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.

Blue Flamingo Resort Key West

New Town

$820

per person

Nov 16 - Nov 19

found 18 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

8.6/10 Excellent! (2,652 reviews)

It was a nice hotel. It was very clean quiet they had two Swimming Pool pools so that made it nice for the kids at one pool primarily and the adults at the other the walk-up bars were nice and close.

Reviewed on Sep 16, 2026

The Marker Key West Harbor Resort

Key West Historic District

$1,163

per person

Nov 16 - Nov 19

found 18 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (1,003 reviews)

Southernmost Beach Resort and Guesthouses

Old Town Key West

$1,066

per person

Nov 16 - Nov 19

found 18 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

8.6/10 Excellent! (3,560 reviews)

The property should have advertised that it was off season and there were amenities closed. The beach was closed the pool was closed. Those were two reasons we chose this resort. We also had a noise issue with the room and the front desk staff tried to give us ear plugs instead of trying to find another room.

Reviewed on Sep 16, 2026

Parrot Key Hotel & Villas

Northside Resort

$845

per person

Nov 16 - Nov 19

found 18 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9/10 Wonderful! (1,460 reviews)

Eden House

Key West Historic District

$1,098

per person

Nov 16 - Nov 19

found 18 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9/10 Wonderful! (1,003 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

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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

$1,057

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

San Jose (SJC) to Miami (MIA)

9.2/10 Wonderful! (1,422 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

3 Night Adventure vacations in Florida Keys

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

Blue Flamingo Resort Key West

New Town

$820

per person

Nov 16 - Nov 19

found 18 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

8.6/10 Excellent! (2,652 reviews)

It was a nice hotel. It was very clean quiet they had two Swimming Pool pools so that made it nice for the kids at one pool primarily and the adults at the other the walk-up bars were nice and close.

Reviewed on Sep 16, 2026

The Marker Key West Harbor Resort

Key West Historic District

$1,163

per person

Nov 16 - Nov 19

found 18 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (1,003 reviews)

Southernmost Beach Resort and Guesthouses

Old Town Key West

$1,066

per person

Nov 16 - Nov 19

found 18 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

8.6/10 Excellent! (3,560 reviews)

Reviewed on Sep 16, 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.

Lime Tree Bay Resort

Save 100% on your flight

$720

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip flight included

Raleigh (RDU) to Miami (MIA)

9.4/10 Exceptional! (1,479 reviews)

100% recommended

Reviewed on Sep 16, 2026

Hawks Cay Resort

Save 100% on your flight

$928

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip flight included

Raleigh (RDU) to Miami (MIA)

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

Beautiful resort

Reviewed on Sep 15, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$1,057

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

San Jose (SJC) to Miami (MIA)

9.2/10 Wonderful! (1,422 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

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! (3,605 reviews)

"The property should have advertised that it was off season and there were amenities closed. The beach was closed the pool was closed. Those were two reasons we chose this resort. We also had a noise issue with the room and the front desk staff tried to give us ear plugs instead of trying to find ..."

Reviewed on Sep 16, 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! (1,011 reviews)

"Beautiful resort"

Reviewed on Sep 15, 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 8,263 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.