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

SUREWINDS ESTATE - Carefree Contemporary Caribbean Style

Bedrooms 5
Half Baths1
Space 4,500 sq ft
Property type villa
Minimum Stay 4 - 7 nights


About the property

Large Main House plus apartment with flexible spaces overlooking the sea


Begun in 2005 and completed in the fall of 2012, Surewinds Estate has been a labor of love. It is designed for carefree island living…… no worries, barefeet, open windows and gentle breezes. The architectural style is classic Caribbean, (think masonry construction, ceiling fans, and colonial stonework ), updated with tropical hardwoods, an open floor plan, contemporary finishes and expansive outdoor living spaces.

Surewinds Estate, as its name implies, was sited to fully capture the cooling trade winds, which bathe the house in a continual ocean breeze. There is no greater luxury than living in an open air home where you can truly experience the sights and sounds of your natural surroundings. (Just in case the wind changes, the bedrooms are air conditioned.) From sunrise to sunset there are views to excite the eye and calm the senses.

Green Cay Plantation is on the south side of St. Thomas in Frenchman’s Bay Estate, centrally located between Charlotte Amalie and Red Hook. The house and attached apartment, overlook the beach at Bolongo Bay which is the home of the USVI Diving Club. There are no neighbors, no street lights and no traffic. Green Cay Plantation is a newly gated community featuring both luxury villas and year round island homes. The plantation roads are wide and safe for jogging, biking and kids at play. Surewinds is located at the end of a cul-de-sac so a stray car seldom passes by.

The four story, 4,500 sf layout of this property invites all sorts of possibilities. It is ideal for 4 couples, a large family seeking a separate in-law apartment, 2 family units, or a wedding party. With 4 ½ bathrooms, 2 ½ kitchens and sleeping space for up to 16 guests both privacy and convenience are well served. WE ALSO OFFER THE OPTION OF RENTING JUST THE MAIN HOUSE FOR GROUPS OF LESS THAN 11 GUESTS. THIS INCLUDES THE POOL AREA, ONLY THE LOWER LEVEL APARTMENT WOULD BE GATED OFF. SEE THE SEPARATE LISTING UNDER VILLA SUREWINDS.)

The Surewinds décor can be described as “put your feet up” casual. White slip covers are easily bleached. The watchword here is “clean and simple”. There is little clutter, so there’s less to worry about. The stainless modern kitchens are fully supplied for “real” cooking , and the electronics are state-of-the art (so you don’t get tooooo relaxed)! There is great space for entertaining, both indoor and out (as in a wedding). In-house catering by a noted island chef is available at an additional cost.

Main House, Main Floor: Open floor plan kitchen /dining / living room, powder room, laundry utility room, master suite (queen bed) w/ whirlpool tub and outdoor shower.

Main House, Pool Level: Bedroom 1 (queen bed + queen sofa bed), Bedroom 2 (queen bed + single bed + single futon), Den Bedroom 3 (trundle bed w/ 2 twins).

Apartment , Main Floor: Open floor plan kitchen / dining / living room (queen sofa bed)

Apartment , Lower Level: Oversized bedroom (queen bed + 2 twin beds (trundle)), Full bath

Finally here are some details to consider as you plan your vacation:

*This is a quiet, private setting. You will have to find your hustle and bustle elsewhere.

*We have done our best to make the house “child-safe” by gating the pool area, but nothing can replace parental supervision in a home that’s perched on a hill.

*Only the Main House / Main Floor is accessible without climbing at least a dozen stairs. There is a single stair at the front entrance, so wheelchair access is limited. If you are traveling with children, we suggest this house for Ages 3+, but we will let you be the judge.

*There are ceiling fans in every room, the 4 main bedrooms are air-conditioned. The breeze is fabulous!

* The 11’x 14’ pool is 9’ at the deep end, and about 3’ at the shallow end. It’s great for lounging, quick cool downs and some active pool play, but it’s NOT for diving or swimming laps (unless your laps are very short!).

2015 - 16 RATES:


12/15/210 – 1/5/2015, $7,250/week ($1,036/night)

1/6/2016 - 4/30/2016, $7.000/week ($1,000/night)

5/1/2016 – 7/31/2016, $6,200/week

8/1/2015 – 11/14/2016, $6,000/week

11/15/2016 – 1/5/2017, $7,800/week

More Details

Sandra Wright
Member since: 2012
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
March 6, 2018

About Sandra Wright

The Wright family has owned a vacation home in St. Thomas since 1985. As Connecticut Yankees, the climate first drew us to STT, but we have grown to love the island as our second home. Our son Jordan is the talented builder of this amazing home, which we hope will soon become a retirement home for us, and the vacation destination of choice for our children and grand children.

