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.

CW Resort

CA $893

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Nice hotel.

Reviewed on Oct 12, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

CA $2,241

per person

Jan 1 - Jan 7

found 18 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) 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 $1,069

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

Saddlebrook Resort

Wesley Chapel South

CA $1,038

per person

Dec 17 - Dec 24

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Tampa (TPA)

8/10 Very good! (172 reviews)

Every one was kind a helpful. Had a great time with my son.

Reviewed on Oct 11, 2026

Landing Palmetto Apartments

CA $1,388

per person

Dec 23 - Dec 28

found 11 hours 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

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5* Ski holidays in South Tampa

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

The Adaline

Hyde Park

CA $1,577

per person

Dec 17 - Dec 24

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Tampa (TPA)

9.6/10 Exceptional! (75 reviews)

The best part about this apartment is its location: right by Bayshore, 10 min walking distance from Hyde Park, and in short driving distance from everything S Tampa. The apartment is cute, spacious, quiet, and well equipped. The host provided comprehensive info ahead of check-in so getting in the apartment was smooth.

Reviewed on Oct 11, 2026

The Gemma by Brightwild

Save 100% on your flight

CA $15,300

per person

Dec 25 - Dec 31

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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 $9,646

per person

Jan 1 - Jan 7

found 18 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Tampa (TPA)

9.8/10 Exceptional! (97 reviews)

Beach view and staff

Reviewed on Oct 9, 2026

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3 Night Ski holidays in South Tampa

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

CW Resort

CA $893

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Nice hotel.

Reviewed on Oct 12, 2026

The Avalon Club

Save 100% on your flight

CA $1,069

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)

Reviewed on Oct 7, 2026

Wyndham Grand Clearwater Beach

CA $934

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.4/10 Exceptional! (3,946 reviews)

This was my third time staying at the Wyndham Grand Clearwater Beach, and once again, it did not disappoint! Every visit reminds me why I keep coming back. From the moment we arrived, the check-in process was smooth, welcoming, and professional. The hotel is beautiful, exceptionally clean, and perfectly located right on the beachfront, offering a wonderful atmosphere for a relaxing getaway. The pool bar is absolutely amazing, with a fantastic atmosphere, and the lobby bar is just as impressive! Both are great places to unwind, enjoy a drink, and soak in the vacation vibes. The beachfront location is unbeatable, and the overall experience continues to exceed my expectations. It's clear that the hotel takes pride in providing a clean, comfortable, and enjoyable stay for its guests. Three visits and counting! Wyndham Grand Clearwater Beach continues to be one of my favorite places to stay in Clearwater. I look forward to returning for a fourth visit. Highly recommend!

Reviewed on Oct 13, 2026

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4 Night Ski holidays in South Tampa

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

Hilton St. Petersburg Bayfront

Downtown St. Petersburg

CA $808

per person

Dec 18 - Dec 22

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Tampa (TPA)

7.8/10 Good! (1,185 reviews)

CW Resort

Save 100% on your flight

CA $2,484

per person

Dec 30 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Nice hotel.

Reviewed on Oct 12, 2026

The Hotel Zamora

CA $1,505

per person

Nov 18 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Tampa (TPA)

8.8/10 Excellent! (423 reviews)

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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 $808. 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 25 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 25. With Expedia Rewards, you can earn points towards your next booking.