Keystone Ski Vacations 2026

Photo by Travel Ginger

Top Ski vacation packages in Keystone

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

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Downtown Tampa

Save 100% on your flight

$827

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (938 reviews)

Valet staff was awesome!

Reviewed on Oct 3, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,313

per person

Dec 20 - Dec 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,236 reviews)

Room, pool and bar were amazing. My only complaint was beach too far to walk for afew of the others. Had to buy beach chairs as there were none at beach unless you paid a third party.

Reviewed on Oct 3, 2026

CW Resort

$1,841

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (188 reviews)

Landing Tampa Westshore

Port Tampa City

Save 100% on your flight

$1,100

per person

Nov 11 - Nov 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (199 reviews)

All was wonderful. We had a problem with the concrete curbs. The curb grabbed our bumper and pulled the front end of our bumper off when we had to back out. It has cost us several thousand dollars for the repairs. Otherwise it was a beautiful facility.

Reviewed on Sep 21, 2026

Wyndham Grand Clearwater Beach

$1,048

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (3,914 reviews)

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See all available trips from Columbus to Keystone

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5* Ski vacations in Keystone

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

The Adaline

Hyde Park

$910

per person

Nov 17 - Nov 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (74 reviews)

Fantastic property. The area was quiet and it felt very safe and private. Friendly owners and staff.

Reviewed on Sep 21, 2026

The Gemma by Brightwild

$9,979

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (7 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

Indian Rocks Escape

Save 100% on your flight

$1,501

per person

Nov 6 - Nov 11

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Tampa (TPA)

No 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

$597

per person

Dec 10 - Dec 13

found 13 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (188 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$619

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,236 reviews)

Room, pool and bar were amazing. My only complaint was beach too far to walk for afew of the others. Had to buy beach chairs as there were none at beach unless you paid a third party.

Reviewed on Oct 3, 2026

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Downtown Tampa

Save 100% on your flight

$827

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (938 reviews)

Valet staff was awesome!

Reviewed on Oct 3, 2026

Don't see what you're looking for?

See all available trips from Columbus to Keystone

View all trips

4 Night Ski vacations in Keystone

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

Bay Palms Waterfront Resort - Hotel and Marina

Belle Vista

Save 100% on your flight

$430

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Tampa (TPA)

8.4/10 Very Good! (561 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$724

per person

Dec 10 - Dec 14

found 1 hour ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,236 reviews)

Room, pool and bar were amazing. My only complaint was beach too far to walk for afew of the others. Had to buy beach chairs as there were none at beach unless you paid a third party.

Reviewed on Oct 3, 2026

CW Resort

Save 100% on your flight

$1,188

per person

Dec 23 - Dec 27

found 11 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (188 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Keystone

View all trips

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 $430. 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 $430. 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.