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 ## Top Ski vacation packages in Raccoon Key Price found within the past 48 hours. Click for updated prices. ![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Blue Flamingo Resort Key West New Town $951 per person Apr 12 - Apr 17 found 1 day ago Roundtrip flight included Boston (BOS) to Key West (EYW) 8.2/10 Very Good! (1,957 reviews) We enjoyed our time very much. The shuttle was very convenient. Since there was no cleaning service on Sunday we would have liked extra towels on Saturday but that wasn’t a big deal. Overall enjoyed ourselves very much! Reviewed on Mar 6, 2026 ![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 $1,106 per person Apr 12 - Apr 17 found 1 day ago Roundtrip 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 $1,590 per person Apr 12 - Apr 17 found 1 day ago Roundtrip flight included Boston (BOS) to Key West (EYW) 8.8/10 Excellent! (3,103 reviews) Yes, although it was behind a staircase so it was more obstructed than others around. Reviewed on Mar 7, 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 $1,699 per person Apr 12 - Apr 17 found 1 day ago Roundtrip flight included Boston (BOS) to Key West (EYW) 9/10 Wonderful! (1,052 reviews) Everything was fantastic Reviewed on Mar 3, 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/2026-04-08/2026-04-15/?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. ![The Reach Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/bc3021c3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Reach Key West, Curio Collection by Hilton Old Town Key West $679 per person May 31 - Jun 3 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.6/10 Excellent! (1,004 reviews) Pool View could see ocean from room through trees. Good property, but elevator was broken. Maid service mediocre, they seemed to do their job with a grudge. Food expensive but mediocre in quality. Fortunately many great restaurants very near by. Walk down the beach to the left about 50 yards and you are at Louies Backyard, one of the best on Key West. Reviewed on Mar 6, 2026 ![Casa Marina Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/14292c62_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Casa Marina Key West, Curio Collection by Hilton Old Town Key West Save 100% on your flight $788 per person May 31 - Jun 3 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.4/10 Very Good! (560 reviews) Ocean view room. Very nice staff. Close to lots of attractions. The perfect stay for a first time solo traveler. I will definitely return! Reviewed on Mar 7, 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 $714 per person May 31 - Jun 3 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.2/10 Wonderful! (1,000 reviews) Great location!! Afternoon music by the pool was excellent! Very walkable to great breakfast and dinner options! Reviewed on Mar 7, 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/2026-04-08/2026-04-15/?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. ![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 $848 per person May 25 - May 29 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.8/10 Excellent! (3,103 reviews) Yes, although it was behind a staircase so it was more obstructed than others around. Reviewed on Mar 7, 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 $1,182 per person May 25 - May 29 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.2/10 Wonderful! (532 reviews) Loved this hotel, immaculate. Reviewed on Mar 7, 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 $998 per person May 25 - May 29 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 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/2026-04-08/2026-04-15/?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 $679\. 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 $679\. 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.