Although this is a new rental property for us, we have been renting our other home for 25 years, so we have great on-island support, and understand the needs of Caribbean vacationers.

Sandra Wright purchased this villa in 2012

Why Sandra Wright chose Green Cay Plantation

Besides the amazing architectural detail, Surewinds Estate is somewhat unique in that the floor plan will adapt to groups of all sizes and configurations. Having the separate apartment with a second complete kitchen is a luxury you don't find in many island rentals.

What makes this villa unique

By opening Surewinds to the breeze you will take away a true island experience like no other. The 270 degree ocean view affords both sunrise and sunset panoramas that extend all the way to St. Croix. The westward view includes watching the majestic cruise ships and elegant yachts as they arrive and depart Charlotte Amalie harbor.

Guestbook comments from the owner

I wanted to thank you for sharing your beautiful home with us and our family. You have certainly thought of EVERY detail in Surewinds! We had all guests over one night from the Marriott for a BBQ (21 total) and everyone felt at home, comfortable and all wanted to come back again as a group in no more than 5 years. I will surely be the instigator of that for sure! We just absolutely loved Surewinds, felt at home and can't thank you enough for sharing!
Apr 2014
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Green Cay Plantation Villa Accommodation and Amenities

Property Type:
  • villa
  • Guests provide their own meals
Floor Area:
  • 4500 sq ft
House Rules:
  • Max. occupancy: 16
  • pets considered
  • Events Allowed
  • children welcome ...
  • non smoking only
Location Type:
  • Beach View ...
  • Ocean View ...
  • Away From It All
  • Air Conditioning ...
  • Clothes Dryer
  • Hair Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Parking ...
  • Telephone ...
  • Towels Provided ...
  • Washing Machine
  • Coffee Maker ...
  • Dishes & Utensils
  • Dishwasher ...
  • Freezer
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster ...
  • Dining ...
  • Dining Area
  • seating for 12 people
  • 4 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - toilet , jetted tub , outdoor shower , MBR double vanities
    Bathroom 2 - toilet , Main House Powderroom
    Bathroom 3 - toilet , combination tub/shower , Double vanities
    Bathroom 4 - toilet , shower
    Bathroom 5 - toilet , shower
  • 5 Bedrooms, Sleeps 16
  • Bedroom 1 - 1 queen
    Bedroom 2 - 1 queen , 1 sleep sofa /futon , Sleep sofa is queen
    Bedroom 5 - 1 sleep sofa /futon , Sleep sofa is Queen
    Bedroom 3 - 1 queen , 1 twin/ single , 1 sleep sofa /futon
    Bedroom 4 - 2 twin/ single , trundle bed set up
    Bedroom 6 - 1 queen , 2 twin/ single , trundle bed set up ideal for small children
  • All bedrooms are quite large and allow for flexible sleeping arrangements.
  • Books
  • DVD Player
  • Games
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Toys ...
  • Video Library
  • Balcony
  • Boat ...
  • Deck / Patio ...
  • Golf ...
  • Kayak / Canoe ...
  • Outdoor Grill ...
  • Tennis ...
  • Water Sports Gear ...
  • 12 garden chairs
  • Long-term Renters Welcome
  • limited accessibility
Pool / Spa:
  • Heated Pool
  • Private Pool ...
  • arboretum
  • botanical garden
  • churches
  • cinemas
  • duty free shops
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • restaurants
  • ruins
  • synagogues
Leisure Activities:
  • beachcombing
  • boating
  • eco tourism
  • paddle boating
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • deepsea fishing
  • fishing
  • golf
  • jet skiing
  • kayaking
  • paragliding
  • 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


Wonderful! 4.9/5 -
(14 traveler reviews)

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SUREWINDS ESTATE - Carefree Contemporary Caribbean Style
average rating of 4.928571 based on 16 reviews

Island life

  • 5 of 5

Million dollar views in every room. I'll miss waking up to that in the morning.

  • Submitted: Jun 2, 2017
  • Stayed: May 2017
  • Source: HomeAway
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Beautiful home for a family reunion

  • 5 of 5

Wow!, were the words from each and every family member when we walked through the door. We picked Surewinds for our family reunion and it was the best choice we could have made. There were 16 people in our group and there was more than enough room for everyone to spread out. The home was beautifully constructed and decorated and the views were endless. The home was so well equipped we had everything we needed for great family meals, dips in the pool, and gear so we could enjoy the local beaches. It even smelled fantastic with aromatherapy scents infused through out the home. At the end of the day, we could come back and unwind with games around the beautiful and large dining table. The home sits at the end of a cul-de-sac so not only was it serene, there was plenty of room to park a few extra cars.

