Condo

Calypso Condo at Gentle Winds

Photo gallery for Calypso Condo at Gentle Winds

Living room with beach beyond
Living room view showing the upper gallery/loft/office level above.
View from the screened veranda with your rum punches waiting.
View of pool, beach shack and palapas on the sand.
Here's a wall of paintings by local artists with the lawn and ocean just outside

Reviews

10 out of 10
Exceptional
3 bedrooms3 bathroomsSleeps 8171.9 sq m

Popular amenities

  • Beach view
  • Dryer
  • Washer
  • Parking available
  • Kitchen

Explore the area

View map
Christiansted, St Croix
  • Cane Bay
  • Sugar Beach
    ‪11 min drive‬
  • Cane Bay Beach
    ‪13 min drive‬
  • Christiansted (STX-Henry E. Rohlsen)
    ‪22 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

Bedroom 3

1 Queen Bed

Office 1

1 Double Sofa Bed

3 bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 3

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Garden
Dining area

About this property

Calypso Condo at Gentle Winds

Walk across the lawn and you are in the ocean with a salt water pool and snack shack serving delicious food at your disposal. As you may know, Gentle Winds Condominiums is consistently ranked #1 in Specialty Housing based on travelers’ reviews. It is located between Salt River Bay and the rain forest on forty landscaped acres and consequently is uncrowded and thanks to rocky outcroppings on either end of the beach it has the feel of a private tropical paradise.

Couples and families alike will enjoy Calypso Condo, a three
bedroom, three en-suite bath unit on two levels with two master suites, two open patios and one screened patio,
cathedral ceilings and central air conditioning.


The private development of 66 units is located on 40 acres of beautifully landscaped grounds amidst surrounding wild vegetation and has its own white sand beach surrounded by a protecting coral reef. It combines the amenities of an exclusive resort with the charm of a friendly neighborhood. There are permanent tikis and lounge chairs on the beach, a
beautiful new salt water swimming pool, a four-hole pitch and put golf course, two tennis courts (lined for pickle-ball as well), a half-court basketball court, jungle gym, ping-pong, shuffle board court, corn-hole board and a recreation room with games and a
library. We are also the only destination with a machine to keep the sandneatly 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 gas BBQ as well as solid wood cabinets, granite counter tops, a mahogany bar and sliding glass doors in the tubs and walk-in shower.

For families with children, there is an extensive array of sports
equipment and sand toys in the attached storage room, a hand made three story doll house and family board games. The separate but attached storage room is suitable for storing scuba gear and contains a variety of sports equipment including snorkeling equipment, basket balls, noodles and kites

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. 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 (loft over the two story living room) has a pull-out queen sofa bed. The gorgeous plantation shutters set off the attached patio which contains the gas BBQ, table and chairs and a view of the surrounding forest.

The downstairs guest room on the land side has two twin beds which can be pushed together to make a king and a view of the landscaped grounds with the tropical vegetation beyond. All bedrooms in the unit have black-out curtains as well as sheers. All rooms have overhead fans and all en-suite full baths are equipped with safety/grab bars.

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. It's
the only building that looks directly out on the water where can see lawn,
sand and waves rolling in without worrying about the afternoon sun pouring
in as we face directly north.

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 bio-luminescence as well as day tours to
see the wildlife and mangroves. It is just a twenty 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 that is listed in the hand-out magazine "This Week in St. Croix."

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
A booster chair and Pack and Play are available.
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Remove personal items and take out the rubbish
Turn off the lights, lock the doors and return the keys
Return parking pass.
Failure to complete these may result in a negative review from the host.
Glass bottles should be thrown in the dumpster outside before leaving and the barcart and basic kitchen staples should be replenished before leaving.
All reservations must have phone or email communication with host within 48 hours after the time of booking.

