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All listings in Florida

Incredible sailboat rentals in Florida, United States.

Page 3 of 5102 listings

4 Hour Private Charter in Destin, FL! Crab Island, Snorkeling, Dolphins & More!
Sailing in Destin · 6 guests

4 Hour Private Charter in Destin, FL! Crab Island, Snorkeling, Dolphins & More!

5.0
$150/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
2 Hour Sunset River Cruise for up to 6 people in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

2 Hour Sunset River Cruise for up to 6 people in Fort Lauderdale

5.0
$150/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
Parasailing Adventure in West Palm Beach
Adventures in Riviera Beach · 12 guests

Parasailing Adventure in West Palm Beach

New
$99/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
Sailing  Miami and Key Biscayne on board Catamaran Lagoon 450F
Sailing in Miami · 13 guests

Sailing Miami and Key Biscayne on board Catamaran Lagoon 450F

5.0
$450/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 Key Biscayne $250/Hr - $41.66/Person
Sailing in Key Biscayne · 10 guests

Sail From Key Biscayne $250/Hr - $41.66/Person

New
Superowner
$195/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
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
60’ Mariah Catamaran Events and Party Boat with Captain and Crew
Events in Fort Lauderdale · 49 guests

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

New
Superowner
Best of 2025
$900/hour
Sail from Boynton Beach to Lake Boca - $200/Hour - $33.33/Person
Sailing in Boynton Beach · 12 guests

Sail from Boynton Beach to Lake Boca - $200/Hour - $33.33/Person

New
Superowner
$126+/hour
42' Wanderlust - The Best Sailing Cat in the Market
Sailing in Sarasota · 12 guests

42' Wanderlust - The Best Sailing Cat in the Market

New
$449+/hour
Instant Book
AZIMUT 45 BEST YACHT IN MIAMI
Powerboats in Miami · 11 guests

AZIMUT 45 BEST YACHT IN MIAMI

New
Superowner
$300/hour
42' Luxury Catamaran Sailboat
Sailing in Miami · 6 guests

42' Luxury Catamaran Sailboat

New
$275/hour
Stunning Azimut 65 flybridge
Events in Miami · 13 guests

Stunning Azimut 65 flybridge

New
$300+/hour
Searay Sundancer 60¨ in North Miami Beach, Florida
Events in Aventura · 12 guests

Searay Sundancer 60¨ in North Miami Beach, Florida

4.0
$400/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
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
55ft "Poseidon SR" Sea Ray Flybridge Power MegaYacht Charter in Tampa, Florida
Events in Tampa · 13 guests

55ft "Poseidon SR" Sea Ray Flybridge Power MegaYacht Charter in Tampa, Florida

New
$801/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
Smooth Sailing: Charter the Elegant 43 Beneteau Today!
Sailing in Fort Lauderdale · 8 guests

Smooth Sailing: Charter the Elegant 43 Beneteau Today!

New
$200/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

Sailing Reviews in Florida

  1. WA

    Warren

    4 Hour Private Charter in Destin, FL! Crab Island, Snorkeling, Dolphins & More!

    Thank you guys so much for everything! What an amazing adventure you guys had for us. The Dolphin show was incredible and the sailing experience was awesome. We are so lucky to get matched up with y’all 😊 For anyone looking for a great way to sail around Destin and do some sightseeing with some crab island fun y’all need not look any further. A++++ Charter

  2. MM

    Mike

    4 Hour Private Charter in Destin, FL! Crab Island, Snorkeling, Dolphins & More!

    Tracy & Ladd are true professionals, and a generally good time. The offering was exactly as presented and they catered to the specific requests we had. The boat is great and their knowledge of the area helped make this a fantastic afternoon on the water. I would highly recommend you book this if you are looking for a private charter in the Destin, FL area!

  3. 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. 🙌

  4. 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!

  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. JR

    Jenna

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

    Brian and his captains were great! They provided us with an amazing experience boating throughout Sanibel/Ft Myers. The boat was spacious, they let us jump in and swim, and even made us reservations at the marina restaurant without being asked - which was a huge help as it was crowded. Will book again!