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Windwardside Cottage: Quaint, Quiet, Romantic, Spa, Great Ocean View & Gardens

(30 Reviews)

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Last updated: 03/24/2017
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:1-7 nights
  • Sleeps:2
  • Bedrooms:1
  • Bathrooms:1
  • Property type:Cottage
  • Internet:Yes
  • Pets considered:No
  • Wheel chair accessible:No

About the Property

1BR Oceanview Vacation Rental St. John, Virgin Islands USA

Windwardside Guest Cottage is the smallest of the Calabash Cottages group but our guests love it. Our goal in constructing Windwardside Guest Cottage was to provide a romantic haven packed with amenities but at a reasonable price. We have many honeymoon guests that choose Windwardside Guest Cottage for precisely this reason It is a budget home that won’t make you feel like you have made any compromises. But the cottage is not only for honeymoon couples- it is a quaint and lovely cottage for any visitors to the island that want an intimate experience of our beautiful island with a gorgeous view.

IMPORTANT INFO ABOUT RATES AND POLICIES: Our rental week runs from Sunday to Sunday. We have two rates: Low season from April 16 to December 14 and High season from December 15 to April 15. The rates are as listed. The only additional charge is 12.5% hotel tax. We do not collect a damage deposit. Our 20 year relationship with guests has taught us that this is not necessary. We treat our guests with respect and we have found that they return the favor. There are no extra costs for reservations, cleaning or service. If you encounter any additional charges when requesting a detailed quote it would be from the advertising site where you found us. Calabash Cottages is an established company and information about our rentals is easily found..

Car Rentals: Since the purchase of Homeaway and VRBO by Expedia we have seen an attachment at the bottom of our ads with them encouraging guests to book car rentals through their site. Because of our unique location we strongly advise against that. You do need a 4 wheel drive vehicle. We have for over 20 years done business with a very reliable company, Courtesy Car Rental. We believe in them enough that we forgo the commission they would give us and to apply it as a discount to your car rental. Please discuss car rentals with us before reserving. Our most important interest is in satisfying our customers. But the recent take over of our advertising sites by large corporations is constructing communication barriers. We can always be contacted directly.

We have numerous storage areas in a compact home with a a view that rivals any on the island. At Windwardside Guest Cottage you will wake up in a four poster bed to a gorgeous view of the Caribbean sea framed by palm trees. You could easily create a post card from the view of this adorable cottage.
The interior has a queen-size, four-poster bed, a small seating area, a kitchenette and a breakfast bar. The furnishings are both tasteful and cheerful. The covered porch has a dining area and two lounging chairs where you can enjoy the trade winds or good book while watching the sailboats pass by. A small gas grill is also available if you prefer to prepare your meals over looking the sea. A shower garden opens onto an uncovered deck. There you can have a relaxing evening soak in the hot tub under a starry Caribbean sky. The hot tub also has a wide view of the sea and total privacy.
In short Windwardside Guest Cottage offers a serene location, fabulous view, charming furnishings, a private hot tub, kitchenette and bbq, plus the dedicated staff of Calabash Cottages who will organize your vacation from start to finish all for the price of a hotel room. We provide snorkel gear, beach chairs and a cooler and a beach umbrella

We also include amenities that you may never need on our casual island (including an iron and a blow dryer) because we want you to be able to travel as light and carefree as possible. Please read reviews from out former guests. We hope to host you on our next visit to St. John.
Send email


Member since: 1998

Speaks: english
Response time: Within 12 hours
Response Rate: 100%
Calendar last updated: 03/24/2017

Property Type

  • Cottage

House Rules

  • Max. occupancy 2
  • Not Suitable For Children
  • Pets Not Allowed

Accommodation Type

  • Vacation Rental


  • Guests Provide Their Own Meals


  • Wheelchair Inaccessible

Bedrooms: 1 Bedroom, Sleeps 2, Beds for 2

Bathrooms: 1 Bathroom

  • Bathroom: toilet, shower, outdoor shower

    Toilet, sink and vanity indoors. Outdoor shower....moreless

  • Spacious enclosed outdoor shower with shower garden


  • Books
  • CD Player
  • DVD Player
  • Radio
  • Stereo
  • Television:

    For use with dvds only. Dvd's provided...moreless

  • Video Library


  • Adventure
  • Away From It All
  • Romantic


  • Churches
  • Duty Free Shops
  • Forests
  • Health/Beauty Spa
  • Library
  • Reefs
  • Restaurants
  • Ruins

Local Services & Businesses

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

Leisure Activities

  • Beachcombing
  • Bird Watching
  • Boating
  • Eco Tourism
  • Horseback Riding
  • Shopping
  • Sight Seeing
  • Walking

Location Type

  • Beach View
  • Mountain
  • Mountain View
  • Near The Ocean
  • Ocean View:

    Great views of ocean from covered porch. Wake up in a four poster bed with a water view framed by palm fronds....moreless

  • Village
  • Water View

Sports & Adventure Activities

  • Deepsea Fishing
  • Fly Fishing
  • Hiking
  • Kayaking
  • Parasailing
  • Sailing
  • Scuba Diving Or Snorkeling
  • Snorkeling
  • Snorkeling/Diving
  • Sound/Bay Fishing
  • Swimming
  • Tennis
  • Wind-Surfing


