Title: Keewaydin Island Ski Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/6337231/0b8ef5b6-2083-4cdb-97c8-d4b5fcbc1cee.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Keewaydin Island Ski Vacations ## Book a Ski Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 ## Top Ski vacation packages in Keewaydin 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 Save 100% on your flight $456 per person May 15 - May 19 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 9.2/10 Wonderful! (704 reviews) The pools and Lazy river was awesome. Condos a little outdated but nice Reviewed on Mar 3, 2026 ![The Perry Hotel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 Save 100% on your flight $597 per person May 15 - May 19 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 9.6/10 Exceptional! (477 reviews) Such a beautiful hotel! Both the rooftop and outside pool were heated and absolutely delightful! They have a boat that will take you down the river and drop you off at Barefoot Beach. You can stay as long as you like as boat comes back every hour. The food at the rooftop restaurant (The Tigress) was one of the best dinners we’ve had in a long time! Highly recommend this hotel! Will be coming back! Reviewed on Mar 4, 2026 ![Hilton Marco Island Beach Resort and Spa](https://images.trvl-media.com/lodging/1000000/20000/17600/17575/65dd4041_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Marco Island Beach Resort and Spa South End Save 100% on your flight $797 per person May 5 - May 9 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 9/10 Wonderful! (1,714 reviews) The Hilton is excellent, if one wants more updated decor this may not be for that traveler It meet the reds for this trip a sunshine break! Reviewed on Mar 3, 2026 ![Marriott Sanibel Harbour Resort & Spa](https://images.trvl-media.com/lodging/1000000/10000/3100/3079/0ef86cd3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Sanibel Harbour Resort & Spa Punta Rassa Save 100% on your flight $875 per person May 20 - May 25 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 8.4/10 Very Good! (1,005 reviews) Unfortunately we had the unpleasant experience of staying at the Captiva Tower. So, no the pool was not enjoyable because of the sewer smell coming from the parking lot. I spoke to management and they did apologize for the lack of service, amenities and cleanliness of Captiva Tower and did refund some of our money. So, staff are great at the front desk. Reviewed on Mar 3, 2026 ![Bellasera Resort](https://images.trvl-media.com/lodging/1000000/10000/4800/4760/d22f3ec7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bellasera Resort Old Naples Save 100% on your flight $949 per person May 5 - May 9 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 9.6/10 Exceptional! (2,225 reviews) Love it, best in the area Reviewed on Mar 5, 2026 Don't see what you're looking for? See all available trips from Columbus to Keewaydin Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-05/2026-04-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=APF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski vacations in Keewaydin 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/f4e5c65a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sundial Beach Resort & Spa Mid Island Save 100% on your flight $1,239 per person May 20 - May 25 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 8.6/10 Excellent! (2,600 reviews) The room was good condition, we enjoyed the pickleball courts. The food was pricey and just so so quality. Reviewed on Mar 1, 2026 ![The Ritz-Carlton Naples, Tiburón](https://images.trvl-media.com/lodging/1000000/790000/788300/788295/a653a1be_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton Naples, Tiburón $1,691 per person Apr 29 - May 3 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 9.4/10 Exceptional! (620 reviews) Very nice accomodations. Reviewed on Jan 12, 2026 ![Naples Beach Club, A Four Seasons Resort](https://images.trvl-media.com/lodging/1000000/10000/9800/9786/ce10cbd7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Naples Beach Club, A Four Seasons Resort Coquina Sands $3,066 per person Apr 29 - May 3 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 8.8/10 Excellent! (3 reviews) Don't see what you're looking for? See all available trips from Columbus to Keewaydin Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-05/2026-04-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=APF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski vacations in Keewaydin Island Price found within the past 48 hours. Click for updated prices. ![Marriott Sanibel Harbour Resort & Spa](https://images.trvl-media.com/lodging/1000000/10000/3100/3079/0ef86cd3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Sanibel Harbour Resort & Spa Punta Rassa Save 