Title: Raccoon Key Ski Vacations 2026 | Expedia.com ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Raccoon Key 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 Raccoon Key Price found within the past 48 hours. Click for updated prices. ![Havana Cabana at Key West ](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/62539afb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Havana Cabana at Key West New Town Save 100% on your flight $907 per person Apr 15 - Apr 18 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.8/10 Excellent! (1,698 reviews) Clean room, comfy bed Reviewed on Mar 6, 2026 ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/546caf1e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Southernmost Beach Resort and Guesthouses Old Town Key West Save 100% on your flight $1,130 per person Apr 15 - Apr 18 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.8/10 Excellent! (3,103 reviews) No but the ocean was only 1 block away Reviewed on Mar 6, 2026 ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pier House Resort & Spa Key West Historic District Save 100% on your flight $1,587 per person May 20 - May 24 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9/10 Wonderful! (1,052 reviews) Everything was fantastic Reviewed on Mar 3, 2026 ![The Marker Key West Harbor Resort](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/15d13ee3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Marker Key West Harbor Resort Key West Historic District $1,363 per person May 20 - May 24 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.2/10 Wonderful! (1,000 reviews) The carpet is old and stained. The pool is a good time and the staff is very friendly. The cleaning staff is a bit aggressive and could leave more than 1 towel per person but all and all a nice place. Reviewed on Mar 5, 2026 Don't see what you're looking for? See all available trips from Columbus to Raccoon Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-07/2026-04-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski vacations in Raccoon Key Price found within the past 48 hours. Click for updated prices. ![Havana Cabana at Key West ](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/62539afb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Havana Cabana at Key West New Town Save 100% on your flight $907 per person Apr 15 - Apr 18 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.8/10 Excellent! (1,698 reviews) Clean room, comfy bed Reviewed on Mar 6, 2026 ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/546caf1e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Southernmost Beach Resort and Guesthouses Old Town Key West Save 100% on your flight $1,130 per person Apr 15 - Apr 18 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.8/10 Excellent! (3,103 reviews) No but the ocean was only 1 block away Reviewed on Mar 6, 2026 Don't see what you're looking for? See all available trips from Columbus to Raccoon Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-07/2026-04-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski vacations in Raccoon Key Price found within the past 48 hours. Click for updated prices. ![Havana Cabana at Key West ](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/62539afb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Havana Cabana at Key West New Town $1,093 per person Apr 19 - Apr 23 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.8/10 Excellent! (1,698 reviews) Clean room, comfy bed Reviewed on Mar 6, 2026 ![The Key West Hotel](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/dab63efc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Key West Hotel Key West Historic District Save 100% on your flight $1,536 per person May 20 - May 24 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.2/10 Wonderful! (532 reviews) Bali bar was the best! Will stay again! Reviewed on Mar 2, 2026 ![Lighthouse Hotel - Key West Historic Inns](https://images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/70163bf1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lighthouse Hotel - Key West Historic Inns Old Town Key West Save 100% on your flight $1,448 per person May 20 - May 24 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9/10 Wonderful! (903 reviews) Perfect hotel for the perfect Key West vacation. The location, staff and beautiful blooming orchids made our stay extra special! I loved that Hemmingway’s House was across the street. Reviewed on Mar 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Raccoon Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-07/2026-04-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Planning your Raccoon Key ski vacation #### What are some things I should consider when booking a Raccoon Key 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 Raccoon Key ski packages? Right now, ski trips start at just $907\. Prices and availability are subject to change. Additional terms may apply. #### Can I book a beginner ski package in Raccoon Key? Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Raccoon Key. 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 Raccoon Key cost? Sensational ski trips to Raccoon Key start from $907\. 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 Raccoon Key? The best time to hit the slopes in Raccoon Key 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 Raccoon Key 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 Raccoon Key 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 Raccoon Key with Expedia? Simple search and fantastic filters make it easy to find, build, and book your dream Raccoon Key ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy. ## 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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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](https://expedia.com/Raccoon-Key-Vacation-Rentals.d180164.Travel-Guide-VacationRentals)[ Car Rentals in Raccoon Key ](https://expedia.com/Car-Rentals-In-Raccoon-Key.d180164.Car-Rental-Guide)[ Raccoon Key Vacations ](https://expedia.com/Raccoon-Key.d180164.Destination-Travel-Guides)[ Things to do in Raccoon Key ](https://expedia.com/Things-To-Do-In-Raccoon-Key.d180164.Travel-Guide-Activities) \* 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