Florida Keys Kid friendly Vacations

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Flight and Kid friendly hotel deals in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

New Town
CA $1,547
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Key West (EYW)
8.6/10 Excellent! (2,606 reviews)
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
CA $1,887
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Miami (MIA)
9.2/10 Wonderful! (1,360 reviews)
Excepcional hotel

Reviewed on Aug 21, 2026

Hawks Cay Resort

Hawks Cay Resort

CA $2,106
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Miami (MIA)
8.2/10 Very good! (1,009 reviews)
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

CA $1,959
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Miami (MIA)
9/10 Wonderful! (246 reviews)
Shuttle driver was driving while in personal FaceTime call. Did not move to help with van door which was hard to close. The resort is beautiful and we really enjoyed the amenities.

Reviewed on Aug 19, 2026

Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

CA $2,073
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Miami (MIA)
8.8/10 Excellent! (1,006 reviews)
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5* Kid friendly holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
CA $1,887
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Miami (MIA)
9.2/10 Wonderful! (1,360 reviews)
Excepcional hotel

Reviewed on Aug 21, 2026

Don't see what you're looking for?
See all available trips from Columbus to Florida Keys
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3 Night Kid friendly holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
CA $968
per person
Oct 13 - Oct 16
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (1,360 reviews)
Excepcional hotel

Reviewed on Aug 21, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
CA $2,412
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (3,469 reviews)
Parking and resort fees expensive for what you get.

Reviewed on Aug 21, 2026

Hawks Cay Resort

Hawks Cay Resort

CA $1,527
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very good! (1,009 reviews)
Don't see what you're looking for?
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4 Night Kid friendly holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

CA $956
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (1,004 reviews)
Hawks Cay Resort

Hawks Cay Resort

CA $1,280
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
8.2/10 Very good! (1,009 reviews)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
CA $3,234
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
8.8/10 Excellent! (3,469 reviews)
Parking and resort fees expensive for what you get.

Reviewed on Aug 21, 2026

Don't see what you're looking for?
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Plan the perfect family-friendly vacation in Florida Keys with Expedia

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

Whether it's luxurious or cheap, family vacations in Florida Keys 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 Florida Keys.

Are there cheap family vacations to Florida Keys?

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 Florida Keys 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 Florida Keys?

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

Can I find luxury family vacations in Florida Keys?

If you're looking for a luxury family vacation to Florida Keys, 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 Florida Keys.

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 Florida Keys 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.

Kid friendly Hotels in Florida Keys

Hawks Cay Resort

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL
  • 2 hours drive from Duval Street
Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Hawks Cay Resort
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
  • 10 min walk from Duval Street
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (3,549 reviews)
"Parking and resort fees expensive for what you get."

Reviewed on Aug 21, 2026

Southernmost Beach Resort and Guesthouses
Islander Resort

Islander Resort

82100 Overseas Highway Islamorada FL
  • 3 hours drive from Duval Street
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.4/10 Exceptional! (1,108 reviews)
"Room clean and lovely. Breakfast was great with a beautiful view."

Reviewed on Aug 21, 2026

Islander Resort
See all 8,253 properties in Florida Keys
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $63
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $78
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Snorkler waving underwater in Key West

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

CA $85
per adult
86% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
See all activities in Florida Keys

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.