Captiva Island Ski Holidays

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Top flight + Ski hotel deals in Captiva Island

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

Wiggins Pass Chalet

£1,207
per person
25 Oct - 1 Nov
found 2 hours ago
Return flight included
Manchester (MAN) to Fort Myers (RSW)
9.6/10 Exceptional! (281 reviews)
The Perry Hotel Naples

The Perry Hotel Naples

£1,278
per person
25 Oct - 1 Nov
found 2 hours ago
Return flight included
Manchester (MAN) to Fort Myers (RSW)
9.6/10 Exceptional! (970 reviews)
Front desk staff-awesome Valet staff- great Roof top manager and waitress. RUDE. Everyone else was terrific and property was clean, etc.

Reviewed on 7 Aug 2026

Bellasera Resort

Bellasera Resort

Old Naples
£1,792
per person
25 Oct - 1 Nov
found 2 hours ago
Return flight included
Manchester (MAN) to Fort Myers (RSW)
9.6/10 Exceptional! (2,307 reviews)
Landing Furnished Apartments - Naples, FL

Landing Furnished Apartments - Naples, FL

£1,382
per person
25 Oct - 1 Nov
found 2 hours ago
Return flight included
Manchester (MAN) to Fort Myers (RSW)
9.8/10 Exceptional! (7 reviews)
Close by beach and 5th avenue

Reviewed on 10 Jul 2026

Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

Coquina Sands
£2,709
per person
25 Oct - 1 Nov
found 2 hours ago
Return flight included
Manchester (MAN) 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 2 Aug 2026

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5* Ski holidays in Captiva Island

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

The Ritz-Carlton Naples, Tiburón

£2,671
per person
25 Oct - 1 Nov
found 2 hours ago
Return flight included
Manchester (MAN) to Fort Myers (RSW)
9.2/10 Wonderful! (671 reviews)
Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

Coquina Sands
£2,709
per person
25 Oct - 1 Nov
found 2 hours ago
Return flight included
Manchester (MAN) 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 2 Aug 2026

The Ritz-Carlton, Naples

The Ritz-Carlton, Naples

Pelican Bay
£3,578
per person
25 Oct - 1 Nov
found 2 hours ago
Return flight included
Manchester (MAN) to Fort Myers (RSW)
9.2/10 Wonderful! (501 reviews)
Beautiful resort. Staff was wonderful and food was amazing.

Reviewed on 3 Aug 2026

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Planning your Captiva Island ski holiday

How can I book the best ski holiday to Captiva Island in 2026/2027?

Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Captiva Island. Just choose your dates and see what’s available. You might prefer a hotel with a heated outdoor pool, or a private chalet for après ski parties; either way, use the property filters to your ideal match. If ski-in-ski-out is important, use the map view to find those idyllic slopeside properties.

How can I find cheap Captiva Island ski holidays?

Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Captiva Island accommodation a little further from the lifts and go self-catering to cut back on eating out. Sort your search results by price to find options from £1,207. Prices and availability are subject to change. Additional terms may apply.

Can I book last-minute ski holidays to Captiva Island?

Use our handy last-minute deals page to look for ski holidays to Captiva Island at a steal. If your dates are fixed, simply input the details and see what specials are available.

What should I consider when booking family ski holidays in Captiva Island?

Captiva Island is well set up for kids. For the teeniest ski-woks, day care in the snow is a blast. As they get older, they love whizzing around on the hill in ski school. Choose a hotel near the lifts and nursery slopes to save a whole lot of ski-carrying hassle in the mornings. With all that extra time and energy, you can take your sweet time to find a family-favourite bolthole on the mountain for hot chocolate with marshmallows ski breaks.

Can I book all-inclusive ski holidays to Captiva Island?

All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Captiva Island. If not, consider booking your flights and accommodation together to save money that way instead.

When's the best time of year to plan a ski trip to Captiva Island?

Ski season in Captiva Island generally starts around December and slopes off around April. Keep an eye on the snow forecasts though, as you can often find some brilliant deals at the start or end of the season, when it’s also much quieter.

How can I find the best deals on Captiva Island ski holiday packages?

If you can be flexible with your ski holiday dates, avoid school holidays and instead buckle up your boots at the start or end of season. Sort your search results by price and look out for self-catered accommodation to save on notoriously expensive ski-resort drinking and dining.

Can I book a Captiva Island ski trip with free cancellation and/or flexible dates?

If you’re not 100% sure on plans or just want peace of mind, choose a ski holiday with free cancellation. You can use our free cancellation filter to find properties in Captiva Island that offer it.

Why should I book a ski holiday package in Captiva Island with Expedia?

Schuss your way to the slopes with Expedia’s smooth booking process. From flights to hotels and even car hire, you’ll find everything you need to plan the ultimate winter wonderland ski holiday.

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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. Flight-inclusive packages are ATOL protected.