We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

All listings in Florida

Incredible sailboat rentals in Florida, United States.

Page 3 of 5104 listings

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

Parasailing Adventure in West Palm Beach

New
$109person
3-Hour Daytime Cruise in Destin, Florida
Sailing in Destin · 6 guests

3-Hour Daytime Cruise in Destin, Florida

5.0
$150hour
50' Chris White Design, Cruising Catamaran rental in beautiful Ponce Inlet Florida.
Sailing in Ponce Inlet · 6 guests

50' Chris White Design, Cruising Catamaran rental in beautiful Ponce Inlet Florida.

5.0
$26person
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
"Real Gone Daddy"  Yacht Charter in West Palm Beach, FL
Sailing in West Palm Beach · 13 guests

"Real Gone Daddy" Yacht Charter in West Palm Beach, FL

New
$524hour
Luxurious 40ft Leopard Catamaran - ALL INCLUSIVE
Sailing in Treasure Island · 6 guests

Luxurious 40ft Leopard Catamaran - ALL INCLUSIVE

New
$215-$500hour
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
Casa Sul Mare - Home on the sea
Events in Jupiter · 12 guests

Casa Sul Mare - Home on the sea

5.0
$750-$1,000hour
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
Sail from Delray Beach to Lake Boca - $150/Hr - $30/Person
Sailing in Delray Beach · 10 guests

Sail from Delray Beach to Lake Boca - $150/Hr - $30/Person

New
Superowner
Best of 2023
$30person
"Boldly Go" Yacht Charter in Tampa, FL
Sailing in Bay Pines · 6 guests

"Boldly Go" Yacht Charter in Tampa, FL

New
$202hour
''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
$382hour
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
Romantic Sunset Cruise with Bottle of Champagne - 2023 Luxury Motorboat
Tours in North Bay Village · 10 guests

Romantic Sunset Cruise with Bottle of Champagne - 2023 Luxury Motorboat

New
$99person
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
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-$950hour
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
Stunning Luxe 60' White Princess Yacht
Events in Fort Lauderdale · 13 guests

Stunning Luxe 60' White Princess Yacht

New
Superowner
$750hour
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
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
Searay Sundancer 60¨ in North Miami Beach, Florida
Events in Aventura · 12 guests

Searay Sundancer 60¨ in North Miami Beach, Florida

4.0
$400hour

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. 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!

  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. 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!