100% on your flight $579 per person Apr 30 - May 3 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 8.4/10 Very Good! (1,005 reviews) Unfortunately we had the unpleasant experience of staying at the Captiva Tower. So, no the pool was not enjoyable because of the sewer smell coming from the parking lot. I spoke to management and they did apologize for the lack of service, amenities and cleanliness of Captiva Tower and did refund some of our money. So, staff are great at the front desk. Reviewed on Mar 3, 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 Save 100% on your flight $711 per person May 21 - May 24 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 9.6/10 Exceptional! (477 reviews) Such a beautiful hotel! Both the rooftop and outside pool were heated and absolutely delightful! They have a boat that will take you down the river and drop you off at Barefoot Beach. You can stay as long as you like as boat comes back every hour. The food at the rooftop restaurant (The Tigress) was one of the best dinners we’ve had in a long time! Highly recommend this hotel! Will be coming back! Reviewed on Mar 4, 2026 ![Bellasera Resort](https://images.trvl-media.com/lodging/1000000/10000/4800/4760/d22f3ec7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bellasera Resort Old Naples Save 100% on your flight $1,011 per person Apr 16 - Apr 19 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Fort Myers (RSW) 9.6/10 Exceptional! (2,225 reviews) Love it, best in the area Reviewed on Mar 5, 2026 Don't see what you're looking for? See all available trips from Columbus to Keewaydin Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-05/2026-04-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=APF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski vacations in Keewaydin Island Price found within the past 48 hours. Click for updated prices. ![Courtyard by Marriott Fort Myers Cape Coral](https://images.trvl-media.com/lodging/1000000/30000/22400/22386/ffbd89e9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard by Marriott Fort Myers Cape Coral Save 100% on your flight $270 per person Apr 7 - Apr 11 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 8.2/10 Very Good! (1,002 reviews) Staff was great and pool was relaxing. Reviewed on Mar 4, 2026 ![Tween Waters Island Resort & Spa](https://images.trvl-media.com/lodging/1000000/180000/170800/170769/a5c54d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tween Waters Island Resort & Spa Save 100% on your flight $610 per person May 15 - May 19 found 1 day ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW) 8.6/10 Excellent! (1,002 reviews) The bed and pillows were awful 😖 Reviewed on Mar 1, 2026 ![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 Save 100% on your flight $456 per person May 15 - May 19 found 1 day ago Roundtrip flight included Boston (BOS) to Fort Myers (RSW) 9.2/10 Wonderful! (704 reviews) The pools and Lazy river was awesome. Condos a little outdated but nice Reviewed on Mar 3, 2026 Don't see what you're looking for? See all available trips from Columbus to Keewaydin Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-05/2026-04-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=APF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Planning your Keewaydin Island ski vacation #### What are some things I should consider when booking a Keewaydin Island 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 Keewaydin Island ski packages? Right now, ski trips start at just $270\. Prices and availability are subject to change. Additional terms may apply. #### Can I book a beginner ski package in Keewaydin Island? Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Keewaydin Island. 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 Keewaydin Island cost? Sensational ski trips to Keewaydin Island start from $270\. 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 Keewaydin Island? The best time to hit the slopes in Keewaydin Island 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 Keewaydin Island 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 Keewaydin Island 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 Keewaydin Island with Expedia? Simple search and fantastic filters make it easy to find, build, and book your dream Keewaydin Island ski vacation in just a few clicks. 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](https://expedia.com/Keewaydin-Island-Vacation-Rentals.d6337231.Travel-Guide-VacationRentals)[ Car Rentals in Keewaydin Island ](https://expedia.com/Car-Rentals-In-Keewaydin-Island.d6337231.Car-Rental-Guide)[ Keewaydin Island Vacations ](https://expedia.com/Keewaydin-Island.d6337231.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 even more - get up to 20% on select hotels 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