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Florida Keys Activities

Looking to make the most of your Florida Keys vacation? Look no further! Browse our collection of trips, tours, and activities in the Florida Keys. Browse by location, category, or price range, learn more about the trip, and then book directly with the tour operators. It couldn’t be easier!

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21’ AquaSport CC Full Day Rental

With Sand Dollar Boat Rentals - Islamorada
In the Upper Keys
Enjoy our beautiful waters on your own schedule with our boat rentals! From as short as 4 hours to multiple days, we have the perfect boat for you and your crew!
Duration: 8 Hours
Starting from: $425
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Full Day Charter

With Ultra Grand Slam
In the Lower Keys
Book your Florida Keys Fishing Vacation with one of the best charter fishing guides in the area. Captain Magnus Nilsson is The Key West Fishing Viking and his First Mate Ross Baker – who has caught over 3600 Billfish – is Key West Famous!
Duration: 8 Hours
Starting from: $1300
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Private Sandbar

With Sole Watersports
In the Middle Keys
It’s Sun and Fun on the 2 Hour Excursion! This two hour excursion is for up to 6 passengers.
Duration: 2 Hours
Starting from: $450
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Dolphin Research Center Day Tour

With Up The Keys
In the Lower Keys
With your friendly & knowledgeable tour guide, this 6 ½ hour VIP tour of the South Keys & Dolphin Research Center will amaze you! This tour will take you half-way up the Florida Keys and over the iconic 7-Mile Bridge.
Duration: 6.5 Hours
Starting from: $159
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21’ AquaSport CC Multi Day Rental

With Sand Dollar Boat Rentals - Islamorada
In the Upper Keys
Enjoy our beautiful waters on your own schedule with our boat rentals! From as short as 4 hours to multiple days, we have the perfect boat for you and your crew!
Duration: 2+ Days
Starting from: $700
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Reach Resort Fun Cat Rental

With Barefoot Billy's
In the Lower Keys
If you’re looking for a laidback and fun hour on the waters of Key West, or full day at the beach, nothing is better than our chaise lounge on a catamaran with an electric motor. The FunCat is easy to use and perfect for the laidback sailor.
Duration: 1 to 8 Hours
Starting from: $60
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Kayak/SUP Rental - 5 Days

With PADDLE! the Florida Keys
In the Upper Keys
We never run out of gear…. Please call us if you want to rent today! Free delivery from mm 100 to mm 80. Or we will strap to the top of your car or truck. We will lend you the straps and padding at no extra cost.
Duration: 5 Days
Starting from: $100
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Stand-Up Paddle board

With Sand Dollar Boat Rentals - Islamorada
In the Upper Keys
Paddle the crystal clear shallows of the Atlantic Ocean. See sharks, turtles and dozens of species of tropical fish and corals.
Duration: 2 Hours
Starting from: $30
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Casa Marina Fun Cat Rental

With Barefoot Billy's
In the Lower Keys
Want to relax and spend some time on the beautiful Key West waters? Try our chaise lounge on a catamaran with an electric motor. Or as we call it: the FunCat!
Duration: 1 to 8 Hours
Starting from: $60
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Private Sunset Sail

With Danger Charters
In the Lower Keys
Enjoy the yachting lifestyle with a 65ft skipjack sailing schooner reserved exclusively for your use on the Danger Charters Private Sunset Sail. A full selection of 8 fine wines and 5 premium beers along with a delectable array of gourmet appetizers make this private charter truly unique. Celebrate your special occasion with the spectacular beauty of the Key West sunset aboard the island’s top-rated sailing cruise.
Duration: 2 Hours
Starting from: $3200
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