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Calypso Condo - Family Friendly Beachfront Elegance at Gentle Winds

Barbara Flanagan

Member since: 2008
Call Owner
Enter your email address to view the phone number
Speaks: english, french, spanish
Bedrooms 3
Property type condo
Minimum Stay 5 nights

Barbara Flanagan

Member since: 2008
Speaks: english, french, spanish
Response time:
Within 12 hours
Response rate:
Calendar last updated:
April 30, 2015
Call Owner
Enter your email address to view the phone number
Book with confidence
Book with confidence
Guaranteed, secure, with no booking fees
Add vacation protection services to your booking
Three services to protect your trip:
Protect your payments in case you need to cancel.
Guarantee the rental meets your expectations
Ensure you're prepared in case of accidental damage.

Calypso Condo - Family Friendly Beachfront Elegance at Gentle Winds

Bedrooms 3
Property type condo
Minimum Stay 5 nights


St. Croix Condo Rental Photos and Description

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

Gentle Winds Condominiums is consistently ranked #1 Specialty Housing based on travelers’ reviews and Calypso Condo consistently receives Awards of Excellence each year as well. 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 if it is needed. 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 providing the perfect environment for snorkeling and swimming. 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 and a recreation room with books, ping-pong, and a shuffle board court. 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, 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 video 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. 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, 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 sofa bed where two individuals can sleep 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 and is decorated in a jungle motif. All beds in the unit have foam toppers and all rooms have overhead fans and en-suite full baths. 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 and perhaps you'll see one of our resident mongooses on the way.

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. Go to our web site for more details and pictures.

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 (Owner)
Member since: 2008
Call Owner
Enter your email address to view the phone number
Speaks: english, french, spanish
Response time:
Within 12 hours
Response rate:
Calendar last updated:
April 30, 2015

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 three dogs, one cat and five 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
  • 1 of 11

Why HomeAway

Bedrooms 3
Property type condo
Minimum Stay 5 nights
Book with confidence
Book with confidence
Guaranteed, secure, with no booking fees
Add vacation protection services to your booking
Three services to protect your trip:
Protect your payments in case you need to cancel.
Guarantee the rental meets your expectations
Ensure you're prepared in case of accidental damage.


based on 42 traveler reviews

Write a Review
Calypso Condo - Family Friendly Beachfront Elegance at Gentle Winds
average rating of 4.952381 based on 53 reviews

Loved the condo!

  • 5 of 5

We just returned from Barbara's condo, and absolutely loved it. The condo has everything you will need to make your vacation complete. Barbara was wonderful about answering questions and making suggestions before the trip and there is plenty of information about the island once you arrive. We enjoyed every balcony and the screened porch. There were plenty of beach towels and linens for the five of us. Beds were comfortable and kitchen is well stocked. Friends stayed in the building next door, and their condo was clearly a rental unit---Barbara's condo is a home.

Gentle Winds is a lovely complex with a good swimming beach and pool. The snack shack on the beach has good and reasonably priced food and drinks. The staff was friendly and helpful. The other guests were friendly and polite. This is not a party place and the island, in general, is quiet and low key. We enjoyed the location in relation to everywhere we wanted to go/explore. It felt very safe and is well maintained.

We would stay at Barbara's condo again, without hesitation! Car is recommended

  • Submitted: Apr 14, 2015
  • Stayed: Apr 2015
  • Source: VRBO, from HomeAway
Owner's Response: Providing a home away from home is exactly what we strive to provide. I'm so glad that that is the feeling that came across.

Look no further!

  • 5 of 5

My two girlfriends joined me for 10 days at this condo. We each had our own bedroom and bathroom, it was perfect. The weather was 80 degrees every day. We visited the pool and the snack shack daily. It was never crowded or noisy and everyone was welcoming. Each evening we would sit on one of the two decks that overlooked the Caribbean and enjoy a glass of wine before heading to dinner. We also appreciated the location of the condo as it was located near many great restaurants.

If you are looking for a beautiful place decorated with local art then look no further. Gentle Winds has everything you could ask for and more!

  • Submitted: Apr 4, 2015
  • Stayed: Mar 2015
  • Source: VRBO, from HomeAway
Owner's Response: Many people mention the central location of Gentle Winds as being terribly convenient. And I'm so glad that you enjoyed the original art on the walls. I know I do. We're looking forward to having you back.
Edmond, Okalhoma, USA

Beautiful island, friendly people, ideally situated condo

  • 4 of 5

Took the family on a holiday over Christmas break to St. Croix, US Virgin Islands. Was looking for an upper end hotel that could hold 5 people but gave up trying. Found this condo located on the NorthEast side of St. Croix on the grounds of the Gentle Winds community of condominiums. The owner, Barbara, was extremely helpful with information on the condo, grounds, things to do, etc. I am a pretty difficult individual to please (which is why I only gave it a good rating) but it is definitely good. Fully furnished condo, two nice size bedrooms downstairs, with a 3rd bedroom upstairs (along with a good size sitting room and two balconies). Each bedroom had its own bathroom and shower. Very well-appointed condo with everything one needs to cook, rest, relax, and enjoy the truly beautiful grounds, beach, and Caribbean waters. The Gentle Winds has a nice size pool and a fabulous snack shack that serves up great sandwiches and beverages. Great place to meet folks visiting as well as owners. We only went out for dinners which were excellent. Can't say enough about the friendly natives and mainlanders who have retired on the island. Very helpful people and very clean island. I've been around the Caribbean, Central and South America and St. Croix is tops when it comes to clean. Plenty of family activities on the grounds - tennis, modest "golf course," shuffle board, ping pong, and this bean bag toss game. If you like water, this spot has beautiful, clear, and warm waters wtih coral reefs right off the beach - fabulous ocean life too!) Overall, just a marvelous time (weather was fantatistic too - 72 at night low 80s during the day..sunny through our seven day stay). So, go for it and stay at the Calypso Condo. Great location and very responsive owner.

