Toll Free: 888-693-7676
Island Getaways Villa Rentals St John, USVI

Villa Madeira - Chocolate Hole

Villa Madeira built in 2008 is now available for short term rental.  Sitting on 3/4 of an acre tucked into a quaint south shore hillside 420″ above sea level this villa is very conveniently located.  Less than a ten minutes to Cruz Bay.  Expansive ocean views of the south, west and to the north.  Overlooking Hart Bay, Chocolate Hole, Great Cruz Bay and Cruz Bay as well as views of St. Thomas and our fabulous sunsets. Villa Madeira is constructed with quality and care which includes Anderson doors and windows, poured concrete walls and beautiful stone work.  The two story pods connected by breezeways surround the terracotta tiled patio that offers a swimming pool, four-person hot tub, wet bar and gas grill.  Each of the three bedroom suites offer covered patios and capture the expansive water views of St. Thomas and the West  Shore of St. John.  The gourmet kitchen includes cherry cabinets, granite countertops and stainless steel appliances.  The kitchen, great room, dining room and 1/2 bath are tiled throughout and offer both indoor and outdoor dining options.  The lush landscaping includes tropical flowering plants and fruit trees.  All three master suites, the Blackbeard’s Suite, the Anne Bonny Suite and the Calico Jack Suite all have private baths with shower windows looking out to the incredible ocean views.  The Great Room has a/c and ceilings fans as well as each bedroom suite.  The suites also include cable tv, telephones and alarm clocks.  Please note the pool furniture in the drone photos has been replaced with grey sling chaise lounges and 2 umbrellas seen in the close up pool photo. Also the 2 chairs, table and telescope have been removed from the Blackbeard Suite deck and there is now 2 chaise lounges and a snack table for your enjoyment.

 

Amenities

  • Gourmet Kitchen
  • 2 Drip Coffee Makers
  • Coffee Grinder
  • Blender
  • 4 slice Toaster
  • Toaster Oven
  • Crock Pot
  • Triple Filtration Water System
  • Formal Dining and Living Room areas
  • Three Master Suites all with Queen Beds
  • Three and one half baths
  • Great Room with Air Conditioning, Three Suites with Air Conditioning
  • Blackbeard Suite  includes flat screen tv w/ Dish Service & DVD player
  • Anne Bonny Suite includes flat screen tv w/ Dish Service & DVD player
  • Calico Jack Suite includes flat screen tv w/ Dish Service & DVD player
  • Great Room includes Sony 32" LCD TV with Dish Service & DVD Player
  • Surround Digital Theatre System with Surround Sound including 5 disc CD and Blue Tooth Option
  • Wireless DSL
  • Bose Docking Station Access with Audio Cord
  • Selection of Books & DVD's
  • Linens & Bath Towels
  • Iron/Ironing board
  • Hair dryers in each bathroom
  • Salt Swimming Pool w/ stairs & bench seating 18' X 12' - depth 3-5 ft
  • Sundance Deluxe four person Jacuzzi
  • Washer & Dryer
  • Weber Gas Barbecue Grill
  • Beach Chairs, Towels, Coolers & Bag
  • Binoculars
  • Safes in the Calico Jack and Anne Bonney Suites for your valuables
  • 40kw Automatic Generator

Weekly Rates

Winter 2026
January 3, - April 17, 2026
1-4 Guests/2 Suites = $6,475
5-6 Guests/3 Suites = $7,175

Summer 2026
April 18 - December 14, 2026
1-2 Guests/ 1 Suite = $4,500
3-4 Guests/2 Suites = $4,900
5-6 Guests/3 Suites = $5,400

Holiday Rates 2026 > 2027

Thanksgiving 2026
November 21-28, 2026
1 - 6 Guests = $5400 All Suites

Holidays 2026/2027
December 15, - January 5, 2027
1 - 6 Guests = $9450 All Suites

Presidents Week 2027
February 13 - 20, 2027
1-6 Guests = $7850

Maximum occupancy 6 Guests
This is a non smoking villa
Minimum Stay: 7 nights
Weekly rates are based on double occupancy, un-rented bedrooms will remain locked & unoccupied during your stay
Accepts children of all ages
Only St. John vehicle rentals are permitted
Our office is closed on Sunday; no arrivals or departures are permitted

Availability

Available
Booked
August 2026
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Reservations / Payment Info

Weekly rates are based on double occupancy, un-rented bedrooms will remain locked & unoccupied during your stay

Children of all ages are welcome!

Check in time is 3:00pm - Check out time is 9:00am if guests are arriving the day of your departure and 10:00am if otherwise.

We support St. John Rental Jeep Companies & recommend Bougainvillea Leasing for our guests, however you are welcome to rent from any St. John Agency. 

This is a non smoking villa

Deposit Information: A deposit of 50% of the total rent is required to confirm your reservation. The balance is due 60 days prior to arrival. The deposit is refunded if re-rented, less 20% administrative costs. Not included in the rental rates is a Virgin Islands Hotel Tax of 12.5%, a Service Fee of 4.5% and a $1,000.00 refundable security deposit. This villa accepts payment by check or bank wire.

Contact Us

Island Getaways Inc
PO Box 1504
St John, VI 00831

Toll Free: 1-888-693-7676
Local: 340-693-7676
Fax: 340-693-8923

e: kathy@islandgetawaysinc.com

Property Facts

Miles to Cruz Bay: TBD
Miles to Coral Bay: TBD
1875 sq. ft. enclosed living space

1817 sq. ft. exterior decking

420' above sea level

Built in 2008
Split A/C units in each bedroom
Nearest beaches: Hart Bay & Chocolate Hole
Northshore beaches: 15 minute drive