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    All listings in Florida

    Incredible sailboat rentals in Florida, United States.

    4.8
    (740 Reviews)

    Page 1 of 4 • 89 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Sunset Sails: Explore the Open Waters of Tampa, Florida
    Sailing in Tampa · 6 guests

    Sunset Sails: Explore the Open Waters of Tampa, Florida

    5.0
    $225/hour
    Instant Book
    Cabbage Key, Captiva Day Trip 1-6 people Captained
    Powerboats in Iona · 6 guests

    Cabbage Key, Captiva Day Trip 1-6 people Captained

    5.0
    $95+/hour
    2017 Robertson and Caine Leopard 40 - Luxury Catamaran
    Sailing in Saint Petersburg · 12 guests

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    5.0
    Superowner
    Best of 2025
    $300+/hour
    Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin
    Sailing in Shalimar · 6 guests

    Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin

    5.0
    $150/hour
    38ft Leopard Catamaran in Cape Canaveral
    Sailing in Cape Canaveral · 6 guests

    38ft Leopard Catamaran in Cape Canaveral

    5.0
    $250/hour
    Catamaran Party Boat 50' (42-Person Max) Includes: Captain and Crew
    Sailing in Miami Beach · 42 guests

    Catamaran Party Boat 50' (42-Person Max) Includes: Captain and Crew

    5.0
    Superowner
    Best of 2025
    $800/hour
    The Ultimate Catamaran Party Boat | Up to 49 Passengers!
    Events in Miami · 49 guests

    The Ultimate Catamaran Party Boat | Up to 49 Passengers!

    4.8
    Superowner
    Best of 2025
    $900/hour
    Instant Book
    Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht
    Sailing in Saint Petersburg · 6 guests

    Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

    5.0
    $205+/hour
    38’ Lagoon Catamaran Charter In Miami, Florida
    Sailing in Miami · 13 guests

    38’ Lagoon Catamaran Charter In Miami, Florida

    5.0
    $299/hour
    Luxury Catamaran located in Downtown Miami
    Sailing in Miami · 12 guests

    Luxury Catamaran located in Downtown Miami

    5.0
    $219+/hour
    Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida
    Tours in Fort Lauderdale · 6 guests

    Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

    5.0
    Superowner
    $119+/hour
    Catamaran Party Boat up to 49 people. Includes: 1-Captain, 2-Mates
    Sailing in Miami Beach · 49 guests

    Catamaran Party Boat up to 49 people. Includes: 1-Captain, 2-Mates

    5.0
    Superowner
    Best of 2025
    $900/hour
    Catamaran Party Boat (49 Max) Includes: 1-Captain, 1-Mate and 1-Bartender
    Sailing in Miami Beach · 49 guests

    Catamaran Party Boat (49 Max) Includes: 1-Captain, 1-Mate and 1-Bartender

    5.0
    Superowner
    Best of 2025
    $800/hour
    Let's go Sailing in Miami!
    Sailing in Miami · 6 guests

    Let's go Sailing in Miami!

    5.0
    $45+/hour
    Instant Book
    Sailing From West Palm Beach, FL - $200/Hour - $33.33/Person
    Sailing in West Palm Beach · 12 guests

    Sailing From West Palm Beach, FL - $200/Hour - $33.33/Person

    4.5
    Superowner
    $125+/hour
    ALL FEES INCLUDED! Endeavor 43 Sailboat Charter out of Miami.
    Sailing in Miami · 4 guests

    ALL FEES INCLUDED! Endeavor 43 Sailboat Charter out of Miami.

    5.0
    Superowner
    $75+/hour
    Catamaran Party Boat with Captain & Crew – Up to 42 Guests!
    Sailing in Miami Beach · 42 guests

    Catamaran Party Boat with Captain & Crew – Up to 42 Guests!

    4.7
    Superowner
    Best of 2025
    $900/hour
    Luxury Lagoon 440 Sailing Catamaran in Key West
    Sailing in Key West · 6 guests

    Luxury Lagoon 440 Sailing Catamaran in Key West

    5.0
    $250/hour
    48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil
    Sailing in Miami · 13 guests

    48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil

    5.0
    $187+/hour
    Enjoy a memorable sailing experience aboard this beautiful Jeanneau 389
    Sailing in West Palm Beach · 8 guests

    Enjoy a memorable sailing experience aboard this beautiful Jeanneau 389

    5.0
    $105+/hour
    Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max
    Powerboats in Fort Lauderdale · 6 guests

    Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max

    4.8
    Superowner
    $113+/hour
    Instant Book
    Morgan 382 Sailboat for charter in Pensacola, Florida
    Sailing in Pensacola · 6 guests

    Morgan 382 Sailboat for charter in Pensacola, Florida

    5.0
    $75/hour
    Discover Miami on this Sea Ray Yacht Charter
    Events in Miami · 12 guests

    Discover Miami on this Sea Ray Yacht Charter

    5.0
    $100/hour
    “Exclusive Escape, Unlimited Adventure on our Yacht”
    Events in Miami · 14 guests

    “Exclusive Escape, Unlimited Adventure on our Yacht”

    5.0
    $300/hour

    Top Destinations Nearby

    Sailing Reviews in Florida

    1. JE

      Jackie

      “Exclusive Escape, Unlimited Adventure on our Yacht”

      Truly had the best time with the crew and on the boat. Booking went so smoothly and the crew gave us the best time celebrating our bride. Will book with them again in the future!

    2. AJ

      Ashley

      Luxury Catamaran located in Downtown Miami

      Liam was great! We had a group of people ranging from 1 years old to 87 years old. Everyone had a fun time on the boat. Highly recommend booking with them!

    3. JB

      Julia

      “Exclusive Escape, Unlimited Adventure on our Yacht”

      This was the best experience ever. The boat is even better in person. The crew is so amazing and really made sure we were taken care of. I would highly recommend booking this and will definitely use them next time I’m in town. They communicate very quickly and the experience was seamless. It was such a special moment for the bachelorette party we were on. I can’t say enough good things honestly. It was fantastic!!

    4. Clarisse

      Clarisse

      2017 Robertson and Caine Leopard 40 - Luxury Catamaran

      Listing was awesome! Captain Dan and his crew were amazing and worked with my bachelorette party so well! Could not recommend them more.

    5. Kieron

      Kieron

      2017 Robertson and Caine Leopard 40 - Luxury Catamaran

      Bailey's luxury catamaran was gorgeous and the sunset cruise we took for my husband's 40th birthday with family was a very special experience. Captain Dave and Emma were so nice and accommodating for our group of 12. They provided us with ice and beverages as well as utensils and napkins for the catered platters we brought. We were also able to connect to the sound system to play our music for the entire trip. We had perfect weather and got to see dolphins frolicking prior to heading out into the Gulf for a gorgeous sail and stunning sunset!

    6. MJ

      Mollie

      48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil

      What a wonderful day with a great captain and a great boat.

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