Important information

You need to know

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
On-site parties or group events are strictly prohibited
This property uses a grey water recycling system
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 fire extinguisher, a first aid kit and a deadlock

We should mention

This property does not have any lifts
A car is recommended for transport to and from this property

About the area

Christiansted

Located in Christiansted, this condo is on the beach. Cane Bay and Carribbean Cinemas St Croix are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Salt River Bay National Historical Park and Little Princess Estate. Travelling with kids? Consider Cruzan Gardens and St. George Village Botanical Garden. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Christiansted, St Croix

What's nearby

  • Salt River Bay National Historical Park - 1 min walk - 0.2 km
  • Sugar Beach - 11 min drive - 8.7 km
  • Cane Bay Beach - 13 min drive - 10.5 km
  • St. Croix Government House - 15 min drive - 11.7 km
  • Shoys Beach - 23 min drive - 16.6 km

Getting around

  • Christiansted (SSB-St. Croix Seaplane Base) - 16 min drive

Restaurants

  • ‪La Reine Chicken Shack - ‬11 min drive
  • ‪Blues Backyard BBQ - ‬11 min drive
  • ‪Little Caesars Pizza - ‬12 min drive
  • ‪Little Caesars - Kmart - ‬12 min drive
  • ‪AMA Cane Bay - ‬16 min drive

Frequently asked questions

Does Calypso Condo at Gentle Winds have a pool?

Yes, this property has an outdoor pool.

Is Calypso Condo at Gentle Winds pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Calypso Condo at Gentle Winds ?

Check-in begins at 4:00 PM.

What time is check-out at Calypso Condo at Gentle Winds ?

Checkout is at 10:00 AM.

Where is Calypso Condo at Gentle Winds located?

This Christiansted condo building is on the beach, 0.2 mi (0.4 km) from Salt River Bay National Historical Park, and within 6 mi (10 km) of Cane Bay and Little Princess Estate. Sugar Beach and Cruzan Gardens are also within 6 miles (10 km).

Reviews

10

Exceptional

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy
Rating 10 - Excellent. 144 out of 149 reviews
Rating 8 - Good. 5 out of 149 reviews
Rating 6 - Okay. 0 out of 149 reviews
Rating 4 - Poor. 0 out of 149 reviews
Rating 2 - Terrible. 0 out of 149 reviews

Reviews

10/10 Excellent

Heather K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

First tropical vacation!

Comfortable and very roomy for our family of four. Loved the views. Especially enjoyed the pool at night hearing the waves and watching the palm trees in the breeze.
Stayed 6 nights in Jun 2025

10/10 Excellent

Nadine H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great accommodation and beautiful location

We loved calypso cottage. Plenty of room, nice furnishings, well equipped kitchen. We lived being so close to beach and pool.
Stayed 7 nights in Dec 2024

10/10 Excellent

Donna A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gentle Winds Family and Friends Vacation

Had a great vacation at Gentle Winds. Great location for large group traveling together. Each had there own place to lay their head however, were able to all be together at beach, pool, and food shack.
Stayed 7 nights in Jul 2023

10/10 Excellent

Suzy S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gentle Winds

This was our 3rd time here. We had a great time and we love the property!!!
Stayed 7 nights in Apr 2024

10/10 Excellent

LeAnne Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spring Break

We had a great stay. We found this location very nice situated between Christiansted & Frederiksted. We loved all the snorkeling equipment to use on our stay. Thank you
Stayed 7 nights in Apr 2023

10/10 Excellent

Tom B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Gentle Winds condo

Had a great stay at the condo, very well appointed and comfortable, kitchen well stocked with accessories if you choose to cook. Pool is very nice and the Snack Shack never disappoints. Will be back!
Stayed 14 nights in Aug 2023

10/10 Excellent

chris t.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to relax

Condo was great, centrally located on the island. Owner was very responsive to questions asked of her. Entire group enjoyed spending time at the pool after a day at the beach.
Stayed 7 nights in Aug 2022

10/10 Excellent

Gwen S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet, relaxing getaway!

