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All listings in Key West

Great sailboat rentals near Key West, Florida.

Page 1 of 17 listings

Captained 42' Sailing Catamaran with 3 cabins and all the toys
Sailing in Key West · 6 guests

Captained 42' Sailing Catamaran with 3 cabins and all the toys

5.0
$320/hour
33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

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

4.6
$199+/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
$210/hour
Captained 80' Sailing Schooner Charter In Key West, Florida
Sailing in Key West · 32 guests

Captained 80' Sailing Schooner Charter In Key West, Florida

5.0
$475+/hour
45ft Lagoon | Somewhere
Sailing in Key West · 12 guests

45ft Lagoon | Somewhere

New
$740+/hour
"Satisfaction" Morgan 41 Classic Sailboat for Charter in Key West
Sailing in Key West · 6 guests

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

New
$351/hour
Luxury 46' Lagoon Catamaran in Key West and Dry Tortugas
Sailing in Key West · 12 guests

Luxury 46' Lagoon Catamaran in Key West and Dry Tortugas

New
$560+/hour

Sailing Reviews in Key West

  1. Brandon

    Brandon

    Captained 42' Sailing Catamaran with 3 cabins and all the toys

    Highly recommended Captain Aaron and his crew Brook... they did an amazing job of hosting and tending to our wants. Very nice boat with ample toys and things to do on the water. Will definitely join them again. ⭐️⭐️⭐️⭐️⭐️

  2. CD

    Carina

    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 !

  3. Bobby

    Bobby

    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. JF

    Jessica

    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!

  5. JS

    Jad

    Captained 80' Sailing Schooner Charter In Key West, Florida

    Amazing ship, a piece of history, great crew, and an excellent experience. Highly recommended!

  6. Maggie

    Maggie

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

    We had the BEST time ever, wouldn’t change a thing!!! Absolutely book this immediately!