Title: Casey Key Ski Vacations 2026 | Expedia.com

![](https://images.trvl-media.com/place/6167273/96af2e52-c240-40b9-93fb-f5a0cccd5b8b.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Casey Key Ski Vacations

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

- ##  
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## Top Ski vacation packages in Casey Key

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

![Legacy Hotel at IMG Academy](https://images.trvl-media.com/lodging/23000000/22890000/22882300/22882236/31e6e20e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Legacy Hotel at IMG Academy

Save 100% on your flight

$553

per person

Apr 13 - Apr 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

9/10 Wonderful! (959 reviews)

Room was good. Staff was very good

Reviewed on Feb 26, 2026

![SeaSpray Resort](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/5b42b650_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### SeaSpray Resort

Save 100% on your flight

$902

per person

May 22 - May 25

found 21 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

9.6/10 Exceptional! (95 reviews)

VERY ENJOYABLE /STAFF WAS EXCELLENT

Reviewed on Mar 8, 2026

![Bali Hai Beachfront Resort and Spa](https://images.trvl-media.com/lodging/37000000/36290000/36286200/36286167/03108394_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bali Hai Beachfront Resort and Spa

Save 100% on your flight

$1,171

per person

May 21 - May 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

8.6/10 Excellent! (662 reviews)

Staff was very nice and rooms were very clean. I had a great time with my son and I can't wait to come back.

Reviewed on Mar 1, 2026

![Compass Hotel by Margaritaville Anna Maria Sound](https://images.trvl-media.com/lodging/42000000/41970000/41961400/41961327/e1f2d8a8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Compass Hotel by Margaritaville Anna Maria Sound

$1,020

per person

Apr 16 - Apr 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

9.4/10 Exceptional! (1,970 reviews)

Greatvfriendly staff

Reviewed on Mar 6, 2026

![1200 Tree Bay ](https://images.trvl-media.com/lodging/99000000/98220000/98218200/98218188/b41221f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 1200 Tree Bay 

Save 100% on your flight

$5,088

per person

May 12 - May 19

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Sarasota (SRQ)

No reviews

Don't see what you're looking for?

See all available trips from Columbus to Casey Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SRQ&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Ski vacations in Casey Key

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

![The St. Regis Longboat Key Resort](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/6b2968af_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The St. Regis Longboat Key Resort

Save 100% on your flight

$2,886

per person

Apr 13 - Apr 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

9.8/10 Exceptional! (63 reviews)

great property great service expensive but worth it in my opinion

Reviewed on Feb 20, 2026

Don't see what you're looking for?

See all available trips from Columbus to Casey Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SRQ&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Ski vacations in Casey Key

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

![Legacy Hotel at IMG Academy](https://images.trvl-media.com/lodging/23000000/22890000/22882300/22882236/31e6e20e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Legacy Hotel at IMG Academy

$483

per person

Apr 29 - May 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

9/10 Wonderful! (959 reviews)

Room was good. Staff was very good

Reviewed on Feb 26, 2026

![SeaSpray Resort](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/5b42b650_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### SeaSpray Resort

Save 100% on your flight

$902

per person

May 22 - May 25

found 21 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

9.6/10 Exceptional! (95 reviews)

VERY ENJOYABLE /STAFF WAS EXCELLENT

Reviewed on Mar 8, 2026

![Bali Hai Beachfront Resort and Spa](https://images.trvl-media.com/lodging/37000000/36290000/36286200/36286167/03108394_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bali Hai Beachfront Resort and Spa

Save 100% on your flight

$1,171

per person

May 21 - May 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

8.6/10 Excellent! (662 reviews)

Staff was very nice and rooms were very clean. I had a great time with my son and I can't wait to come back.

Reviewed on Mar 1, 2026

Don't see what you're looking for?

See all available trips from Columbus to Casey Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SRQ&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Ski vacations in Casey Key

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

![Tropical Beach Resorts](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/f85b62a5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tropical Beach Resorts

South Village

Save 100% on your flight

$568

per person

May 18 - May 22

found 1 day ago

Roundtrip flight included

New York (LGA) to Sarasota (SRQ)

9.4/10 Exceptional! (5,331 reviews)

Loved the access to the beach to watch amazing sunsets. The large pool was amazing! Our room was lovely - appreciated the kitchen. Unique setting - a combinatioin of properties joined together. A short drive to the central section of Siesta Key. We very much enjoyed our stay!

Reviewed on Mar 8, 2026

![Cedar Cove Resort and Cottages](https://images.trvl-media.com/lodging/9000000/8100000/8099700/8099611/0a89d66d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cedar Cove Resort and Cottages

Save 100% on your flight

$1,271

per person

Apr 30 - May 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

9.2/10 Wonderful! (492 reviews)

Everything was perfect cant wait to go back

Reviewed on Feb 10, 2026

![Captiva Beach Resort](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3d46ab53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Captiva Beach Resort

South Village

Save 100% on your flight

$581

per person

May 2 - May 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

9/10 Wonderful! (1,206 reviews)

Upon arriving at the resort, found this place to be charming. Our room had a kitchenette with small dining table and 4 chairs, 2 queen beds - which were very comfortable and a nice bathroom. The court yard was lovely! The pool was nice as well! Beach access about a 3-4 minute walk away from the resort. Lastly, I want to give a shoutout to the staff in the office. They could not have been nicer! Plan on booking another stay at Captive Beach resort next year.

Reviewed on Feb 21, 2026

Don't see what you're looking for?

See all available trips from Columbus to Casey Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SRQ&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Planning your Casey Key ski vacation

####  What are some things I should consider when booking a Casey Key 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 Casey Key ski packages? 

Right now, ski trips start at just $483\. Prices and availability are subject to change. Additional terms may apply. 

####  Can I book a beginner ski package in Casey Key? 

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Casey Key. 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 Casey Key cost? 

Sensational ski trips to Casey Key start from $483\. 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 Casey Key? 

The best time to hit the slopes in Casey Key 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 Casey Key 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 Casey Key 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 Casey Key with Expedia? 

Simple search and fantastic filters make it easy to find, build, and book your dream Casey Key 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 Casey Key

](https://expedia.com/Cheap-Flights-To-Casey-Key.d6167273.Travel-Guide-Flights)[

Casey Key Hotels

](https://expedia.com/Casey-Key-Hotels.d6167273.Travel-Guide-Hotels)[

Vacation Rentals in Casey Key

](https://expedia.com/Casey-Key-Vacation-Rentals.d6167273.Travel-Guide-VacationRentals)[

Car Rentals in Casey Key

](https://expedia.com/Car-Rentals-In-Casey-Key.d6167273.Car-Rental-Guide)[

Casey Key Vacations

](https://expedia.com/Casey-Key.d6167273.Destination-Travel-Guides)[

Things to do in Casey Key

](https://expedia.com/Things-To-Do-In-Casey-Key.d6167273.Travel-Guide-Activities)

\* 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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