SUREWINDS - Contemporary Villa and Apartment Combo
Surewinds 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 concrete finishes and expansive outdoor living spaces.
Surewinds, 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. and we do have a generator for when the power is down!) From sunrise to sunset there are views to excite the eye and calm the senses.
Green Cay 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 is a newly gated community featuring both luxury villas and year round island homes. The neighborhood 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 4-5 couples, a large family seeking a separate in-law apartment, 2 or 3 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.
The Surewinds décor can be described as “put your feet up” casual.. 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 wi-fi is in place. 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, primary bedroom suite (queen bed) w/ whirlpool tub and outdoor shower. Main House, Pool Level: Bedroom 1 (king bed + queen sofa bed), Bedroom 2 (queen bed + single bed), 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
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 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!). Finally, if you are traveling with fewer than10 people you have the option of renting just the main house. see listing 769129.
Our prices include all fees. No hidden fees.
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Events allowed: family gatherings, birthday parties, weddings
$400 event charge to pay for a water delivery.
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Pets
No pets allowed
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Smoking
Smoking is not permitted
Unfortunately, this property cannot accommodate more than 16 guests and any reservations above 16 cannot be accepted.
Evidence of smoking inside will incur a damage fee.
Important information
You need to know
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 50
Note from host: $400 event charge to pay for a water delivery.
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
St. Thomas
Located in Green Cay Plantation, a neighbourhood in St. Thomas, this villa is next to a golf course and near the beach. The area's natural beauty can be seen at Bolongo Bay and Sapphire Beach. Discover the area's water adventures with jet skiing, kayaking and scuba diving nearby, or enjoy the great outdoors with ecotours.
St. Thomas (SPB-St. Thomas Seaplane Base) - 14 min drive
Restaurants
The Tap & Still - 6 min drive
Paradise Point - 9 min drive
Shorebird - 6 min drive
Stir It Up - 6 min drive
The Smoking Rooster - 6 min drive
Frequently asked questions
Does SUREWINDS - Contemporary Villa and Apartment Combo have a pool?
Yes, this property has an outdoor pool.
How much does it cost to stay at SUREWINDS - Contemporary Villa and Apartment Combo ?
As of 8 May 2026, prices found for a 1-night stay for 2 adults at SUREWINDS - Contemporary Villa and Apartment Combo on 18 May 2026 start from £772, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is SUREWINDS - Contemporary Villa and Apartment Combo pet-friendly?
No, pets are not allowed at this property.
How much is parking at SUREWINDS - Contemporary Villa and Apartment Combo ?
On-site parking is available at the property.
What time is check-in at SUREWINDS - Contemporary Villa and Apartment Combo ?
Check-in begins at 1:30 PM.
What time is check-out at SUREWINDS - Contemporary Villa and Apartment Combo ?
Checkout is at 11:00 AM.
Where is SUREWINDS - Contemporary Villa and Apartment Combo located?
Located in Green Cay Plantation, this golf villa is within 2 miles (3 km) of Frenchman's Bay, Limetree Beach and Bluebeards Beach. Bolongo Bay and Morningstar Beach are also within 3 miles (5 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The house and the view were amazing. Very comfortable furnishings and well stocked with provisions. It was a destination within itself but served as a home base for adventures all around St Thomas. Our group had a wonderful time and found ourselves conveniently located between the two main towns. Our rental car made it all very doable.
Deborah F.
Stayed 7 nights in Mar 2026
Response from VrboOwner on 2 Apr 2026
Wonderful group!! Hope you will visit us again!! All the best, Sandra
This was a beautiful villa in a beautiful location. All of my friend's and family wanted to stay longer! Sandra is a great hostess and was very available and amicable.
amanda b.
Stayed 4 nights in Mar 2025
Response from VrboOwner on 3 Apr 2025
Thanks again Amanda. It is always fun to be part of a guests special memories! Wishing you well.
our 2 children their spouses and our 6 grandchildren ages 13 to 20 had a great time. Wonderful house in a wonderful location with a great host. great base for a St Thomas retreat
FRED W.
Stayed 10 nights in Dec 2023
Response from VrboOwner on 3 Jan 2024
So happy to hear it was a great trip. All the best and Happy New Year!
Surewinds is a beautiful property. The only thing I want to point out is that there is no air conditioning in the main areas, just sleeping, it did get rather warm some days during the day. Other than that it’s perfection!
