Raccoon Key Kid friendly Vacations

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Flight and Kid friendly hotel deals in Raccoon Key

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

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

CA $1,430

per person

Nov 27 - Nov 30

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (1,398 reviews)

We thoroughly enjoyed our time here! The grounds are beautiful. The staff was great. The rooms are very clean and housekeeping did a great job each day. I loved the robes that were provided! The buildings are old, yes. And the floor in our room was uneven. Not desirable but not a deal breaker. Bar and bar staff was great. Breakfast was great for a continental. Plenty of options and fresh cut fruit every day. We’d definitely return!

Reviewed on Sep 17, 2026

Southernmost House - Adult Exclusive

Old Town Key West

CA $3,734

per person

Nov 25 - Dec 2

found 18 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Key West (EYW)

9.4/10 Exceptional! (1,001 reviews)

Southernmost House is like an adult Disney World. There isn't enough stars to rate it. Staff are the hardest working people Ive ever met. they cater to your every need like your royalty. And clean, you could eat off the floors and even outside. Such a beautiful and historical place not to mention right next to the most famous place in Key West the bouy . Close to plenty shopping and restaurants. I could go on and on all I can say is you have to stay here to see for yourselves

Reviewed on Sep 17, 2026

The Marker Key West Harbor Resort

Key West Historic District

CA $1,985

per person

Nov 27 - Nov 30

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (1,003 reviews)

Location is one of the best in west west off the busy area but yet in the middle of everything. Will def be going back here.

Reviewed on Sep 17, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $1,810

per person

Nov 27 - Nov 30

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

8.6/10 Excellent! (3,560 reviews)

Lighthouse Suites Collection

Old Town Key West

CA $1,898

per person

Oct 26 - Oct 30

found 7 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Key West (EYW)

No reviews

My favorite place now. Won’t stay anywhere else. Lost track of the amount of my Key West stays, but this place has been the the most memorable.

Reviewed on Sep 13, 2026

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3 Night Kid friendly holidays in Raccoon Key

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

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $1,810

per person

Nov 27 - Nov 30

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

8.6/10 Excellent! (3,560 reviews)

The Gardens Hotel

Old Town Key West

CA $2,101

per person

Nov 27 - Nov 30

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.8/10 Exceptional! (1,003 reviews)

Great historical Key West vibe. The staff are excellent and knowledgeable. It was a great find.

Reviewed on Sep 17, 2026

The Marker Key West Harbor Resort

Key West Historic District

CA $1,985

per person

Nov 27 - Nov 30

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (1,003 reviews)

Location is one of the best in west west off the busy area but yet in the middle of everything. Will def be going back here.

Reviewed on Sep 17, 2026

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4 Night Kid friendly holidays in Raccoon Key

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

Heron House - Adult Only

Old Town Key West

CA $1,651

per person

Oct 26 - Oct 30

found 7 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Key West (EYW)

9.2/10 Wonderful! (1,158 reviews)

The Key West Hotel

Key West Historic District

CA $2,648

per person

Nov 23 - Nov 27

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9.2/10 Wonderful! (562 reviews)

Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

Ella's Cottages - Key West Historic Inns

Old Town Key West

CA $2,021

per person

Nov 23 - Nov 27

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9.4/10 Exceptional! (496 reviews)

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What are some benefits of booking a family-friendly vacation?

Whether it's luxurious or cheap, family vacations in Raccoon 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 Raccoon Key.

Are there cheap family vacations to Raccoon 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 Raccoon 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 Raccoon Key?

Yes, you'll find plenty of all-inclusive family vacation packages for Raccoon 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 Raccoon 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 Raccoon Key or something a bit more relaxed.

Can I find luxury family vacations in Raccoon Key?

If you're looking for a luxury family vacation to Raccoon 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 Raccoon 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 Raccoon 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.