Ski Vacations in South Tampa 2026

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Flight and Ski hotel deals in South Tampa

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

La Tortuga Historic Downtown Pass A Grille

Pass-a-Grille

CA $1,248

per person

Nov 20 - Nov 25

found 1 hour ago

Roundtrip non-stop flight included

Ottawa (YOW) 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

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

CA $2,850

per person

Dec 29 - Jan 4

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

The property was amazing. Very well maintained and the staff was great. Everyone was very friendly and helpful. We have no complaints and will be staying again soon.

Reviewed on Oct 12, 2026

The Westin Sarasota

Central Sarasota

Save 100% on your flight

CA $2,060

per person

Nov 13 - Nov 20

found 16 hours ago

Roundtrip non-stop flight included

Buffalo (BUF) to Tampa (TPA)

9.2/10 Wonderful! (1,178 reviews)

Very clean, friendly staff, very pleasant stay. Rooftop has the best views and centrally located.

Reviewed on Oct 14, 2026

Landing Palmetto Apartments

CA $1,388

per person

Dec 23 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Sarasota (SRQ)

9/10 Wonderful! (71 reviews)

The apartment had everything we needed. The bathroom vanity was a pedestal sink with no counter space for toiletries.

Reviewed on Oct 12, 2026

The Hotel Zamora

Save 100% on your flight

CA $1,352

per person

Nov 13 - Nov 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

8.8/10 Excellent! (423 reviews)

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5* Ski holidays in South Tampa

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

The Tampa EDITION

Downtown Tampa

CA $1,543

per person

Dec 11 - Dec 14

found 18 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Tampa (TPA)

9.4/10 Exceptional! (426 reviews)

The Gemma by Brightwild

CA $3,901

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) 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

The St. Regis Longboat Key Resort

CA $6,955

per person

Dec 23 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.8/10 Exceptional! (97 reviews)

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3 Night Ski holidays in South Tampa

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

Ocean Club Treasure Island Hotel

Sunshine Beach

CA $913

per person

Nov 23 - Nov 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

The property was amazing. Very well maintained and the staff was great. Everyone was very friendly and helpful. We have no complaints and will be staying again soon.

Reviewed on Oct 12, 2026

CW Resort

CA $1,149

per person

Nov 26 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Great property

Reviewed on Oct 13, 2026

The Avalon Club

CA $1,134

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.4/10 Exceptional! (608 reviews)

Great place to stay with the family. Rooms were clean and spacious. Parking was easy. Walkable to many stores and restaurants. Very close to the beach, and the hotel has everything needed for your beach day: towels, chairs, umbrellas, floaties, and sand toys.

Reviewed on Oct 7, 2026

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4 Night Ski holidays in South Tampa

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

CW Resort

Save 100% on your flight

CA $1,965

per person

Dec 27 - Dec 31

found 22 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Great property

Reviewed on Oct 13, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

CA $2,130

per person

Dec 26 - Dec 30

just found

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

The property was amazing. Very well maintained and the staff was great. Everyone was very friendly and helpful. We have no complaints and will be staying again soon.

Reviewed on Oct 12, 2026

The Avalon Club

Save 100% on your flight

CA $2,284

per person

Dec 27 - Dec 31

found 22 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

9.4/10 Exceptional! (608 reviews)

Reviewed on Oct 7, 2026

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What are some benefits when booking ski vacations in South Tampa?

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 South Tampa?

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 South Tampa, 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 South Tampa with some as cheap as CA $913. 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 South Tampa. 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 22 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 South Tampa.

Can I book all-inclusive ski vacations in South Tampa?

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 South Tampa 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 South Tampa'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 South Tampa?

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 South Tampa. 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 22. With Expedia Rewards, you can earn points towards your next booking.