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    Incredible sailboat rentals in Florida Keys, United States.

    Average of 12 reviews in this area.
    12 listings
    "Marathon Traveller" Robertson & Caine Leopard 44
    hour$344
    Super Owner6 guests

    "Marathon Traveller" Robertson & Caine Leopard 44

    "Satisfaction" Morgan 41 Classic Sailboat for Charter in Key West
    hour$351
    Super Owner6 guests

    "Satisfaction" Morgan 41 Classic Sailboat for Charter in Key West

    41' Island Trader Ketch in Key West, Florida!
    hour$199
    6 guests

    41' Island Trader Ketch in Key West, Florida!

    80' Sailing Schooner Charter In Key West, Florida
    hour$950
    32 guests

    80' Sailing Schooner Charter In Key West, Florida

    Seawind 1260 41' Makai, in Key West FL
    day$1,795
    12 guests

    Seawind 1260 41' Makai, in Key West FL

    Seawind 1260 41' Honu Kai, in Key West FL
    day$1,795
    12 guests

    Seawind 1260 41' Honu Kai, in Key West FL

    Leopard 48' Catamaran, 4 Cabins in Key West
    day$2,115
    12 guests

    Leopard 48' Catamaran, 4 Cabins in Key West

    Seawind 1160 38' Go Slow in Key West FL 12 Guests
    day$640
    12 guests

    Seawind 1160 38' Go Slow in Key West FL 12 Guests

    Leopard 44 Luxury Catamaran Charter in Florida Keys
    hour$200
    6 guests

    Leopard 44 Luxury Catamaran Charter in Florida Keys

    Full Day Private Charter in Key West, Florida
    day$985
    6 guests

    Full Day Private Charter in Key West, Florida

    Boating Guide - Florida Keys Sailing

    Rent or charter a sailboat for a memorable experience in Florida Keys.

    Are you ready for a fun adventure out on the open water onboard a sailboat in Florida Keys? Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Florida Keys is a wonderful sailboat rental destination.

    Using GetMyBoat to book your next sailing experience.

    Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

    Search for the perfect experience now and book your dream day out on the water.

    GetMyBoat customer reviews for Sailing in Florida Keys.

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

      Sunset Cruise was responsive throughout the entire process & more than accommodating. Both Eric & Mark were with us through our experience & were nothing but pleasurable and made the day great. I highly recommend Sunset cruise & this boat !

    2. Alex
      Alex
      41' Island Trader Ketch in Key West, Florida!

      We had an absolutely amazing experience out on the boat. The captain and crew were amazing and so kind and accommodating. The dog was the cherry on top too - cutest thing ever.

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

      Great owner and communications the captain Nate and first Mate Mark were wonderful , would highly recommend Hightide for a nice sail or snorkeling

    4. PK
      Petri
      41' Island Trader Ketch in Key West, Florida!

      Smooth sailing. Spacious and beautiful boat with professional and corteous crew guaranteed an excellent afternoon. Thank you.

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

      We spent four hours as a family together - it was a great adventure. I highly recommend this experience!

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

      Great boat, great crew. We had a great time!!

    GetMyBoat has 12 listings for Sailing experiences in Florida Keys with 12 reviews.

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