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

$1,430

per person

Dec 30 - Jan 1

found 10 hours ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (2,736 reviews)

Tranquility Bay Beachfront Hotel and Resort

$1,526

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Miami (MIA)

8.8/10 Excellent! (1,007 reviews)

Cheeca Lodge & Spa

Matecumbe

$3,151

per person

Dec 30 - Jan 3

found 11 hours ago

Roundtrip flight included

Jacksonville (JAX) to Miami (MIA)

9.2/10 Wonderful! (1,492 reviews)

The Marker Key West Harbor Resort

Key West Historic District

$1,838

per person

Dec 30 - Jan 1

found 10 hours ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,033 reviews)

needs to be refurbished

Reviewed on Oct 27, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

$1,683

per person

Dec 30 - Jan 1

found 10 hours ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (3,630 reviews)

The entire stay was perfect! See you next year!!

Reviewed on Oct 29, 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

$3,151

per person

Dec 30 - Jan 3

found 11 hours ago

Roundtrip flight included

Jacksonville (JAX) to Miami (MIA)

9.2/10 Wonderful! (1,492 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.

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

$1,438

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Miami (MIA)

9/10 Wonderful! (296 reviews)

The view from our room was outstanding. However, there was a horrible smell that kept floating on the wind from another part of the property- it smelled like sewage. The cleaning staff weren't great, and the woman who checked us in didn't give us any info on how to find our room. The rest of the staff were very helpful. The room itself didn't have enough lighting. There was a full length mirror outside the bathroom, but there wasn't any light to see yourself in.

Reviewed on Oct 29, 2026

Cheeca Lodge & Spa

Matecumbe

$1,755

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Miami (MIA)

9.2/10 Wonderful! (1,492 reviews)

Tranquility Bay Beachfront Hotel and Resort

$1,526

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Miami (MIA)

8.8/10 Excellent! (1,007 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.

Orchid Key Inn - Adults Only

Old Town Key West

Save 100% on your flight

$824

per person

Nov 30 - Dec 4

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Key West (EYW)

9.8/10 Exceptional! (1,001 reviews)

We loved this motel. The pool area is secluded and private. The staff are amazing. The room was so nice. We will be back.

Reviewed on Oct 29, 2026

The Marker Key West Harbor Resort

Key West Historic District

$2,481

per person

Dec 30 - Jan 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

9.2/10 Wonderful! (1,033 reviews)

needs to be refurbished

Reviewed on Oct 27, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

$2,296

per person

Dec 30 - Jan 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

8.6/10 Excellent! (3,630 reviews)

The entire stay was perfect! See you next year!!

Reviewed on Oct 29, 2026

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! (3,660 reviews)

"The entire stay was perfect! See you next year!!"

Reviewed on Oct 29, 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! (1,000 reviews)

"Lots of amenities and great staff will be coming back to this location"

Reviewed on Oct 28, 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 8,273 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.