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Upper Keys

Upper Keys Trips & Tours

From Long Key all the way up to North Key Largo, you’ll find world class fishing, both backcountry and offshore, great dining options, incredible snorkeling, and of the course the world famous Islamorada Sandbar! Classy, quiet, and packed with things to do, the Upper Keys are a great choice for your Florida Keys vacation.

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22.5’ Hurricane SunDeck 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: $395
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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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25’ Sportsman - Center Console Half 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: 4 Hours
Starting from: $395
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Single Kayak

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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22' Blue Hurricane 150 hp 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: $750
Learn More

Double Kayak

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: $40
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Full Day Offshore Charter - 42' Liberty

With DirtyBoat Charters LLC
In the Upper Keys
Full-day Offshore Charter offered is 8+ hours, hunting Mahi-Mahi offshore. Again, we start by catching live bait at the reef, then head out to one of The Humps, the undersea mountains in the Atlantic of Islamorada. On the way we troll a simple spread for that “out of the blue” bite, all the while looking for diving birds or floating debris.
Duration: 8 Hours
Starting from: $1800
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22' Robalo Center Console Half 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: 4 Hours
Starting from: $295
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Kayak/SUP Rental - 3 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: 3 Days
Starting from: $100
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21’ FunDeck 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: $750
Learn More
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