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    All listings in Florida

    Incredible sailboat rentals in Florida, United States.

    4.8
    (642 Reviews)

    Page 3 of 5 • 105 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    42' Luxury Catamaran Sailboat
    Sailing in Miami · 6 guests

    42' Luxury Catamaran Sailboat

    New
    $285/hour
    Leopard 53 Power Catamaran (25-ft wide deck space)
    Powerboats in Fort Lauderdale · 12 guests

    Leopard 53 Power Catamaran (25-ft wide deck space)

    New
    $400+/hour
    Sail from Delray Beach to Lake Boca
    Sailing in Delray Beach · 12 guests

    Sail from Delray Beach to Lake Boca

    1.0
    Superowner
    $125+/hour
    45' Luxury Sailing Catamaran Charter
    Sailing in Saint Petersburg · 6 guests

    45' Luxury Sailing Catamaran Charter

    5.0
    $300+/hour
    Passport 40 Sailboat in Key West - Comfortable Sailing for Up to 6 Guests
    Sailing in Key West · 6 guests

    Passport 40 Sailboat in Key West - Comfortable Sailing for Up to 6 Guests

    New
    $150/hour
    Private Yacht Tour — Miami Skyline Sunset Cruise with Bottle of Champagne
    Tours in Miami Beach · 10 guests

    Private Yacht Tour — Miami Skyline Sunset Cruise with Bottle of Champagne

    New
    Superowner
    $159+/hour
    Sailing Adventure on Bay in Miami on Tartan Sailboat!
    Sailing in Key Biscayne · 6 guests

    Sailing Adventure on Bay in Miami on Tartan Sailboat!

    5.0
    $100/hour
    57' Fountaine Pajot Sailing Catamaran - A Luxury Experience
    Sailing in Fort Lauderdale · 12 guests

    57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

    5.0
    $450/hour
    Sail from Boynton Beach to Lake Boca
    Sailing in Boynton Beach · 12 guests

    Sail from Boynton Beach to Lake Boca

    New
    Superowner
    $126+/hour
    Luxury Catamaran Party Lagoon 50 in Fort Lauderdale, Florida
    Sailing in Fort Lauderdale · 12 guests

    Luxury Catamaran Party Lagoon 50 in Fort Lauderdale, Florida

    New
    $370/hour
    Luxury 50ft Sea Ray Sedan Bridge 2005 | Premium Yacht Experience in Miami
    Events in Miami · 13 guests

    Luxury 50ft Sea Ray Sedan Bridge 2005 | Premium Yacht Experience in Miami

    New
    $250/hour
    Day Sails & Sunset Cruises – Downtown St. Petersburg, FL – 36’ Catalina Yacht
    Sailing in Saint Petersburg · 6 guests

    Day Sails & Sunset Cruises – Downtown St. Petersburg, FL – 36’ Catalina Yacht

    New
    $206+/hour
    Hunter 450 Passage Yacht - Sail From Key Biscayne
    Sailing in Key Biscayne · 10 guests

    Hunter 450 Passage Yacht - Sail From Key Biscayne

    New
    Superowner
    $250/hour
    50 Luxury Sailing Catamaran in Miami
    Sailing in Fort Lauderdale · 12 guests

    50 Luxury Sailing Catamaran in Miami

    5.0
    $390/hour
    50ft Luxury Great White Catamaran Charter – Up to 42 Guests in Miami!
    Sailing in Miami Beach · 42 guests

    50ft Luxury Great White Catamaran Charter – Up to 42 Guests in Miami!

    New
    Superowner
    Best of 2026
    $850/hour
    Best Sea Ray Sundancer 40ft in Miami | Perfect for Parties & Cruises
    Events in Miami · 14 guests

    Best Sea Ray Sundancer 40ft in Miami | Perfect for Parties & Cruises

    New
    $250/hour
    Parasailing Adventure in West Palm Beach
    Adventures in Riviera Beach · 12 guests

    Parasailing Adventure in West Palm Beach

    New
    $99/hour
    ⛵️ MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)
    Events in Miami Beach · 49 guests

    ⛵️ MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)

    New
    Superowner
    $750+/hour
    Sun, Luxury & Fun | Sea Ray Flybridge 52ft in Miami
    Events in Miami · 14 guests

    Sun, Luxury & Fun | Sea Ray Flybridge 52ft in Miami

    New
    $350/hour
    Hunter 336 Sailing Yacht Charter in Palm Beach, Florida
    Sailing in North Palm Beach · 4 guests

    Hunter 336 Sailing Yacht Charter in Palm Beach, Florida

    New
    $125/hour
    Miami Sunset Sailing Cruise with Open Bar, Appetizers, DJ on 60ft Catamaran
    Sailing in Miami Beach · 49 guests

    Miami Sunset Sailing Cruise with Open Bar, Appetizers, DJ on 60ft Catamaran

    New
    $1,500/hour
    Luxe 75ft Sailing Catamaran Serving Key West & Miami Florida
    Events in Key West · 12 guests

    Luxe 75ft Sailing Catamaran Serving Key West & Miami Florida

    New
    $14,750/night
    46 Sport Bridge Yacht
    Events in Miami Beach · 12 guests

    46 Sport Bridge Yacht

    New
    $240+/hour
    "Thea Marie" Yacht Charter in Riviera Beach, FL
    Sailing in Riviera Beach · 49 guests

    "Thea Marie" Yacht Charter in Riviera Beach, FL

    New
    $1,288/hour

    Top Destinations Nearby

    Sailing Reviews in Florida

    1. GS

      Grant

      Sailing Adventure on Bay in Miami on Tartan Sailboat!

      Wonderful experience. The boat functioned perfectly and was a blast. Great communication from the owner Don.

    2. Blue

      Blue

      50 Luxury Sailing Catamaran in Miami

      Leo and crew were fantastic, and my friends and I had a blast out on the water! Can't wait to do it again.

    3. EL

      Eric

      45' Luxury Sailing Catamaran Charter

      Great experience. Fantastic captain and admiral. Wonderful time had by all!!

    4. RH

      Roger

      Sailing Adventure on Bay in Miami on Tartan Sailboat!

      Great vessel. Well maintained. Up to date equipment. Very relaxed.

    5. erkan

      erkan

      57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

      Crew , boat , owner … they were the best !

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