Lower Florida Keys Adventure Vacations 2025/2026

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Top Adventure vacation packages in Lower Florida Keys

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

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$531

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,722 reviews)

The staff was great.

Reviewed on Oct 14, 2025

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$780

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,005 reviews)

Beautifully designed, comfortable beds, quiet and peaceful grounds.

Reviewed on Oct 14, 2025

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$1,041

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,005 reviews)

Everything was excellent, except poor TV service in room.

Reviewed on Oct 13, 2025

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$893

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.4/10 Very Good! (347 reviews)

The views were great! Water access was perfect! Had a lot of issues with house keeping? We stayed 8 nights and had no housekeeping 3 of those days, even after I complained the first time? No towels, washclothes, bed not made. Normal housekeeping duties were not done? After the last time I had to go speak with the front desk and they did refund me $200.00. It was something but I expected a lot more for what we paid for our stay. Staff was very polite!

Reviewed on Oct 14, 2025

Havana Cabana at Key West

New Town

Save 100% on your flight

$633

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.8/10 Excellent! (1,761 reviews)

I loved this place! Complementary drinks! My room was super clean with a get view. This will be my go to the next time I’m in The Keys.

Reviewed on Oct 12, 2025

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3 Night Adventure vacations in Lower Florida Keys

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

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$531

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,722 reviews)

The staff was great.

Reviewed on Oct 14, 2025

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$780

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,005 reviews)

Beautifully designed, comfortable beds, quiet and peaceful grounds.

Reviewed on Oct 14, 2025

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$1,041

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,005 reviews)

Everything was excellent, except poor TV service in room.

Reviewed on Oct 13, 2025

Don't see what you're looking for?

See all available trips from Columbus to Lower Florida Keys

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4 Night Adventure vacations in Lower Florida Keys

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

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$579

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,025 reviews)

Definitely have to say the staff was so nice makeable helpful. We even decide to extend our stay

Reviewed on Oct 11, 2025

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$740

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,005 reviews)

Beautifully designed, comfortable beds, quiet and peaceful grounds.

Reviewed on Oct 14, 2025

Ella's Cottages - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$824

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (375 reviews)

Everything was well-kept and clean, the delivered breakfast baskets were wonderful (and a LOT of food!), and the staff were all friendly, welcoming, and helpful. I was travelling alone but always felt perfectly safe, and even stayed an extra night! The hotel is also very conveniently located, right next to a stop on the Duval Loop bus stop.

Reviewed on Oct 14, 2025

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See all available trips from Columbus to Lower Florida Keys

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How can I book the best Lower Florida Keys adventure trips?

Choose your own adventure in Lower 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 Lower Florida Keys family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Lower 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 Lower 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 Lower Florida Keys adventure vacation for couples?

Book a Lower 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 Lower 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 Lower 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.