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Windswept 2: Oceanfront, Spectacular Views, Pool, Nearby Beach

Bedrooms 2
Space 1,500 sq ft
Property type condo
Minimum Stay 7 nights


About the property

Condo, 2 Bedrooms + Attached Unit, 2 Baths, (Sleeps 4)

Windswept Water Island Update Post Hurricanes Irma & Maria: December 9, 2017

As you know, Hurricanes Irma and Maria roared across the Virgin Islands in September 2017. Water Island took a direct hit from both of these Category 5 storms. We are happy and grateful to report that no lives were lost on Water Island but many of our friends suffered extensive property losses. Windswept stood strong, sustaining modest damage. Repairs will be completed within the next couple of months. We are accepting reservations for rental March, 2018. Happily, the Windswept Palm remains standing. Honeymoon Beach lost its shelter and Heidi’s and Dinghy’s were severely damaged but, in true Water Island fashion, locals banded together to repair what they could. Both Heidi’s and Dinghy’s are open for business and the beach has been cleared of all storm debris. It will be some time before the shelter returns, but we have no doubt that we will see it again someday. The island is green again. Power has been restored to Water Island. . We’re saddened by the destruction that our little island paradise encountered but know that 2018 will bring nothing but good cheer!

Water Island was described as 'A Homeland Treasure' in the front page, feature article of the Boston Globe travel section (December 6, 2009).

Windswept 2 is a newly constructed (2009) two bedroom, two bathroom oceanfront, semi-attached condominium perched on a cliffside. It is one of five condominiums located on this 1.3 acre property with breathtaking views from every window. At night enjoy the sparkling lights of St. Thomas across the bay. Listen to the waves crashing against the rocks, the trade winds blowing and taste the salt from the ocean on your lips.

Enjoy your morning coffee on either the front or back lanai watching the cruise ships arrive in St. Thomas Harbor. In the evening, enjoy cocktails at the swim up bar, in the 12X30 shared pool, overlooking Flamingo Bay. If you tire of lounging around the pool, the warm turquoise waters of the Caribbean can be enjoyed at Honeymoon Beach, which is a short five minute ride in the four person golf cart available during your stay. You will find Heidi's Honeymoon Grill on the beach offering lunch most days of the week. New for the 2013-2014 season is Dinghy's on the beach which offers lunch, dinner and drinks seven days a week. On Saturday evenings, you can enjoy the true island experience of an excellent gourmet dinner, served by Heidi, on the beach (In season). Relax with the sound of the water lapping at the shore and the sun setting over the ocean.

For a change of pace, St. Thomas is ten minutes away by public ferry offering shopping and world class restaurants. If golf is your passion, the beautiful golf course, Mahogany Run is located on St. Thomas. After enjoying the city amenities, return to quiet, laid back Water Island where golf carts out number vehicles.

Inquire if additional space needed. This villa can be rented with VRBO #331951.

Keywords: Tropical paradise, high end, surrounded by mesmerizing views, turquoise water, gorgeous nearby beach

More Details

Charles & Karen Dumond
Member since: 2009
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
April 17, 2018

About Charles & Karen Dumond

My wife and I live in Falmouth, Maine. I am a retired Portland firefighter and my wife is a retired nurse. We love to travel, meet new people and see amazing places. We love living on the rugged coast of Maine most of the time. Our winters can be long and we always look forward to escaping to the warm tropics.

Charles & Karen Dumond purchased this condo in 2009

Why Charles & Karen Dumond chose Estate Western Water Island

A few years ago, friends told us about a piece of oceanfront property in the Caribbean that housed an old five-unit military barrack. Our friends were looking for four other couples to build a total of five units on the site. While my wife and I never considered the possibility of owning oceanfront property in the Caribbean, this seemed like a great opportunity. Without even discussing it, my wife and I looked at each other and said 'yes'.

In 2006, we put a down payment on the property, before even seeing it. We had never heard of Water Island! If our adult children did something like this, we would call them irresponsible!

Stepping on the property for the first time was unbelievable. How could we not have known about Water Island? The pictures we had seen just didn't come close to the amazing views all around. Maybe we weren't so crazy after all! This was definitely one of those 'Once in a lifetime opportunities!' We knew immediately that owning a vacation home on this spot was going to be very special. We could not believe that we had been lucky enough to fall into this and kept waiting for everything to fall apart!

For the next three years, we planned and worked towards completing this villa from our home in Maine. No easy feat, and lots of 'oh by the ways!' Building on an island is difficult enough, doing it from a distance, adds to the fun!!!

In the Fall of 2009, our vacation villa was completed adjacent to the villa of our good friends. We started sharing it with family and close friends. Their first reactions on seeing Water Island and Windswept were: 'Unbelievable, gorgeous, breathtaking!'

In 2010, we had our first rental guests. We consider ourselves fortunate to have wonderful guests who enjoy Windswept and Water Island as much as we do. We love to hear that we have helped them have a relaxing vacation and truly get away from it all. We get a lot of satisfaction from helping people create lasting memories and hope you are our next guest!

