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.
Amara Cay Resort

Amara Cay Resort

Matecumbe
Save 100% on your flight
CA $1,592
per person
Dec 9 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
8.8/10 Excellent! (1,318 reviews)
Very clean resort. The pool was fabulous. The tiki bar was great. Stall friendly and helpful. Truly enjoyed my stay!

Reviewed on Oct 6, 2026

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

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

Save 100% on your flight
CA $2,172
per person
Dec 9 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
9/10 Wonderful! (281 reviews)
Clean, comfortable rooms. On site amenities were fantastic!

Reviewed on Oct 6, 2026

Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
Save 100% on your flight
CA $2,226
per person
Dec 9 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (1,471 reviews)
Islander Resort

Islander Resort

Matecumbe
Save 100% on your flight
CA $2,410
per person
Dec 9 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
9.4/10 Exceptional! (1,132 reviews)
We got the poolside cabana king and it was perfect! Resort was immaculate! Already want to go back!

Reviewed on Oct 6, 2026

Hawks Cay Resort

Hawks Cay Resort

CA $1,764
per person
Nov 9 - Nov 14
found 18 hours ago
Roundtrip non-stop flight included
Bangor (BGR) to Miami (MIA)
8.2/10 Very good! (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
Save 100% on your flight
CA $2,226
per person
Dec 9 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (1,471 reviews)
Don't see what you're looking for?
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3 Night Kid friendly holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

Save 100% on your flight
CA $1,455
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (281 reviews)
Clean, comfortable rooms. On site amenities were fantastic!

Reviewed on Oct 6, 2026

Islander Resort

Islander Resort

Matecumbe
CA $1,619
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.4/10 Exceptional! (1,132 reviews)
We got the poolside cabana king and it was perfect! Resort was immaculate! Already want to go back!

Reviewed on Oct 6, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
CA $1,753
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
Onsite parking was $50 a day. We were given a room with the view of the dumpster and construction area. The beach was mostly non-existent and had sea grass that smelled heavily like cow manure. Onsite restaurant prices were ridiculous $123 dollars for two appetizers, two Pepsi's, and a Mahi plate all eaten while enduring the cow manure smell. We had our do not disturb on our room, housecleaning waited till the last day after their work hours to let us know they would like to clean the room. The very small room had the window air conditioner vent propped with a hotel brochure and blowed directly across the bed and was very noisy.

Reviewed on Oct 6, 2026

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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 $722
per person
Nov 16 - Nov 20
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (1,010 reviews)
Clean rooms, excellent staff. Great sunset!

Reviewed on Oct 6, 2026

Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
Save 100% on your flight
CA $5,267
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
9.2/10 Wonderful! (1,471 reviews)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
CA $3,534
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
Onsite parking was $50 a day. We were given a room with the view of the dumpster and construction area. The beach was mostly non-existent and had sea grass that smelled heavily like cow manure. Onsite restaurant prices were ridiculous $123 dollars for two appetizers, two Pepsi's, and a Mahi plate all eaten while enduring the cow manure smell. We had our do not disturb on our room, housecleaning waited till the last day after their work hours to let us know they would like to clean the room. The very small room had the window air conditioner vent propped with a hotel brochure and blowed directly across the bed and was very noisy.

Reviewed on Oct 6, 2026

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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 3 outdoor pools, a full-service spa, and 2 poolside bars. Our guests praise the pool and the helpful staff in ...
8.6/10 Excellent! (3,626 reviews)
"Onsite parking was $50 a day. We were given a room with the view of the dumpster and construction area. The beach was mostly non-existent and had sea grass that smelled heavily like cow manure. Onsite restaurant prices were ridiculous $123 dollars for two appetizers, two Pepsi's, and a Mahi plate ..."

Reviewed on Oct 6, 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! (1,134 reviews)
"We got the poolside cabana king and it was perfect! Resort was immaculate! Already want to go back!"

Reviewed on Oct 6, 2026

Islander Resort
See all 8,208 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 $59
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
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

CA $82
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
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.