Florida Keys Adventure Vacations
Book a Adventure Hotel + Flight or Car together to unlock savings
Top Adventure vacation packages 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 $532, price is now $352 per person
$352
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
9.2/10 Wonderful! (1,201 reviews)
This was my first visit to Cheeca Lodge but many prior visits to Islamorada. I was disappointed. The maid did not show up the 1st day. There were dirty dishes on the walkway for 3 days (I finally called). The ice machine was broken in my building (3 days to repair) and the bathroom faucet handle came off! Staff at check-in did not offer the wi-fi info upon arrival, and I had to call back for it. Upon exiting, no feedback was requested like "How was your stay?" Dirty bar glasses left out for 2 days at the beach area lights. Just not a well run hotel.
Reviewed on Oct 3, 2025
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Save 100% on your flight
Price was $838, price is now $499 per person
$499
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.6/10 Excellent! (1,015 reviews)
Property was excellent and offered everything you could want. Paddle boards, fishing, jet skis, kayak, snorkeling, plenty of romantic spots with chairs and hammocks, beach chairs, umbrellas and clean pools. We enjoyed ourselves. Although we didn’t bring our dog, we enjoyed the many pets enjoying themselves. It was great to see a truly pet friendly hotel and the families enjoying their time with their dogs. Couldn’t have asked for a cleaner resort.
Reviewed on Oct 3, 2025
Hawks Cay Resort
Save 100% on your flight
Price was $1,132, price is now $680 per person
$680
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8/10 Very Good! (1,007 reviews)
Impeccable cleanliness. The Salt and Ash dining was one of the best meals of my life.
Reviewed on Oct 3, 2025
Tranquility Bay Beachfront Hotel and Resort
Save 100% on your flight
Price was $799, price is now $510 per person
$510
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.8/10 Excellent! (1,005 reviews)
Me encantó en todos los sentidos. Volvería con toda seguridad.
Reviewed on Sep 25, 2025
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton
Save 100% on your flight
Price was $494, price is now $361 per person
$361
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.8/10 Excellent! (1,282 reviews)
My second time staying here. Great spot for food, wine and a marina out back for your boat.
Reviewed on Oct 5, 2025
Don't see what you're looking for?
See all available trips from Columbus to Florida Keys
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 $532, price is now $352 per person
$352
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
9.2/10 Wonderful! (1,201 reviews)
This was my first visit to Cheeca Lodge but many prior visits to Islamorada. I was disappointed. The maid did not show up the 1st day. There were dirty dishes on the walkway for 3 days (I finally called). The ice machine was broken in my building (3 days to repair) and the bathroom faucet handle came off! Staff at check-in did not offer the wi-fi info upon arrival, and I had to call back for it. Upon exiting, no feedback was requested like "How was your stay?" Dirty bar glasses left out for 2 days at the beach area lights. Just not a well run hotel.
Reviewed on Oct 3, 2025
Don't see what you're looking for?
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.
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Save 100% on your flight
Price was $838, price is now $499 per person
$499
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.6/10 Excellent! (1,015 reviews)
Property was excellent and offered everything you could want. Paddle boards, fishing, jet skis, kayak, snorkeling, plenty of romantic spots with chairs and hammocks, beach chairs, umbrellas and clean pools. We enjoyed ourselves. Although we didn’t bring our dog, we enjoyed the many pets enjoying themselves. It was great to see a truly pet friendly hotel and the families enjoying their time with their dogs. Couldn’t have asked for a cleaner resort.
Reviewed on Oct 3, 2025
Hawks Cay Resort
Save 100% on your flight
Price was $1,132, price is now $680 per person
$680
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8/10 Very Good! (1,007 reviews)
Impeccable cleanliness. The Salt and Ash dining was one of the best meals of my life.
Reviewed on Oct 3, 2025
Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $1,462, price is now $911 per person
$911
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Shreveport (SHV) to Key West (EYW)
9/10 Wonderful! (1,005 reviews)
Great location, walkable to everywhere!
Reviewed on Oct 5, 2025
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.
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Save 100% on your flight
Price was $1,309, price is now $834 per person
$834
per person
Nov 4 - Nov 8
found 7 hours ago
Roundtrip non-stop flight included
Shreveport (SHV) to Miami (MIA)
8.6/10 Excellent! (1,015 reviews)
Property was excellent and offered everything you could want. Paddle boards, fishing, jet skis, kayak, snorkeling, plenty of romantic spots with chairs and hammocks, beach chairs, umbrellas and clean pools. We enjoyed ourselves. Although we didn’t bring our dog, we enjoyed the many pets enjoying themselves. It was great to see a truly pet friendly hotel and the families enjoying their time with their dogs. Couldn’t have asked for a cleaner resort.
Reviewed on Oct 3, 2025
Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $1,615, price is now $1,068 per person
$1,068
per person
Dec 5 - Dec 9
found 1 hour ago
Roundtrip non-stop flight included
Akron (CAK) to Key West (EYW)
9/10 Wonderful! (1,005 reviews)
Great location, walkable to everywhere!
Reviewed on Oct 5, 2025
Cheeca Lodge & Spa
Matecumbe
Save 100% on your flight
Price was $1,584, price is now $1,053 per person
$1,053
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Springfield (SGF) to Miami (MIA)
9.2/10 Wonderful! (1,201 reviews)
This was my first visit to Cheeca Lodge but many prior visits to Islamorada. I was disappointed. The maid did not show up the 1st day. There were dirty dishes on the walkway for 3 days (I finally called). The ice machine was broken in my building (3 days to repair) and the bathroom faucet handle came off! Staff at check-in did not offer the wi-fi info upon arrival, and I had to call back for it. Upon exiting, no feedback was requested like "How was your stay?" Dirty bar glasses left out for 2 days at the beach area lights. Just not a well run hotel.
Reviewed on Oct 3, 2025
Don't see what you're looking for?
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
Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. ...
8.6/10 Excellent! (2,767 reviews)
"I loved the variety of restaurants and the location. It was perfect for my daughter and I, we will be back! Thank you 🤗"
Reviewed on Oct 2, 2025
Hawks Cay Resort
61 Hawks Cay Blvd, Marathon, FL
Stay at this 4-star luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8/10 Very Good! (1,012 reviews)
Great family vacation stay in villa
"Amazing views and villas are great for family vacation stays. Wonderful balconies Beautiful resort overall."
Reviewed on Sep 28, 2025
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,210 reviews)
"Amazing!"
Reviewed on Oct 2, 2025
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.