What makes this condo unique

Coffee in the morning on the front patio while watching the sun come up over the tip of St. Thomas as the cruise ships enter St. Thomas Harbor. Dinner time drinks at the swim up bar as the sun sets in the west. Riding around the island in the golf cart and stopping for lunch at the beach. Saturday night dinner on Honeymoon Beach as the sun sets and the Monday night movies at the beach. Quiet evenings with the only sound being the waves crashing against the rocks below and the trade winds blowing.


Estate Western Water Island Condo Accommodation and Amenities

Property Type:
  • condo
  • Guests provide their own meals
Floor Area:
  • 1500 sq ft
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 4
  • Max. adults: 4
  • Min. age of primary renter: 21
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
Location Type:
  • Beach ...
  • Near The Ocean ...
  • Oceanfront ...
  • Town ...
  • Away From It All
  • Family
  • Romantic
  • Air Conditioning ...
  • Alarm Clock
  • Basic Soaps
  • Ceiling Fans
  • Clothes Dryer
  • Filtered Water
  • Hair Dryer
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided
  • Living Room
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking Off Street
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • Water Cooler
  • Wireless Internet
  • 4 Ring Stove
  • Blender
  • Catering Available ...
  • Coffee Grinder
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher
  • Freezer
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator
  • Stove
  • Stove
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 4 people
  • 2 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
  • Bathroom one has open shower with glass block wall and river rock floor.
  • 2 Bedrooms, Sleeps 4
  • King size beds (1), Twin or Single Beds (2) Extra long twin beds can be converted to king bed. Inquire about availability of attached unit, VRBO #331951 for additional capacity.
  • Books ...
  • Games ...
  • Satellite / Cable ...
  • Television
  • Balcony ...
  • Barbecue
  • Beach Chairs
  • Beach Towels
  • Deck / Patio ...
  • Golf ...
  • Golf Cart
  • Lanai / Gazebo ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Outdoor Grill Gas
  • Patio
  • Porch / Veranda
  • Small Cooler
  • Unscreened Porch / Veranda
  • Water Sports Gear ...
  • Long-term Renters Welcome
  • wheelchair inaccessible ...
Pool / Spa:
  • Communal Pool ...
  • bay/sound
  • cinemas
  • duty free shops
  • health/beauty spa
  • marina
  • museums
  • reefs
  • restaurants
Leisure Activities:
  • beachcombing
  • boating
  • shelling
  • shopping
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • hiking
  • jet skiing
  • kayaking
  • paragliding
  • parasailing
  • pier fishing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • swimming
  • tennis
  • wind-surfing
Four person golf cart, Property Manager on island, Whole house UV water filtration system. All water in the house is safe to drink.


Wonderful! 4.9/5 -
(34 traveler reviews)

94% Complete
5% Complete
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Windswept 2: Oceanfront, Spectacular Views, Pool, Nearby Beach
average rating of 4.9411764 based on 34 reviews
Cumberland Foreside Maine

Great stay! You can’t go wrong with Windswept 2! Great owners!

  • 5 of 5

Very nice stay! One of the nicest homes you can stay at on Water Island. Owners are very involved and take great care of Windswept 2. Enjoy your part of paradise!

  • Submitted: Mar 13, 2018
  • Stayed: February 2018
  • Source: VRBO, from HomeAway
Owner's Response: Thank-you very much. We are very glad that you enjoy Windswept and Water Island.
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0 0
Rockwall tx

Lovely, well equipped home

  • 5 of 5

We rented both windswept condos and our family had a wonderful time on this island, and felt at home in these well equipped rentals. Windswept 2 is the nicest of the two condos, clean and considering the environment of the salty sea air, is in pretty good shape. Windswept 1 is in need of some repair, and cleaning, but is also lovely and well equipped. We plan on making this a yearly family trip and if these are available on our next trip, we won't have to think twice about where to stay. Windswept is the way to go!

  • Submitted: Jul 27, 2017
  • Stayed: July 2017
  • Source: HomeAway
Owner's Response: Joanna, We are happy that you enjoyed your stay at Windswept on Water Island. Thank-you for your thoughtful review and the opportunity to address the problems that you found. I appreciate our followup email conversation and will take care of the issues discussed. We will look forward to having you back again soon. Regards, Karen
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1 0

First Class all the way

  • 5 of 5

Beautiful property. Open the doors and sleep with the waves crashing. Great pool. We have been to Water Island 4 times and we will come back again. I just hope this property is still available. We appreciate the Dummonds sharing this gem with us.

