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All listings in Florida Keys

Incredible sailboat rentals in Florida Keys, United States.

Page 1 of 18 listings

22ft Sea Fox 226 Commander for Family fun or Fishing!
Powerboats in Tavernier · 8 guests

22ft Sea Fox 226 Commander for Family fun or Fishing!

5.0
$75/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
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
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
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

New
$320/hour
THE ONE AND ONLY GRADY WHITE FREEDOM
Fishing in Marathon · 8 guests

THE ONE AND ONLY GRADY WHITE FREEDOM

New
$150/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
$600+/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

Sailing Reviews in Florida Keys

  1. Brian

    Brian

    22ft Sea Fox 226 Commander for Family fun or Fishing!

    Great boat, great service. Professional and prompt with everything. Went above and beyond to make sure everything went smoothly and as planned. Would highly recommend. Great boat, speakers, etc.

  2. MD

    Michael

    22ft Sea Fox 226 Commander for Family fun or Fishing!

    Absolutely phenomenal experience. From the call the day before to make sure I had everything needed to the friendly service- will be coming back plenty!

  3. NV

    Nivaa

    22ft Sea Fox 226 Commander for Family fun or Fishing!

    Highly recommend Braxton for charter rentals.. excellent service and we had a great time with him

  4. Tristan

    Tristan

    22ft Sea Fox 226 Commander for Family fun or Fishing!

    Braxton Why Knott Exclusive Rentals is super awesome and a class act. Everything went great- we snorkelled the reefs he recommended at chicken and hen and saw dolphins on our ride. Smooth and flawless, highly recommended . Check out their website for all the cool spear fishing trips they do!

  5. Nicole

    Nicole

    22ft Sea Fox 226 Commander for Family fun or Fishing!

    Everything about our experience was absolutely stellar from start to finish. The boat was fantastic, Braxton was extremely helpful not only educating on the boat itself but provided great information on routes & places to visit. We had a wonderful day snorkeling the lighthouse and hanging out at Islamorada Sandbar. We will definitely book this again on our next trip to the Keys.

  6. LR

    Lori

    Luxury Lagoon 440 Sailing Catamaran in Key West

    Awesome boat!! Ashley was very helpful and easy to communicate with. Nils, the captain was very welcoming and informative as we cruised around looking for sea life. We saw turtles, dolphins and even a hammerhead shark. It was such a relaxing day. Thanks Ashley and Nils for making our day great.