Florida Keys Kid friendly Vacations 2026

Top Kid friendly vacation packages in Florida Keys

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

Tranquility Bay Beachfront Hotel and Resort

$761

per person

Dec 8 - Dec 12

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Miami (MIA)

8.8/10 Excellent! (1,006 reviews)

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$861

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.2/10 Wonderful! (1,471 reviews)

Hawks Cay Resort

Save 100% on your flight

$831

per person

Dec 8 - Dec 12

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Miami (MIA)

8.2/10 Very Good! (1,006 reviews)

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

$819

per person

Dec 7 - Dec 11

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (281 reviews)

Clean, comfortable rooms. On site amenities were fantastic!

Reviewed on Oct 6, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

$1,349

per person

Nov 6 - Nov 8

just found

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

8.6/10 Excellent! (3,606 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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5* Kid friendly vacations in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$861

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.2/10 Wonderful! (1,471 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

3 Night Kid friendly vacations in Florida Keys

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

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

$687

per person

Dec 8 - Dec 11

found 19 hours ago

Roundtrip flight included

Cleveland (CLE) to Miami (MIA)

9/10 Wonderful! (281 reviews)

Clean, comfortable rooms. On site amenities were fantastic!

Reviewed on Oct 6, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

$855

per person

Dec 7 - Dec 10

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (3,606 reviews)

Reviewed on Oct 6, 2026

Islander Resort

Matecumbe

$818

per person

Dec 8 - Dec 11

found 19 hours ago

Roundtrip flight included

Cleveland (CLE) 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

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4 Night Kid friendly vacations in Florida Keys

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

The Pelican Key Largo Cottages

Save 100% on your flight

$358

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9/10 Wonderful! (1,010 reviews)

Clean rooms, excellent staff. Great sunset!

Reviewed on Oct 6, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$861

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.2/10 Wonderful! (1,471 reviews)

Gilbert's Resort

Save 100% on your flight

$550

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8.6/10 Excellent! (1,005 reviews)

Amamos Gilber, el lugar es muy familiar

Reviewed on Oct 6, 2026

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How can I find the best family vacation packages in Florida Keys?

For fam-tastic vacation packages in Florida Keys, check the family-friendly filter and add child-charming amenities, like water parks and pools. Read reviews written by other broods to be sure your chosen stay packs plenty of rest and play.

How can I book family-friendly vacations in Florida Keys on a budget?

For family- and wallet-friendly trips, filter your search results by budget. You can also sort by price. When bringing the whole brigade on a budget, consider staying in low season or outside the city or. To save more coin, accommodation with a kitchen can be your friend—a bowl of pasta at home is always cheaper than feeding the team at a restaurant.

What does a family trip to Florida Keys cost?

You could book your amazing family trip to Florida Keys just $358. But with so many brilliant breaks on offer, there’s something for every wallet. Prices and availability are subject to change. Additional terms may apply.

Can I book an all-inclusive Florida Keys family vacation package?

Check the all-inclusive filter for an all-you-could-ever-wish-for family vacay. Click more of your favorite filters for even more extravagance. Perhaps an ocean view, spa, or hot tub. Maybe a water park, epic kids club, or activities galore.

How can I plan a fun family vacation in Florida Keys?

Search for stays with kid-satisfying extras, like water parks, and teenage-friendly free Wi-Fi, so they can post about all their vacation adventures for all their buddies back home. Book up local attractions, excursions, and experiences—and they might even put their phone down for a few minutes.

How can I find Florida Keys family vacation deals?

Delightful deals often dwell outside high season, so move your travel dates around for top deals. You can also book up a little away from the major Florida Keys landmarks to save cash. Whenever you wish to travel, sort your search results by deals for the most brilliant bargains.

Can I book a Florida Keys family vacation package with free cancellation and/or flexible dates?

Free cancellation makes for a hassle-free family vacation. Filter by payment option to find fully flexible trips, including buy now, pay later options.

Why should I book my Florida Keys family trip with Expedia?

You can easily find fun for all the family with the super-handy filters. It’s easy to build your dream kid-friendly vacation in just a few clicks. And you can bundle your accommodation, airfare, and car rental in just a few more.

Top Kid friendly Florida Keys Hotels

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 ...

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 ...

8.6/10 Excellent! (3,623 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

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)

Families like: Outdoor pools, miniature golf, on the beach, bicycle rentals

Travelers say...

"We got the poolside cabana king and it was perfect! Resort was immaculate! Already want to go back!"

Reviewed on Oct 6, 2026

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.