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    Captain

    Florida Keys Boat Rentals [From $75/Hour]

    5.0
    (399 Reviews)

    Page 2 of 5 • 97 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Luxury Sailing Catamaran in Key West
    Sailing in Key West · 10 guests

    Luxury Sailing Catamaran in Key West

    5.0
    $250hour
    Yamaha 242XE - Top of line entertainment boat for any adventure - Islamorada
    Powerboats in Islamorada · 11 guests

    Yamaha 242XE - Top of line entertainment boat for any adventure - Islamorada

    5.0
    Superowner
    $150hour
    31ft Contender Center Console - Captained Custom Tours in Islamorada, Florida
    Powerboats in Islamorada · 6 guests

    31ft Contender Center Console - Captained Custom Tours in Islamorada, Florida

    5.0
    $150hour
    Luxury Adventure Boat: Brabus of the Seas - Up to 13ppl - Islamorada/Key Largo
    Events in Islamorada · 13 guests

    Luxury Adventure Boat: Brabus of the Seas - Up to 13ppl - Islamorada/Key Largo

    5.0
    Superowner
    $225-$349hour
    41' Island Trader Ketch in Key West, Florida!
    Sailing in Stock Island · 6 guests

    41' Island Trader Ketch in Key West, Florida!

    4.9
    $162-$199hour
    Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)
    Sailing in Key West · 12 guests

    Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)

    4.6
    $175-$200hour
    Choose your own adventure exploring the last frontier of Florida, the Lower Florida Keys! Amazing Float Plans and secluded sandbars!
    Powerboats in Cudjoe Key · 6 guests

    Choose your own adventure exploring the last frontier of Florida, the Lower Florida Keys! Amazing Float Plans and secluded sandbars!

    5.0
    Snoozed - Active 03 Jul 2024
    Wake Surf Wake Skate In Key West, Florida
    Tours in Key West · 6 guests

    Wake Surf Wake Skate In Key West, Florida

    5.0
    $225hour
    All-Inclusive, Captain-Led Adventure Awaits! Snorkel, Sandbar, and More
    Powerboats in Islamorada · 6 guests

    All-Inclusive, Captain-Led Adventure Awaits! Snorkel, Sandbar, and More

    5.0
    $125-$150hour
    Hydrasport 6-Hour Private Charter in Key West
    Powerboats in Key West · 6 guests

    Hydrasport 6-Hour Private Charter in Key West

    5.0
    $142hour
    25ft Premier Pontoon
    Tours in Marathon · 16 guests

    25ft Premier Pontoon

    New
    $72hour
    21ft Sea Hunt 207 Triton Center Console for Rent in Key Largo Florida!
    Powerboats in Key Largo · 6 guests

    21ft Sea Hunt 207 Triton Center Console for Rent in Key Largo Florida!

    5.0
    $98hour
    Newer Key West Party Boat for 36 people!
    Powerboats in Key West · 36 guests

    Newer Key West Party Boat for 36 people!

    5.0
    $550hour
    80' Sailing Schooner Charter In Key West, Florida
    Sailing in Key West · 32 guests

    80' Sailing Schooner Charter In Key West, Florida

    5.0
    $475-$950hour
    2020 Sailfish 270 WAC Charter in Key West!
    Powerboats in Key West · 6 guests

    2020 Sailfish 270 WAC Charter in Key West!

    5.0
    $675day
    2022 Yamaha 252EX Islamorada, FL
    Powerboats in Key Largo · 10 guests

    2022 Yamaha 252EX Islamorada, FL

    New
    $135hour
    Rum Runner Bar Boat in Key West, Florida
    Powerboats in Key West · 12 guests

    Rum Runner Bar Boat in Key West, Florida

    5.0
    $150hour
    Private Tiki Boat Charters for up to 18 Passengers
    Events in Islamorada · 18 guests

    Private Tiki Boat Charters for up to 18 Passengers

    New
    $333-$400hour
    Sandbar Charter and Island Tour
    Powerboats in Key West · 6 guests

    Sandbar Charter and Island Tour

    New
    $200hour
    EXCLUSIVE Brand New 2023 Axopar 25ft Cross Top
    Events in Key Largo · 6 guests

    EXCLUSIVE Brand New 2023 Axopar 25ft Cross Top

    New
    $150-$205hour
    Mako Marine 33' Express Cabin
    Powerboats in Islamorada · 6 guests

    Mako Marine 33' Express Cabin

    5.0
    $250hour
    21' Shearwater - Captained Islamorada Sandbar, Snorkeling, or Sunset Cruise
    Powerboats in Islamorada · 5 guests

    21' Shearwater - Captained Islamorada Sandbar, Snorkeling, or Sunset Cruise

    5.0
    $125hour
    Fun Keys Charter in Islamorada
    Tours in Islamorada · 6 guests

    Fun Keys Charter in Islamorada

    New
    $175-$200hour
    Tiki Bar Boat in Key West
    Powerboats in Key West · 6 guests

    Tiki Bar Boat in Key West

    New
    $125hour

    Top Destinations Nearby

    Florida Keys Reviews

    1. AJ

      Alan

      All-Inclusive, Captain-Led Adventure Awaits! Snorkel, Sandbar, and More

      Excellent trip, great communication, knowledgeable skipper, made the day special, will book again if we ever come back

    2. BB

      Brianna

      31ft Contender Center Console - Captained Custom Tours in Islamorada, Florida

      We had a great time with Rene! He was communicative and a great host!

    3. Erin

      Erin

      All-Inclusive, Captain-Led Adventure Awaits! Snorkel, Sandbar, and More

      Captain Jim was fantastic! We had a charter out to the Islamorada sand bar- the ride was fun and Captain Jim set us up with a lily pad and paddle board to enjoy our time at the sandbar. Plus he had so much info to share with us! Cannot recommend enough and will be in contact next time in Islamorada.

    4. LR

      Lori

      Luxury Sailing Catamaran in Key West

      Awesome boat!! Ashley was very helpful and easy to communicate with. Nils, the captain was very welcoming and informative as we cruised around looking for sea life. We saw turtles, dolphins and even a hammerhead shark. It was such a relaxing day. Thanks Ashley and Nils for making our day great.

    5. JA

      Jody

      Luxury Sailing Catamaran in Key West

      Five stars isn't enough! The catamaran is beautiful, and the crew was extremely accommodating. Captain Nils and First Mate Patrick are top notch seamen and gentlemen to boot. Took us to all the best spots to enjoy the beauty and majesty of Key West!!! We cant recommend them highly enough!

    6. Thibaut

      Thibaut

      31ft Contender Center Console - Captained Custom Tours in Islamorada, Florida

      I am French and I am living in Miami for the past 22 years and I am used to go in Islamorada and rent boat, Rene was amazing and brought us to some amazing places I had the best day ever in the keys, if you go there Rene is the guy to call, super nice person, beautiful boat, you won’t regret it. Thanks again Rene for your kindness and hospitality 😊

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