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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)

If we do not have the availability you need, please inquire about VRBO # 331951.

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 an hour
Response rate:
Calendar last updated:
April 25, 2017

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 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:
  • Max. occupancy: 4
  • non smoking only
  • pets not allowed
  • Minimum Age Limit for Renters ...
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 ...
  • DVD Player
  • Games ...
  • Satellite / Cable ...
  • Television
  • Balcony ...
  • Barbecue
  • Beach Chairs
  • Beach Towels
  • Binoculars
  • 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 -
(29 traveler reviews)

Windswept 2: Oceanfront, Spectacular Views, Pool, Nearby Beach
average rating of 4.9310346 based on 29 reviews
Grand Forks, ND

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: Jan 2017
  • Source: VRBO, from HomeAway
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1 0

Unbelievably perfect

  • 5 of 5

Everything you could possibly want! Perfect vacation for family, including 20 and 22 year old daughters Plenty of activities Day trip to St. Thomas made us really happy to be on Water Island

  • Submitted: Dec 30, 2016
  • Stayed: Dec 2016
  • Source: VRBO, from HomeAway
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Portland, Maine


  • 5 of 5

My husband and I spent 2 weeks at Windswept 2 and it will forever be the benchmark for future vacations. Karen and Chuck are so attentive and responsive. The condo is well maintained and well appointed. Being able to wake to the sunrise every morning was very special. The pool was very refreshing and a great way to start and end the day. It was quiet and peaceful.

Honeymoon beach was a highlight and the snorkeling was great, so many fish to see as well as the turtles. The food at Dinghy's was great and the staff were a lot of fun. It was great to explore the island in the golf cart. We had Jacquie shop for us and it was wonderful to have food at the condo when we got there. Went into St. Thomas a couple of times and the ferry is so convenient.

Cannot say enough about how wonderful Windswept II and Water Island are.

This is the most relaxing vacation I have ever been on in the Caribbean and look forward to returning some day.

  • Submitted: Nov 18, 2016
  • Stayed: Oct 2016
  • Source: VRBO, from HomeAway
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1 0

A Gem overlooking the Ocean

  • 5 of 5

We had a wonderful stay at Windswept 2 in July 2016. It's a cozy, 2-story, tropical condo that shares a pool and courtyard area with three similar residences. It was comfortable, clean as a whistle, and well-maintained. There were numerous supplies provided that I'd stressed about forgetting to pack: bug spray & zappers, flashlights, & batteries, drinking water, coffee, beach towels, scuba gear -- all left for guest comfort and much appreciated. The internet and TV worked fine. There was a washer & dryer, although we packed amply and didn't need to use it. The air conditioning and ceiling fans in the two upstairs bedrooms helped us all sleep well (and many other rentals on the Island have no A/C, so beware if you are going there in the summer.) The downstairs has no A/C, but with the constant breeze through the jalousie windows, it was OK. The breeze also kept the mosquitos and bugs away, as we never saw any there. We miss the sound of the wind on the hilltop (Windswept is aptly named!) and the beautiful view of St. Thomas and the twinkling lights at night.

We were on Water Island for a family event and reunion, and many relatives were staying at a different, larger and more pricey rental where the A/C was out way more than it worked, and there were some plumbing and various maintenance issues. It was such a pleasure after staying there for a few days to head back to the comforts of Windswept 2, where all was in order and everything worked! This even extended to the included golf cart (the mode of transportation on this tiny island.) Our Windswept cart worked better than any that our friends & relatives rented.

Windswept 2 is up on a ridge overlooking the ocean. When you take the golf cart to the end of the block, there is a sign that says: "Stop, Den Go!" Only problem I had as our designated driver (who is also admittedly directionally impaired), was that I didn't know where to go! I took many wrong turns and got lost a couple of times. Water Island is tiny and only has a few roads, but they aren't really marked, so keep that in mind. It actually added to the fun in retrospect, but if it rains or you're in a rush, try to find a map of the island that shows where everything is located.

Water Island's Honeymoon Beach is great, with a bar/casual restaurant at each end: Heidi's and Dinghy's, which had great frozen drinks and movie & karaoke nights. Side trips were Mountaintop on St. Thomas and a bus tour of St. John (via ferry).

  • Submitted: Aug 30, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
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  • 4 of 5

The service was prompt and spot on. The unit has sunrise and sunset views over the ocean - incredible.

  • Submitted: Mar 28, 2016
  • Stayed: Mar 2016
  • Source: VRBO, from HomeAway
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K & J

  • 5 of 5

This was the most relaxing and easy vacation I have ever had! Windswept 2 is a home away from home on what feels like a deserted island! Breezy, quiet, and tranquil with all the modern accommodations to make it feel like home or better! If you are into shopping, St Thomas is just a short water taxi ride away, but we preferred the peace and quite on Water Island. Karen and Chuck are available for all and any questions and made us feel like family. We were sad to leave and look forward to returning some day.

  • Submitted: Jan 6, 2016
  • Stayed: Dec 2015
  • 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

Estate Western Water Island Condo Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Summer/Fall 2017
Apr 1 2017 - Dec 22 2017
7 night minimum stay
Holiday 2017
Dec 23 2017 - Jan 5 2018
7 night minimum stay
Winter 2018
Jan 6 2018 - Mar 30 2018
7 night minimum stay
My Standard Rate
7 night minimum stay

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

Please ask the owner or check their rental agreement when booking the property.
Enter dates for accurate pricing