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$100-$300
All listings in Florida

Incredible sailboat rentals in Florida, United States.

Page 2 of 351 listings

Parasailing Adventure in West Palm Beach
Adventures in Riviera Beach · 12 guests

Parasailing Adventure in West Palm Beach

New
$109person
Large Catamaran sailing on the Biscayne Bay from Miami
Sailing in Miami · 13 guests

Large Catamaran sailing on the Biscayne Bay from Miami

5.0
$270-$430hour
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
$250hour
4-Hour Private Charter in Destin, Florida! Crab Island, Snorkeling, Dolphins & More!
Sailing in Destin · 6 guests

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

5.0
$150hour
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
$150hour
40 ft Jeanneau Sloop Charter in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

40 ft Jeanneau Sloop Charter in Fort Lauderdale

5.0
$100-$110hour
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
$300hour
Private Sunset Cruise (2-Hours) in Destin, Florida
Powerboats in Destin · 6 guests

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

5.0
$175hour
36 YELLOWFIN   Sunset Cruises / Sandbar Party / Intercoastal Cruise
Fishing in Bay Pines · 6 guests

36 YELLOWFIN Sunset Cruises / Sandbar Party / Intercoastal Cruise

5.0
$150hour
Enjoy Miami in SEA RAY 45FT!!
Events in Miami Beach · 13 guests

Enjoy Miami in SEA RAY 45FT!!

New
Superowner
Best of 2023
$140hour
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

New
$300hour
PONTOON IN HAULOVER  Final Price No Hidden Fees 1h Free On Week Days 10ppl
Powerboats in Sunny Isles Beach · 11 guests

PONTOON IN HAULOVER Final Price No Hidden Fees 1h Free On Week Days 10ppl

New
Superowner
$160hour
Sail From Key Biscayne $195/Hr - $40/Person
Sailing in Key Biscayne · 6 guests

Sail From Key Biscayne $195/Hr - $40/Person

New
Superowner
Best of 2023
$195hour
Sailing Cataraman 48ft "Bubble"
Sailing in Miami · 12 guests

Sailing Cataraman 48ft "Bubble"

New
$177person
2016 Bali Sailing Cataraman 45ft
Events in Sunny Isles Beach · 12 guests

2016 Bali Sailing Cataraman 45ft

New
$270-$400hour
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
$125hour
Sea Ray 270 SDX Luxury Deck Boat Rental in Riverview, Florida
Powerboats in Riverview · 10 guests

Sea Ray 270 SDX Luxury Deck Boat Rental in Riverview, Florida

New
$160hour
Classic 1970 Sail Yacht
Sailing in West Palm Beach · 4 guests

Classic 1970 Sail Yacht

New
$150person
"Boldly Go" Yacht Charter in Tampa, FL
Sailing in Bay Pines · 6 guests

"Boldly Go" Yacht Charter in Tampa, FL

New
$202hour
The "Original Redneck Pontoon" Crab Island / Dolphin / Snorkeling Adventures
Powerboats in Destin · 6 guests

The "Original Redneck Pontoon" Crab Island / Dolphin / Snorkeling Adventures

New
$110hour
Tampa Bay - Clearwater Area with a perfect & elegant Carver Mariner 38 x 190$/h
Powerboats in Tampa · 12 guests

Tampa Bay - Clearwater Area with a perfect & elegant Carver Mariner 38 x 190$/h

New
$250hour
Day Sail, Sun Rise & Sun Set, Special Event Guided Charter, Si hablo Español
Sailing in Aventura · 7 guests

Day Sail, Sun Rise & Sun Set, Special Event Guided Charter, Si hablo Español

New
$130-$150hour
Experience the Magic of Charm! | Luxury Private Catamaran Charter Service in South Florida and the Bahamas
Miami · 12 guests

Experience the Magic of Charm! | Luxury Private Catamaran Charter Service in South Florida and the Bahamas

New
$300hour
45´ Sea Ray Express Cruiser. Luxury Yacht in Aventura, North Miami.
Sailing in North Miami Beach · 13 guests

45´ Sea Ray Express Cruiser. Luxury Yacht in Aventura, North Miami.

New
$150-$200hour

Sailing Reviews in Florida

  1. LH

    Laura

    Large Catamaran sailing on the Biscayne Bay from Miami

    We had a great experience on the boat. Captain is super kind, helpful and even very entertaining for a child we had on board. Very fun crew and a very pleasant day, route and atmosphere. Boat has all you need for a short or long term rental. Thanks for having us!

  2. MM

    Mike

    4-Hour Private Charter in Destin, Florida! 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. 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!