Southwest Florida Ski Holidays

Book a Ski Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to £335 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Planning your Southwest Florida ski holiday

How can I book the best ski holiday to Southwest Florida in 2025/2026?

Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Southwest Florida. 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 Southwest Florida ski holidays?

Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Southwest Florida 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 . Prices and availability are subject to change. Additional terms may apply.

Can I book last-minute ski holidays to Southwest Florida?

Use our handy last-minute deals page to look for ski holidays to Southwest Florida 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 Southwest Florida?

Southwest Florida 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 Southwest Florida?

All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Southwest Florida. 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 Southwest Florida?

Ski season in Southwest Florida 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 Southwest Florida 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 Southwest Florida 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 Southwest Florida that offer it.

Why should I book a ski holiday package in Southwest Florida 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.

Top Ski Southwest Florida Hotels

Villa Margarita Sparkles
Villa Margarita Sparkles
Englewood, FL
  • 59 min drive from Siesta Key Beach
Stay at this cottage in Englewood. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Englewood Beach and Stump Pass Beach State Park are located ...
9.6/10 Exceptional! (132 reviews)
"Loved it. Convenient location and had everything we needed."

Reviewed on 11 Jun 2025

Villa Margarita Sparkles
Beach getaway! Unit 3
Beach getaway! Unit 3
Sarasota, FL
  • 8 min drive from Siesta Key Beach
Stay at this apartment in Sarasota. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Lido Beach and Siesta Key Beach are located nearby.
9.6/10 Exceptional! (149 reviews)
Perfect beach getaway
"My husband and I were looking for a nice small place within a close proximity to the beach for our Memorial Day weekend getaway-this property was just about perfect for our purposes. Small but clean and well-kept unit with all basic features; quiet neighborhood (which was very important to us); 5-10 ..."

Reviewed on 27 May 2025

Beach getaway! Unit 3
Pool home with western exposure on fresh water canal
Pool home with western exposure on fresh water canal
Cape Coral, FL
  • 2 hours drive from Siesta Key Beach
Stay at this family-friendly holiday home in Cape Coral. Enjoy free Wi-Fi, private pools and a water park. Popular attractions Royal Tee Golf Club and Palmetto-Pine ...
9.8/10 Exceptional! (140 reviews)
Family vacation
"We came to visit family and had a wonderful time! A great house and location. The pool was amazing! Greg was an excellent host and responded quickly. We’ll return for another visit!"

Reviewed on 31 May 2025

Pool home with western exposure on fresh water canal
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

More holidays you might like

* 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.