Ski Vacations in South Naples 2026

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Flight and Ski hotel deals in South Naples

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

Landing Fort Myers Near Highland Pines

Daniels Corridor

Save 100% on your flight

CA $824

per person

Dec 11 - Dec 17

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

9.2/10 Wonderful! (14 reviews)

Very Clean

Reviewed on Sep 9, 2026

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

Save 100% on your flight

CA $1,064

per person

Dec 11 - Dec 17

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

CA $1,112

per person

Dec 11 - Dec 17

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

9.2/10 Wonderful! (1,012 reviews)

The Perry Hotel Naples

Save 100% on your flight

CA $1,353

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

We had such a wonderful experience here! ❤️ This is a great place to come with the family. The atmosphere was welcoming, the food was delicious, and everyone made us feel right at home. We’re visiting from Miami, and we’re so glad we found this place! We would definitely recommend it to other families and would love to come back again. ⭐️⭐️⭐️⭐️⭐️

Reviewed on Sep 21, 2026

Landing Apartments Fort Myers near Olympia Pointe

Save 100% on your flight

CA $869

per person

Dec 11 - Dec 17

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

8.8/10 Excellent! (9 reviews)

Great pool,comfortable room.

Reviewed on Mar 27, 2026

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5* Ski holidays in South Naples

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

Sundial Beach Resort & Spa

Mid Island

Save 100% on your flight

CA $1,826

per person

Dec 11 - Dec 17

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

8.6/10 Excellent! (2,690 reviews)

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

CA $4,611

per person

Oct 26 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Buffalo (BUF) to Fort Myers (RSW)

9.6/10 Exceptional! (34 reviews)

Excellent hotel vacation, relaxation, family rest and enjoyment. Enjoyed our stay!! Highly recommended.

Reviewed on Sep 19, 2026

The Ritz-Carlton Naples, Tiburón

CA $2,125

per person

Oct 23 - Oct 28

found 6 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

9.2/10 Wonderful! (681 reviews)

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3 Night Ski holidays in South Naples

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

The Perry Hotel Naples

Save 100% on your flight

CA $576

per person

Oct 26 - Oct 29

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Reviewed on Sep 21, 2026

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

CA $824

per person

Nov 13 - Nov 16

found 7 hours ago

Roundtrip non-stop flight included

Buffalo (BUF) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

Hyatt Vacation Club at Coconut Cove, Bonita Springs

CA $858

per person

Nov 13 - Nov 16

found 7 hours ago

Roundtrip non-stop flight included

Buffalo (BUF) to Fort Myers (RSW)

9.2/10 Wonderful! (1,012 reviews)

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4 Night Ski holidays in South Naples

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

The Perry Hotel Naples

Save 100% on your flight

CA $1,013

per person

Oct 22 - Oct 26

found 2 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Reviewed on Sep 21, 2026

Olde Marco Island Inn and Suites

Olde Marco

CA $1,139

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

8.8/10 Excellent! (1,001 reviews)

Tween Waters Island Resort & Spa

CA $1,243

per person

Oct 28 - Nov 1

found 14 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

8.6/10 Excellent! (1,005 reviews)

My husband and I were able to check in right on time. We were given a helpful overview of the property, a map, and list of the numerous amenities (complimentary kayaks, bikes, beach towels, pools and hot tubs, as well as the many restaurants, shops, rentals, and beach services) and opening and closing times said amenities. Prices for amenities and rentals were reasonable in my opinion. The restaurants range in price from reasonable to upscale dining. Our room was exactly as pictured. The entire property including the private beach - which was just across the road - were exceptionally clean. My only complaint was our bed was very firm for our tastes. The Gulf side beach was gorgeous. We saw many shore birds and dolphins. The bay side features a large marina and manatees in the cove. All staff we encountered were very friendly and helpful. We stayed in mid September and it appeared that most of the rooms were filled, but it was still very relaxing, quiet, and uncrowded. The location is excellent. It's easy to find off the main road through the islands and it's only a short drive to the attractions and beaches in both Sanibel and Captiva. Overall I would recommend and would stay here again.

Reviewed on Sep 20, 2026

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

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 Naples?

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 Naples, 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 Naples with some as cheap as CA $576. 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 Naples. 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 35 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 Naples.

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

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 Naples 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 Naples'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 Naples?

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 Naples. 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 35. With Expedia Rewards, you can earn points towards your next booking.