Title: Five Cays Ski Vacations 2026 | Expedia.com

![](https://images.trvl-media.com/place/11672/d2d90a11-08a9-4e50-887d-b91554f7945e.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Five Cays Ski Vacations

## Book a Ski Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to $1,045 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

## Top Ski vacation packages in Five Cays

Price found within the past 48 hours. Click for updated prices.

![Windsong on the Reef](https://images.trvl-media.com/lodging/3000000/2430000/2422200/2422198/12b8b359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Windsong on the Reef

Grace Bay

Save 100% on your flight

$1,942

per person

May 2 - May 9

found 2 days ago

Roundtrip flight included

Boston (BOS) to Providenciales (PLS)

9.2/10 Wonderful! (1,003 reviews)

Everything was perfect and beautiful. Good food. All great

Reviewed on Mar 1, 2026

![Dream Villas Provo](https://images.trvl-media.com/lodging/97000000/96370000/96368700/96368651/a01ea79e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Dream Villas Provo

$2,535

per person

May 2 - May 9

found 2 days ago

Roundtrip flight included

Boston (BOS) to Providenciales (PLS)

9/10 Wonderful! (58 reviews)

Excellent location. Walking distance to 2 restaurants, small store across street. Very clean and modern. Comfortable beds. Everything you need for a relaxing beach vacation!

Reviewed on Feb 26, 2026

![Bungalows at Windsong on the Reef](https://images.trvl-media.com/lodging/2000000/1800000/1793300/1793291/bb54e1cd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bungalows at Windsong on the Reef

Grace Bay

Save 100% on your flight

$2,256

per person

May 2 - May 9

found 2 days ago

Roundtrip flight included

Boston (BOS) to Providenciales (PLS)

9/10 Wonderful! (84 reviews)

The staff was wonderful, our room was spotless and very comfortable, the beach was beautiful

Reviewed on Feb 19, 2026

![Beachfront at Windsong on the Reef](https://images.trvl-media.com/lodging/21000000/20850000/20846500/20846403/159db57d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Beachfront at Windsong on the Reef

Grace Bay

Save 100% on your flight

$2,830

per person

May 22 - May 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.2/10 Wonderful! (117 reviews)

Great room. Lovely resort, friendly staff. Easy access to town

Reviewed on Feb 15, 2026

![The Park at Grace Bay](https://images.trvl-media.com/lodging/121000000/120070000/120063400/120063392/08207d46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Park at Grace Bay

Grace Bay

Save 100% on your flight

$2,969

per person

May 22 - May 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

No reviews

Don't see what you're looking for?

See all available trips from Columbus to Five Cays

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-02/2026-04-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MDS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Ski vacations in Five Cays

Price found within the past 48 hours. Click for updated prices.

![Beachfront at Windsong on the Reef](https://images.trvl-media.com/lodging/21000000/20850000/20846500/20846403/159db57d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Beachfront at Windsong on the Reef

Grace Bay

Save 100% on your flight

$2,830

per person

May 22 - May 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.2/10 Wonderful! (117 reviews)

Great room. Lovely resort, friendly staff. Easy access to town

Reviewed on Feb 15, 2026

![Rock House](https://images.trvl-media.com/lodging/73000000/72070000/72061500/72061427/3ee4de3b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Rock House

Save 100% on your flight

$5,568

per person

May 2 - May 9

found 2 days ago

Roundtrip flight included

Boston (BOS) to Providenciales (PLS)

9.6/10 Exceptional! (322 reviews)

Everything was absolutely amazing

Reviewed on Mar 2, 2026

![The Shore Club Turks and Caicos](https://images.trvl-media.com/lodging/16000000/15440000/15438900/15438835/fb1fd0ea_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Shore Club Turks and Caicos

Long Bay

Save 100% on your flight

$3,154

per person

May 22 - May 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.4/10 Exceptional! (871 reviews)

Beautiful hotel with excellent service

Reviewed on Feb 28, 2026

Don't see what you're looking for?

See all available trips from Columbus to Five Cays

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-02/2026-04-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MDS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Ski vacations in Five Cays

Price found within the past 48 hours. Click for updated prices.

