Florida Keys Adventure Vacations
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Top Adventure vacation packages in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Save 100% on your flight
Price was $1,098, price is now $665 per person
$665
per person
Jun 13 - Jun 17
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9/10 Wonderful! (192 reviews)
Beautiful property, lots to do on the property. We found lighting in the rooms to be a little lacking, especially in the coffee bar area. The rooms are really small but we kind of knew that going in, the balcony was a great extension of space. Clean and lots of staff around to help with anything.
Reviewed on May 14, 2026
Cheeca Lodge & Spa
Matecumbe
Save 100% on your flight
Price was $1,210, price is now $763 per person
$763
per person
Jun 13 - Jun 17
just found
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.2/10 Wonderful! (1,323 reviews)
Exelente service but the room need more clean and attention
Reviewed on May 11, 2026
The Reach Key West, Curio Collection by Hilton
Old Town Key West
Price was $1,361, price is now $876 per person
$876
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
8.6/10 Excellent! (1,006 reviews)
Very nice. Location was easy to walk to places and beach was right there! Staff were pleasant and helpful. We will definitely go back.
Reviewed on May 14, 2026
Hyatt Centric Key West Resort and Spa
Key West Historic District
Price was $1,364, price is now $921 per person
$921
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
9/10 Wonderful! (1,003 reviews)
Very friendly and helpful stuff. Specially, Mr. Sasa. He’s always there to help you.!
Reviewed on May 13, 2026
Ocean Key Resort - A Noble House Resort
Key West Historic District
Price was $1,513, price is now $1,062 per person
$1,062
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
The location was perfect and close to restaurants, bars etc on Duvall Street. Also excellent location for the famous Key West sunsets. The rooms were spacious and clean. The pool was very enjoyable. The staff at the valet parking were extremely friendly and very helpful.
Reviewed on Apr 27, 2026
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View all trips5* 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
Price was $1,210, price is now $763 per person
$763
per person
Jun 13 - Jun 17
just found
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.2/10 Wonderful! (1,323 reviews)
Exelente service but the room need more clean and attention
Reviewed on May 11, 2026
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View all trips3 Night Adventure vacations in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Blue Flamingo Resort Key West
New Town
Price was $1,152, price is now $677 per person
$677
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
8.4/10 Very Good! (2,190 reviews)
Was only overnight. Wish I could’ve stayed longer
Reviewed on May 14, 2026
Oceans Edge Key West Resort, Hotel & Marina
Price was $1,311, price is now $783 per person
$783
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
9/10 Wonderful! (1,872 reviews)
Everything about oceans edge was wonderful! The rooms were beautiful! The beds and pillows do comfortable! The view was beautiful! The property and pool lovely. Loved the marina view! The shuttle to downtown was great and the drivers - esp Jeffrey! And the food and drinks at Yellowfin Restaurant was amazing! I look forward to returning and will recommend Oceans Edge to my family and friends
Reviewed on May 12, 2026
Pier House Resort & Spa
Key West Historic District
Price was $1,471, price is now $897 per person
$897
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
9/10 Wonderful! (1,103 reviews)
We really enjoyed our stay at the Pier House and will definitely come back. We are not big spa people so we would like to try an oceanfront room next time. But our room was great. The beds were very comfortable. We had a fun time visiting the Chart Room and sitting on the beach at night. Perfect location to all the activities!
Reviewed on May 10, 2026
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View all trips4 Night Adventure vacations in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Amara Cay Resort
Matecumbe
Save 100% on your flight
Price was $898, price is now $573 per person
$573
per person
Jun 13 - Jun 17
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.8/10 Excellent! (1,269 reviews)
Beautiful location, very helpful staff and just an exquisite experience. Food was excellent. Loved every second.
Reviewed on May 13, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Save 100% on your flight
Price was $1,296, price is now $766 per person
$766
per person
Jul 14 - Jul 18
found 22 hours ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
9/10 Wonderful! (192 reviews)
Beautiful property, lots to do on the property. We found lighting in the rooms to be a little lacking, especially in the coffee bar area. The rooms are really small but we kind of knew that going in, the balcony was a great extension of space. Clean and lots of staff around to help with anything.
Reviewed on May 14, 2026
Cheeca Lodge & Spa
Matecumbe
Save 100% on your flight
Price was $1,210, price is now $763 per person
$763
per person
Jun 13 - Jun 17
just found
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.2/10 Wonderful! (1,323 reviews)
Exelente service but the room need more clean and attention
Reviewed on May 11, 2026
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See all available trips from Columbus to Florida Keys
View all tripsFind awesome Florida Keys adventure vacations
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
Book a stay at this beach 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 ...
8.8/10 Excellent! (3,314 reviews)
Great Atmosphere and friendly staff
Reviewed on May 14, 2026
Hawks Cay Resort
61 Hawks Cay Blvd Marathon FL
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! (1,002 reviews)
Love this place
Reviewed on May 14, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
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! (1,310 reviews)
Exelente service but the room need more clean and attention
Reviewed on May 11, 2026
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.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
