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
$567
per person
Sep 23 - Sep 26
found 12 hours ago
Roundtrip non-stop flight included
Spokane (GEG) to Miami (MIA)
9/10 Wonderful! (246 reviews)
I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff.
Reviewed on Aug 23, 2026
Cheeca Lodge & Spa
Matecumbe
$622
per person
Sep 23 - Sep 26
found 12 hours ago
Roundtrip non-stop flight included
Spokane (GEG) to Miami (MIA)
9.2/10 Wonderful! (1,360 reviews)
I didnt have a great stay here, but I am scouting a place for family reunion. I think I will give it another shot. Could have just been a fluke. The grounds were impeccably maintained. The dock was great. Wish they had more than one class for Teaching kids to fish. Most of the Staff was great. Food was good. For some reason I really felt like we did not belong. Glared at by employees, bad room way in the back, terrible metal scrapping noise that started at 11pm each night. Weird barn type door between bathroom and bedroom, kids loved playing on it. Adults not so much. I think I will try it again, not on a holiday and maybe in the main part of hotel.
Reviewed on Aug 23, 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
$622
per person
Sep 23 - Sep 26
found 12 hours ago
Roundtrip non-stop flight included
Spokane (GEG) to Miami (MIA)
9.2/10 Wonderful! (1,360 reviews)
I didnt have a great stay here, but I am scouting a place for family reunion. I think I will give it another shot. Could have just been a fluke. The grounds were impeccably maintained. The dock was great. Wish they had more than one class for Teaching kids to fish. Most of the Staff was great. Food was good. For some reason I really felt like we did not belong. Glared at by employees, bad room way in the back, terrible metal scrapping noise that started at 11pm each night. Weird barn type door between bathroom and bedroom, kids loved playing on it. Adults not so much. I think I will try it again, not on a holiday and maybe in the main part of hotel.
Reviewed on Aug 23, 2026
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See all available trips from Columbus to Florida Keys
View all trips3 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
$567
per person
Sep 23 - Sep 26
found 12 hours ago
Roundtrip non-stop flight included
Spokane (GEG) to Miami (MIA)
9/10 Wonderful! (246 reviews)
I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff.
Reviewed on Aug 23, 2026
Cheeca Lodge & Spa
Matecumbe
$622
per person
Sep 23 - Sep 26
found 12 hours ago
Roundtrip non-stop flight included
Spokane (GEG) to Miami (MIA)
9.2/10 Wonderful! (1,360 reviews)
I didnt have a great stay here, but I am scouting a place for family reunion. I think I will give it another shot. Could have just been a fluke. The grounds were impeccably maintained. The dock was great. Wish they had more than one class for Teaching kids to fish. Most of the Staff was great. Food was good. For some reason I really felt like we did not belong. Glared at by employees, bad room way in the back, terrible metal scrapping noise that started at 11pm each night. Weird barn type door between bathroom and bedroom, kids loved playing on it. Adults not so much. I think I will try it again, not on a holiday and maybe in the main part of hotel.
Reviewed on Aug 23, 2026
Don't see what you're looking for?
See all available trips from Columbus to Florida Keys
View all trips4 Night Adventure vacations in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa
Matecumbe
$882
per person
Oct 28 - Nov 1
found 24 hours ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
9.2/10 Wonderful! (1,360 reviews)
I didnt have a great stay here, but I am scouting a place for family reunion. I think I will give it another shot. Could have just been a fluke. The grounds were impeccably maintained. The dock was great. Wish they had more than one class for Teaching kids to fish. Most of the Staff was great. Food was good. For some reason I really felt like we did not belong. Glared at by employees, bad room way in the back, terrible metal scrapping noise that started at 11pm each night. Weird barn type door between bathroom and bedroom, kids loved playing on it. Adults not so much. I think I will try it again, not on a holiday and maybe in the main part of hotel.
Reviewed on Aug 23, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
$961
per person
Oct 29 - Nov 2
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
9/10 Wonderful! (246 reviews)
I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff.
Reviewed on Aug 23, 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
- 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 ...
8.8/10 Excellent! (3,565 reviews)
"The pool had fun activities all the days we were there. The food was really good at the restaurant on site."
Reviewed on Aug 24, 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 ...
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 ...
9.2/10 Wonderful! (1,422 reviews)
"I didnt have a great stay here, but I am scouting a place for family reunion. I think I will give it another shot. Could have just been a fluke. The grounds were impeccably maintained. The dock was great. Wish they had more than one class for Teaching kids to fish. Most of the Staff was great. Food ..."
Reviewed on Aug 23, 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.
Things to do
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
$69
per adult
88% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
