We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

All listings in Florida Keys

Incredible sailboat rentals in Florida Keys, United States.

Page 1 of 17 listings

Luxury Sailing Catamaran in Key West
Sailing in Key West · 10 guests

Luxury Sailing Catamaran in Key West

5.0
$250hour
Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

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

4.6
$175-$200hour
41' Island Trader Ketch in Key West, Florida!
Sailing in Stock Island · 6 guests

41' Island Trader Ketch in Key West, Florida!

4.9
$162-$199hour
Private Catamaran Charter in Marathon
Sailing in Marathon · 6 guests

Private Catamaran Charter in Marathon

5.0
Snoozed - Active 03 May 2024
80' Sailing Schooner Charter In Key West, Florida
Sailing in Key West · 32 guests

80' Sailing Schooner Charter In Key West, Florida

5.0
$475-$950hour
"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
$351hour
31feet SeaRay Sundancer - Enjoy!!!
Events in Florida · 8 guests

31feet SeaRay Sundancer - Enjoy!!!

New
$1,350day

Sailing Reviews in Florida Keys

  1. MS

    Mary

    Private Catamaran Charter in Marathon

    We had the most beautiful day on the water with Jack. Weather was perfect. So relaxing. Just sat back and enjoyed. We saw dolphins a few times. We got to take in the most beautiful sunset ever. Highly recommend Jack as your captain!!

  2. LR

    Lori

    Luxury 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.

  3. JA

    Jody

    Luxury Sailing Catamaran in Key West

    Five stars isn't enough! The catamaran is beautiful, and the crew was extremely accommodating. Captain Nils and First Mate Patrick are top notch seamen and gentlemen to boot. Took us to all the best spots to enjoy the beauty and majesty of Key West!!! We cant recommend them highly enough!

  4. 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 !

  5. JT

    Jeff

    Private Catamaran Charter in Marathon

    Beautiful and comfortable catamaran with everything you’ll need. Everything was super easy. Plenty of parking at the marina. Had a great time sailing and snorkeling on a beautiful February day!

  6. 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.