From the beginning, the owner Sandra was so pleasant to talk to and had a wealth of information on St. Thomas. Since it was the first time for everyone in our family, she even told us where to shop for reasonably priced groceries and where we could find all the amenities we needed. Sandra was such a delight that we knew we had made the right choice with Surewinds for such an important occasion. We would highly recommend Sandra and this home to anyone wanting a luxurious home away from home.

  • Submitted: Aug 26, 2016
  • Stayed: August 2016
  • Source: VRBO, from HomeAway
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Ashland, MO, United States

St Thomas Birthday 2015

  • 5 of 5

SureWinds was everything and more than what we expected it to be. We had a group of 4 couples that went on this trip. We rented the apartment below the pool which gave us lots of room to spread out. We all had a great time at the house! We had no issues at all during the week. I don't think any of us had to use the air conditioning due to the great breezes.

The house is located in a great spot. We liked that it was located in a gated community. We were very comfortable with going on morning walks around the subdivision. The house is secluded so you don't have neighbor issues. The views are outstanding!

My wife and I stayed in the Master suite on the upper level. We loved the outdoor shower! Taking a shower looking out at the awesome view was amazing! The main level with Kitchen, Dining, Hearth room, living room, and Master was very spacious and comfortable!! Kitchen had everything we needed for the meals we prepared.

The house location on the island was perfect for us! We took out almost every morning to go site seeing. Being centrally located it was never more than 20 minutes from anywhere we went. We often went to the beach bar right down the road to the east called Iggies. Many nights we went to Red Hook where there was dining and night life.

Sandra the owner was very pleasant to deal with before and after the stay!! She answered all our questions so we were prepared for the trip. One of the guys forgot his sunglasses and she located them and mailed them back to him.

We rarely go back to the same vacation spot because we like to try new things! When we go back to St Thomas we will definitely stay here again!!

  • Submitted: Apr 19, 2015
  • Stayed: March 2015
  • Source: VRBO, from HomeAway
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Lovely retreat!

  • 5 of 5

I took my son, daughter-in-law, and three teenage grandchildren to St. Thomas for spring break. I could not have chosen a more perfect place to stay. The beauty is obvious in the photos....and the photos don't lie! There was plenty of room to stretch out and the bedroom arrangements were just great. We loved having a pool and grill and the views from the house were magnificent. We enjoyed watching sunrises, sunsets and the beautiful full moon during our trip. Also had a great view of cruise ships calling at St. Thomas. The house was fully equipped and even had beach towels and snorkel equipment. I'd recommend this lovely retreat for families, groups of couples....anyone wanting a beautiful place to stay on St. Thomas!

  • Submitted: Apr 16, 2015
  • Stayed: March 2015
  • Source: VRBO, from HomeAway
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The pictures don't lie

  • 5 of 5

The views are fabulous and the home is gorgeous. We hosted a family party here and the layout worked great. Our guests were taking pictures as soon as they arrived. The homeowners were kind to offer suggestions in our planning too. Easily accessible by car to nearby beaches and food, but located on a quiet and private road. Home is fully furnished and well maintained. The driveway is a bit too steep for some but was amusing. So happy we booked our week here and thank the homeowners for their lovely home!

  • Submitted: Jun 22, 2014
  • Stayed: June 2014
  • Source: VRBO, from HomeAway
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New York, New York

Wonderful Villa

  • 4 of 5

We had 3 families stay in Surewinds for a week in St. Thomas and it was a wonderful house with great amenities and views. Plenty of space in a great location. I suggest this villa for any family or families looking for a luxury villa in St. Thomas.

  • Submitted: May 18, 2014
  • Stayed: May 2014
  • Source: VRBO, from HomeAway
Owner's Response: Once again, so nice to be a small part of another family's special time together. We look forward to your anniversary visit!
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Nearest Airport
5 Miles
Cyril B. King, Charlotte Amalie
Nearest Barpub
0.25 Miles
Abi Bar
Nearest Ferry
4 Miles
Charlotte Amalie or Red Hook to Tortola, St. John
Nearest Beach
0.5 Miles
Bolongo Bay
Car: necessary

St. Thomas offers every amenity available in a tropical setting. Surewinds is centrally located so that no activity is more than 15-20 minutes from your doorstep.

The sport fishing, day sailing charters and duty-free shopping is among the best in the world.




Additional information about rental rates

Refundable damage deposit $500

We also offer the Main House without the apartment for groups of less than 10 people. The apartment is not rented separately. Inquire about rates.

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.

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