Fleming Key Kid friendly 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 Kid friendly hotel deals in Fleming Key

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

Park Central South Beach

South Beach

Save 100% on your flight

CA $1,630

per person

Dec 13 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

8.6/10 Excellent! (1,952 reviews)

It was ok. good for one night before the cruise. We got stuck in the elevator so it was kind of scary. They moved our room and gave us a little compensation for our food for the inconvenience but still not the best hotel around. It was a little run down and old. Pictures make it look a lot better than it is. Staff was really nice though

Reviewed on Oct 1, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $20,306

per person

Dec 25 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) 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

Bentley Hotel South Beach

South Beach

Save 100% on your flight

CA $2,095

per person

Dec 13 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

9.4/10 Exceptional! (1,145 reviews)

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

CA $2,406

per person

Nov 1 - Nov 7

found 2 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Key West (EYW)

9.4/10 Exceptional! (1,001 reviews)

We arrived at Key West just after 12 noon on a Sunday. I was planning to just leave our luggage’s at the hotel since check in time was at 4pm. Catherine was the one that greeted us and help us out on our check in process. She was very professional and very friendly. We got our room ready right away and we didn’t have to wait until check in time at 4PM. Our room was right by the pool, it was clean, has a full size fridge and small microwave, some kitchen amenities (plates, cups, silverware’s) and a dehumidifier. The bathroom is clean and very spacious (shower area). We thought it will be loud since it’s close to the pool and the bar but the whole time we were there it was nice and quiet. There’s are near by restaurants, shops and coffee shops but I suggest to rent a scooter to get to the port area if you have any plans on going to any boating trips (it’s a good 20-30 mins walk from the hotel). We met dean on our 2nd day and he was very friendly and make sure to give us our parking pass for the scooter that we rented. Dean and Catherine definitely made our stay special. And we will definitely come back to stay at this facility on our next trip to Key West. I highly recommend this place if you want a relaxing, laidback stay at Key West.

Reviewed on Oct 1, 2026

EAST Miami Residences

Brickell

Save 100% on your flight

CA $2,741

per person

Nov 1 - Nov 7

found 19 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

9.2/10 Wonderful! (151 reviews)

beatiful place

Reviewed on Sep 30, 2026

Don't see what you're looking for?

See all available trips from Columbus to Fleming Key

View all trips

5* Kid friendly holidays in Fleming Key

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

Miami Vacation Rentals - Downtown

Downtown Miami

Save 100% on your flight

CA $2,414

per person

Dec 25 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

9/10 Wonderful! (92 reviews)

Really enjoyed the area and the room and view was awesome!!!!

Reviewed on Oct 1, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $20,306

per person

Dec 25 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) 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

EAST Miami Residences

Brickell

Save 100% on your flight

CA $2,741

per person

Nov 1 - Nov 7

found 19 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

9.2/10 Wonderful! (151 reviews)

beatiful place

Reviewed on Sep 30, 2026

Don't see what you're looking for?

See all available trips from Columbus to Fleming Key

View all trips

3 Night Kid friendly holidays in Fleming Key

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

Fontainebleau Miami Beach Private Luxury Suites

Mid Beach

Save 100% on your flight

CA $1,042

per person

Nov 23 - Nov 26

found 17 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

7/10 Good! (74 reviews)

The room was give it to us was so dirty, we talk with the people in charge and the said just that was only room available, I submit the pictures of the room to get reimbursement because I left the hotel and get another one.

Reviewed on Sep 3, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $12,421

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip flight included

Toronto (YYZ) 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

1 Hotel South Beach

South Beach

Save 100% on your flight

CA $1,964

per person

Dec 8 - Dec 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

9.4/10 Exceptional! (1,644 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Fleming Key

View all trips

4 Night Kid friendly holidays in Fleming Key

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

The Local House

South Beach

Save 100% on your flight

CA $994

per person

Nov 16 - Nov 20

found 19 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

9.2/10 Wonderful! (1,002 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $18,011

per person

Dec 24 - Dec 28

found 1 day 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

1 Hotel South Beach

South Beach

Save 100% on your flight

CA $3,249

per person

Dec 12 - Dec 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

9.4/10 Exceptional! (1,644 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 of booking a family-friendly vacation?

Whether it's luxurious or cheap, family vacations in Fleming Key are among the most memorable experiences you'll ever have with your family. It can be a great way to bond and explore new destinations with the people you love most. Plus, it's easy to keep an eye on your little ones without having to worry about how they are with a sitter back home. You may even meet some other families and establish long-lasting friendships.

How can I find the best family-friendly vacations?

Using search filters makes finding the perfect family-friendly vacation easy. You can implement the search filter for family-friendly accommodations specifically, but that's just the beginning. You'll also find search filters for price range along with the desired number of bedrooms, so you can ensure you have enough space for everyone you want to bring to Fleming Key.

Are there cheap family vacations to Fleming Key?

Price varies quite a bit, ranging from to . The price you'll be paying depends on a variety of factors, and you can filter for them all. You can implement a filter for your budget limitations and also remove any 4- and 5-star stays from your search. You can even filter by accommodation type, which can present you with cheap alternatives to what is typically considered standard.

When should I book family-friendly vacation packages?

The right time to book family-friendly vacation packages in Fleming Key depends on what you're looking for. If you're looking to save, booking during least popular month tends to be cheaper compared to the rest of the year, though that's not always a guarantee. Keep in mind that the off-season and the busy season differ from place to place, with family-friendly vacations in Canada being very different compared to options in France and Spain, for example.

Can I book an all-inclusive family vacation in Fleming Key?

Yes, you'll find plenty of all-inclusive family vacation packages for Fleming Key. To see what's available, just select the all-inclusive filter on your search.

How can I book the best family activity vacation?

If you're looking to make the most out of the available activities in Fleming Key, you'll need to consider what your family likes to do. Cater your itinerary to your family's interests, and you'll create memories that you and your kids will hold on to for the rest of your lives whether it's family ski vacations in Fleming Key or something a bit more relaxed.

Can I find luxury family vacations in Fleming Key?

If you're looking for a luxury family vacation to Fleming Key, you can use search filters to find the best options available. Activate the filter for 5-star packages to only see the best of the best. Plus, you'll find a range of first-class flights available to make even the journey there top-of-the-line.

How can I search for family vacation deals?

Finding deals is easy when you take advantage of the array of available search filters. You can set budget limitations and remove 4- and 5-star options from your search. If you don't want to miss out on your favourite amenities, however, you can consider travelling during , which often have lower prices because of the off-season in Fleming Key.

Can I book a family vacation package that is fully refundable?

If you're looking for a fully refundable reservation, you won't have to look far on Expedia. Quite a few properties in Fleming Key are fully refundable. You can search for this feature, but always make sure to check the specific property's policies and requirements before booking.

Why should I book my family trip with Expedia?

When you book with Expedia, you can book your accommodation and your flight together, with some discounts available for doing both at once. Additionally, you may be able to enjoy special discounts with Expedia Rewards that will earn you points you can then put toward discounts for subsequent bookings.