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Surewinds Estate - Carefree Contemporary Caribbean Style

(13 Reviews)

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As seen from the closest beach at Bolonga Bay Resort. Apartment is lower left.


Last updated: 04/22/2017
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:5-7 nights
  • Sleeps:16
  • Bedrooms:5
  • Bathrooms:4.5
  • Property type:Villa
  • Internet:Yes
  • Pets considered:Yes
  • Wheel chair accessible:N/A

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

Send email


Member since: 2012

Speaks: english
Response time: Within 12 hours
Response Rate: 100%
Calendar last updated: 04/22/2017

Property Type

  • Villa
  • 4500 sq. ft.

House Rules

  • Max. occupancy 16
  • Events Allowed
  • Children Welcome:

    Probably best for children who can manage stairways safely, although we do have gates for stairways....moreless

  • Non Smoking Only
  • Pets Considered

Accommodation Type

  • Vacation Rental


  • Guests Provide Their Own Meals


  • Long-Term Renters Welcome
  • Limited Accessibility

Bedrooms: 5 Bedrooms, Sleeps 16, Beds for 12-16

  • Bedroom 1: 1 queen


  • Bedroom 2: 1 queen, 1 sleep sofa /futon

    Sleep sofa is queen...moreless

  • Bedroom 5: 1 sleep sofa /futon

    Sleep sofa is Queen...moreless

  • Bedroom 3: 1 queen, 1 twin/ single, 1 sleep sofa /futon


  • Bedroom 4: 2 twin/ single

    trundle bed set up...moreless

  • Bedroom 6: 1 queen, 2 twin/ single

    trundle bed set up ideal for small children...moreless

  • All bedrooms are quite large and allow for flexible sleeping arrangements....moreless

Bathrooms: 4 Bathrooms, 1 Half Bathroom

  • Bathroom 1: toilet, jetted tub, outdoor shower

    MBR double vanities...moreless

  • Bathroom 2: toilet

    Main House Powderroom...moreless

  • Bathroom 3: toilet, combination tub/shower

    Double vanities...moreless

  • Bathroom 4: toilet, shower


  • Bathroom 5: toilet, shower



  • Books
  • DVD Player
  • Games


  • Away From It All


  • Arboretum
  • Botanical Garden
  • Churches
  • Cinemas
  • Duty Free Shops
  • Health/Beauty Spa
  • Library
  • Live Theater
  • Marina
  • Museums
  • Restaurants
  • Ruins
  • Synagogues

Local Services & Businesses

  • ATM/Bank
  • Groceries
  • Hospital
  • Massage Therapist
  • Medical Services

Leisure Activities

  • Beachcombing
  • Boating
  • Eco Tourism
  • Paddle Boating
  • Scenic Drives
  • Shelling
  • Shopping
  • Sight Seeing
  • Walking
  • Wildlife Viewing

Location Type

  • Beach View:

    Bolongo Bay Beach Resort is at the bottom of the hill....moreless

  • Ocean View:

    270 degree view includes St. John, Buck Island and on a clear day St. Croix which is 26 miles away....moreless

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


  • Dining:

    Additional dining on pool level and in apartment...moreless

  • Dining Area
  • Seating for 12 people


  • Air Conditioning:

    Bedrooms are air-conditioned....moreless

  • Clothes Dryer
  • Hair Dryer
  • Internet:

    Wi-Fi ...moreless

  • Iron & Board
  • Linens Provided
  • Living Room:

    2 separate living rooms, 3 TV areas...moreless

  • Parking:

    Parking for several cars in driveway....moreless

  • Telephone:

    Local outgoing, excellent cellular service...moreless

  • Towels Provided:

    Includes beach towels...moreless

  • Washing Machine


  • Kitchen:

    (3) Main House has large open plan kitchen/dining area on main floor, and bar kitchen on lower level. Apartment has full galley kitchen w/ breakfast bar....moreless

  • Microwave:


  • Oven:

    (2) ...moreless

  • Pantry Items:

    crock Pot, electric griddle, hand mixer, blender...moreless


  • Balcony
  • Boat:

    Readily available to rent bareboat or captained charters...moreless

  • Deck / Patio:

    (6) Decks with views off every room....moreless

  • Tennis:

    Available at nearby resorts...moreless

  • Water Sports Gear:

    Some in house, also available for rent or purchase at all major resorts...moreless

Pool / Spa

  • Heated Pool


Write a review 4.9
from 13 traveler reviews
Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
Winter 2017
Jan 6 - Apr 30, 2017
5 night min stay
May 1 - Jul 31, 2017
5 night min stay
FALL 2017
Aug 1 - Nov 18, 2017
5 night min stay
Holiday 2017-2018
Nov 19 - Jan 6, 2018
7 night min stay

My Standard Rate
5 night min stay

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:

Policy available by contacting owner when booking

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Last updated: 04/22/2017
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates


5 Miles
Nearest Airport
Cyril B. King, Charlotte Amalie
0.25 Miles
Nearest Barpub
Abi Bar
4 Miles
Nearest Ferry
Charlotte Amalie or Red Hook to Tortola, St. John
0.5 Miles
Nearest Beach
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.


Owner info

Year Purchased: 2012

About the owner: 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.

Why the Owner Chose Bolongo, St. Thomas, USVI:
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.

The Unique Benefits at this Villa:
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.

Contact us

Speaks: english
Response time: Within 12 hours
Response Rate: 100%
Calendar last updated: 04/22/2017

Send email

Links to more information:

Guestbook comments from the owner

1 of 2


  • As seen from the closest beach at Bolonga Bay Resort. Apartment is lower left.

    As seen from the closest beach at Bolonga Bay Resort. Apartment is lower left.

  • Pool deck above the apartment.

    Pool deck above the apartment.

  • Open floor plan w/ loads of space.

    Open floor plan w/ loads of space.

  • Main House Stainless Kitchen with hi-tech concrete counters.

    Main House Stainless Kitchen with hi-tech concrete counters.

  • Master Bedroom.

    Master Bedroom.

  • Pool bar.

    Pool bar.

  • Apartment Living /dining area w/ queen sofabed.

    Apartment Living /dining area w/ queen sofabed.

  • Gated entryway into Green Cay Plantation.

    Gated entryway into Green Cay Plantation.

  • Sunsets beyond compare.

    Sunsets beyond compare.

  • 7 a.m. Nautical Parade

    7 a.m. Nautical Parade

  • ...and watch 'em roll away again....

    ...and watch 'em roll away again....

  • Both ends of the rainbow from the deck

    Both ends of the rainbow from the deck

  • Perched on a hill with nothing between you and the deep blue sea.

    Perched on a hill with nothing between you and the deep blue sea.

  • Pool.


  • Main House Livingroom into diningroom.

    Main House Livingroom into diningroom.

  • Dining by the sea.

    Dining by the sea.

  • Pooldeck into the Pool bar room.

    Pooldeck into the Pool bar room.

  • Apartment Kitchen.

    Apartment Kitchen.

  • The closest beach (you overlook it).

    The closest beach (you overlook it).

  • Sunset view over Green Cay.

    Sunset view over Green Cay.

  • Sunrise.


  • Watchin' the ships roll in.....

    Watchin' the ships roll in.....

  • Space to relax and entertain

    Space to relax and entertain

VRBO #448096

This listing was first published here in 2012.

Date last modified - Sunday, April 23, 2017

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