Lower Florida Keys Adventure Vacations 2026/2026

Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top Adventure vacation packages in Lower Florida Keys

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

Blue Flamingo Resort Key West

New Town

Save 100% on your flight

$954

per person

Jan 2 - Jan 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8/10 Very Good! (1,693 reviews)

Staff is amazing & very accommodating, the property is designed very nicely, with family in mind, nice property to stay at when in key west. Salvador, Adrian definitely know how to take care of their guest :)

Reviewed on Dec 2, 2025

Oceans Edge Key West Resort, Hotel & Marina

$1,285

per person

Jan 2 - Jan 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

My stay at this hotel was absolutely outstanding! From the moment I arrived, I felt welcomed and well taken care of. The staff were incredibly professional, friendly, and always ready to help with anything I needed.

Reviewed on Dec 1, 2025

The Gardens Hotel

Old Town Key West

$1,567

per person

Feb 6 - Feb 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

Great breakfast, convenient location. Staff is very friendly. Rooms are nice and the garden area is pretty. I read all of the reviews and the hype around the place so it fell short of my expectations. If I had just gone there and not read the reviews I may have enjoyed it more. I would go back but I had stayed at places as nice or nice for my needs for what I believe to be better value. That being said I am glad I stayed there

Reviewed on Nov 20, 2025

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$1,846

per person

Jan 2 - Jan 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,006 reviews)

Lovely hotel, great room and ideal location.

Reviewed on Nov 30, 2025

Southernmost Beach Resort and Guesthouses

Old Town Key West

Save 100% on your flight

$1,577

per person

Jan 2 - Jan 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (2,844 reviews)

Clean room. Staff was friendly pool and beach were great

Reviewed on Dec 1, 2025

Don't see what you're looking for?

See all available trips from Columbus to Lower Florida Keys

View all trips

3 Night Adventure vacations in Lower Florida Keys

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

The Perry Hotel & Marina Key West

Save 100% on your flight

$642

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,151 reviews)

Had a very nice stay and most likely will return my next trip down. Beautiful hotel and friendly staff. Snorkel/dive boat only steps away. Biking (or golf cart) is the way to go in Key West. Very scenic. You can bring your own or rent one right at Perry for only $20 for the day. Only negative is the rooster in the middle of the morning, every single morning, all morning long. Think "My Cousin Vinnie." After googling the history of roosters in the Keys, I learned that there isn't anything that can be done, so it's certainly not the fault of the hotel. So, let's go with, "They add to the charm of the Keys!" Yeah, let's go with that. I'll leave you with ***fried Hogfish sandwich*** at Hogfish Bar & Grill only a couple of blocks away. You'll thank me later.

Reviewed on Dec 1, 2025

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$663

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

My stay at this hotel was absolutely outstanding! From the moment I arrived, I felt welcomed and well taken care of. The staff were incredibly professional, friendly, and always ready to help with anything I needed.

Reviewed on Dec 1, 2025

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$863

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,044 reviews)

I had a wonderful time. The staff was very nice and accommodating. The room was cool. Great location. I would definitely stay there again!

Reviewed on Dec 1, 2025

Don't see what you're looking for?

See all available trips from Columbus to Lower Florida Keys

View all trips

4 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

$677

per person

Jan 12 - Jan 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

My stay at this hotel was absolutely outstanding! From the moment I arrived, I felt welcomed and well taken care of. The staff were incredibly professional, friendly, and always ready to help with anything I needed.

Reviewed on Dec 1, 2025

The Key West Hotel

Key West Historic District

$1,270

per person

Jan 12 - Jan 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (505 reviews)

Beautiful private oasis

Reviewed on Nov 25, 2025

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$710

per person

Jan 12 - Jan 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.6/10 Exceptional! (1,002 reviews)

One of the best resorts my family and I have been to in awhile. We stayed in the 2 bedroom condo which was absolutely beautiful and had every single thing we needed for our stay. The vibe at three pet

Reviewed on Dec 2, 2025

Don't see what you're looking for?

See all available trips from Columbus to Lower Florida Keys

View all trips

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.