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 - ## 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 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 $610 per person May 14 - May 20 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 ![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 $6,967 per person Apr 19 - Apr 23 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![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 $1,926 per person May 13 - May 20 found 1 day ago Roundtrip flight included Boston (BOS) 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 ![The Sunny](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145283/edbd844f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Sunny Ocean Four Save 100% on your flight $1,021 per person Apr 30 - May 3 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.4/10 Very Good! (72 reviews) Great location, beach, pool, and friendly staff. Reviewed on Mar 11, 2026 ![Hilton Cabana Miami Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/18200/18107/0760f366_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Cabana Miami Beach Resort Mid Beach $627 per person May 14 - May 20 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 7.8/10 Good! (610 reviews) Pros: Hotel room is clean, great location, beach is just behind the hotel. Cons: I had high expectation from this resort as it is a “Hilton” hotel. Customer service was mid. I asked for extra duvet/comforter since the blanket we had was really thin. It wasn’t given to us until the next day after we asked the third time. 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/2026-04-11/2026-04-18/?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 $1,224 per person Apr 12 - Apr 16 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 ![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 $6,967 per person Apr 19 - Apr 23 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![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 $3,160 per person Apr 12 - Apr 16 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.4/10 Exceptional! (1,451 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 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/2026-04-11/2026-04-18/?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 6 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 $3,008 per person Apr 30 - May 3 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 $7,451 per person May 22 - May 25 found 1 day ago Roundtrip 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/2026-04-11/2026-04-18/?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. ![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 ![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 $6,967 per person Apr 19 - Apr 23 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![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! (1,451 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 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/2026-04-11/2026-04-18/?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 $610\. 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 $610\. 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. ![](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