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$100-$300

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All listings in Florida

Incredible sailboat rentals in Florida, United States.

5.0

(400 Reviews)

Page 1 of 3 • 50 listings

Sailing in Treasure Island · 12 guests

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

5.0

$225-$350hour

Sailing in Shalimar · 6 guests

Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin

5.0

$150hour

Powerboats in Miami · 15 guests

51ft Trimaran-Catamaran Sailing Yacht Charter in Miami, Florida

5.0

Snoozed - Active 02 Jan 2025

Sailing in Miami · 13 guests

38’ Lagoon Catamaran Charter In Miami, Florida

5.0

Superowner

$299hour

Sailing in Fort Walton Beach · 6 guests

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

5.0

$149hour

Sailing in Saint Petersburg · 6 guests

Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

5.0

$205-$230hour

Sailing in Fernandina Beach · 6 guests

30' Kurt Hughes Cruising Catamaran rental in Fernandina Beach, Florida

4.8

$300hour

Powerboats in West Palm Beach · 12 guests

Luxury Sport Boats Rental

5.0

$200hour

Tours in Fort Lauderdale · 6 guests

Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

5.0

Superowner

$119-$125hour

Powerboats in Sunny Isles Beach · 10 guests

Set sail with our luxurious Sea Ray 300 Yacht!!

New

$200hour

Sailing in Key West · 10 guests

Luxury Sailing Catamaran in Key West

5.0

$250hour

Powerboats in Deerfield Beach · 10 guests

30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida

5.0

$200hour

Powerboats in Fort Lauderdale · 6 guests

Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max

4.8

Superowner

$113-$171hour

Sailing in Green Cove Springs · 6 guests

64' Roberts Sailing Ketch for Charter in Jacksonville Area

5.0

$138-$217hour

Sailing in West Palm Beach · 6 guests

Sailing From West Palm Beach, FL - $150/Hour - $30/Person

4.7

Superowner

Best of 2023

$150hour

Powerboats in Deerfield Beach · 10 guests

Ultimate Intercoastal Cruiser and Sandbar party boat in Deerfield Beach, Florida

5.0

$125hour

Sailing in Treasure Island · 6 guests

John’s Pass: Sailing, dolphins and sightseeing

5.0

$200hour

Sailing in Stock Island · 6 guests

41' Island Trader Ketch in Key West, Florida!

4.9

$162-$199hour

Sailing in North Palm Beach · 4 guests

Hunter 336 Sailboat! Relaxing Sailing Palm Beach

5.0

$120hour

Sailing in Stuart · 6 guests

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

5.0

$225hour

Sailing in Key West · 12 guests

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

4.6

$175-$200hour

Sailing in Marathon · 6 guests

Private Catamaran Charter in Marathon

5.0

Snoozed - Active 03 May 2024

Sailing in Panama City · 12 guests

Full or Half Day Private Charter Aboard 50' Ohana in Panama City, Florida

5.0

$299-$320hour

Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale Bahamas Sailing Charters

5.0

$119-$120hour

Top Destinations Nearby

Sailing Reviews in Florida

Kathy
April, 2024
Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida
A glorious day at sea! Do yourself a favor and book this experience! You won’t regret it! Feeling at ease on the water and really enjoying the element was what were were striving for! As a local realtor, I make sure to enjoy what this beautiful place has to offer and this is one of them!
Lauren
April, 2024
Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin
Wonderful time out on the water with Captain Bill! Very accommodating, kind and knowledgeable. Weather wasn’t cooperative but he was able to be flexible and come up with an alternative itinerary. Definitely recommend!
Shajira
March, 2024
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Celebrated my 40th alongside my family on David and Emma’s catamaran and it turned out better than I would’ve ever imagined! Emma was the best captain and she was even more awesome with the kids. We went during spring break and their recommendations on where to go with the kids was just perfect. David was great with communicating with me since before I even booked the trip, and answered all the questions I had promptly. We all had such a great time, made so many memories and will definitely be booking with David and Emma again!!
Meghan
March, 2024
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
We booked David's boat for a bachelorette/30th birthday party and had a BLAST. David, and his daughter, Emma, were absolutely amazing. They were easy to get in contact with and responded promptly. Their boat was modern and perfect for what we were looking for. They even added some decorations and heart shaped sunglasses! We thought that was so thoughtful. If you're looking for a boat in St. Pete beach, I highly recommend this one!
Daziah
March, 2024
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
My family and I had an absolutely amazing time with David & his daughter! The took us to see dolphins, we got to jump off the boat, it was just wonderful. 10/10 would recommend. I can’t wait to book again!!
BO
Brian
April, 2024
Luxury Sport Boats Rental
2nd time booking - always the best experience. Would recommend to anyone looking for a great day on the water! Amazing experience