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Calypso Condo - Family Friendly Beachfront Elegance at Gentle Winds

62 Reviews
Bedrooms 3
Property type condo
Minimum Stay 5 nights

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Minimum Stay
5 nights


Northcentral Condo Rental Photos and Description

Condo, 3 Bedrooms/3Baths + Loft with Queen Sofa Bed

Gentle Winds Condominiums is consistently ranked #1 in Specialty Housing based on travelers’ reviews. Honeymooners, couples and families alike will enjoy the amenities at Gentle Winds and Calypso Condo, a three bedroom, three en-suite bath unit on two levels with two master suites, cathedral ceilings and central air conditioning. Prices vary according to the number of persons staying making it attractive to couples as well as families.

Being located on the second floor allows you to safely open all the floor-to-ceiling screened windows at night to allow the Trade Winds to blow through and allows you to be lulled to sleep by the sound of the surf. The private development of 66 units is located on 40 acres of beautifully landscaped grounds and has its own white sand beach set off from the public surrounded by a protecting coral reef. It combines the amenities of an exclusive resort with the charm of a friendly neighborhood. There are permanent palapas and lounge chairs on the beach, a beautiful new salt water swimming pool, a snack shack with freshly prepared food and drink, a four-hole pitch and put golf course, two tennis courts, a half-court basketball court, jungle gym, ping-pong, shuffle board court and a recreation room with game tables and a library. A Pirates Cove for children has been constructed nearby with a ship's bow, wheel, look-out and sand toys. We are also the only destination with a machine to keep the sand neatly raked which is also shallow and light enough not to disturb the turtle nests.

Completely renovated, Calypso Condo was designed to meet the needs of a wide clientele. For the adults, there is a sophisticated decor with multiple original works of art in every room, two master suites, a fully stocked bar, 40” HDTV with a large collection of DVDs, a MP3 compatible stereo system, WiFi and a gas BBQ. For families with children, there is an extensive array of sports equipment and sand toys, a hand made three story doll house, family board games and a comprehensive library of children’s movies with its separate TV set. Special furniture for infants and toddlers is available on request. The separate but attached storage room is suitable for storing scuba gear and contains a variety of sports equipment including snorkeling equipment, tennis rackets, basket balls and two sets of golf clubs.

The main floor master bedroom with its magnificent floor-to-ceiling hand carved mirror and luxurious king size bed with silk skirt and pillows is perfect for a couple or honeymooners. It opens directly onto the screened veranda where vacation memories will be created watching the swaying palms and listening to the surf. The two adjacent bathrooms provide his and hers privacy with lots of room to spread out. All rooms have overhead fans so you can choose between tropical breezes or a completely air conditioned house.

The upstairs master bedroom with queen bed is perfect for adults that would like to set themselves off from the rest of the family or for children that would like to be on their own. It has its own TV and DVD player, individual air conditioning (in addition to the central air conditioning) in case the downstairs wants breezes but the upstairs wants A/C, an en suite bath and a very large outdoor deck where one can watch the waves roll in or sit under the stars sipping an evening cocktail or just listen to the soothing sounds of the surf.

The upstairs gallery has a pull-out queen sofa bed and has a combination VHS/TV for playing the children’s movies. The gorgeous plantation shutters set off the attached patio which contains the gas BBQ, table and chairs.

The downstairs guest room on the land side has two twin beds, a view of the landscaped grounds with the tropical vegetation beyond. All bedrooms in the unit have beds with foam toppers and blackout curtains as well as sheers. All rooms have overhead fans and all en-suite full baths are equipped with safety/grab bars The living room and gallery fans are programmable and will adjust their speed according to the room temperature.

The great room is two stories high, has wall to wall windows and looks out on the screened veranda with the lush tropical landscaping and beach beyond. Even the veranda has an overhead fan to assure that the tropical breezes never stop flowing. It’s just a short walk across the lawn to feel the warm waters of the Caribbean lapping at your feet.

Gentle Winds is located on the exclusive north shore, half way between Christiansted and Cane Bay, home of the famous Wall at Cane Bay known throughout the world by diving enthusiasts. It is adjacent to Salt River Preserve where there are dive boats by day and kayak tours at night to see the phosphorescence as well as day tours to see the wildlife and mangroves. It is just a ten minute drive to Christiansted where tours leave daily for Buck Island, a national underwater preserve where there is a trail for snorkelers to follow.

To the east is the Buccaneer Hotel Golf Course located along the water with magnificent vistas and to the west is the Championship Robert Trent Jones Carambola Golf Course. The Divi Carina Casino is located to the south east. There is horse back riding to the west and deep sea fishing is available just next door at Salt River Marina. There is a special event or activity almost every night of the week throughout the island.

