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All listings in Florida

Incredible sailboat rentals in Florida, United States.

Page 3 of 5101 listings

Catamaran Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami · 42 guests

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

1.0
Superowner
Best of 2025
$800/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
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
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
Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins
Sailing in Fort Walton Beach · 6 guests

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

5.0
$110+/hour
23’ Bayliner Beautiful Boat In Miami
Sailing in Miami · 9 guests

23’ Bayliner Beautiful Boat In Miami

New
$115/hour
40ft party power catamaran for 13 on sand bar!
Sailing in Sunny Isles Beach · 12 guests

40ft party power catamaran for 13 on sand bar!

New
Superowner
$280+/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
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
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
Hunter 450 Passage Yacht - Sail From Key Biscayne
Sailing in Key Biscayne · 10 guests

Hunter 450 Passage Yacht - Sail From Key Biscayne

New
Superowner
$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
42' Luxury Catamaran Sailboat
Sailing in Miami · 6 guests

42' Luxury Catamaran Sailboat

New
$285/hour
Sailing Adventure on Bay in Miami on Tartan Sailboat!
Sailing in Key Biscayne · 6 guests

Sailing Adventure on Bay in Miami on Tartan Sailboat!

5.0
$100/hour
Luxury Catamaran Party |  Lagoon 50
Sailing in Miami · 12 guests

Luxury Catamaran Party | Lagoon 50

New
$399/hour
Sail from Boynton Beach to Lake Boca
Sailing in Boynton Beach · 12 guests

Sail from Boynton Beach to Lake Boca

New
Superowner
$126+/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
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
Parasailing Adventure in West Palm Beach
Adventures in Riviera Beach · 12 guests

Parasailing Adventure in West Palm Beach

New
$99/hour
65ft Pershing Yacht for Luxury Charter and Miami Fun!
Events in Miami · 13 guests

65ft Pershing Yacht for Luxury Charter and Miami Fun!

New
$450/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
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
Hanse 418 Cruising Monohull Rental in Hollywood, Florida
Sailing in Hollywood · 12 guests

Hanse 418 Cruising Monohull Rental in Hollywood, Florida

New
$250/hour

Sailing Reviews in Florida

  1. PA

    Peggy

    30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida

    Our party of six adults and three children had the best time with Mike and his beautiful Jupiter 30. The boat was in immaculate order, had plenty of seating for all of us, and was safe for the kids to roam around on. A great sound system kept both kids and adults entertained. Mike truly is the best captain one can ask for. Quick to respond to our requests before the trip, and attentive, safe and positive during it. 10/10 from our whole party of nine

  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. 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!

  5. 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!

  6. 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!