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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Great for couples traveling together!!! Privacy, Incredible sunset views! Enjoy

Bedrooms 2
Space 2,300 sq. ft.
Property type house
Minimum Stay 3 nights


About the property

This villa is private, set away and yet close to all that town offers!

This is a private two story villa which overlooks Pillsbury sound toward St. Thomas. Every single night you can enjoy beautiful sunsets on your very large private porches. Each story of the home provides privacy. This is a complete concrete structure, very safe, secure for you family. The villa has a downstairs studio apartment with its own AC, washer dryer, bathroom, mini fridge and toaster. The downstairs has just as incredible a view as the upstairs. The upstairs of the home is complete with temperdedic mattress, AC in the bedroom, bath, full kitchen, living room, large private porches complete with outdoor dining and seating area. The house has all comforts including surrounding gardens and paths. Outdoor gas grill, 3 fridges, Wifi, flat screen tvs with Roku.

Benjamin Shepherd
Member since: 2014
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
April 23, 2017

About Benjamin Shepherd

I am a painter, sculptor and stone mason.

Benjamin Shepherd purchased this house in 2014

Why Benjamin Shepherd chose Great Cruz Bay

It is romantic, private, perfect for friends and families with children. It is easy to walk into town, grocery stores and to the Westin. Plenty of parking if you decided to rent a car. Itality group takes excellent care of its properties. We also met you at the ferry and escort you to the villa, grocery store or rental car agency. We do all we can to ensure a perfect stay

What makes this house unique

The outdoor patio has a beautiful teak table and is wide and long. It is one of those pieces which draws you into enchanted evenings and long conversations. From the patio you can see all of Pillsbury sound from sunrise to gorgeous sunset that view is yours. At nights you see all the lights of St. Thomas and all the noises the gardens and island has to offer.


Great Cruz Bay Estates House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 2300 sq. ft.
House Rules:
  • Max. occupancy: 6
  • pets considered
  • children welcome
Location Type:
  • Downtown ...
  • Ocean View ...
  • Adventure
  • Away From It All
  • Romantic
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Internet ...
  • Linens Provided
  • Living Room
  • Parking
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven ...
  • Pantry Items
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 12 people
  • 2 Bathrooms
  • Master - toilet , shower
    downstairs - toilet , shower
  • 2 Bedrooms, Sleeps 6
  • Master - 1 queen , Upstairs bedroom
    Downstairs/ studio apartment - 2 twin/ single , 1 sleep sofa /futon , The two twin beds can be pushed together to form queen
  • All bedrooms have AC, are private, have own baths and closets
  • Books
  • DVD Player
  • Stereo
  • Television ...
  • Balcony
  • Deck / Patio
  • Golf ...
  • Outdoor Grill
  • Tennis ...
  • wheelchair inaccessible
  • botanical garden
  • churches
  • festivals
  • health/beauty spa
  • library
  • playground
  • recreation center
  • restaurants
  • ruins
Leisure Activities:
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • gambling casinos
  • horseback riding
  • luaus
  • paddle boating
  • photography
  • scenic drives
  • shelling
  • shopping
  • shuffleboard
  • sight seeing
  • walking
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • golf privileges optional
  • hiking
  • jet skiing
  • kayaking
  • parasailing
  • pier fishing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
wifi available


Wonderful! 4.8/5 -
(12 traveler reviews)

Great for couples traveling together!!! Privacy, Incredible sunset views! Enjoy
average rating of 4.75 based on 12 reviews

Great place to stay

  • 5 of 5

Nice place located close to Cruz Bay, but still very private. House had everything we needed and privacy for two couples. The best feature of the house was the outside deck that had a great view of the water and neighboring St. Thomas. The outside table is great for morning coffee and before and after dinner drinks. Jen the property manager is a super sweet woman who is always available if needed. I would certainly recommend this property to anyone.

