Fleming Key Ski Vacations

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence
Better together
Save up to CA $4,200 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

Flight and Ski hotel deals in Fleming Key

Price found within the past 48 hours. Click for updated prices.

YotelPad Miami

Downtown Miami

Save 100% on your flight

CA $1,045

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

8.4/10 Very good! (525 reviews)

The dirtiest place I’ve ever visited. Had to keep my shoes on while I wasn’t in the bed. Service was inexistant and staff was rude…

Reviewed on Sep 28, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $18,387

per person

Dec 7 - Dec 14

found 5 hours ago

Roundtrip flight included

Ottawa (YOW) to Miami (MIA)

8/10 Very good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Miami Vacation Rentals - Brickell

Brickell

Save 100% on your flight

CA $2,152

per person

Dec 3 - Dec 9

found 5 hours ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8.8/10 Excellent! (570 reviews)

Miami Vacation Rentals - Downtown

Downtown Miami

Save 100% on your flight

CA $1,929

per person

Dec 3 - Dec 9

found 5 hours ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

9/10 Wonderful! (92 reviews)

Amazing

Reviewed on Sep 21, 2026

Hotel Riu Plaza Miami Beach

Mid Beach

Save 100% on your flight

CA $2,161

per person

Dec 19 - Dec 26

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

8.2/10 Very good! (1,180 reviews)

The rooms were clean. I can't say immaculate, but they were clean. The staff was very kind and helpful, which made us stay very pleasant. Actually the staff is the best part of the day. The breakfast is just OK. They could do better with meal selection. Now the café/American food is amazing. The beach view and access are wonderful overall I can't complain. It was a great day.

Reviewed on Sep 29, 2026

Don't see what you're looking for?

See all available trips from Columbus to Fleming Key

View all trips

5* Ski holidays in Fleming Key

Price found within the past 48 hours. Click for updated prices.

Kimpton EPIC Hotel by IHG

Downtown Miami

Save 100% on your flight

CA $1,712

per person

Dec 24 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

9/10 Wonderful! (2,598 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $18,387

per person

Dec 7 - Dec 14

found 5 hours ago

Roundtrip flight included

Ottawa (YOW) to Miami (MIA)

8/10 Very good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Miami Vacation Rentals - Downtown

Downtown Miami

Save 100% on your flight

CA $1,929

per person

Dec 3 - Dec 9

found 5 hours ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

9/10 Wonderful! (92 reviews)

Amazing

Reviewed on Sep 21, 2026

Don't see what you're looking for?

See all available trips from Columbus to Fleming Key

View all trips

3 Night Ski holidays in Fleming Key

Price found within the past 48 hours. Click for updated prices.

Pelican Grand Beach Resort - A Noble House Resort

East Fort Lauderdale

Save 100% on your flight

CA $857

per person

Nov 19 - Nov 22

found 7 hours ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8.8/10 Excellent! (1,731 reviews)

The pelican was the first place I took my baby daughter on vacation 21 years ago. This was a nostalgic return for us and unfortunately, it was extremely disappointing. The lazy river was not operational. This is a major factor in why I booked here. Nothing said, no indication of price reduction, nothing. I wouldn’t have booked here had I known. That might be funny to some, but remember, this was a return trip with my daughter with a lot of nostalgia. It was a factor for me. Big strike one. The mandatory Vale parking was almost $100 Canadian per night. Unacceptable. Strike 2. Due to life circumstances I needed to change from a king bed Suite to a double or two queen suite because instead of my ex-girlfriend, it was my daughter that was with me, so they instantly charged me $50 American PER NIGHT to change from a king bed to Queen. Give me a break. I’m not new. Strike three. I will not be returning to the pelican.

Reviewed on Sep 29, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $6,460

per person

Nov 22 - Nov 25

found 22 hours ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8/10 Very good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Pelican Hotel

South Beach

Save 100% on your flight

CA $1,032

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

9.2/10 Wonderful! (506 reviews)

Excellent hotel. I will be back. Lovely. Such friendly staff on all levels and accommodating. Top notch. Thank you!

