Title: Ski Vacations in Chokoloskee Island 2026 | Expedia.ca ![](https://images.trvl-media.com/place/3000430940/6a686070-6a7c-41a9-b800-f0b3cf385f24.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chokoloskee Island Ski Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Noel Benadom - ## 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 Chokoloskee Island Price found within the past 48 hours. Click for updated prices. ![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 $955 per person Apr 10 - Apr 13 found 1 day ago Roundtrip flight included Toronto (YYZ) to Fort Myers (RSW) 9.2/10 Wonderful! (704 reviews) The 2 room condo was huge& had everything you could ask for. The surroundings were beautiful. Reviewed on Jan 30, 2026 ![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 $1,264 per person Apr 10 - Apr 14 found 23 hours ago Roundtrip flight included Detroit (DTW) to Fort Myers (RSW) 9.6/10 Exceptional! (477 reviews) yes everything was amazing! Reviewed on Feb 3, 2026 ![LaPlaya Beach & Golf Resort - A Noble House Resort](https://images.trvl-media.com/lodging/1000000/30000/25200/25199/d2442103_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LaPlaya Beach & Golf Resort - A Noble House Resort Vanderbilt Beach CA $3,288 per person Mar 15 - Mar 20 found 7 hours ago Roundtrip flight included Detroit (DTW) to Fort Myers (RSW) 9/10 Wonderful! (1,000 reviews) The best part is that this hotel is right on the beach. We only stayed two nights because this hotel is very expensive, and the restaurant is very expensive. Reviewed on Feb 1, 2026 ![Marriott Sanibel Harbour Resort & Spa](https://images.trvl-media.com/lodging/1000000/10000/3100/3079/ac9a3a07_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Sanibel Harbour Resort & Spa Punta Rassa CA $1,270 per person Mar 11 - Mar 16 found 6 hours ago Roundtrip flight included Detroit (DTW) to Fort Myers (RSW) 8.4/10 Very Good! (1,005 reviews) Nice room and perfect location Reviewed on Feb 1, 2026 ![Landing Fort Myers near Heritage Palms](https://images.trvl-media.com/lodging/119000000/118250000/118241800/118241763/89f56210_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Landing Fort Myers near Heritage Palms CA $1,061 per person Apr 17 - Apr 24 found 21 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Fort Myers (RSW) 6/10 (2 reviews) The rental was nice. I just wish they had toilet paper ready, something to cover the door in the bedroom. There was not 100% privacy. Reviewed on Oct 21, 2025 Don't see what you're looking for? See all available trips from Columbus to Chokoloskee Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MRK&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski holidays in Chokoloskee Island Price found within the past 48 hours. Click for updated prices. ![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 $2,502 per person Mar 24 - Mar 29 found 1 day ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 8.6/10 Excellent! (2,581 reviews) Very clean room, staff was very nice. All of the pools were clean and everything was very nice and well taken care of. Reviewed on Jan 30, 2026 ![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 $9,724 per person Mar 14 - Mar 21 found 1 hour ago Roundtrip flight included Halifax (YHZ) to Fort Myers (RSW) 6/10 (2 reviews) ![The Ritz-Carlton Naples, Tiburón](https://images.trvl-media.com/lodging/1000000/790000/788300/788295/75f45fbf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton Naples, Tiburón CA $2,605 per person Apr 10 - Apr 14 found 23 hours ago Roundtrip flight included Detroit (DTW) to Fort Myers (RSW) 9.4/10 Exceptional! (609 reviews) Very nice accomodations. Reviewed on Jan 12, 2026 Don't see what you're looking for? See all available trips from Columbus to Chokoloskee Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MRK&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski holidays in Chokoloskee Island Price found within the past 48 hours. Click for updated prices. ![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 $955 per person Apr 10 - Apr 13 found 1 day ago Roundtrip flight included Toronto (YYZ) to Fort Myers (RSW) 9.2/10 Wonderful! (704 reviews) The 2 room condo was huge& had everything you could ask for. The surroundings were beautiful. Reviewed on Jan 30, 2026 ![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 $1,500 per person Mar 17 - Mar 20 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Fort Myers (RSW) 9.6/10 Exceptional! (477 reviews) yes everything was amazing! Reviewed on Feb 3, 2026 ![LaPlaya Beach & Golf Resort - A Noble House Resort](https://images.trvl-media.com/lodging/1000000/30000/25200/25199/d2442103_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LaPlaya Beach & Golf Resort - A Noble House Resort Vanderbilt Beach CA $1,902 per person Apr 10 - Apr 13 found 1 day ago Roundtrip flight included Toronto (YYZ) to Fort Myers (RSW) 9/10 Wonderful! (1,000 reviews) The best part is that this hotel is right on the beach. We only stayed two nights because this hotel is very expensive, and the restaurant is very expensive. Reviewed on Feb 1, 2026 Don't see what you're looking for? See all available trips from Columbus to Chokoloskee Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MRK&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski holidays in Chokoloskee Island Price found within the past 48 hours. Click for updated prices. ![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 $1,264 per person Apr 10 - Apr 14 found 23 hours ago Roundtrip flight included Detroit (DTW) to Fort Myers (RSW) 9.6/10 Exceptional! (477 reviews) yes everything was amazing! Reviewed on Feb 3, 2026 ![Edison Beach House](https://images.trvl-media.com/lodging/12000000/11760000/11753200/11753200/fb0b7d7c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Edison Beach House CA $1,277 per person Apr 8 - Apr 12 found 1 day ago Roundtrip flight included Toronto (YYZ) to Fort Myers (RSW) 9.4/10 Exceptional! (1,554 reviews) This is an excellent hotel really well maintained. Pool is super nice and heated. It also is also in a great location. Near a bunch of restaurants and a farmers market on the weekend. Reviewed on Feb 2, 2026 ![LaPlaya Beach & Golf Resort - A Noble House Resort](https://images.trvl-media.com/lodging/1000000/30000/25200/25199/d2442103_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LaPlaya Beach & Golf Resort - A Noble House Resort Vanderbilt Beach CA $2,154 per person Apr 10 - Apr 14 found 23 hours ago Roundtrip flight included Detroit (DTW) to Fort Myers (RSW) 9/10 Wonderful! (1,000 reviews) The best part is that this hotel is right on the beach. We only stayed two nights because this hotel is very expensive, and the restaurant is very expensive. Reviewed on Feb 1, 2026 Don't see what you're looking for? See all available trips from Columbus to Chokoloskee Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MRK&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the ultimate ski vacation in Chokoloskee Island #### What are some benefits when booking ski vacations in Chokoloskee 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 Chokoloskee 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 Chokoloskee 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 Chokoloskee Island with some as cheap as CA $955\. 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 Chokoloskee 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 32 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 Chokoloskee Island. #### Can I book all-inclusive ski vacations in Chokoloskee 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 Chokoloskee 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 Chokoloskee 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 Chokoloskee 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 Chokoloskee 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 32\. 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 Chokoloskee Island ](https://expedia.ca/Cheap-Flights-To-Chokoloskee-Island.d553248635976468286.Travel-Guide-Flights)[ Chokoloskee Island Hotels ](https://expedia.ca/Chokoloskee-Island-Hotels.d553248635976468286.Travel-Guide-Hotels)[ Chokoloskee Island Vacation Rentals ](https://expedia.ca/Chokoloskee-Island-Vacation-Rentals.d553248635976468286.Travel-Guide-VacationRentals)[ Chokoloskee Island Car Rentals ](https://expedia.ca/Car-Rentals-In-Chokoloskee-Island.d553248635976468286.Car-Rental-Guide)[ Chokoloskee Island Vacations ](https://expedia.ca/Chokoloskee-Island.d553248635976468286.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