  • Submitted: Mar 7, 2017
  • Stayed: Feb 2017
  • Source: VRBO, from HomeAway
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Very clean and nice!

  • 4 of 5

First Jenny the villas manager was amazing! Always there when needed. The place was great and comfortable! Everything you could possibly need in the kitchen. The patio was so nice to sit out morning and night. We stayed with our close friends and it was nice we had our privacy as they did also. I heard it was for sale hopefully it won't sell so we can return.

  • Submitted: Mar 5, 2017
  • Stayed: Feb 2017
  • Source: VRBO, from HomeAway
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Greensboro, NC

Location, view, convenience and ambiance

  • 5 of 5

This property was perfect for three ladies celebrating one of our 50th birthdays. The location simply cannot be beat, 2 minute drive from Cruz Bay.

The view was not to be believed, the sunset and sparkling lights of St. Thomas coming up each evening was magnificent.

This is a funky little house perfect for us. It has an unusual set up with one bedroom up and one down (you have to go outside to access the bottom floor - absolutely not a problem). Each bedroom was air conditioned but the rest of the main floor was open to the breezes. A very deep porch keeps things pleasant and we loved the open air feel of the home. For such a small space it had everything we needed, wash and dryer, two refrigerators, beach chairs, towels and cooler, kitchen is fully equipped. We lived on the porch, no need to turn the tv on, the best show is outside.

  • Submitted: Feb 27, 2017
  • Stayed: Feb 2017
  • Source: HomeAway
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House is well situated very well stocked and the porch is spectacular great for sunset watching.

  • 5 of 5

Property manager Jennifer is terrific!

  • Submitted: Feb 18, 2017
  • Stayed: Feb 2017
  • Source: HomeAway
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Overlooking Paradise!

  • 5 of 5

Beautiful porch!!!!!!! That makes the entire property just an oasis.

Two couples stayed at this lovely property for the past 5 days and we just had a great time. Everything we needed was there and the place was clean and tidy!

Jennifer, the host, was so fantastic. She picked us up and even dropped us at the grocery store (bringing us cloth bags to help) on our first afternoon.

Every morning an iguana stuck it's head out on a nearby tree. The washer and dryer was an added treat. The chickens nearby will sing you lullabies and rouse you in the morning.....

Thanks for a great stay!

  • Submitted: Feb 9, 2017
  • Stayed: Feb 2017
  • Source: HomeAway
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Comfortable home with a breathtaking view and convenient location

  • 5 of 5

Great house with all the comforts of home ! Very close to Cruz bay and the perfect layout for two couples or a couple with adult children ! We were welcomed by Jenny and she was so friendly and gave us some great advice about Some great spots to visit while on St John . She told us she would be available if needed for any problems / questions we had ! This was an exceptional offer of service that was greatly appreciated!

Would not recommend trying to walk anywhere however as the roads are very steep and busy near the property.

  • Submitted: Jan 14, 2017
  • Stayed: Jan 2017
  • Source: HomeAway
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Nearest Barpub
1 Miles
Beach Bar
Nearest Ferry
1 Miles
St. John
Nearest Motorway
0.1 Miles
Hwy 10
Nearest Restaurant
1 Miles
Nearest Beach
0.5 Miles
Great Cruz Bay
Car: recommended

St. John is mostly US National Park. The beaches are the most private and pristine in all the Caribbean. Private boat tours into the BVI include exploring underwater caves, lunches at sandy floor beach bars, and dinners with beautiful sunsets!


Rates & Availability

Great Cruz Bay Estates House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
My Standard Rate
3 night minimum stay
Notes: Rates are based on 4 guests; add $25 per night, per additional guest

Additional information about rental rates

Property Damage Protection $99
Pet Fee $125

We meet all our guests at the ferry dock and escort them to the villa. We answer any questions and help you get groceries or your rental car.

Owner's Cancellation Policy

100% refund if canceled at least 30 days before arrival date.

Enter dates for accurate pricing

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