Reviewed on Sep 27, 2026

Don't see what you're looking for?

See all available trips from Columbus to Fleming Key

View all trips

4 Night Ski holidays in Fleming Key

Price found within the past 48 hours. Click for updated prices.

Shore View Hotel

Hollywood Beach

Save 100% on your flight

CA $833

per person

Nov 2 - Nov 6

found 9 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

9.4/10 Exceptional! (49 reviews)

Room was not clean- kitchen sink in particular was filthy. Check in was terrible- no one at the office, stood outside for 45 mins waiting for someone to answer the phone. Would not stay here again.

Reviewed on Apr 27, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $21,371

per person

Dec 24 - Dec 28

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

8/10 Very good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Miami Vacation Rentals - Brickell

Brickell

Save 100% on your flight

CA $1,409

per person

Dec 5 - Dec 9

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

8.8/10 Excellent! (570 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Fleming Key

View all trips

What are some benefits when booking ski vacations in Fleming Key?

If you're interested in skiing, there's nothing quite like a ski vacation. These trips are designed to allow you to enjoy being on the slopes and relax in tranquil and convenient accommodations at the end of the day. Amenities on ski trips can be pretty upscale, so it's easy to relax in a hot tub or at a spa in between your skiing excursions. Plus, they can put you right next to the slopes. You'll even find a variety of different vacation types available whether you're looking for family friendly, cheap, or even last minute ski vacations.

How can I book the best ski vacation in Fleming Key?

It is most important to implement the ski filter in your search when trying to find a ski vacation that will make you happy. Using the filter will automatically remove any entries that don't offer the skiing opportunities you want. After that, you'll need to think about what specifically you want from Fleming Key, and think about the time of year that's best to visit.

How can I find cheap ski vacations?

Cheap ski vacations are readily available in Fleming Key with some as cheap as CA $833. You can see the cheapest options by sorting your accommodation choices by price, which automatically puts the least-expensive results at the top of the list. You may also want to consider an accommodation with a kitchen, so you can cook instead of eating out.

Can I book ski packages?

Yes, ski packages are readily available throughout Fleming Key. All you have to do is put in your travel dates and see what's available. When you book a ski package, you may be able to enjoy discounts with savings of up to 40 when you book your accommodation and your flight together.

What should I consider when booking family ski vacations?

The key to a successful family ski vacation is ensuring that your family is kept happy and entertained. Consider what your family members are interested in and the kind of vacation they want. If they have little skiing experience, for example, you may want to opt for an accommodation that offers ski lessons or a kid's club. Various slope difficulties may be essential in providing opportunities for everyone at Fleming Key.

Can I book all-inclusive ski vacations in Fleming Key?

Yes, all-inclusive ski trips are available and may be precisely what you're looking for. All you have to do is include the filter for all-inclusive stays, and your search results will only show the accommodations that provide this handy feature that allows you to plan your entire trip to Fleming Key in advance.

What's the best time of year to plan a ski trip?

The apparent answer to when you should plan a ski trip is in winter, but other details are important too. If you book for Fleming Key's high season around January and February, you'll likely find increased prices. It's generally best to opt for the early or late season in December and April, as prices tend not to be quite as high.

How can I find the best deals on ski packages in Fleming Key?

When you're looking for cheap ski vacations, there are a few factors you can take advantage of to help get the best deals. Travelling during the off-season can be cheaper since there's more availability. However, the beginning and end of the season tend to be the most affordable for skiing.

Can I book a ski vacation that's fully refundable?

Being fully refundable is a feature you'll find on several accommodation packages in Fleming Key. You can even search for it explicitly using a filter for full refundability.

Why should I book a ski vacation package with Expedia?

When you book with Expedia, you'll find everything you need for cheap ski vacations, luxury ski vacations and everything in between in one central location. You may even be able to enjoy discounts for booking your accommodation and your flight together with savings of up to 40. With Expedia Rewards, you can earn points towards your next booking.