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All listings in Florida

Incredible sailboat rentals in Florida, United States.

Page 2 of 491 listings

21ft Sun Tracker 20 Party Barge {Catch a Vibe}
Powerboats in Fort Lauderdale · 6 guests

21ft Sun Tracker 20 Party Barge {Catch a Vibe}

5.0
$100/hour
Let's go Sailing in Miami!
Sailing in Miami · 6 guests

Let's go Sailing in Miami!

5.0
$45+/hour
Instant Book
Discover Miami on this Sea Ray Yacht Charter
Events in Miami · 13 guests

Discover Miami on this Sea Ray Yacht Charter

5.0
$90/hour
Sailing From Pompano Beach, FL
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.5
Superowner
$125+/hour
50' Party Boat Catamaran in Miami ($1,200  PER HOUR)
Sailing in Miami Beach · 42 guests

50' Party Boat Catamaran in Miami ($1,200 PER HOUR)

4.8
$1,100/hour
Leopard 40 Cruising Catamaran for Up to 6 People in Stuart, FL with Captain Paul
Sailing in Stuart · 6 guests

Leopard 40 Cruising Catamaran for Up to 6 People in Stuart, FL with Captain Paul

5.0
$225/hour
Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami · 42 guests

Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender

3.0
Superowner
Best of 2025
$800/hour
Instant Book
Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)

4.6
$199+/hour
Fort Lauderdale Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale Bahamas Sailing Charters

5.0
$130+/hour
Sail Miami! Beautiful Beneteau 43 Cruising Monohull
Sailing in Miami · 10 guests

Sail Miami! Beautiful Beneteau 43 Cruising Monohull

5.0
$170/hour
The Best Boat For You And Your Friends NERO
Events in Miami · 13 guests

The Best Boat For You And Your Friends NERO

New
Superowner
$365+/hour
60' Sailing Party Catamaran in Miami Florida ($1,300 PER HOUR)
Travel in Miami Beach · 49 guests

60' Sailing Party Catamaran in Miami Florida ($1,300 PER HOUR)

4.6
$1,300/hour
Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!
Powerboats in Miami · 10 guests

Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!

4.3
$100+/hour
Luxurious 40ft Leopard Catamaran - Captain Included
Sailing in Saint Petersburg · 6 guests

Luxurious 40ft Leopard Catamaran - Captain Included

5.0
Superowner
Best of 2025
$315+/hour
40ft party catamaran for 13 on sand bar!
Sailing in Sunny Isles Beach · 12 guests

40ft party catamaran for 13 on sand bar!

New
Superowner
$280+/hour
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
ALL INCLUDED | 35ft Luxury Scarab Sportster Sport Boat
Powerboats in West Palm Beach · 12 guests

ALL INCLUDED | 35ft Luxury Scarab Sportster Sport Boat

5.0
$280/hour
Instant Book
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
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
Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins
Sailing in Fort Walton Beach · 6 guests

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

5.0
$110+/hour
Instant Book
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
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
50ft Luxury Great White Catamaran Charter – Up to 42 Guests in Miami!
Sailing in Miami Beach · 42 guests

50ft Luxury Great White Catamaran Charter – Up to 42 Guests in Miami!

New
Superowner
Best of 2025
$850/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

Sailing Reviews in Florida

  1. DG

    Darla

    21ft Sun Tracker 20 Party Barge {Catch a Vibe}

    Our group of 6 had the BEST time with Captain Porshia! The communication was phenomenal, she called the day before to discuss our desired itinerary, meet location, and any needs we may have. We had a prompt departure, and Porshia was very knowledgeable of boating and the area. Porshia was not only friendly but also very helpful and made sure all of our needs were taking care of. 10/10… HIGHLY RECOMMEND!!! We will definitely be back.

  2. IL

    Iryna

    Let's go Sailing in Miami!

    What an amazing day we had celebrating my dad's birthday! We spent the day sailing and trying out paddle boarding, and Captain Rod made the experience even more enjoyable with his friendliness and great service. The food we ordered was absolutely delicious too!

  3. WD

    Wayne

    Let's go Sailing in Miami!

    Steve and Rodrigo were great start to finish! Our goal was to build on our sailing experience, and they are both great teachers, letting us take the helm as much as we wanted and providing tons of useful insight. Not to mention they're both good guys, and we'd absolutely recommend them for any kind of outing you have in mind.

  4. CR

    Cara

    Let's go Sailing in Miami!

    I highly recommend Captain Steven and Rodrigo for your boating needs. Spending the afternoon on their 40ft sailboat, Mystiko, was a slice of heaven…we could not have asked for a better experience. They found a perfect spot to let our family take a swim, had an amazing playlist that set the mood, and they organized an absolutely incredible charcuterie board and steak/salmon barbecue for my sister’s birthday. It was positively sublime. Thank you, Captain Steven and Rodrigo!

  5. CR

    Cecelia

    Let's go Sailing in Miami!

    We had a lovely time for my birthday. It was a perfect day for sailing and Capt. Steven's Benneteau is beautiful. We paid a little extra for Capt Steven and Rodrigo to grill some steaks for us while my party took a swim. It was a special experience to sit in the lagoon at the end of key Biscayne and smell the grill while we sat in the water. The steaks were amazing! high quality and perfectly cooked. We ate the them with pieces of brie cheese and it was the best food we had tasted in 12 months. Capt. Rodrigo went above and beyond and his wife helped him design a whole charcuterie board with fruit and nuts and delicious cheese and fine salami. Capt. Steve and Rodrigo were great company as well as excellent hosts. The day was perfect, this was money well spent. I would go sailing with them again and again.

  6. DC

    DEBBIE

    Let's go Sailing in Miami!

    Capt Steven and his assistant were a pleasure to sail with. They communicated with us constantly to understand the experience we wanted, and how best to deliver it. They were also flexible. They anticipated our needs and exceeded our expectations. We will definitely book with them again!