Florida Keys Adventure Vacations 2026

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Top Adventure vacation packages in Florida Keys

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

Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight

$1,089

per person

Dec 22 - Dec 25

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Miami (MIA)

8.8/10 Excellent! (1,006 reviews)

Villa was clean. Staff was very polite, knowledgeable. There was a problem with the toilet and it was taken care of. A shower outside of the pool area would be very helpful in washing off sandy feet, also a door mat. Silverware was very cheap, could be better. It's the small things that could make it great.

Reviewed on Oct 20, 2026

Cheeca Lodge & Spa

Matecumbe

$1,478

per person

Dec 20 - Dec 24

found 1 day ago

Roundtrip flight included

Kansas City (MCI) to Miami (MIA)

9.2/10 Wonderful! (1,471 reviews)

Southernmost Beach Resort and Guesthouses

Old Town Key West

$1,298

per person

Nov 19 - Nov 22

found 3 hours ago

Roundtrip non-stop flight included

Austin (AUS) to Key West (EYW)

8.6/10 Excellent! (3,636 reviews)

Hawks Cay Resort

$1,515

per person

Dec 20 - Dec 24

found 1 day ago

Roundtrip flight included

Kansas City (MCI) to Miami (MIA)

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

Over priced for quality of rooms.

Reviewed on Oct 18, 2026

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

$1,244

per person

Dec 20 - Dec 24

found 1 day ago

Roundtrip flight included

Kansas City (MCI) to Miami (MIA)

9/10 Wonderful! (281 reviews)

We've stayed at many places over the years . This place and the room that we had were the best . Waking up in bed to a view of the ocean can't be beat. It is situated on the most luxurious of all the keys.. can't wait to return .

Reviewed on Oct 19, 2026

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5* Adventure vacations in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe

$1,478

per person

Dec 20 - Dec 24

found 1 day ago

Roundtrip flight included

Kansas City (MCI) 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

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3 Night Adventure 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

$930

per person

Dec 22 - Dec 25

found 4 hours ago

Roundtrip flight included

Louisville (SDF) to Miami (MIA)

9/10 Wonderful! (281 reviews)

Reviewed on Oct 19, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$1,289

per person

Dec 22 - Dec 25

found 4 hours ago

Roundtrip flight included

Louisville (SDF) to Miami (MIA)

9.2/10 Wonderful! (1,471 reviews)

Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight

$1,089

per person

Dec 22 - Dec 25

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Miami (MIA)

8.8/10 Excellent! (1,006 reviews)

Reviewed on Oct 20, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

4 Night Adventure vacations in Florida Keys

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

Orchid Key Inn - Adults Only

Old Town Key West

Save 100% on your flight

$918

per person

Dec 20 - Dec 24

found 14 hours ago

Roundtrip flight included

Columbus (CMH) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

Lime Tree Bay Resort

Save 100% on your flight

$1,175

per person

Dec 24 - Dec 28

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Miami (MIA)

9.4/10 Exceptional! (1,527 reviews)

We always stay at Lime Tree Bay. If you find yourself driving down U.S. 1, be sure to stop and enjoy the Exceptional Service, Beauty, and one of the Best stays we have loved many times, in Layton, Lime Tree Bay and the Keys await you!

Reviewed on Oct 19, 2026

Hawks Cay Resort

Save 100% on your flight

$1,059

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Cedar Rapids (CID) to Miami (MIA)

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

Over priced for quality of rooms.

Reviewed on Oct 18, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

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How can I book the best Florida Keys adventure trips?

Choose your own adventure in Florida Keys, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.

How can I plan the perfect Florida Keys family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Florida Keys. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.

Can I book all-inclusive Florida Keys adventure vacation packages?

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.

Why should I book a Florida Keys adventure vacation for couples?

Book a Florida Keys couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.

How can I find the best deals on adventure packages in Florida Keys?

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.

Can I book an adventure vacation package in Florida Keys with free cancellation and/or flexible dates?

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.

Why should I book a Florida Keys adventure trip with Expedia?

Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.

Top Adventure Florida Keys Hotels

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 ...

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 ...

8.2/10 Very Good! (1,007 reviews)

"Over priced for quality of rooms."

Reviewed on Oct 18, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

3 hours drive from Duval Street

Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...

See all 8,301 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.