Title: Ski Vacations in Little Gasparilla Island 2026 | Expedia.ca ![](https://images.trvl-media.com/place/146453/85f773f7-8432-4bfe-9807-94101b761832.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Little Gasparilla Island Ski Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Tom Hunt - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Flight and Ski hotel deals in Little Gasparilla Island Price found within the past 48 hours. Click for updated prices. ![Hotel Tampa Riverwalk](https://images.trvl-media.com/lodging/1000000/30000/22400/22354/e58c12ba_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Tampa Riverwalk Downtown Tampa CA $1,585 per person Feb 8 - Feb 14 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Sarasota (SRQ) 7/10 Good! (1,744 reviews) Loved the restaurant, breakfast was no nonsense and as expected. Reviewed on Dec 17, 2025 ![Innovation Hotel](https://images.trvl-media.com/lodging/83000000/82990000/82988300/82988281/61b55ef1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Innovation Hotel CA $1,925 per person Feb 3 - Feb 10 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Fort Myers (RSW) 9.8/10 Exceptional! (527 reviews) We had a great time! Modern design, great service and friendly. Reviewed on Dec 14, 2025 ![Hyatt Vacation Club at Coconut Cove, Bonita Springs](https://images.trvl-media.com/lodging/1000000/1000000/991200/991114/fedffc57_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Vacation Club at Coconut Cove, Bonita Springs CA $2,196 per person Feb 3 - Feb 10 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Fort Myers (RSW) 9.2/10 Wonderful! (704 reviews) The place was fabulous!!! Everyone was fabulous! Only issue was that the adult pool was not just adults. Parents would leave their kids in it and they would yell and splash. Reviewed on Dec 18, 2025 ![The Perry Hotel Naples](https://images.trvl-media.com/lodging/103000000/102390000/102386400/102386398/0ad2742c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Perry Hotel Naples CA $1,641 per person Feb 3 - Feb 10 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Fort Myers (RSW) 9.6/10 Exceptional! (477 reviews) The rooftop amenities were fabulous Reviewed on Dec 19, 2025 ![Compass Hotel by Margaritaville Anna Maria Sound](https://images.trvl-media.com/lodging/42000000/41970000/41961400/41961327/8b0dc5d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Compass Hotel by Margaritaville Anna Maria Sound CA $1,832 per person Mar 1 - Mar 8 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Sarasota (SRQ) 9.4/10 Exceptional! (1,843 reviews) The breafest was fresh and yummy and the staff was amazing. We loved the bartender! Reviewed on Dec 18, 2025 Don't see what you're looking for? See all available trips from Columbus to Little Gasparilla Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=RSW&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski holidays in Little Gasparilla Island Price found within the past 48 hours. Click for updated prices. ![The Adaline](https://images.trvl-media.com/lodging/97000000/96050000/96044100/96044015/2cb71c62_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Adaline Hyde Park CA $1,059 per person Jan 23 - Jan 26 found 23 hours ago Roundtrip flight included Toronto (YTO) to Sarasota (SRQ) 9.6/10 Exceptional! (53 reviews) Very cute place! Feels like home. It’s in a walkable area really close to a lot of stores and food options. I enjoyed staying here! Reviewed on Dec 1, 2025 ![Sundial Beach Resort & Spa](https://images.trvl-media.com/lodging/1000000/10000/2000/1939/5481c209_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sundial Beach Resort & Spa Mid Island CA $2,300 per person Feb 24 - Mar 2 found 13 hours ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 8.6/10 Excellent! (2,581 reviews) Very clean, fun activities for the kids. Reviewed on Nov 29, 2025 ![Naples Beach Club, A Four Seasons Resort](https://images.trvl-media.com/lodging/1000000/10000/9800/9786/e6518097_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Naples Beach Club, A Four Seasons Resort Coquina Sands CA $4,433 per person Feb 18 - Feb 22 found 18 hours ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 6/10 (2 reviews) Don't see what you're looking for? See all available trips from Columbus to Little Gasparilla Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=RSW&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski holidays in Little Gasparilla Island Price found within the past 48 hours. Click for updated prices. ![Matanzas Inn Bayside Resort and Marina](https://images.trvl-media.com/lodging/3000000/2670000/2665100/2665085/fc463bf9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Matanzas Inn Bayside Resort and Marina CA $1,006 per person Feb 18 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 9.2/10 Wonderful! (1,001 reviews) got the 2 bdr unit next to office. rooms were great, check inn easy, pool and hot tub made it very