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.
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

New Town
$672
per person
Nov 18 - Nov 21
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
8.6/10 Excellent! (2,652 reviews)
The place was clean and staff were very friendly. The room was nicely appointed. The non-Tesla chargers were all broken which was disappointing but I was able to trickle charge. One elevator was also out but another one nearby was available and quick. Overall, very nice and I’d likely stay again but the lack of a charger when it was billed as being available was a disappointment.

Reviewed on Sep 18, 2026

Hawks Cay Resort

Hawks Cay Resort

Save 100% on your flight
$919
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Miami (MIA)
8.2/10 Very Good! (1,006 reviews)
The place are beautiful!!! The staff were very nice and welcoming!!! We booked the 3 bedroom premium villa which is upgraded and little bigger it was really cool we love it , the only thing was that we had an issue with the Wifi we complained the moment we found out they said we send someone no one come!!! We keeping asking and asking we went to the front desk we will send the IT guy in hour we were there for 5 days he never come!!!!! The Arcade room and fitness room Was open 8-5 nothing to do after 5pm very disappointed, the water park was closed the Dolphin was closed no Dolphin!!! Restaurant is little over priced!!!! The place is very beautiful !!!

Reviewed on Sep 17, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Save 100% on your flight
$993
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Miami (MIA)
9/10 Wonderful! (258 reviews)
We had an excellent stay at Three Waters Resort in Islamorada. Everything about the property was great from start to finish. Our room was very clean, comfortable, and well maintained, and the entire resort was beautiful and inviting. One of the things we really enjoyed was all of the included amenities. We took advantage of the complimentary kayaks, and they also had bikes available for guests to use at no additional charge. It was a great way to get out, explore, and enjoy the area. The fire pits at night were another highlight. Sitting outside by the fire was the perfect way to end the day and really added to the relaxing Keys atmosphere. Overall, we had a fantastic experience. The property was clean, the amenities were excellent, and there honestly wasn’t anything we could complain about. We would absolutely stay at Three Waters again and highly recommend it to anyone visiting Islamorada!

Reviewed on Sep 15, 2026

Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

$839
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Miami (MIA)
8.8/10 Excellent! (1,009 reviews)
The room was clean and the pools were excellent! But everything else was just average, and I don't know that I'd say it was worth a $50/day resort fee (what does this cover? Why not just put it in the room rate?) We stayed 4 nights and by the third night we had to ask to have someone come by and bring fresh towels. I'm used to seeing signs at hotels that state for environmental reasons they may only clean rooms every so often, but there was no such indication. Our room was off at the edge of the resort, by the fitness room which meant every time someone came in the building, the whole building shook when the door slammed behind them. So much for getting a nice sleep-in on vacation because this started at 5 or 6 am. I can definitely see the benefit to staying here with a larger group, families and friends staying in one of the villas. But as a couple, I probably wouldn't come back.

Reviewed on Sep 15, 2026

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Save 100% on your flight
$2,068
per person
Nov 20 - Nov 27
found 2 hours ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
8.6/10 Excellent! (1,176 reviews)
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5* Adventure vacations in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
Save 100% on your flight
$1,632
per person
Nov 18 - Nov 22
found 19 hours ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
9.2/10 Wonderful! (1,422 reviews)
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3 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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Save 100% on your flight
$882
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (258 reviews)
We had an excellent stay at Three Waters Resort in Islamorada. Everything about the property was great from start to finish. Our room was very clean, comfortable, and well maintained, and the entire resort was beautiful and inviting. One of the things we really enjoyed was all of the included amenities. We took advantage of the complimentary kayaks, and they also had bikes available for guests to use at no additional charge. It was a great way to get out, explore, and enjoy the area. The fire pits at night were another highlight. Sitting outside by the fire was the perfect way to end the day and really added to the relaxing Keys atmosphere. Overall, we had a fantastic experience. The property was clean, the amenities were excellent, and there honestly wasn’t anything we could complain about. We would absolutely stay at Three Waters again and highly recommend it to anyone visiting Islamorada!

Reviewed on Sep 15, 2026

Eden House

Eden House

Key West Historic District
$954
per person
Nov 18 - Nov 21
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
9/10 Wonderful! (1,003 reviews)
We love Eden house, this was our 5th stay and itcontinues to improve.

Reviewed on Sep 18, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
$1,148
per person
Nov 18 - Nov 21
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
Location is one of the best in west west off the busy area but yet in the middle of everything. Will def be going back here.

Reviewed on Sep 17, 2026

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4 Night Adventure vacations in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Lime Tree Bay Resort

Lime Tree Bay Resort

$596
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Miami (MIA)
9.4/10 Exceptional! (1,479 reviews)
100% recommended

Reviewed on Sep 16, 2026

Hawks Cay Resort

Hawks Cay Resort

Save 100% on your flight
$919
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Miami (MIA)
8.2/10 Very Good! (1,006 reviews)
The place are beautiful!!! The staff were very nice and welcoming!!! We booked the 3 bedroom premium villa which is upgraded and little bigger it was really cool we love it , the only thing was that we had an issue with the Wifi we complained the moment we found out they said we send someone no one come!!! We keeping asking and asking we went to the front desk we will send the IT guy in hour we were there for 5 days he never come!!!!! The Arcade room and fitness room Was open 8-5 nothing to do after 5pm very disappointed, the water park was closed the Dolphin was closed no Dolphin!!! Restaurant is little over priced!!!! The place is very beautiful !!!

Reviewed on Sep 17, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Save 100% on your flight
$993
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Miami (MIA)
9/10 Wonderful! (258 reviews)
We had an excellent stay at Three Waters Resort in Islamorada. Everything about the property was great from start to finish. Our room was very clean, comfortable, and well maintained, and the entire resort was beautiful and inviting. One of the things we really enjoyed was all of the included amenities. We took advantage of the complimentary kayaks, and they also had bikes available for guests to use at no additional charge. It was a great way to get out, explore, and enjoy the area. The fire pits at night were another highlight. Sitting outside by the fire was the perfect way to end the day and really added to the relaxing Keys atmosphere. Overall, we had a fantastic experience. The property was clean, the amenities were excellent, and there honestly wasn’t anything we could complain about. We would absolutely stay at Three Waters again and highly recommend it to anyone visiting Islamorada!

Reviewed on Sep 15, 2026

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Find 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

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 ...
Southernmost Beach Resort and Guesthouses
Hawks Cay Resort

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 ...
8.2/10 Very Good! (1,000 reviews)
"The place are beautiful!!! The staff were very nice and welcoming!!! We booked the 3 bedroom premium villa which is upgraded and little bigger it was really cool we love it , the only thing was that we had an issue with the Wifi we complained the moment we found out they said we send someone no one ..."

Reviewed on Sep 17, 2026

Hawks Cay Resort
Cheeca Lodge & Spa

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 ...
Cheeca Lodge & Spa
See all 8,273 properties in Florida Keys
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

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

$69
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$41
per adult
88% of travellers recommend
Key West Conch Tour Train
See all activities in Florida Keys

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.