Keystone Ski Vacations 2026

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Top Ski vacation packages in Keystone

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

CW Resort

Save 100% on your flight

$699

per person

Nov 5 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (132 reviews)

Nos gustó el ambiente amplio y limpio.

Reviewed on Sep 10, 2026

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$830

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,150 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,276

per person

Nov 23 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,190 reviews)

SkyBeach Resort

Greater Pinellas Point

Save 100% on your flight

$996

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (889 reviews)

Love this hidden gem 💎

Reviewed on Sep 9, 2026

La Tortuga Historic Downtown Pass A Grille

Pass-a-Grille

Save 100% on your flight

$1,000

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (36 reviews)

A six page contract with a ton of strict rules can’t move furniture, can’t touch tv, can’t leave sand in any place, leave a/c at 78 degrees etc etc., all these subject to fines. My a/c was pouring water all night and was fixed next morning. There is nobody at the hotel you can reach, that’s why everything is virtual. I don’t recommend it if you are looking for a relax vacation.

Reviewed on Jun 18, 2026

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5* Ski vacations in Keystone

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

The Adaline

Hyde Park

$967

per person

Nov 12 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (74 reviews)

The Gemma by Brightwild

Save 100% on your flight

$2,366

per person

Oct 28 - Oct 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (6 reviews)

The Jade House is in an excellent location only a block from the beach and short walk to restaurants, shops, and bars. Communication with the management company was difficult through Expedia. Even when I called directly, one of the three client service agents was not helpful whatsoever. However, once I was given the number to text, communication was much better. The pool/ hot tub area is perfect. The house is very comfortable. Only decks are narrow (only stand); ocean view is from one of theses.

Reviewed on Jul 30, 2026

The Ritz-Carlton, Sarasota

Central Sarasota

$1,342

per person

Oct 13 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,018 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Keystone

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3 Night Ski vacations in Keystone

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

CW Resort

$436

per person

Oct 28 - Oct 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (132 reviews)

Nos gustó el ambiente amplio y limpio.

Reviewed on Sep 10, 2026

Hyatt Regency Clearwater Beach Resort and Suites

Save 100% on your flight

$456

per person

Oct 28 - Oct 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (2,303 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

$568

per person

Nov 18 - Nov 21

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,190 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Keystone

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4 Night Ski vacations in Keystone

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

Turtle Beach Resort

Save 100% on your flight

$756

per person

Oct 13 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (363 reviews)

Great location. Friendly staff and nice amentities.

Reviewed on Sep 9, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$992

per person

Nov 23 - Nov 27

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

9.2/10 Wonderful! (591 reviews)

Beautiful private beach. Room was nice. Amenities were great. Housekeeping could have been a little better.

Reviewed on Sep 11, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,254

per person

Nov 24 - Nov 28

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,190 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Keystone

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What are some things I should consider when booking a Keystone 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 Keystone ski packages?

Right now, ski trips start at just $436. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Keystone?

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

Sensational ski trips to Keystone start from $436. 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 Keystone?

The best time to hit the slopes in Keystone 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 Keystone 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 Keystone 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 Keystone with Expedia?

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