  • Dining:

    Two dining tables are provided, one in the kitchenette and one on the covered porch facing a beautiful view of the bay....moreless

  • Dining Area
  • Seating for 2 people


  • Alarm Clock
  • Basic Soaps
  • Ceiling Fans
  • Filtered Water
  • Free Local Calls
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided:

    Sheets, towels, beach towels, robes...moreless

  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking
  • Parking Off Street
  • Safe
  • Telephone
  • Toilet Paper
  • Towels Provided
  • Wireless Internet


  • Blender
  • Coffee Grinder
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Kitchen:

    Kichenette includes 2 burner stove top, toaster oven, sink, small refrigerator, utensils, pots pans, coffee maker and coffee grinderindoor...moreless

  • Kitchenette
  • Mini Refrigerator
  • Refrigerator
  • Stove
  • Stove
  • Toaster


  • Balcony
  • Beach Chairs
  • Beach Towels
  • Beach Umbrellas
  • Deck / Patio:

    Covered porch with great water and mountain view...moreless

  • Deck Furniture
  • Large Cooler
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Porch Furniture
  • Small Cooler
  • Unscreened Porch / Veranda
  • Water Sports Gear:

    snorkel gear provided...moreless

  • Wood Deck

Pool / Spa

  • Hot Tub:

    Located on private deck, open to stars with ocean view...moreless

  • Outdoor Hot Tub


Write a review 4.9
from 30 traveler reviews
Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
High Season
Dec 15 - Apr 15, 2017
7 night min stay

Low Season 2017
Apr 16 - Dec 14, 2017
7 night min stay

High Season 2017/18
Dec 15 - Apr 15, 2018
7 night min stay

Low Season 2018
Apr 16 - Dec 14, 2018
7 night min stay


Additional information about rental rates



There is an additional 12.5% hotel tax that will be added to the weekly rate.


12/15 - 4/15 $1610/weekly (2 Guests).

4/16 - 12/14 $1330/weekly (2 Guests).

Hotel tax in the Virgin Islands is increasing to 12.5% as of January 1, 2016.

For larger groups the guest cottage can be rented along with the neighboring Windwardside Main House.

For that option, or to see our other cottage for two, Sago Cottage, please see our additional listings on the St. John page.

Check or money order. 50% at time of reservation. Balance due 30 days before arrival.

Manager's cancellation policy:

Policy available by contacting manager when booking

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Last updated: 03/24/2017
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
2.5 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.


Manager info

Year Purchased: 1996

About: We are thirty year residents of St. John. My husband is a retired builder and we designed this home together. We built Windwardside in 1996 and have managed it as part of the Calabash Cottages group for over 20 years. Calabash Cottages offers charming and private cottages and villas in quiet secluded locations. Our main focus is to provide an assortment of options for couples in a tranquil setting. We and our staff always do our best to insure your precious vacation time is well spent at one of our Calabash Cottages. We are very happy to answer any questions to help you decide if Windwardside Guest Cottage or one of our other Calabash Cottages is a good fit for you.

Why Calabash Boom, Johns Folly, St. John, USVI:
We love Coral Bay and wanted to design a home that did not tower over the hillside but fit into it's natural surroundings. The shape and orientation allowed of this property allowed us to do just that while still offering fabulous views. We love quiet natural settings, tropical gardens and ocean views and we appeal to visitors who are looking for just that.

The Unique Benefits at this Cottage:
Windwardside Guest Cottage will make you fall in love with the view from the front porch. The first thing you will see in the morning right from your four poster bed is the palm fronds waving in the breeze. This compact cottage offers many amenities. It is also a great choice for two couples when rented with Windwardside Main House as each has a lot of privacy.

Contact us

Speaks: english
Response time: Within 12 hours
Response Rate: 100%
Calendar last updated: 03/24/2017

Send email

Links to more information:



  • Exterior of Windwardside Guest Cottage

    Exterior of Windwardside Guest Cottage

  • Morning view from deck

    Morning view from deck

  • Covered porch

    Covered porch

  • View from deck

    View from deck

  • view from Windwardside

    view from Windwardside

  • View with palm

    View with palm

  • Bathroom


  • Maho Bay, 15 minutes from the cottage.

    Maho Bay, 15 minutes from the cottage.

  • A visit to the ruins of Annaberg Sugar mill is a must.  Great snorkeling nearby.

    A visit to the ruins of Annaberg Sugar mill is a must. Great snorkeling nearby.

  • Exterior dining table

    Exterior dining table

  • Sitting area

    Sitting area

  • Chairs on deck

    Chairs on deck

  • Covered porch

    Covered porch

  • Floor plan showing Winwardside Guest Cottage and Main House

    Floor plan showing Winwardside Guest Cottage and Main House

  • Shower garden

    Shower garden

  • Salt Pond Bay: located 10 minutes from cottage and also accesses two trails.

    Salt Pond Bay: located 10 minutes from cottage and also accesses two trails.

  • Excellent snorkeling on island.  Gear provided

    Excellent snorkeling on island. Gear provided

  • Gorgeous beaches surround the island.  Francis Bay is about a 12 minute drive.

    Gorgeous beaches surround the island. Francis Bay is about a 12 minute drive.

VRBO #10284

This listing was first published here in 2001.

Date last modified - Sunday, March 26, 2017

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