We stayed at the house December 24-December 30. There were 14 of us ranging in age from 3-71. The house came fully stocked with everything needed. The pool was pretty small but it was great for the morning/evening swims before and after the days at the beaches. The views from the balcony were amazing!
Accommodated our 3 generation family perfectly. View outstanding, easy to find, lots of space for all to relax or share our daily experiences. Kitchen well equiped as we have some great cooks in family. Pool was great to kick back, cool off and visit. Visited a different beach everyday, snorkeled, went on a snorkeling charter. Saw turtles, eagle ray, porpoise, and many colorful fish. Very memorable trip.
Janet D.
Stayed 7 nights in Nov 2023
Response from VrboOwner on 28 Nov 2023
This was a lovely family group! 5 star all around.
Thank you again and Happy Holidays!!
Our stay at this property was absolutely amazing! From the moment we arrived, we were blown away by the breathtaking views and the spacious, well-designed layout of the home. It was the perfect getaway for our group, offering both comfort and luxury.The space was immaculately clean, beautifully decorated, and had everything we needed to feel at home. Waking up to the stunning island scenery every morning was truly unforgettable. The location was ideal, allowing us to fully immerse ourselves in the beauty and culture of the island.Everything about our stay exceeded expectations—from the peaceful atmosphere to the top-notch amenities. Whether relaxing on the balcony, exploring the area, or simply enjoying quality time together, this property provided the perfect backdrop for an unforgettable trip.We highly recommend this place to anyone looking for a dream getaway! Can’t wait to come back!
House and setting beautiful. Incredible views and terrific breezes. House has lots of amenities, lovely furnishings, but very, very accommodating to the 3 generations on the trip. We had a couple of hiccups but property manager very responsive, I mean fast. We had one car, but mainly used a taxi service, James, we met at Compass Point Marina who gave us good prices for group .excursions. Also used Paradise car rental, probably the best experience with car rental in 20 years. Overall, would recommend to anyone, with no qualifiers.
Daniel M.
Stayed 5 nights in Jun 2023
Response from VrboOwner on 4 Jul 2023
Always so happy to have a 3gen family like our own. Come again someday! All the best. Sandra
Archival
10/10 Excellent
Mark L.
10 May 2013
Great Family Destination
We had 15 people ranging in age from 2 years to 83.
The property was at the end of the road and overlooking the beautiful blue waters of
Charlotte Amalie. The VRBO listing photo's were very appealing and when we first
entered the property, there were nothing but ooo's and aaahhhh's. It was clean, neat
and everything was in its place. Very well equipped with laundry, linens, towels and more.
The property was in excellent condition and decorated and fit up nicely. The kitchen
was a little small for the "four cooks" who wanted to cook at the same time, but furnished
with just about everything we needed.
The pool was smaller than we anticipated but served its purpose well. The pool area was
pretty much the gathering place at any time of the day or evening.
The owner, Sandra Wright, was very helpful in fielding questions prior to our visit and we
did not have to bug her while we were there.
I would highly recommend this property to friends and relatives.
We had the most enjoyable time at Iggies which is a restaurant on the beach just 5 minutes away. From the pool patio, you can actually see the restaurant.
This was a special family event that we will never forget. For many reasons!
Mark L.
Response from VrboOwner on 22 Mar 2020
I am so happy we could be a small part of a very special family vacation.
The view was amazing and the house was great! It came with a small pool and a relaxing environment. Only complaint is there wasn't AC in every room so some of the rooms were hot. Besides that, we would happily come back again.
This was an excellent villa in the USVI. Clean, plenty of space for a large group, outstanding views and close to many world class beaches. Would love to come back!
We had a group of 15. We met up my sister's family and my mom and the house was huge and accommodated all of us. We ran out of water in the property but the property manager responded quick to come out and get it refilled for us. The house is super breezy no matter how hot it was. Definitely worth renting!
Our stay was wonderful. We were a group of 15, and we were all able to sleep comfortably. The views were amazing, and the pool was great for the kids. The house is equipped with all the essentials and more. We would definitely stay here again.
Janet C.
Stayed 6 nights in Mar 2022
Verified
6/10 Okay
Shelby B.
