Legacy Trail Ski Vacations

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    Save up to CA $4,200 when you book a flight and hotel together*
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Flight and Ski hotel deals in Legacy Trail

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

The Westin Sarasota

Central Sarasota
CA $808
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,151 reviews)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
CA $1,259
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,128 reviews)
The Hotel Zamora

The Hotel Zamora

CA $1,036
per person
Oct 25 - Oct 31
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
8.8/10 Excellent! (388 reviews)
The hotel is beautiful and very clean. Great amenities, close to great restaurants and beautiful stretch of the beach. Lovely service, staff weee friendly and very helpful. Rachel at the hotel restaurant was amazing. We had a beautiful weekend. Will definitely visit again.

Reviewed on Aug 21, 2026

CW Hotel

CW Hotel

CA $1,087
per person
Oct 25 - Oct 31
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (48 reviews)
The Avalon Club

The Avalon Club

CA $1,218
per person
Oct 25 - Oct 31
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (581 reviews)
We liked the clean room & the staff we didn’t like the noise of the other guest when we were trying to sleep

Reviewed on Aug 19, 2026

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5* Ski holidays in Legacy Trail

Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota

Central Sarasota
CA $2,613
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,017 reviews)
I had an excellent experience from the moment I arrived at the hotel. The staff were incredibly polite, friendly, and welcoming. I immediately felt comfortable and at home. Thank you for making my stay such a warm and pleasant experience!

Reviewed on Aug 21, 2026

The Gemma by Brightwild

The Gemma by Brightwild

CA $4,361
per person
Oct 9 - Oct 12
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) 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 St. Regis Longboat Key Resort

The St. Regis Longboat Key Resort

CA $8,251
per person
Nov 5 - Nov 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.8/10 Exceptional! (88 reviews)
Great staff and close attention to detail. Helpful all around. Great restaurants.

Reviewed on Aug 14, 2026

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3 Night Ski holidays in Legacy Trail

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

The Hotel Zamora

CA $774
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.8/10 Excellent! (388 reviews)
The hotel is beautiful and very clean. Great amenities, close to great restaurants and beautiful stretch of the beach. Lovely service, staff weee friendly and very helpful. Rachel at the hotel restaurant was amazing. We had a beautiful weekend. Will definitely visit again.

Reviewed on Aug 21, 2026

CW Hotel

CW Hotel

CA $827
per person
Nov 13 - Nov 16
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (48 reviews)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
CA $823
per person
Oct 1 - Oct 4
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.6/10 Exceptional! (1,128 reviews)
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4 Night Ski holidays in Legacy Trail

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

CA $789
per person
Sep 23 - Sep 27
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (1,341 reviews)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
CA $869
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,128 reviews)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

CA $832
per person
Nov 12 - Nov 16
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (2,412 reviews)
I loved that this property was on the edge of a quiet beautiful neighborhood for walking my dog. Very clean and cared for! Probably the best bed I’ve ever had in a rental. I would stay here again and recommend to others.

Reviewed on Aug 21, 2026

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Plan the ultimate ski vacation in Legacy Trail

What are some benefits when booking ski vacations in Legacy Trail?

If you're interested in skiing, there's nothing quite like a ski vacation. These trips are designed to allow you to enjoy being on the slopes and relax in tranquil and convenient accommodations at the end of the day. Amenities on ski trips can be pretty upscale, so it's easy to relax in a hot tub or at a spa in between your skiing excursions. Plus, they can put you right next to the slopes. You'll even find a variety of different vacation types available whether you're looking for family friendly, cheap, or even last minute ski vacations.

How can I book the best ski vacation in Legacy Trail?

It is most important to implement the ski filter in your search when trying to find a ski vacation that will make you happy. Using the filter will automatically remove any entries that don't offer the skiing opportunities you want. After that, you'll need to think about what specifically you want from Legacy Trail, and think about the time of year that's best to visit.

How can I find cheap ski vacations?

Cheap ski vacations are readily available in Legacy Trail with some as cheap as CA $774. You can see the cheapest options by sorting your accommodation choices by price, which automatically puts the least-expensive results at the top of the list. You may also want to consider an accommodation with a kitchen, so you can cook instead of eating out.

Can I book ski packages?

Yes, ski packages are readily available throughout Legacy Trail. All you have to do is put in your travel dates and see what's available. When you book a ski package, you may be able to enjoy discounts with savings of up to 33 when you book your accommodation and your flight together.

What should I consider when booking family ski vacations?

The key to a successful family ski vacation is ensuring that your family is kept happy and entertained. Consider what your family members are interested in and the kind of vacation they want. If they have little skiing experience, for example, you may want to opt for an accommodation that offers ski lessons or a kid's club. Various slope difficulties may be essential in providing opportunities for everyone at Legacy Trail.

Can I book all-inclusive ski vacations in Legacy Trail?

Yes, all-inclusive ski trips are available and may be precisely what you're looking for. All you have to do is include the filter for all-inclusive stays, and your search results will only show the accommodations that provide this handy feature that allows you to plan your entire trip to Legacy Trail in advance.

What's the best time of year to plan a ski trip?

The apparent answer to when you should plan a ski trip is in winter, but other details are important too. If you book for Legacy Trail's high season around January and February, you'll likely find increased prices. It's generally best to opt for the early or late season in December and April, as prices tend not to be quite as high.

How can I find the best deals on ski packages in Legacy Trail?

When you're looking for cheap ski vacations, there are a few factors you can take advantage of to help get the best deals. Travelling during the off-season can be cheaper since there's more availability. However, the beginning and end of the season tend to be the most affordable for skiing.

Can I book a ski vacation that's fully refundable?

Being fully refundable is a feature you'll find on several accommodation packages in Legacy Trail. You can even search for it explicitly using a filter for full refundability.

Why should I book a ski vacation package with Expedia?

When you book with Expedia, you'll find everything you need for cheap ski vacations, luxury ski vacations and everything in between in one central location. You may even be able to enjoy discounts for booking your accommodation and your flight together with savings of up to 33. With Expedia Rewards, you can earn points towards your next booking.

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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.