Keywords: family friendly,on the water, condominium, resort, villa, vacation rental, home, honeymoon, tropical getaway, exclusive, luxury beachfront, beautifully decorated, green, gated community, snorkeling supplies furnished,

More Details
  • children welcome
  • non smoking only
  • pets not allowed
  • wheelchair inaccessible

Barbara Flanagan
Member since: 2008
Speaks: english, french, spanish
Response time:
Within a few hours
Response rate:
Calendar last updated:
October 17, 2016
Call Owner

About Barbara Flanagan

I am a retired school teacher who has a horse boarding facility in Gardnerville, Nevada. I like to travel, garden and remodel houses. I have two dogs, one cat and three horses that I don't have time to ride.

Barbara Flanagan purchased this condo in 2011

Why Barbara Flanagan chose St. Croix

I was looking for a location that was warm and sunny in the winter. I have relatives who have been happy with their condo here at Gentle Winds for the last 30 years and it seemed a natural. I have always enjoyed snorkeling and never get tired of watching fish in their natural habitat. In addition, the Gentle Winds location is private and never feels over crowded.

What makes this condo unique

Being able to walk out on the beach whenever I feel like it is the height of luxury to me. Even in the summer, when you are in the shade at the beach with the trade winds blowing, the weather is perfect for reading and catching up on novels. With two master suites on two levels it's great for having family and friends visit.

Guestbook comments from the owner

The condo was perfect for a family of six. The unit is updated, clean and tasteful. The only odd part I found was that you had to leave from the front of the unit and walk around to back to get to the beach. Views are great. Beach is magnificent. Beach bar was fun. My sons and I snorkeled right off the beach at the complex and saw brain coral, barracuda, and a stingray. Sunny every day. About 30 mins. to airport about 20 mins. to Christiansted. Be aware the major activity is sunning on the beach or pool. We thought it was perfect - first time in six month we had all our young adult children with us at the same time. Family really reconnected.
Jan 2014
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based on 62 traveler reviews

Calypso Condo - Family Friendly Beachfront Elegance at Gentle Winds
average rating of 4.951613 based on 73 reviews
Montville nj

Calypso Condo still lives up to its name

  • 5 of 5

In Greek mythology Calypso was a nymph of exceptional beauty who lived on a hidden island and kept a lover her prisoner for years. Perhaps that's why the Flanagans named their Gentle Winds home "Calypso", a beautiful place where you wouldn't mind being held captive for years.

This was the second time that our family (husband, 16-year old, 13-year-old and 9-year old, plus my parents in their mid-70's) was fortunate enough to spend 9 days on St. Croix staying at Calypso Condo. The word "condo" though doesn't do it justice. Calypso becomes your home for the time you are there.

Calypso still has every amenity you could possibly desire. Toiletries in the bathroom, novels on the bookshelf, a well-stocked bar and some sunscreen (hats, too) await you upon your arrival so that you can start relaxing without doing that first run to the supermarket upon landing. Furnishings are clean, fresh, comfortable and stylish, loads of local art adorn the brightly-painted walls.

We love when the Shack opens its' shutters each day around 11 so the kids can get their fruit daiquiris. Food is always fresh and everyone had a favorite "drink of the day". The Caribbean Sea beckons with its warm, lapping waves and snorkeling right off the beach, but at night the Gentle Winds pool lights are irresistible for that night swim.

Its a tough decision to leave Gentle Winds to explore the island but when you do, we recommend Rainbow Beach in Frederiksted, the beach restaurant and activities are a fun way to spend a day. Crab races on the boardwalk in Christiansted was a highlight. Un Amore has fresh Italian specialties that will inspire you to order something from every course with a wine selection to match. One day set your alarm and drive the 40 minutes or so to see the sunrise at Point Udall. The drive on this part of the island is gorgeous in the pre-dawn hours.

Lots more recommendations in the Calypso Condo Guest Book. Snag this place if it is available.

  • Submitted: Aug 23, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
Owner's Response: Wow! What a terrific review. Thanks a million. Glad your kids enjoyed the fruit daiquiris at the snack shack.
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Wonderful, once again!

  • 5 of 5

Calypso Condo at Gentle Winds is just perfect! This is our 2nd year staying 2 weeks per year, always clean, well stocked with games, toys, tennis equipment, beach gear, golf clubs and balls, etc... Any issue we've had Angela has happily taken care of within the same day. This condo is centrally located and whether you just want to sit by the huge pool and soak up the sun or be super active and go diving, snorkeling, and horseback riding, this is the place for you! We have 4 kids and they loved the basketball court, ping pong table, shuffle board, and board games. The condo is designed so our family could spread out into the 3 bedrooms/3 baths/ 3 balconies.