  • Submitted: Jul 6, 2017
  • Stayed: June 2017
  • Source: VRBO, from HomeAway
Owner's Response: Daniel & Deborah, Thank-you for taking the time to write this nice review. We look forward to having you as our guests again soon. Chuck & Karen
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0 0

Everything we expected

  • 5 of 5

Our stay at Windswept 2 was very nice. The home has everything you need. The kitchen, bathrooms, linens etc were all well supplied. The beds are very comfortable as is the living room furniture. A/C in bedrooms was good. It is a very nice home. The views are fantastic. Cruise ships in the front and rear of the home. The pool is nice if you don't wish to go to Honeymoon Beach. We loved our stay here and would recommend Windswept 2 and Water Island to anyone looking for a nice relaxing vacation. We hope to be able to return one day. Our dealings with the property owners was very good.

  • Submitted: Jul 4, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: Mike & Heather, Thank-you for your kind review. We look forward to having you return to Water Island, as our guests at Windswept, in the near future. Chuck & Karen
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0 0

A Slice of Paradise!

  • 5 of 5

We've now stayed/visited all 4 USVI and agree Windswept 2 on Water Island is our favorite spot!! It's perfect with a very easy pace vibe, only golf carts to explore the island & very friendly locals. Doug, who oversees the property, met us at the dock after a quick water taxi ride to Water Island. He was very welcoming & showed us around the condo. It was comforting knowing he was close by, if we needed anything.

Windswept 2 is a piece of paradise with amazing views. We were awakened by a beautiful sunrise as cruise ships headed into St. Thomas & evenings captured amazing sunsets while enjoying a glass of wine, poolside. It definitely lives up to its name with tropical breezes, never turned on the A/C.

It just doesn't get any better!!

Owners, Chuck & Karen, have thought of everything to meet the needs of their guests. They factor in all the comforts of home with high quality linens, towels, beach towels, beach chairs, snorkeling gear & the list goes on. The condo has been well maintained and VERY clean. They've thought of everything so all we needed to do was relax & enjoy our week.


They contacted us before our trip to answer any last minute questions. Having Celiac can make traveling tricky and they made suggestions that worked out very well. We were able to call Heidi, owner of Heidi's Honeymoon Grill, and she had gluten free buns/wraps to meet our needs. The grill is right on Honeymoon Beach and serves delicious food!! Dinghy is another spot on the other end of the beach & we enjoyed their live music a few times.

Honeymoon Beach is absolutely gorgeous! We loved snorkeling right off the beach and observing the resident sea turtles.

It was very sad leaving our little slice of paradise, but look forward to returning to Windswept 2 in the future with family or friends!!!!

  • Submitted: May 3, 2017
  • Stayed: April 2017
  • Source: VRBO, from HomeAway
Owner's Response: Dick & Kathy, Thank-you for taking the time to write this lovely review of Windswept and Water Island. We appreciate having you as our guests. Chuck & Karen Dumond
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1 0
Grand Forks

Great experience and aptly named

  • 5 of 5

Our family of 4 just returned from a week long stay on Water Island. We loved the unique experience of being on a less inhabited island where the pace was slow and the views great. Even when cruise ship groups visited Honeymoon Beach we never felt it was over run. We loved waking up each morning to the sunrise out our master bedroom window and counting the cruise ships heading to port in St. Thomas. Sunsets from the pool or from a quick golf cart drive up to sw corner of the island were spectacular! The owners were amazingly prompt and helpful in responding during the booking process. The information they shared ahead of time was much appreciated in making plans of what to bring. We have rented in other locations in the US and feel these owners truly set the stage for us "feeling at home" with high quality linens and towels, books, games, beach gear, nice array of staples in the kitchen etc. We enjoyed bingo night at the pavilion and meeting the locals who we found very friendly. For those planning to book I would recommend considering making flight plans that bring you to St. Thomas by mid afternoon and not fly out until late morning in order to avoid hassles with planning for ferry plans that sync with airline plans. We loved being on Water Island and our great accommodations so much that we only left the island twice to explore St. Thomas and cancelled our plans for additional island hopping. We hope to come back someday and bring others with to rent Windswept 1 and II together for a fun time!

  • Submitted: Jan 12, 2017
  • Stayed: January 2017
  • Source: VRBO, from HomeAway
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Nearest Airport
2 Miles
Cyril King (STT)
Nearest Barpub
1 Miles
Dinghy's at Honeymoon Beach
Nearest Ferry
0.5 Miles
Water Island to St. Thomas
Nearest Golf
1 Miles
Mahogany Run on St. Thomas
Nearest Restaurant
1 Miles
Tickles at Crown Bay Marina on St. Thomas
Nearest Beach
0.5 Miles
Car: not necessary

Owner is happy to assist with activity information on request.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Tax Rate 12.5%

Additional rental nights are prorated. Cancellations more than 60 days prior to arrival will receive a full refund minus a $75.00 administrative fee. Cancellations within 60 days of arrival will forfeit payment.

Arrival day is flexible.

Cancellation policy: Deposit will be returned, minus $75.00 administrative fee, if cancellation is made more than sixty days prior to arrival date. If cancellation is within sixty days of arrival date, the deposit will not be returned but can be used towards a future booking.

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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