Deck, hot tub, and view - Windwardside Main House - St. John
courtyard, bedroom and main house - Windwardside Main House - St. John
courtyard - Windwardside Main House - St. John
bedroom - Windwardside Main House - St. John
bedroom and courtyard - Windwardside Main House - St. John
dining room and view - Windwardside Main House - St. John
living room - Windwardside Main House - St. John
kitchen - Windwardside Main House - St. John
porch and view - Windwardside Main House - St. John
porch - Windwardside Main House - St. John
bedroom - Windwardside Main House - St. John
lounge area - Windwardside Main House - St. John
main house bathroom - Windwardside Main House - St. John
hot tub and view - Windwardside Main House - St. John
blueprint of the property (windwardside guest cottage is located on the right) - Windwardside Main House - St. John
Windwardside is an elegant retreat with a beautiful view and lush tropical gardens
Hosted by Calabash


This traditional West Indian style home consists of multiple buildings with a large central courtyard. The mainhouse consists of two buildings: the first is a detached bedroom / bathroom with a veranda that looks over the courtyard, gardens and sea; the second is the “great house”. The great house is entered though a roomy screened-in porch which holds a beautifully furnished dining room and a cushioned window seating area. There is a full kitchen and living room, an adjoining bath, plus an inviting covered porch overlooking the sea. Larger groups can rent Windwardside guest cottage as an additional bedroom.


Full Kitchen
Hot Tub


Mountain biking
Horseback riding


Not Child friendly
Parking Included
There is a gravel lot that is shared with "Windwardside Guest Cottage" which is next door to Windwardside Main House
Not Wheelchair Accessible


These directions are for planning purposes only. You may find that construction projects, traffic, weather, or other events may cause conditions to differ from the map results, and you should plan your route accordingly. You must obey all signs or notices regarding your route.
Check in
Check out
Add date
Add date
1 guest
Enter dates and number of guests to view the total trip price, including additional fees and any taxes.
Report this listing


Property Manager

Policies and Rules

Check In: 4PM - Flexible
For first time visitors to the islands or if “it’s been a while” we prefer to meet you at the dock on St. John. We will then take you to pick up your rental car and stop for groceries before showing you out to the house. If you feel quite familiar with the island we can also arrange to meet you in Coral Bay. Whoever shows you into the house will give you a basic orientation and also go over the map. They will discuss your interests and make suggestions to help you enjoy your stay on the island as much as possible. They will point out some of the best beaches, snorkel spots, hiking trails, restaurants and shops. Feel free to ask them any questions that will enhance your stay. Our greeters are all enthusiastic residents of the island that are hoping to make your vacation as much fun as possible.
Read more
Check Out: 10AM
No parties or events
No pets
No smoking
House Rules
House rules? Have a wonderful vacation, please conserve water, and let us no if there are any repairs needed or anyway we can make your vacation more enjoyable.
Refundable Damage Deposit
We do not collect a damage deposit. We treat our guests with care and ove the years we have found the return the favor.
Cancellation Policy
In case of a cancellation any we make every attempt to refill the vacancy. In that case we refund your payment with out any cancellation or administrative fee. If we need to create a last minute discount in order to fill your week that discount will be deducted from you refund. If we are not able to refill the time held for you no refunds or rescheduling is possible. We highly encourage our guests to obtain trip cancellation insurance.
Read more
© Calabash and Houfy Inc. Unauthorized use and/or duplication of this material without express and written permission from this page's author and/or owner is strictly prohibited. Excerpts and links may be used, provided that full and clear credit is given to Calabash and Houfy Inc. with appropriate and specific direction to the original content.
For more information, please visit the Houfy's copyright and trademark policy

Windwardside Main House - St. John is a Villa located in St. John, U.S. Virgin Islands. This Villa is available for short term lodging and accommodates 2 guests
Windwardside Main House - St. John has 1 bedroom, 2 bathrooms and was listed on Houfy on Jan 2018

Listing # 2045 - 64 Views