South Naples Ski Vacations 2026

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Top Ski vacation packages in South Naples

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

Chadwick Cove Resort & Marina

$454

per person

Oct 25 - Oct 28

found 1 day ago

Roundtrip flight included

New York (NYC) to Fort Myers (RSW)

9.4/10 Exceptional! (22 reviews)

The Perry Hotel Naples

Save 100% on your flight

$934

per person

Oct 20 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (970 reviews)

A great accidental find for a short overnight trip.

Reviewed on Aug 7, 2026

Shell Island Beach Club

East End

Save 100% on your flight

$993

per person

Oct 10 - Oct 17

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

9.6/10 Exceptional! (24 reviews)

Great place to stay on the beach! Woman at the front desk was rude!

Reviewed on Jun 7, 2026

Landing Fort Myers - Eastwood Village

Eastwood Village

Save 100% on your flight

$633

per person

Sep 22 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

10/10 Exceptional! (2 reviews)

Nice place

Reviewed on Mar 25, 2026

Landing Apartments Fort Myers near Olympia Pointe

Save 100% on your flight

$564

per person

Sep 16 - Sep 22

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 vacations in South Naples

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

Sundial Beach Resort & Spa

Mid Island

$1,185

per person

Oct 25 - Oct 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (2,675 reviews)

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$3,208

per person

Oct 20 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (25 reviews)

**⭐⭐⭐⭐⭐ A five-star experience — for our pet too!** Our stay at the Four Seasons Resort Naples was simply spectacular from start to finish. From check-in, we were welcomed with genuine warmth, and the attention to detail was felt in every corner: impeccable rooms, breathtaking views of the Gulf of Mexico, and service that anticipates every need before you even ask. What truly surprised us was how well they treated our dog. The staff asked for him by name, brought him water during our walks around the resort, and the "canine concierge" recommended nearby pet-friendly parks and areas. It was clear that for them, pets aren't just "tolerated" — they're genuinely welcomed and pampered. Between the spa, the exceptional restaurants, and the white sand beaches, every moment felt like a well-deserved luxury. Without a doubt, one of the best resorts we've ever stayed at, both for us and for our four-legged companion. We'll definitely be back!

Reviewed on Aug 2, 2026

The Ritz-Carlton, Naples

Pelican Bay

$1,833

per person

Sep 9 - Sep 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (501 reviews)

Beautiful resort. Staff was wonderful and food was amazing.

Reviewed on Aug 3, 2026

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3 Night Ski vacations in South Naples

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

Chadwick Cove Resort & Marina

$454

per person

Oct 25 - Oct 28

found 1 day ago

Roundtrip flight included

New York (NYC) to Fort Myers (RSW)

9.4/10 Exceptional! (22 reviews)

The Perry Hotel Naples

$654

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

9.6/10 Exceptional! (970 reviews)

A great accidental find for a short overnight trip.

Reviewed on Aug 7, 2026

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

$591

per person

Oct 15 - Oct 18

just found

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,015 reviews)

My husband and I enjoyed our time at the resort. The staff were incredibly welcoming and helpful with all our needs and the dining options were fantastic for the area. However, the main pool area felt like a state of chaos as kids were screaming running all around the pool deck and paying to attention to other people in the pool. I would not classify that as relaxing.

Reviewed on Aug 7, 2026

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4 Night Ski vacations in South Naples

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

Casa Ybel Resort

Mid Island

Save 100% on your flight

$627

per person

Sep 26 - Sep 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (391 reviews)

Great place to stay. Always check your invoice because they had extra charges on my bill and place a huge hold on CC for deposit and takes time for return. It could be the bank too. They also charged me by error and refunded but still haven’t received after few days.the amenities were great and the beach! Also entrance with wood little bridge really scared us. I believe they fixed while we were there. Lots of bugs !! Maybe property should clean up trees and fumigate because we were bit by noseeums

Reviewed on Aug 5, 2026

Tween Waters Island Resort & Spa

Save 100% on your flight

$716

per person

Oct 17 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,004 reviews)

Everything excellent Excellent

Reviewed on Aug 7, 2026

The Perry Hotel Naples

$643

per person

Oct 19 - Oct 23

found 18 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

9.6/10 Exceptional! (970 reviews)

A great accidental find for a short overnight trip.

Reviewed on Aug 7, 2026

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What are some things I should consider when booking a South Naples 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 South Naples ski packages?

Right now, ski trips start at just $454. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in South Naples?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in South Naples. 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 South Naples cost?

Sensational ski trips to South Naples start from $454. 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 South Naples?

The best time to hit the slopes in South Naples 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 South Naples 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 South Naples 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 South Naples with Expedia?

Simple search and fantastic filters make it easy to find, build, and book your dream South Naples ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.