enjoyable. my only complaint was i only booked for 1 night. will be my stop when return Reviewed on Dec 18, 2025 ![Innovation Hotel](https://images.trvl-media.com/lodging/83000000/82990000/82988300/82988281/61b55ef1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Innovation Hotel CA $1,351 per person Feb 18 - Feb 22 found 18 hours ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 9.8/10 Exceptional! (527 reviews) We had a great time! Modern design, great service and friendly. Reviewed on Dec 14, 2025 ![The Perry Hotel Naples](https://images.trvl-media.com/lodging/103000000/102390000/102386400/102386398/0ad2742c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Perry Hotel Naples CA $1,111 per person Feb 18 - Feb 22 found 18 hours ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 9.6/10 Exceptional! (477 reviews) The rooftop amenities were fabulous Reviewed on Dec 19, 2025 Don't see what you're looking for? See all available trips from Columbus to Little Gasparilla Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=RSW&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the ultimate ski vacation in Little Gasparilla Island #### What are some benefits when booking ski vacations in Little Gasparilla Island? 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 Little Gasparilla Island? 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 Little Gasparilla Island, 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 Little Gasparilla Island with some as cheap as CA $1,006\. 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 Little Gasparilla Island. 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 41 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 Little Gasparilla Island. #### Can I book all-inclusive ski vacations in Little Gasparilla Island? 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 Little Gasparilla Island 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 Little Gasparilla Island'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 Little Gasparilla Island? 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 Little Gasparilla Island. 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 41\. With Expedia Rewards, you can earn points towards your next booking. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Top Ski Vacation Destinations > - [Ski vacations in Whistler ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/4115/Whistler) > - [Ski vacations in Banff ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/4332/Banff) > - [Ski vacations in Mont Tremblant ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/55374/Mont-Tremblant) > - [Ski vacations in Jasper ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/8028/Jasper) > - [Ski vacations in Jackson ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/180006/Jackson) > - [Ski vacations in France ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/59/France) > - [Ski vacations in Quebec ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/180017/Quebec) > - [Ski vacations in Queenstown ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/3611/Queenstown) > - [Ski vacations in Lake Louise ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/10115/Lake-Louise) > - [Ski vacations in Nelson ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6194600/Nelson) > - [Ski vacations in Kitzbuhel ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6346453/Kitzbuehel) > - [Ski vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/174/Switzerland) > - [Ski vacations in La Plagne ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6034464/La-Plagne) > - [Ski vacations in St Gervais ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/3000402612/St-Gervais-Sur-Mare) > - [Ski vacations in Austria ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/11/Austria) > - [Ski vacations in Germany ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/64/Germany) > - [Ski vacations in Wengen ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6186871/Wengen) > - [Ski vacations in Ontario ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/2680/Ontario) > - [Ski vacations in Colorado ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/207/Colorado) ## More Vacations Ideas [Flights to Little Gasparilla Island ](https://expedia.ca/Cheap-Flights-To-Little-Gasparilla-Island.d553248635976193817.Travel-Guide-Flights)[ Little Gasparilla Island Hotels ](https://expedia.ca/Little-Gasparilla-Island-Hotels.d553248635976193817.Travel-Guide-Hotels)[ Little Gasparilla Island Vacation Rentals ](https://expedia.ca/Little-Gasparilla-Island-Vacation-Rentals.d553248635976193817.Travel-Guide-VacationRentals)[ Little Gasparilla Island Car Rentals ](https://expedia.ca/Car-Rentals-In-Little-Gasparilla-Island.d553248635976193817.Car-Rental-Guide)[ Little Gasparilla Island Vacations ](https://expedia.ca/Little-Gasparilla-Island.d553248635976193817.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app