Everything was great! The condo was clean and cozy with all the amenities that anyone should need. It was a nice relaxing environment. Our only problem was…..our stay wasn’t long enough 😊 We hope to visit again one day. Thank you Barbara for your hospitality!
Stayed 7 nights in Jul 2022

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise

Friends, This property has the home feel. Everything you need, they have. Steps from the beach and pool. If you're feeling lazy, there is a bar / grill within steps from the beach. Need to rest and relax, spend some time at Calypso Condo.
Stayed 6 nights in Mar 2023

10/10 Excellent

Gary K., Tampa, FL

Liked: Cleanliness, check-in, communication, location, listing accuracy

Really Nice Condo

Calypso Condo was nothing less than spectacular. Very well furnished, lots of towels, plenty of dishes and silverware, comfortable chairs and beds, really nice layout, great appliances. Pool was super as was the beach and snack bar. No hot water upon arrival but Angela got the fixed pronto. We will be back.
Stayed 8 nights in Dec 2023

10/10 Excellent

Tom R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

I've stayed in this unit three times in the past year. Great location and unit.

The unit is well appointed with everything you would need for a beach vacation. If you prefer not to eat at restaurants this unit has every thing you can think for to prepare all your meals. Great deal!!
Stayed 5 nights in Nov 2019

10/10 Excellent

S C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet Perfection

Our family spent Christmas week at this oasis. The home provided every single thing you could think you wanted (specially the kitchen). Two separate living spaces, two separate outside spaces, a must for familys. We didnt use any if the water equipment ie snorkles and such because we brought our own but we didn't need to. The property was quiet and offered many spaces a family could enjoy. Corn hole, shuffle board a small library for quiet space. Conveniently located for short trips to either of the city spaces. We will definitely be back. Barbara shares a great deal of lnformation to make the decidion easy.
Stayed 5 nights in Dec 2023

10/10 Excellent

George R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Oceanfront R & R

Group of 6 adults on our annual "Winter Warmer" trip. Condo was just as advertised. It was spacious, clean, naturally cool with beachfront breeze, well stocked for cooking needs (pots, pans, condiments & spices), short walk to pool & beach & overall pretty quiet & relaxing Spent lots of time on beach with plenty of sun, swimming & snorkeling. Prepared & cooked most meals. Good conversation, libations & food at the pool Snack Shack. Great complex for a morning or evening walk/jog. Had a few minor issues that we were able to work around. Overall, a very enjoyable, non-tourist intensive stay. Will consider again in the future.
Stayed 15 nights in Dec 2023

10/10 Excellent

Mark F., St George, UT USA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Carribean delight

This was a fabulous rental, just as advertised. The unit decor and layout were beautiful and the views of the Carribean sea and beach were breathless. The unit had everything a family would need for cooking, sleeping, and recreational activities (snorkels, fins, buoyancy compensators, beach chairs, towels, golf clubs, tennis rackets, games, and more). The Gentle Winds complex was well maintained with a large pool, beach area, and bar. Best of all, the property is away from the hustle and bustle of the towns and tourist areas, but close to the Salt River Conservation Area where we did some kayaking. It was a good base for visiting all parts of the island. Overall, we (4 senior adults) had a fantastic Carribean experience for 2 weeks thanks to the host and her condomium.
Stayed 14 nights in Dec 2022

10/10 Excellent

Barbara M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

ST CROIX a beautiful island with great potential.

Our condo was very nicely decorated and view was perfect. St Croix is a beautiful island and the people were friendly and helpful. We eat the Hamilton and AMA restaurants which were delicious and definitely 5star. Additionally, we breakfastd and lunches at several smaller restaurants and the food and service was very good I wish there were more road signs and street lights. Sun down was around 7 PM when we were there. So we made sure we were back in our unit before dark. I want to write to our President and ask him to assist these people of St. Croix . Having been to both St Thomas and St John, I hope St Croix would have the same type intra structure for safe roads as a car is a necessity here.
Stayed 7 nights in Jun 2023

10/10 Excellent

James W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely condo on St. Croix

