Florida Keys Adventure Vacations 2026

Top Adventure vacation packages in Florida Keys

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

Parrot Key Hotel & Villas

Northside Resort

Save 100% on your flight

$675

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Asheville (AVL) to Key West (EYW)

9/10 Wonderful! (1,460 reviews)

Wonderful stay with my family. Fantastic location. Friendly staff. Large, clean rooms.

Reviewed on Sep 11, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

Save 100% on your flight

$1,364

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Asheville (AVL) to Key West (EYW)

8.6/10 Excellent! (3,560 reviews)

Nice place but no water access and not worth the money. Rooms are very small and TV didn't work. Very little parking at the complex we stayed at.

Reviewed on Sep 12, 2026

The Marker Key West Harbor Resort

Key West Historic District

Save 100% on your flight

$1,266

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Asheville (AVL) to Key West (EYW)

9.2/10 Wonderful! (1,003 reviews)

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

Save 100% on your flight

$1,006

per person

Nov 12 - Nov 15

found 2 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (258 reviews)

Beautiful place Great beds Lots of dining options

Reviewed on Sep 12, 2026

Eden House

Key West Historic District

Save 100% on your flight

$925

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Asheville (AVL) to Key West (EYW)

9/10 Wonderful! (1,003 reviews)

Great hotel , very close to everything, bike hire outside and free car parking. Hotel pool and area is lovey .

Reviewed on Sep 10, 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

Save 100% on your flight

$688

per person

Oct 12 - Oct 16

found 5 hours ago

Roundtrip flight included

Omaha (OMA) to Miami (MIA)

9.2/10 Wonderful! (1,422 reviews)

Property is tired Staff helpful especially when we had a few problems with our room. It was resolved within mins. Excellent service

Reviewed on Sep 12, 2026

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.

Parrot Key Hotel & Villas

Northside Resort

Save 100% on your flight

$675

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Asheville (AVL) to Key West (EYW)

9/10 Wonderful! (1,460 reviews)

Wonderful stay with my family. Fantastic location. Friendly staff. Large, clean rooms.

Reviewed on Sep 11, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

Save 100% on your flight

$1,364

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Asheville (AVL) to Key West (EYW)

8.6/10 Excellent! (3,560 reviews)

Nice place but no water access and not worth the money. Rooms are very small and TV didn't work. Very little parking at the complex we stayed at.

Reviewed on Sep 12, 2026

The Marker Key West Harbor Resort

Key West Historic District

Save 100% on your flight

$1,266

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Asheville (AVL) to Key West (EYW)

9.2/10 Wonderful! (1,003 reviews)

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.

Lime Tree Bay Resort

Save 100% on your flight

$572

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip flight included

Houston (HOU) to Miami (MIA)

9.4/10 Exceptional! (1,479 reviews)

Excellent location with great views, great amenities, great AC, shower door didn’t close all the way and refrigerator door had trouble staying closed, all in all A++++ resort

Reviewed on Sep 12, 2026

Parrot Key Hotel & Villas

Northside Resort

Save 100% on your flight

$1,266

per person

Nov 12 - Nov 16

found 24 hours ago

Roundtrip non-stop flight included

Detroit (DTT) to Key West (EYW)

9/10 Wonderful! (1,460 reviews)

Wonderful stay with my family. Fantastic location. Friendly staff. Large, clean rooms.

Reviewed on Sep 11, 2026

Hawks Cay Resort

Save 100% on your flight

$681

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

Beautiful

Reviewed on Sep 12, 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 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! (3,584 reviews)

"Nice place but no water access and not worth the money. Rooms are very small and TV didn't work. Very little parking at the complex we stayed at."

Reviewed on Sep 12, 2026

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! (1,004 reviews)

"Beautiful"

Reviewed on Sep 12, 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 ...

9.2/10 Wonderful! (1,435 reviews)

"Property is tired Staff helpful especially when we had a few problems with our room. It was resolved within mins. Excellent service"

Reviewed on Sep 12, 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.