The best sailboat rentals in Key West.

Average of 5 reviews in this area.
7 listings

Rent a sailboat for an unforgettable experience in Key West, Florida.

Get ready for a fun adventure when you hit the open water onboard a sailboat in Key West, Florida. 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. Key West, Florida is a wonderful sailboat rental destination.

Using GetMyBoat to rent your next sailboat in Key West.

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.

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GetMyBoat customer reviews for Sailing in Key West.

  1. RF
    41' Island Trader Ketch "Conch West" In Key West, Florida (With Captain Only)

    Highly recommend for a great time!

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