I just spent a week at Calypso Condo with my family of 5, including kids ages 14, 18, and 20. I knew we had made the perfect choice as soon as I received my confirmation of booking from Barbara. I've rented homes and condos through VRBO all over the world over the past 20 years, and can honestly say I've never had an owner provide such a thorough introduction to their property and the area. Barbara's communication remained immediate and incredibly helpful throughout. The condo itself was laid out perfectly for our family. My 14 yo daughter was very comfortable using the fold out sofabed in the loft area above the living room, which left the 2nd floor master suite for my 20 yo and the smaller bedroom with 2 twin beds for my 18 yo. Everyone had their own bathroom, which is great for a bunch of teenagers! The unit was super clean and well-equipped. There is a huge, private locked storage closet immediately adjacent to the front door, which is full of goodies for communal use (e.g. masks, snorkels, fins, beach chairs, etc). The most pleasant surprise, though, was the swimming pool. The photos simply do not do it justice. The pool was quiet and seemed "newer" and "fresher" than it appeared in the photos. Most importantly, we all thought it was one of the absolute most refreshing pools we've ever used. The snack shop was awesome. And there was an abundance of beach chairs, tiki huts, etc on the beach. Rental car is a necessity, which is true for almost any location on St. Croix.
Stayed 7 nights in Jul 2024

10/10 Excellent

Amy P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great rental

Property is very well equipped and comfortable. Beach and pool on site were great and we were able to easily travel around the island from this location. The owner and on site manager were both great during our stay. We would definitely stay here again.
Stayed 7 nights in Jun 2022

10/10 Excellent

Courtney O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Escape from reality

This property was absolutely amazing. Property manager was awesome and went above and beyond when we had flight issues. She truly cares about her guests. House was perfect and property was so beautiful. The snack shack and Nick were awesome for food and drinks at the pool. She had everything you could need right there for you. We were all very happy with our stay here and out of all the places we saw on the island THIS was the best!!!!
Stayed 10 nights in May 2022

10/10 Excellent

Jeff P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Second stay

Great time and already planning another trip. One week too short, planning at least two weeks next time. The island itself still recovering from Covid and slowly opening back up. Next time hopefully more of the shops will be open again. Great experience overall.
Stayed 7 nights in Apr 2022

10/10 Excellent

Paul P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great family vacation

We enjoyed the condo and resort during our stay and we were impressed with how well stocked everything was! Also despite us staying at the height of spring break, the resort was never crowded and there was always a spot at the pool. Look forward to visiting again!
Stayed 7 nights in Mar 2022

10/10 Excellent

Sarah B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spring Break

This is a great property for families. The beach is not crowded and the pool is great! The grounds are well maintained and the beach bar is a perfect addition for drinks and lunch!
Stayed 7 nights in Mar 2022

10/10 Excellent

David M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

It is an amazing property with great space with views of the ocean and a very well stocked unit!!!

Barbara was wonderful to work with, her unit is amazing, everything you would have at home and more and the unit it self is clean and well maintained!!! With great views of the ocean from ever room. The location on the Island is perfect for other off site excursions. This property is a 9 out of 10 the property is beautiful and relaxing and private!
Stayed 6 nights in Mar 2022

10/10 Excellent

Crissy B., Saint Amant, LA

Liked: Cleanliness, check-in, communication, location, listing accuracy

The Calypso Condo was perfect for our family.

There was ample room for 6 adults to spread out and have their own space. The kitchen was well appointed with everything we needed.
Stayed 5 nights in Jan 2022

8/10 Good

Sandra B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good but not excellent

Beautiful views of the ocean. When we first arrived there was a musty smell. After we did a little cleaning it was fine. The condo overall was satisfactory. My personal opinion is it could have been cleaner. Again my personal opinion is there are way too many “Knick knacks.” We had to move things to be able to get our stuff out.
Stayed 5 nights in Feb 2022

10/10 Excellent

Sean N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Island perfection

The property and condo were perfect. Beach, pool, and beach-front drink/lunch shack are amazing. Property owner is wonderful and communicates well. Couldn't ask for more.
Stayed 6 nights in Jan 2022

About the host

Hosted by Barbara Flanagan

Host profile image
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, five barn cats and two horses that I don't have time to ride.

Why they chose this property

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 property unique

We are in the middle of a horseshoe ring of buildings facing the beach. Our view is directly at the water facing north. 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.

Languages:

English, French, Spanish

Premier Host

They consistently provide great experiences for their guests