Top Adventure vacation packages in Florida Keys

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

Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

Save 100% on your flight

$441

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Miami (MIA)

8.8/10 Excellent! (1,298 reviews)

Best marina around!!! Best dockmasters ever!! Great room! Great food! And a great bar!!!

Reviewed on Aug 15, 2025

Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight

$572

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Miami (MIA)

8.8/10 Excellent! (1,006 reviews)

Yes, I recommend this hotel

Reviewed on Aug 18, 2025

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$604

per person

Oct 22 - Oct 25

found 19 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Key West (EYW)

9/10 Wonderful! (1,722 reviews)

Nice rooms. Pool water needs attention due to some algae growth on bottom.

Reviewed on Aug 21, 2025

Hawks Cay Resort

Save 100% on your flight

$804

per person

Sep 21 - Sep 27

found 4 hours ago

Roundtrip flight included

Cleveland (CLE) to Miami (MIA)

8/10 Very Good! (1,008 reviews)

$25 charge per day for parking (like we had an option) TV was not connected, took 2 days and 2 request to get connected. Room phone did not work, had to walk downstairs for any request. Hot water in our bathroom lavatory barely trickled. Bars did not carry non-alcoholic beer (I am a cancer patient and cannot drink regular beer) In general I would expect much more for the price we paid.

Reviewed on Aug 20, 2025

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$1,129

per person

Oct 22 - Oct 25

found 19 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Key West (EYW)

8.4/10 Very Good! (300 reviews)

Room accommodation not satisfactory. Elevator broken, repeated issues with door lock. Hotel not willing to correct issues.

Reviewed on Aug 21, 2025

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5* Adventure vacations in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe

$1,219

per person

Sep 21 - Sep 25

just found

Roundtrip non-stop flight included

Boise (BOI) to Miami (MIA)

9/10 Wonderful! (1,153 reviews)

An amazing hidden gem. From the staff to the hotel you feel like you’re on an island. Everyone is sooo friendly and kind!!! Most amazing stay ever !!

Reviewed on Aug 20, 2025

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3 Night Adventure vacations in Florida Keys

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

Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight

$440

per person

Sep 25 - Sep 28

found 3 hours ago

Roundtrip flight included

Houston (HOU) to Miami (MIA)

8.8/10 Excellent! (1,006 reviews)

Yes, I recommend this hotel

Reviewed on Aug 18, 2025

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$604

per person

Oct 22 - Oct 25

found 19 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Key West (EYW)

9/10 Wonderful! (1,722 reviews)

Nice rooms. Pool water needs attention due to some algae growth on bottom.

Reviewed on Aug 21, 2025

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$1,129

per person

Oct 22 - Oct 25

found 19 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Key West (EYW)

8.4/10 Very Good! (300 reviews)

Room accommodation not satisfactory. Elevator broken, repeated issues with door lock. Hotel not willing to correct issues.

Reviewed on Aug 21, 2025

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4 Night Adventure vacations in Florida Keys

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

The Pelican Key Largo Cottages

Save 100% on your flight

$322

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip flight included

Denver (DEN) to Miami (MIA)

8.8/10 Excellent! (1,005 reviews)

Love the water, nature, close to dining, cvs, near bird sanctuary. Love the area.

Reviewed on Aug 21, 2025

Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight

$572

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Miami (MIA)

8.8/10 Excellent! (1,006 reviews)

Yes, I recommend this hotel

Reviewed on Aug 18, 2025

Hawks Cay Resort

Save 100% on your flight

$558

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip flight included

Denver (DEN) to Miami (MIA)

8/10 Very Good! (1,008 reviews)

$25 charge per day for parking (like we had an option) TV was not connected, took 2 days and 2 request to get connected. Room phone did not work, had to walk downstairs for any request. Hot water in our bathroom lavatory barely trickled. Bars did not carry non-alcoholic beer (I am a cancer patient and cannot drink regular beer) In general I would expect much more for the price we paid.

Reviewed on Aug 20, 2025

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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

11 min walk from Duval Street

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! (2,701 reviews)

"Great stay awesome staff we will definitely stay here again."

Reviewed on Aug 20, 2025

Hawks Cay Resort

61 Hawks Cay Blvd, Marathon, FL

2 hours drive from Duval Street

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! (1,001 reviews)

"So fun. Loved my room and having Dolphin Connection right there for my kids. Food at all the restaurants from poolside to fancy was delicious."

Reviewed on Aug 10, 2025

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL

3 hours drive from Duval Street

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! (1,153 reviews)

"amazing stay"

Reviewed on Aug 21, 2025

See all 8,274 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.