Florida Keys Adventure Vacations
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Top Adventure vacation packages in Florida Keys
- Lighthouse Hotel - Key West Historic Inns
Sep 23 - Sep 28Lighthouse Hotel - Key West Historic Inns + Flight
Old Town Key West5 nights3.5 star property9.0/10 - Wonderful (969 reviews)"Location and location. It's right there, next to the Duval str. and more nice activity around. Front desk Laura helped us with a lot of good information's about Key West."Reviewed July 30, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop$1,078$799found 1 day agoper traveler - Ella's Cottages - Key West Historic Inns
Sep 23 - Sep 28Ella's Cottages - Key West Historic Inns + Flight
Old Town Key West5 nights3.5 star property9.4/10 - Exceptional (489 reviews)"S"Reviewed July 15, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop$1,126$828found 1 day agoper traveler - Ridley House - Key West Historic Inns
Sep 23 - Sep 28Ridley House - Key West Historic Inns + Flight
Key West Historic District5 nights3.5 star property9.2/10 - Wonderful (945 reviews)Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop$1,126$828found 1 day agoper traveler - Isla Bella Beach Resort & Spa
Sep 7 - Sep 12Isla Bella Beach Resort & Spa + Flight
Marathon5 nights5.0 star property9.2/10 - Wonderful (1,210 reviews)Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • Nonstop - The Perry Hotel & Marina Key West
Oct 2 - Oct 6The Perry Hotel & Marina Key West + Flight
Stock Island4 nights4.0 star property9.4/10 - Exceptional (1,309 reviews)"The hotel is nice enough. The staff was very helpful and responsive. One bad thing was the bed. It was hard as a rock and the spring creaked everytime you moved. Both of our backs were screaming by the end of the stay. (4 nights) I must say that we did not complain to staff until checkout because we weren’t going to pack up and move to a different room. Some of the other furniture in the room was very warm out as well. At the restaurant for breakfast the second morning we encountered a very..."Reviewed August 1, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop$1,143$848found 1 day agoper traveler
Discover the most popular places to visit in Florida Keys
What to do in Florida Keys
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
Shipwreck Treasure Museum Tickets
Top Adventure Florida Keys Hotels
Blue Flamingo Resort Key West
Blue Flamingo Resort Key West
Margaritaville Beach House Key West
Margaritaville Beach House Key West
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.
What types of mountain accommodations are available in Florida Keys?
5-star hotels, cozy mountain lodges, and quaint bed and breakfasts are some of the most popular types of mountain accommodations for your vacation to Florida Keys. Don't forget to use the filters to home in the amenities you'd like to have, too. Maybe it's a spacious suite with a mountain view or a traditional lobby with a fireplace—you'll find it all with Expedia's easy-to-use search wizard and wide choice of accommodation.