We spent a lot of time at Cane Bay this year getting our diving certification, and it's only 10 minutes down the road. We also did See Thru Kayaks at night into the bioluminescent bay which is only a minute away. We needed to keep up with emails while on vacation and had no problem; internet connection was more then adequate. We ate most of our meals at the condo and had the best meats from Annaly farms and Seaside. Other items we found at Plaza West, just be really careful buying meat there! Annaly farms has all kinds of meat and it's super fresh! We had a fantastic meal at Blue Water Terrace on the east side of the island and several great meals at Eat at Cane Bay. We also attended several church services at Southgate Baptist Church also on the east side. Great people and great preaching!! We really don't think there's a better place to stay on the island!

  • Submitted: Jul 19, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
Owner's Response: Our location near Cane Bay is great for getting a diving certification, isn't it?
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Madisonville, LA

Gorgeous condo -perfect vacation

  • 5 of 5

Our family, 7 members this time, from 21 to 71 all enjoyed staying from June 6-11 this year. The condo has 3 nice bedrooms and full baths so everyone was extremely comfortable. The owner has decorated the condo so beautiful and interesting, as well as nice little touches for the guests. The views and soft breezes are so special. Everything was provided, except a small amount of food you need to buy. The cupboards are full of spices, basic food supplies, and bathroom needs. There are books, DVDs , wifi, and music. We ate 2 nights at Rowdy Joes, only 10 minutes away, and were a amazed at the food. Hopefully we will be able to come back to this peaceful, safe, and very enjoyable condo.

  • Submitted: Jun 29, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
Owner's Response: Glad you could enjoy our expanded set of DVD's. Come back soon.
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Best family vacation- ever

  • 5 of 5

The condo is just as nice as described. I think it is more important to note that Barbara is an attentive owner. She promptly answered my emails and followed up with us on vacation. Barbara also has a contact person in the area in case the condo has something unexpected happen. My husband and I enjoy snorkeling and the beach at the condo is a nice, easy place to snorkel. The view of the surrounding hills and forest is breathtaking and is visible from land and sea. We would definitely want to vacation at the condo again.

  • Submitted: Jun 26, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
Owner's Response: Being surrounded by forest on one side and the ocean on the other makes for a very restful, tropical vacation, doesn't it?
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Beautiful setting and wonderful accommodations!

  • 5 of 5

The condo was just as described, beautiful! Right on the beach, pool on the property, gorgeous grounds and very clean, comfortable accommodations. Everything went off without a hitch. Beautiful and safe condo, great for large families or groups of friends. All three rooms have its' own bathroom which was wonderful. The kitchen had everything you might need for cooking during your stay. Washer and dryer looked brand new. Three different balconies looked out onto the grounds and ocean. Storage room had pool floats and snorkeling gear for families to borrow. The owner seemed to have thought of everything. Free wi-fi, satellite TV, books, extra covers, towels and linens. Be sure to pack some of your own food from the states as groceries are about double of what they will cost you stateside. Wonderful family vacation!

  • Submitted: Jun 15, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
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Beautiful Calypso Condo

  • 5 of 5

We would highly recommend Calypso Condo to one and all. We have been in love with St. Croix, and with Gentle Winds for years now, and have stayed in various units throughout this lovely community. This condo exceeded all of our expectations. First of all, it is absolutely beautiful, painted in gorgeous sunny gold tones, and decorated with stunning tropical art and furniture. The palm trees on both sides of the unit complete the tropical setting. Having the trees surrounding the condo also adds the sound of birdsong to the other best sound on the island -- the sound of waves.

We were so impressed by how well- supplied this condo is in every respect, from kitchenware to beach and pool toys. Everything in the unit feels very upscale, from the mahogany bar and granite countertops to the lovely china in the kitchen. Games, books, a super TV and DVD system make the place feel like home. Having stayed in other very nice condos at beautiful Gentle Winds, we can tell you that this one has been updated considerably; it is super comfortable and a real treat to inhabit!

Barbara Flanagan (owner) has done a wonderful job with customer service, as well as with refurbishing and maintaining Calypso Condo. She always responded to questions and requests right away. She was not just prompt, but also very direct and pleasant in her communications with us. We felt that if we had experienced any problem, she would have addressed it immediately.

For those of you who have never stayed at Gentle Winds -- it has one of the best beaches on the island, with great snorkeling, swimming, and lunch at the Sandy Toes beach shack. It is also a very friendly community.

We can't imagine anyone not loving this place. Have fun!!!!

  • Submitted: May 10, 2016
  • Stayed: Apr 2016
  • Source: VRBO, from HomeAway
Owner's Response: It really is a friendly community isn't it? I, too, enjoy the view of the palm trees on both sides of the building. I think it really completes the tropical experience. Our DVD collection has really expanded and I am glad you were able to enjoy it. We're looking forward to having you back.
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Car: recommended

St Croix is world famous for Scuba diving and snorkeling. There are many tours including, horse back, jeep and mini bus. There are many museums and ecological sites and museums including beaches where the sea turtles come to lay their eggs. I would consider a day-trip to Buck Island to snorkle along an underwater trail in the national preserve a must-do activity . Boats leave twice a day from Christiansted for a full or half day trip. I would also recommend taking a kayak tour at night to see the phosphorescence in the water when it is disturbed.