![Dream Villas Provo](https://images.trvl-media.com/lodging/97000000/96370000/96368700/96368651/a01ea79e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Dream Villas Provo

Save 100% on your flight

$1,560

per person

May 18 - May 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9/10 Wonderful! (58 reviews)

Excellent location. Walking distance to 2 restaurants, small store across street. Very clean and modern. Comfortable beds. Everything you need for a relaxing beach vacation!

Reviewed on Feb 26, 2026

![The Park at Grace Bay](https://images.trvl-media.com/lodging/121000000/120070000/120063400/120063392/08207d46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Park at Grace Bay

Grace Bay

Save 100% on your flight

$2,084

per person

Apr 2 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

No reviews

![Windsong on the Reef](https://images.trvl-media.com/lodging/3000000/2430000/2422200/2422198/12b8b359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Windsong on the Reef

Grace Bay

Save 100% on your flight

$7,201

per person

Apr 2 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.2/10 Wonderful! (1,003 reviews)

Everything was perfect and beautiful. Good food. All great

Reviewed on Mar 1, 2026

Don't see what you're looking for?

See all available trips from Columbus to Five Cays

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-02/2026-04-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MDS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Ski vacations in Five Cays

Price found within the past 48 hours. Click for updated prices.

![Windsong on the Reef](https://images.trvl-media.com/lodging/3000000/2430000/2422200/2422198/12b8b359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Windsong on the Reef

Grace Bay

Save 100% on your flight

$1,292

per person

May 7 - May 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.2/10 Wonderful! (1,003 reviews)

Everything was perfect and beautiful. Good food. All great

Reviewed on Mar 1, 2026

![Dream Villas Provo](https://images.trvl-media.com/lodging/97000000/96370000/96368700/96368651/a01ea79e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Dream Villas Provo

$1,879

per person

Apr 15 - Apr 19

found 2 days ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9/10 Wonderful! (58 reviews)

Excellent location. Walking distance to 2 restaurants, small store across street. Very clean and modern. Comfortable beds. Everything you need for a relaxing beach vacation!

Reviewed on Feb 26, 2026

![The Shore Club Turks and Caicos](https://images.trvl-media.com/lodging/16000000/15440000/15438900/15438835/fb1fd0ea_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Shore Club Turks and Caicos

Long Bay

Save 100% on your flight

$1,905

per person

May 7 - May 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.4/10 Exceptional! (871 reviews)

Beautiful hotel with excellent service

Reviewed on Feb 28, 2026

Don't see what you're looking for?

See all available trips from Columbus to Five Cays

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-02/2026-04-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MDS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Planning your Five Cays ski vacation

####  What are some things I should consider when booking a Five Cays ski trip package? 

Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in. 

####  How can I find cheap Five Cays ski packages? 

Right now, ski trips start at just $1,292\. Prices and availability are subject to change. Additional terms may apply. 

####  Can I book a beginner ski package in Five Cays? 

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Five Cays. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow. 

####  How much does a ski trip to Five Cays cost? 

Sensational ski trips to Five Cays start from $1,292\. Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply. 

####  When’s the best time of year to plan a ski trip to Five Cays? 

The best time to hit the slopes in Five Cays depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days. 

####  Can I book Five Cays ski packages with airfare? 

Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly. 

####  Can I book a Five Cays ski trip with free cancellation and/or flexible dates? 

Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options. 

####  Why should I book a ski package in Five Cays with Expedia? 

Simple search and fantastic filters make it easy to find, build, and book your dream Five Cays ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy. 

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## More Vacation Ideas

[Flights to Five Cays

](https://expedia.com/Cheap-Flights-To-Five-Cays.d11672.Travel-Guide-Flights)[

Five Cays Hotels

](https://expedia.com/Five-Cays-Hotels.d11672.Travel-Guide-Hotels)[

Vacation Rentals in Five Cays

](https://expedia.com/Five-Cays-Vacation-Rentals.d11672.Travel-Guide-VacationRentals)[

Car Rentals in Five Cays

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Five Cays Vacations

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Things to do in Five Cays

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\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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