Title: Grassy Key Ski Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/2437/83757040-1d80-4589-aea2-a5fe1bb3ba0c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Grassy Key Ski Vacations ## Book a Ski Hotel + Flight or Car together to unlock savings Photo by Monica Ferro ## Top Ski vacation packages in Grassy Key Price found within the past 48 hours. Click for updated prices. ![Solé Miami, A Noble House Resort](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803820/ff03be62_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Solé Miami, A Noble House Resort Ocean Four Save 100% on your flight $606 per person May 20 - May 24 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.6/10 Excellent! (2,052 reviews) The bed hotel in Miami Reviewed on Mar 11, 2026 ![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/5c0d327a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel South Beach South Beach Save 100% on your flight $1,567 per person May 20 - May 24 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.4/10 Exceptional! (1,455 reviews) This hotel is so beautiful and the staff is so kind and accommodating. The pool and beach areas are stunning, the food is delicious, the rooms are spacious, the beds are so comfortable, and the location is perfect. It’s the best hotel experience I’ve ever had, and I can’t wait to go back again! Reviewed on Mar 7, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach Save 100% on your flight $7,352 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![Fontainebleau Miami Beach](https://images.trvl-media.com/lodging/2000000/1200000/1190600/1190549/4c5e4651_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fontainebleau Miami Beach Mid Beach Save 100% on your flight $821 per person May 20 - May 24 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.4/10 Very Good! (7,941 reviews) Overall clean and enjoyable. The refresh lounge needs a refresh! Reviewed on Mar 10, 2026 ![Bay Breeze Premium Apartments By Eskape Collection](https://images.trvl-media.com/lodging/28000000/27610000/27603500/27603405/e068aeb4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bay Breeze Premium Apartments By Eskape Collection Save 100% on your flight $740 per person May 14 - May 20 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.6/10 Excellent! (201 reviews) The staff was super helpful and friendly. They cleaned our room and restocked towels and dishwasher/laundry soap for us on the third day. The kids loved the pool and we spent a lot of time out on the balcony. The neighborhood was quiet and seemed to be full of families. It really was a perfect little place for our family. Reviewed on Mar 10, 2026 Don't see what you're looking for? See all available trips from Columbus to Grassy Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-12/2026-04-19/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski vacations in Grassy Key Price found within the past 48 hours. Click for updated prices. ![EAST Miami Residences](https://images.trvl-media.com/lodging/79000000/78580000/78570600/78570563/759b33fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### EAST Miami Residences Brickell Save 100% on your flight $1,534 per person May 6 - May 10 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9/10 Wonderful! (109 reviews) We loved staying here and will definitely be back! Yes, it is very expensive, but compared to other Miami hotels this one is the best overall deal for what you get. Reviewed on Mar 1, 2026 ![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/5c0d327a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel South Beach South Beach Save 100% on your flight $1,567 per person May 20 - May 24 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.4/10 Exceptional! (1,455 reviews) This hotel is so beautiful and the staff is so kind and accommodating. The pool and beach areas are stunning, the food is delicious, the rooms are spacious, the beds are so comfortable, and the location is perfect. It’s the best hotel experience I’ve ever had, and I can’t wait to go back again! Reviewed on Mar 7, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach Save 100% on your flight $7,352 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) Don't see what you're looking for? See all available trips from Columbus to Grassy Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-12/2026-04-19/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski vacations in Grassy Key Price found within the past 48 hours. Click for updated prices. ![Villas At Hawks Cay Resort](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920083/8638cc9f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Villas At Hawks Cay Resort Save 100% on your flight $957 per person Apr 25 - Apr 28 found 12 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Miami (MIA) 8.4/10 Very Good! (170 reviews) Property was clean and staff were helpful. Would stay again. Reviewed on Mar 11, 2026 ![W South Beach](https://images.trvl-media.com/lodging/1000000/20000/11900/11881/486a329f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### W South Beach South Beach $1,998 per person May 3 - May 6 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.2/10 Wonderful! (1,002 reviews) We waited 2 days and moved 2 rooms before getting our actual room. For that reason the manager upgraded us for the remainder of the week to a 4 bedroom, Oceanfront suite. The property is awesome, but the pool closing at 5:00 is annoying and then closing even earlier for private events is even more annoying. Request a room on the North side of the property to avoid early morning car honking and construction beeps at 7:00 am every day. Reviewed on Mar 2, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $6,601 per person Apr 18 - Apr 21 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) Don't see what you're looking for? See all available trips from Columbus to Grassy Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-12/2026-04-19/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski vacations in Grassy Key Price found within the past 48 hours. Click for updated prices. ![Cavalier Hotel South Beach](https://images.trvl-media.com/lodging/1000000/20000/13600/13579/c0c3faa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cavalier Hotel South Beach South Beach Save 100% on your flight $573 per person May 20 - May 24 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.6/10 Excellent! (1,002 reviews) No view of anything except alley. I don’t need a view I’m there to sleep. Staff very friendly and accommodating. Loved the 1930s decor and the old style music inside and more modern vibe outside. Reviewed on Mar 10, 2026 ![W South Beach](https://images.trvl-media.com/lodging/1000000/20000/11900/11881/486a329f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### W South Beach South Beach $3,438 per person May 1 - May 5 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.2/10 Wonderful! (1,002 reviews) We waited 2 days and moved 2 rooms before getting our actual room. For that reason the manager upgraded us for the remainder of the week to a 4 bedroom, Oceanfront suite. The property is awesome, but the pool closing at 5:00 is annoying and then closing even earlier for private events is even more annoying. Request a room on the North side of the property to avoid early morning car honking and construction beeps at 7:00 am every day. Reviewed on Mar 2, 2026 ![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/4743fa46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Creekside Inn $634 per person May 20 - May 24 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 7.8/10 Good! (1,013 reviews) It’s totally sufficient for the type of hotel. Older but clean. Great location Reviewed on Mar 9, 2026 Don't see what you're looking for? See all available trips from Columbus to Grassy Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-12/2026-04-19/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Planning your Grassy Key ski vacation #### What are some things I should consider when booking a Grassy 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 Grassy Key ski packages? Right now, ski trips start at just $573\. Prices and availability are subject to change. Additional terms may apply. #### Can I book a beginner ski package in Grassy Key? Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Grassy 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 Grassy Key cost? Sensational ski trips to Grassy Key start from $573\. 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 Grassy Key? The best time to hit the slopes in Grassy 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 Grassy 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 Grassy 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 Grassy Key with Expedia? Simple search and fantastic filters make it easy to find, build, and book your dream Grassy 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/Grassy-Key-Vacation-Rentals.d3000451823.Travel-Guide-VacationRentals)[ Car Rentals in Grassy Key ](https://expedia.com/Car-Rentals-In-Grassy-Key.d3000451823.Car-Rental-Guide)[ Grassy Key Vacations ](https://expedia.com/Grassy-Key.d3000451823.Destination-Travel-Guides)[ Things to do in Grassy Key ](https://expedia.com/Things-To-Do-In-Grassy-Key.d3000451823.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.