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All listings in Florida

Incredible sailboat rentals in Florida, United States.

Page 2 of 482 listings

Hunter 336 Sailboat! Relaxing Sailing Palm Beach
Sailing in North Palm Beach · 4 guests

Hunter 336 Sailboat! Relaxing Sailing Palm Beach

5.0
$120/hour
⛵️ Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender

3.0
Superowner
$700+/hour
Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat
Sailing in Saint Pete Beach · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

5.0
$110/hour
Safe and Comfortable 42ft Fountaine Pajot catamaran sailing in West Palm Beach
Sailing in West Palm Beach · 6 guests

Safe and Comfortable 42ft Fountaine Pajot catamaran sailing in West Palm Beach

5.0
$300/hour
Luxury Sailing Experience on Robertson & Caine Leopard 40
Sailing in Saint Petersburg · 12 guests

Luxury Sailing Experience on Robertson & Caine Leopard 40

5.0
Superowner
$799+/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
Leopard 53 Power Catamaran (25-ft wide deck space)
Powerboats in Fort Lauderdale · 12 guests

Leopard 53 Power Catamaran (25-ft wide deck space)

New
$400+/hour
Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!
Powerboats in Miami · 10 guests

Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!

4.3
$100+/hour
60' Sailing Party Catamaran in Miami Florida
Sailing in Miami Beach · 49 guests

60' Sailing Party Catamaran in Miami Florida

4.6
$1,300/hour
Luxurious 40ft Leopard Catamaran - Captain Included
Sailing in Saint Petersburg · 6 guests

Luxurious 40ft Leopard Catamaran - Captain Included

5.0
Superowner
$315+/hour
42' Wanderlust - The Best Sailing Cat in the Market - Sarasota
Sailing in Sarasota · 12 guests

42' Wanderlust - The Best Sailing Cat in the Market - Sarasota

5.0
$499+/hour
Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins
Sailing in Fort Walton Beach · 6 guests

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

5.0
$110+/hour
40ft Jeanneau Sloop Charter in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

40ft Jeanneau Sloop Charter in Fort Lauderdale

5.0
$109+/hour
Aicon 67 Fly  – Elite Luxury Yacht Experience
Events in Miami · 13 guests

Aicon 67 Fly – Elite Luxury Yacht Experience

New
$350/hour
30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida
Powerboats in Deerfield Beach · 10 guests

30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida

5.0
$200/hour
Sun, Luxury & Fun | Sea Ray Flybridge 52ft in Miami
Events in Miami · 14 guests

Sun, Luxury & Fun | Sea Ray Flybridge 52ft in Miami

New
$350/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
Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida
Sailing in West Palm Beach · 12 guests

Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida

5.0
$250/hour
''Razor's Edge'' Yacht Rental in Cape Canaveral, Fl
Events in Cape Canaveral · 11 guests

''Razor's Edge'' Yacht Rental in Cape Canaveral, Fl

5.0
$382/hour
Sail from Delray Beach to Lake Boca
Sailing in Delray Beach · 12 guests

Sail from Delray Beach to Lake Boca

1.0
Superowner
$125+/hour
42' Luxury Catamaran Sailboat
Sailing in Miami · 6 guests

42' Luxury Catamaran Sailboat

New
$285/hour
45' Large Lagoon Catamaran | Private Luxury Charter | Fort Lauderdale
Sailing in Fort Lauderdale · 12 guests

45' Large Lagoon Catamaran | Private Luxury Charter | Fort Lauderdale

New
$350/hour
Private Yacht Tour — Miami Skyline Sunset Cruise with Bottle of Champagne
Tours in Miami Beach · 10 guests

Private Yacht Tour — Miami Skyline Sunset Cruise with Bottle of Champagne

New
Superowner
$159+/hour
45' Luxury Sailing Catamaran Charter
Sailing in Saint Petersburg · 6 guests

45' Luxury Sailing Catamaran Charter

5.0
$300+/hour

Sailing Reviews in Florida

  1. MT

    Michelle

    Hunter 336 Sailboat! Relaxing Sailing Palm Beach

    We had the absolute best time with Gerald. From the moment we stepped on the boat, we were treated like family. His kindness, generosity, and genuine spirit made the entire experience feel so special. What stood out most was not only how much fun we had, but how it truly felt like we made a new friend. Gerald’s knowledge of the area is expert level, and he shared so many great insights that made the day even more enjoyable. This was such a memorable experience for our group, and we cannot recommend him enough. We will absolutely be back.

  2. AK

    ALEXANDER

    Hunter 336 Sailboat! Relaxing Sailing Palm Beach

    Excellent experience from first contact until and beyond offboarding. Very family friendly. Definitely 5* experience. Will book again next time. The trip from the pier to the Atlantic is a great experience by itself. Sailing on the ocean is a dream come true. Enjoy!

  3. ED

    Eric

    Hunter 336 Sailboat! Relaxing Sailing Palm Beach

    We had an incredible time on the water from the get-go. Started off cruising the intercostal waterway and even got off the dock in time to catch an earlier bridge to avoid low tide. We cruised south past Singer Island and Palm Beach. We stopped in the ICW near Palm Beach to put our feet in the water and take in the scenery in peace and quiet. The wind was amenable to sailing so we tacked south for a while then sailed back past Singer Island to make the bridge opening to get us home on time. All in all, couldn’t change a thing about the experience. The vessel was clean, well-equipped and lots of space to relax. There was ample space for beverages and food that we brought onboard and a clean restroom. Definitely would love to sail again with Gerald in the future!

  4. MS

    Mikhail

    Hunter 336 Sailboat! Relaxing Sailing Palm Beach

    The sailing trip we took with Gerald was everything we were looking for! He has years of experience to share, as much as interesting stories to tell. He let's you handle the boat as much as you are comfortable to and teaches you ins and outs of sailing and navigation. We did some swimming off the boat which was a lot of fun! Gerald was so nice to offer us a taste of mangoes from his garden which were simply delicious! Thank you for a great time and conversations, Gerald! Mike&Yana

  5. SH

    Simon

    Safe and Comfortable 42ft Fountaine Pajot catamaran sailing in West Palm Beach

    My wife and I celebrated our anniversary and we had a fabulous time on the water with Cal and Marty. The catamaran is the perfect way to enjoy a cruise up and down the coast with plenty of space to lay in out and relax. They even provided a beautiful spread of fruit and a welcome cocktails. Would highly recommend!

  6. NH

    Nikki

    Luxury Sailing Experience on Robertson & Caine Leopard 40

    I’m so glad I decided to book this vessel! Booking was simple. The communication was accurate, timely, always professional, and with forethought, before the trip. My group was in town for a bachelorette weekend and enjoyed our day sailing with Captain Dan. We departed and returned right on time, which we appreciated as we had a schedule we were trying to adhere to. We also appreciated the blankets as it got windy at some points and we didn’t want to go inside. Overall 10/10 experience. I’d definitely book again!