Windwardside: Quiet, Great View, Hot Tub, Elegantly Appointed, Lush Gardens

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Last updated: 11/27/2015
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:1-7 nights
  • Internet:Yes
  • Pets considered:No
  • Wheel chair accessible:No

Special offer: Holiday Special $500 Off Weekly Rental Details

Property description

Windwardsie 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.

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!


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Property Type

  • Villa

Accommodation Type

  • Vacation Rental


  • Guests Provide Their Own Meals


  • Pets Not Allowed
  • Wheelchair Inaccessible

Bedrooms: 1 Bedroom, Sleeps 2

Bathrooms: 2 Bathrooms


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


  • Adventure
  • Away From It All
  • Romantic


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

Local Services & Businesses

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

Leisure Activities

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

Location Type

  • Mountain
  • Mountain View
  • Near The Ocean
  • Ocean View
  • Rural
  • Water View

Sports & Adventure Activities

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


  • Dining Room
  • Seating for 4 people


  • 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
  • Stove
  • Stove
  • Toaster


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

    Snorkel gear...moreless

  • Wood Deck

Pool / Spa

  • Hot Tub
  • Outdoor Hot Tub


Write a review 5
from 20 traveler reviews

Special offer: Holiday Special $500 Off Weekly Rental

Holiday special $500 off Sunday to Sunday weekly rentals in December! December 13-20 regular rate $2335 now $1835 plus 10% hotel tax. December 20-27 or December 27 - January 3 regular rate $2555 offered at $2055 plus 10% tax. (Hotel Tax increases to 12.5% on January 1, 2016)

Offer for: Dec 13, 2015 - Jan 3, 2016 View calendar

Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
Low Season
Sep 27 - Dec 14, 2015
7 night min stay


Changeover Day: Sunday

High Season
Dec 15 - Apr 15, 2016
7 night min stay


Changeover Day: Sunday

Low Season 2016
Apr 16 - Dec 14, 2016
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)

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.

Please wait... Travel with Confidence

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Last updated: 11/27/2015
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates


20 Miles
Nearest Airport
St. Thomas
1 Miles
Nearest Barpub
Shipwreck Landing
8 Miles
Nearest Ferry
Cruz Bay
1 Miles
Nearest Restaurant
Shipwreck Landing
2 Miles
Nearest Beach
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


Manager 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)

  • Layout showing Main House and neighboring cottage

    Layout showing Main House and neighboring cottage

  • 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

  • living room view

    living room view

VRBO #1249

This listing was first published here in 1998.

Date last modified - Monday, November 30, 2015

Minimum stay: 1-7 nights
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  • Reviews
  • Sleeps
  • Bedrooms
  • Bathrooms
  • Property type
Member since: 1998
Speaks: english
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  • Response time Within an hour
  • Response rate 100%
  • Calendar last updated 11/27/2015

+1340 7766368

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

Coral Bay #210716ha

1 BR  2 BA  Sleeps 2

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