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All listings in Florida

Incredible sailboat rentals in Florida, United States.

Page 3 of 494 listings

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins
Sailing in Fort Walton Beach · 6 guests

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

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

40 ft Jeanneau Sloop Charter in Fort Lauderdale

5.0
$109+/hour
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+/hour
Lagoon 42' Private Sailing Adventure in Florida with Captain Eric
Sailing in Deerfield Beach · 8 guests

Lagoon 42' Private Sailing Adventure in Florida with Captain Eric

5.0
$300/hour
Private Sunset Cruise (2-Hours) in Destin, Florida
Sailing in Fort Walton Beach · 6 guests

Private Sunset Cruise (2-Hours) in Destin, Florida

5.0
$175/hour
40ft party catamaran for 13 on sand bar!
Sailing in Sunny Isles Beach · 12 guests

40ft party catamaran for 13 on sand bar!

New
Superowner
$280+/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
Parasailing Adventure in West Palm Beach
Adventures in Riviera Beach · 12 guests

Parasailing Adventure in West Palm Beach

New
$99/hour
Sailing Adventure on Bay in Miami on Tartan Sailboat!
Sailing in Key Biscayne · 4 guests

Sailing Adventure on Bay in Miami on Tartan Sailboat!

5.0
$100/hour
Instant Book
42' Luxury Catamaran Sailboat
Sailing in Miami · 6 guests

42' Luxury Catamaran Sailboat

New
$300/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
Rent This Lux Sea Ray 33’ Miami Experience
Events in Miami · 12 guests

Rent This Lux Sea Ray 33’ Miami Experience

New
$130+/hour
Top-Rated Miami Boat Rental – Sandbar, Music & Fun!
Events in Miami · 13 guests

Top-Rated Miami Boat Rental – Sandbar, Music & Fun!

New
$250/hour
Catamaran 48 foot luxury sailing cat daily, over night and weekly Excursions
Sailing in Fort Myers Beach · 12 guests

Catamaran 48 foot luxury sailing cat daily, over night and weekly Excursions

5.0
$300/hour
Instant Book
Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1
Sailing in Fort Lauderdale · 4 guests

Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1

New
$50/hour
60’ Mariah Catamaran Events and Party Boat with Captain and Crew
Events in Miami · 49 guests

60’ Mariah Catamaran Events and Party Boat with Captain and Crew

New
Superowner
Best of 2025
$800+/hour
48ft Sailing Catamaran – Day Charter in Miami with Captain
Sailing in Miami · 12 guests

48ft Sailing Catamaran – Day Charter in Miami with Captain

New
$423+/hour
THE ONE AND ONLY GRADY WHITE FREEDOM
Fishing in Marathon · 8 guests

THE ONE AND ONLY GRADY WHITE FREEDOM

New
$150/hour
Set sail with our luxurious Sea Ray 300 Yacht!!
Powerboats in Sunny Isles Beach · 10 guests

Set sail with our luxurious Sea Ray 300 Yacht!!

New
$200/hour
Hunter 336 Sailing Yacht Charter in Palm Beach, Florida
Sailing in North Palm Beach · 4 guests

Hunter 336 Sailing Yacht Charter in Palm Beach, Florida

New
$125/hour
"Thea Marie" Yacht Charter in Riviera Beach, FL
Sailing in Riviera Beach · 49 guests

"Thea Marie" Yacht Charter in Riviera Beach, FL

New
$1,288/hour
44ft Aquila "A Lil Bit Nauti" Yacht Charter in Palmetto, FL
Sailing in Palmetto · 13 guests

44ft Aquila "A Lil Bit Nauti" Yacht Charter in Palmetto, FL

New
$590/hour
Set Sail aboard the Most Photographed Boat in the Tampa Bay Region!
Sailing in Treasure Island · 28 guests

Set Sail aboard the Most Photographed Boat in the Tampa Bay Region!

New
$695/hour
''Aloan at Last''r Mega Yacht Rental in Sarasota, Florida
Events in Sarasota · 13 guests

''Aloan at Last''r Mega Yacht Rental in Sarasota, Florida

New
$1,690/hour

Sailing Reviews in Florida

  1. Becca

    Becca

    Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

    Amazing in every way! Kip & Elizabeth were so kind and accommodating. We got to relax, snorkel, and even saw some dolphins which made the trip extra memorable. Kip was always responsive to messages and the process couldn’t have been more seamless from start to finish. Couldn’t recommend enough!

  2. SS

    Shaun

    40 ft Jeanneau Sloop Charter in Fort Lauderdale

    This was our first time sailing and Captain Dan was amazing 🤩. He is very knowledgeable and accommodating. We sat up front on a couple of bean bags which was perfect and very comfortable. We will definitely do this again. Oh and we saw 👀dolphins 🐬 too. 🙌

  3. Kathy

    Kathy

    40 ft Jeanneau Sloop Charter in Fort Lauderdale

    It was a great choice! Captain Dan welcomed us and prepared us so we would have a most enjoyable and safe trip! We toured beautiful areas, sailed along the coast and a great ocean adventure! We dropped anchor for a swim and lunch and had great conversation !! Thank you and we will be back!

  4. JP

    Jonathan

    Lagoon 42' Private Sailing Adventure in Florida with Captain Eric

    Amazing experience. Exceeded all expectations. I booked a trip for eight family members to celebrate a birthday while on vacation. Captain Eric took us on an afternoon tour of the Florida intercoastal. His boat was incredibly nice and spacious, and Eric was a great host - very friendly and accommodating to all our needs. We hope to book a sailing excursion with him next time we are in the area!

  5. JF

    Joey

    Private Sunset Cruise (2-Hours) in Destin, Florida

    Ladd was our captain for this trip. We couldn’t ask for a better crew than him and Sebastian. We had to delay our trip a day because of a storm but they more than made up for it. They also documented our trip with photos that they emailed to us. It was very relaxing and informative. We also got to see some dolphins. Very nice people. Overall, a 10 star outing!

  6. KW

    Kel

    Private Sunset Cruise (2-Hours) in Destin, Florida

    This was a GREAT trip..Captain Tracy's communication and follow thru was awesome.. although Tracy was unable to captain the boat Captain Ladd and Sebastian created an awesome experience for my girlfriend and I.. we even got up close and personal with the dolphins...I would definitely recommend and will use again