  • Submitted: Jan 19, 2015
  • Stayed: Dec 2014
  • Source: VRBO, from HomeAway
Owner's Response: "Definitely good" can't be all that bad. We'll settle for that. Thanks for finding time to do a review and letting everyone know about the great food at the snack shack and the many activities for families and children. It's interesting to hear that St. Croix is the cleanest island/country that you have visited in your travels in this area.

Great stay!

  • 5 of 5

Just arrived home from a wonderful time on St Croix. Our condo was perfect for our family! The owner goes over and above to help you have a wonderful trip. We love staying here because its not crowded, its very relaxing. The condo had everything we needed to enjoy our stay. Plenty of room for 6 of us. We recommend this condo to everyone. Its a great place to stay.

  • Submitted: Jan 15, 2015
  • Stayed: Jan 2015
  • Source: VRBO, from HomeAway
Owner's Response: We bought this unit because we liked the open feeling the two story living room had without even thinking about the fact that the two stories and the three bedrooms were perfect for a three generation family stay. It has worked out very nicely for all concerned.
Albuquerque, NM

Paradise in Paradise

  • 5 of 5

This was our introduction to the Caribbean and I wanted it to be special for the family. After a day filled with activities (snorkeling, scuba diving, sailing, playing on the beaches), we came home to the best condo in St. Croix! The pictures on the website are exactly what you find when you step through the door. The condo is spectacular and the grounds at Gentle Winds are manicured like a golf course. This is also the first VRBO that we have tried, and Barbara made the process seamless. She is very responsive and accommodating. Thank you for a wonderful vacation. We hope to return next year.

  • Submitted: Oct 26, 2014
  • Stayed: Oct 2014
  • Source: VRBO, from HomeAway
Owner's Response: Exactly as pictured, manicured landscaping, seamless process, coming back next year......we couldn't ask for more Thanks.

A terrific stay at Gentlle Winds

  • 5 of 5

We loved our stay at Calypso Condo in Gentle Winds. When we were choosing which unit to stay, we picked this one since it looked to be nicely appointed. It was even nicer to see in person. The unit is immaculate and has everything you'd want or need during your stay. We never turned on the A/C because of the breezes that were always blowing through the unit. There are sliders in the front and back so it was quite comfortable. We were there during the off season so our restaurant selections were somewhat limited. There are several restaurants nearby. We drove into Christiansted a couple of nights also. We would definitely recommend this unit to someone looking to rent at Gentle Winds.

  • Submitted: Sep 28, 2014
  • Stayed: Sep 2014
  • Source: VRBO, from HomeAway
Owner's Response: It's always nice to hear that it's even nicer in reality than the pictures depicted and quite clean. We are lucky indeed to have Angela as our housekeeper.


Cane Bay
Fort Christiansvaern
Fort Christian Brew Pub
The Terrace Restaurant at the Buccaneer
Salt River Bay National Historical Park and Ecological Preserve
Angry Nates Boathouse & Seafood Emporium
Rum Runners Steaks & Seafood
Off the Wall
"Outdoor pizza right beside the splashing waves. Bingo night can be a worthwhile investment."
Cruzan Rum Distillery -- CLOSED
"Fun to watch the rum bubbling and gurgling away."
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

From $235 Per night

St. Croix Condo Rental Rates

Rental Basis:
per property
Rental rates quoted in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
Peak Season (Xmas Week extra)
Dec 15 2015 - Apr 15 2016
5 night minimum stay
Notes: Rates are based on 2 guests; add $15 per night, per additional guest
Peak Season (Xmas Week extra)
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 Xmas Week extra
Dec 15 2017 - Apr 15 2018
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 10.0%
Notes 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-week cleaning and concierge service to pre-stock unit available at extra charge. Snack Shack closed Sept/Oct, reduced days and hours during the low season. Xmas week is $3,000.00 for 1-6 persons. Refundable damage deposit or credit card information required as well a signed contract for all rentals.

Cancellation Policy

Policy available by contacting owner when booking.
Enter dates to see total


St. Croix Condo Accommodation and Amenities

Property Type:
  • condo
  • floor 2
  • Guests provide their own meals
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
  • 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 ...
  • Pantry Items ...
  • Refrigerator ...
  • Toaster
  • Child's Highchair
  • 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, stainless steel fixtures, rain shower heads and granite counter tops.
  • 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/deck opening to ocean & private A/C
    Convertible bed(s) - 1 sleep sofa /futon , Queen sofa bed on lanai level w/deck 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. The sleeper sofa on the gallery level accommodates 2 people. 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 Game Console ...
  • Video Games ...
  • 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 suitcases and 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. There is a printer and surge protector waiting to be used with your computer as well as a computer and printer to preprint boarding passes in the office. 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.

Partner Offers

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4 - 5 night min stay
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  • 2 BA,
  • Sleeps 6
$5,800 - $12,000 per week
1 - 10 night min stay
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