Rates & Availability

Northcentral Condo Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
Peak Season
Dec 15 2016 - Apr 15 2017
5 night minimum stay
Notes: Rates are based on 2 guests; add $15 per night, per additional guest
Peak Season
Dec 15 2017 - Apr 15 2018
5 night minimum stay
Notes: Rates are based on 2 guests; add $15 per night, per additional guest
Peak Season
Dec 15 2018 - Apr 15 2019
5 night minimum stay
Notes: Rates are based on 2 guests; add $15 per night, per additional guest
My Standard Rate
5 night minimum stay
Notes: Rates are based on 2 guests; add $15 per night, per additional guest

Additional information about rental rates

Tax Rate 12.5%

Five day minimum stay. Minimal cleaning fee added for stays of less than a week ($44 or $22). 5% discount for a two week stay and must mention at time of booking. Mid-stay cleaning included with a two week booking, otherwise mid-week cleaning and concierge service to pre-stock unit is available at extra charge. Snack Shack closed Sept/Oct, reduced days and hours during the low season. Refundable damage deposit or credit card information required as well as a signed contract for all rentals.

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
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Northcentral Condo Accommodation and Amenities

Property Type:
  • condo
  • floor 2
Building Type:
  • building
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 1850 sq. ft.
Location Type:
  • Beach ...
  • Beach View ...
  • Beachfront ...
  • Ocean View ...
  • Oceanfront ...
  • Resort ...
  • Waterfront ...
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Broadband Access
  • Clothes Dryer ...
  • Hair Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Parking ...
  • Parking Off Street ...
  • Telephone ...
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet ...
  • Catering Available ...
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Freezer ...
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 16 people
  • 3 Bathrooms
  • Bathroom 2 - toilet , combination tub/shower
    Bathroom 1 - toilet , combination tub/shower
    Bathroom 3 - toilet , combination tub/shower
  • All bathrooms are newly renovated with gorgeous solid wood cabinets and granite counter tops as well as having new grab/safety bars.
  • 3 Bedrooms, Sleeps 8
  • Bedroom 1 - 1 king , Ground floor facing water,windows open to sound of the surf.
    Bedroom 2 - 2 twin/ single , Ground floor facing tropical landscaping.
    Bedroom 3 - 1 queen , Second floor w/open air deck opening to ocean
    Convertible bed(s) - 1 sleep sofa /futon , Queen sofa bed on lanai level overlooking great room
  • All rooms including the bedrooms have overhead fans in addition to central air conditioning to make sure that the tropical breezes never stop blowing. All beds have memory foam toppers and all bedrooms have two sets of curtains, both sheer and blackout. All bedrooms have chests with six or more drawers plus closets. The gallery level with the sofa bed has a three drawer chest and plantation shutters rather than curtains.
  • Books ...
  • CD Player
  • DVD Player ...
  • Game Room ...
  • Games ...
  • Music Library ...
  • Ping Pong Table
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Toys ...
  • VCR
  • Video Library ...
  • Balcony ...
  • Deck / Patio ...
  • Golf ...
  • Lanai / Gazebo ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Porch / Veranda ...
  • Tennis ...
  • Water Sports Gear ...
  • children welcome ...
  • non smoking only
  • pets not allowed
  • wheelchair inaccessible ...
Pool / Spa:
  • Communal Pool ...
  • arboretum
  • botanical garden
  • churches
  • cinemas
  • coin laundry
  • festivals
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • rain forests
  • recreation center
  • reefs
  • restaurants
  • ruins
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • gambling casinos
  • horseback riding
  • photography
  • scenic drives
  • shelling
  • shopping
  • shuffleboard
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • freshwater fishing
  • golf
  • hiking
  • jet skiing
  • kayaking
  • mountain biking
  • paragliding
  • parasailing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • wind-surfing
Half court basketball, 4 hole pitch and putt golf and shuffle board are available. There is an attached private storage room for sports equipment. Golf clubs and sports equipment such as face masks, fins, basketball, tennis rackets and balls, ping pong, sand toys, doll house and furniture, etc. are included. With three bedrooms, three baths and three decks and an entry with seating and stocked bar (replenished by guests), you'll never feel crowded. There are overhead fans in every room including the veranda to maintain the tropical breezes. The gallery and great room even have 'smart fans' that adjust their speed according to the temperature. We can stock your unit with food before arrival for an extra charge. The sound of the surf can be heard throughout the unit and the views are fantastic from every room.

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