2 Apr 2022
Liked: Check-in, communication
Poorly maintained
From the pictures posted the property looked beautiful. However upon arrival we noticed the pool was deceptively small and dirty with some tiles also broken off at the bottom. The house itself was only somewhat clean:windows were dirty, bugs in picture frames, etc. Also not all the bedrooms had AC units. Not to mention the master bath had terrible water pressure that was no more than a trickle and the master bed mattress was very uncomfortable due to the caved in right side. In addition, the key we were given for the apartment did not work and many of the sliding glass doors in the main house would not lock. The view was the only real draw for this property.
Shelby B.
Stayed 7 nights in Mar 2022
Response from VrboOwner on 24 May 2022
Sadly, these guests have gone out of their way to find fault, because I retained $150 of their security deposit due to damage they caused.
As to the pool…. It is photographed and the dimensions are noted in the listing and in the extensive info packet I send to all guests. As to the “cleanliness” issues. It is difficult to make minor repairs between guests, but all of the items she mentioned had been addressed by our family less than 2 weeks before these guests arrived. I am sorry to disappoint anyone, and regret things didn’t satisfy.
We stayed at Surewinds with a total of 14 people for our wedding in St Thomas and rented both the house an appartment. Everything about our stay was incredible and Sandra was easy to communicate with and got back to me very quickly. The house was absolutely beautiful and we already miss waking up to the sunrise and ocean breezes. The kids spent all of their time in the pool and loved every minute of it. There were plenty of clean linens and lots of beach towels available for our entire group. We did a fair amount of cooking in the house and there were plenty of pots, pans and dishes to accommodate all of us. I would not hesitate to recommend that anyone stay here. We are already thinking of heading back for an anniversary trip.
The description was “spot on” and the house was great for us. Grandparents, 6 adult children and spouses, and 5 grands ages 1 to 9. There were four separate suites for the 4 family units, and the kids loved the pool , with supervision. We could fit 13 around the large dining table and there were several living rooms, including an apartment. We particularly appreciated the plentiful, nice quality towels and linens Our family is already talking about Christmas 2023 for a repeat vacation!
Property- The property was great. It was large enough for 10 people to have separate beds and eat together as a family. We rented the apartment on which was super nice!!!! The patio and pool are great hang out spots for days you want to stay in. The pool is shallow on one end and drops on the other but non swimmers were safe with supervision.
It was a bit warm during the day but the bedrooms have AC. The fans, the windows and open doors provide an amazing breeze for the common areas. Once you make it to the property you will get the hang of the location to tell the drivers or taxis. It is nice and secluded. We rented 2 cars and had plenty parking space. Everything was great for a getaway and the “outdoor” shower in the master was AMAZING!!!! We will rent again when we return to the island.
Communication- Sandra is amazing! She provided recommendations and had maps available in the home. No matter the question she always had an answer within 24 hours (more like 4 hours). I felt very prepared with the directions she provided and the island transportation did not have a problem finding the place. Sandra is the best!
Cons- the 2 minor cons is the trash system and the bugs. These are both an island thing not a house problem. The trash has to be taken to the bottom of the hill and loaded in the big dumpster which requires a car. The kids had a few spider bites from the bedroom downstairs, water bugs, ants and one lizard and one frog (on the patio door) during the stay. It was manageable by a wiping down upon arrival and wiping down after eating. It wasn’t a problem after day 2 but be prepared. I think the home may be vacant most of the time and they kind of settle in. But like I said it wasn’t an issue after day 2.
Overall: I would recommend this home! It is spacious, close to stores and restaurants but will require a taxi or rental car to really explore the island.
We had a fantastic week at Surewinds with our wedding party. The home is huge! Each couple had their own space. The air conditioned bedrooms were much appreciated and comfortable. Sandra is absolutely fantastic to work with. Some of our favorite parts of the house are the master bedroom open-air shower and the huge balcony. Thank you Sandra and Obrien for making Surewinds part of the best week of our life!
Owner Sandra is very nice and responsible. She sent us key and maps information ahead of our trip. I can always contact her easily during my stay. Great view from the house, definitely recommend to everyone!
Surewinds Estate is the perfect property for a big family or group. Massive balconies with spectacular views, lots of comfortable common spaces, big bedrooms. Sandra is a great host! Super attentive and always available.
Cristina H.
Stayed 8 nights in Jun 2021
Response from VrboOwner on 22 Jun 2021
Thank you Cristina. Sorry for getting behind on some maintenance things. We are working on them today! All the best, Sandra
About the host
Hosted by 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.
Why they chose this property
Besides the amazing architectural detail, Surewinds 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 property 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.