together, the guest house provides 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.

The Main House can be rented alone for 2 people, or the Main and Guest can be rented together for up to 4 people. If just the Main House is rented the Guest House will remain vacant and locked.

All rentals run from Saturday to Saturday.

More Details

Property Manager
Bryan and Margaret
Member since: 2009
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
April 27, 2017

Guestbook comments from the manager

"We have loved our stay here at Fair Winds. This is our 10th trip to St. John and we've rented many houses all over the island but none with a view that

compares to the one here! It's like Camelot...gorgeous weather all day and rain during the night. Thanks for sharing your beautiful home.'
Apr 2010
  • 1 of 7


Calabash Boom House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 1000 sq. ft.
House Rules:
  • Max. occupancy: 4
  • non smoking only
  • pets not allowed
Location Type:
  • Mountain ...
  • Near The Ocean ...
  • Ocean View ...
  • Water View
  • Away From It All
  • Budget
  • Family
  • Romantic
  • Activities Guide
  • Alarm Clock
  • Basic Soaps
  • Ceiling Fans
  • Filtered Water
  • Hair Dryer
  • Iron & Board
  • Linens Provided ...
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Parking
  • Telephone ...
  • Thermos Bottle
  • Toilet Paper
  • Towels Provided ...
  • Wireless Internet
  • 4 Ring Stove
  • Blender
  • Coffee Grinder
  • Coffee Maker
  • Cooking Utensils ...
  • Dishes & Utensils
  • Grill
  • Ice Maker
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator ...
  • Stove
  • Toaster
  • Dining Area
  • seating for 4 people
  • 2 Bathrooms
  • Bathroom 2 - toilet , shower
    Bathroom 1 - toilet , shower , outdoor shower , Main House has an outdoor shower only.
  • 2 Bedrooms, Sleeps 4
  • Bedroom 1 - 1 queen
    Bedroom 2 - 1 queen
  • Books
  • CD Player
  • DVD Player
  • Radio
  • Satellite / Cable ...
  • Stereo ...
  • Television
  • Video Library ...
  • Beach Chairs
  • Beach Towels
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Small Cooler
  • Wood Deck
  • 6 garden chairs
  • wheelchair inaccessible
Pool / Spa:
  • Hot Tub ...
  • churches
  • duty free shops
  • reefs
  • restaurants
  • ruins
Leisure Activities:
  • beachcombing
  • bird watching
  • eco tourism
  • horseback riding
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • groceries
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • deepsea fishing
  • fishing
  • hiking
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • sound/bay fishing
  • swimming
  • tennis
  • wind-surfing
Flat screen TV's, Cambridge Sound Works radio/cd with i-pod docking station and MP3 capability provide full media access. Private sunbathing.

Learn more about this vacation rental at the manager's website:


Exceptional! 5/5 -
(7 traveler reviews)

Fair Winds Cottages: Private villa with phenomenal views
average rating of 5.0 based on 14 reviews

All and more!

  • 5 of 5

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

  • Submitted: Apr 13, 2015
  • Stayed: Mar 2015
  • Source: HomeAway
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1 0
Albuquerque New Mexico

Fantastic views! Great house!

  • 5 of 5

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.

  • Submitted: Mar 29, 2015
  • Stayed: Jan 2015
  • Source: HomeAway
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2 0
New England

Couldn't have been better

  • 5 of 5

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.

  • Submitted: Mar 9, 2015
  • Stayed: Oct 2014
  • Source: VRBO, from HomeAway
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2 0

Great Getaway!

  • 5 of 5

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!

  • Submitted: Jan 8, 2015
  • Stayed: Dec 2014
  • Source: VRBO, from HomeAway
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2 0

Once in a Lifetime view!

  • 5 of 5

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!

  • Submitted: May 13, 2014
  • Stayed: Feb 2014
  • Source: HomeAway
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4 0


  • 5 of 5

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.

  • Submitted: Feb 17, 2014
  • Stayed: Feb 2014
  • Source: HomeAway
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1 0


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

Tranquil, tropical getaway, cooled by prevailing Trade Winds and located a mile up a dirt/concrete road. Spectacular 180 degree views of Coral Bay, the East End of St. John and the British Virgin Islands. Memorable sun and moon rises over the Bay. Convenient to beaches, restaurants, shops, grocery stores, hiking trails and boating.


Rates & Availability

Calabash Boom House Rental Rates

Rental Basis:
per property
Manager accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Main and Guest- Low Season
Apr 15 2017 - Dec 15 2017
7 night minimum stay
Main and Guest - High Season
Dec 16 2017 - Apr 13 2018
7 night minimum stay
My Standard Rate

Changeover Day: Saturday
7 night minimum stay

Additional information about rental rates

Tax Rate 12.5%

All rentals are from Saturday to Saturday.

For couples traveling alone we offer just the main house at a reduced rate. The guest house would remain empty and locked.
Main House Only - Low Season 2017 (4/15/17 to 12/15/17): Weekly rate -$1330 plus 12.5% hotel tax.
Main House Only - High Season (12/16/17-4/13/18) $1820 plus 12.5% hotel tax.

Check or money order. No Credit Cards.
50% due at booking, 50% 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

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