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All listings in Florida

Incredible sailboat rentals in Florida, United States.

Page 3 of 493 listings

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
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
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
42' Luxury Catamaran Sailboat
Sailing in Miami · 6 guests

42' Luxury Catamaran Sailboat

New
$275/hour
Parasailing Adventure in West Palm Beach
Adventures in Riviera Beach · 12 guests

Parasailing Adventure in West Palm Beach

New
$99/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
''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
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
Set Sail on a Suncoast Escapade!
Sailing in Treasure Island · 6 guests

Set Sail on a Suncoast Escapade!

New
$225/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
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
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
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
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
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
Luxury Lagoon 450 Catamaran in Key West
Sailing in Fort Lauderdale · 8 guests

Luxury Lagoon 450 Catamaran in Key West

New
$600+/hour
Classic 1970 Sail Yacht
Sailing in West Palm Beach · 4 guests

Classic 1970 Sail Yacht

2.0
$900/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
''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
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

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. 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

  3. 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!

  4. 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. 🙌

  5. 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!

  6. 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!