Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

Map View

All listings in Florida

Incredible sailboat rentals in Florida, United States.

4.8

(981 Reviews)

Page 1 of 4 • 94 listings

Sailing in Tampa · 6 guests

Sunset Sails: Explore the Open Waters of Tampa, Florida

5.0

$225/hour

Powerboats in Iona · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained

5.0

$95+/hour

Sailing in Saint Petersburg · 12 guests

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

5.0

Superowner

Best of 2025

$300+/hour

Sailing in Shalimar · 6 guests

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

5.0

$150/hour

Sailing in Miami · 42 guests

Catamaran Party Boat 50' (42-Person Max) Includes: Captain and Crew

5.0

Superowner

Best of 2025

$800/hour

Events in Miami · 49 guests

The Ultimate Catamaran Party Boat | Up to 49 Passengers!

4.8

Superowner

Best of 2025

$800/hour

Instant Book

Sailing in Saint Petersburg · 6 guests

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

5.0

$205+/hour

Sailing in Miami · 13 guests

38’ Lagoon Catamaran Charter In Miami, Florida

5.0

$299/hour

Sailing in Miami · 12 guests

Luxury Catamaran located in Downtown Miami

5.0

$219+/hour

Sailing in Miami · 49 guests

Catamaran Party Boat up to 49 people. Includes: 1-Captain, 2-Mates

5.0

Superowner

Best of 2025

$800/hour

Sailing in Cape Canaveral · 6 guests

38ft Leopard Catamaran in Cape Canaveral

5.0

$250/hour

Tours in Fort Lauderdale · 6 guests

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

5.0

Superowner

$119+/hour

Events in Miami · 14 guests

“Exclusive Escape, Unlimited Adventure on our Yacht”

5.0

$250/hour

Instant Book

Sailing in Miami Beach · 42 guests

Catamaran Party Boat with Captain & Crew – Up to 42 Guests!

4.8

Superowner

Best of 2025

$800/hour

Sailing in Miami Beach · 49 guests

Catamaran Party Boat (49 Max) Includes: 1-Captain, 1-Mate and 1-Bartender

5.0

Superowner

Best of 2025

$800/hour

Powerboats in Holmes Beach · 8 guests

2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!

4.9

$372+/day

Sailing in Sarasota · 12 guests

42' Wanderlust - The Best Sailing Cat in the Market - Sarasota

5.0

$499+/hour

Instant Book

Sailing in Miami · 4 guests

ALL FEES INCLUDED! Endeavor 43 Sailboat Charter out of Miami.

5.0

Superowner

$75+/hour

Powerboats in Fort Lauderdale · 6 guests

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

5.0

$100/hour

Sailing in Pensacola · 6 guests

Morgan 382 Sailboat for charter in Pensacola, Florida

5.0

$75/hour

Sailing in Key West · 6 guests

Luxury Lagoon 440 Sailing Catamaran in Key West

5.0

$250/hour

Events in Miami · 13 guests

Discover Miami on this Sea Ray Yacht Charter

5.0

$90/hour

Sailing in Miami · 13 guests

48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil

5.0

$187+/hour

Powerboats in Fort Lauderdale · 6 guests

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

4.8

Superowner

$113+/hour

Instant Book

Top Destinations Nearby

Sailing Reviews in Florida

PM
Paulina

Catamaran Party Boat with Captain & Crew – Up to 42 Guests!
My wedding anniversary brought me back here! We obtain their services and we have to say our guest and us had a blast! Very professional services, their food items were great, overall a great and fun experience!
ET
Elliot

Catamaran Party Boat 50' (42-Person Max) Includes: Captain and Crew
Great experience. The crew took care of us the entire time. Would definitely book again.
Zach

2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Could not recommend this vessel and crew more. We rented it for the 4th of July and it was an unforgettable experience for our group. Despite some shaky weather we still had a blast. The boat is incredible and such a fair rate compared to other similar listings. Captain Dave and Joe were AWESOME. Would book again in a heartbeat!
Afolabi

“Exclusive Escape, Unlimited Adventure on our Yacht”
This trip was top class a 10/10 , very respectful captain, good communication and professionalism at its highest . Really appreciate Carlos and the captain.
AP
Albalia

Morgan 382 Sailboat for charter in Pensacola, Florida
We shared our 24th wedding anniversary with Robert and Carly in their beautiful boat. The only thing we regret is not doing this sooner because they are amazing and it is an experience to cherish. You guys are the best and we will definitely be back! Looking forward for that paella next time! Thank you!!!
Deja

2017 Robertson and Caine Leopard 40 - Luxury Catamaran
We can’t thank Captains Dave & Joe enough. From the communication with Bailey, to the overall experience.. everything went smooth and easy. I booked for my friend’s Bachelorette Party and they made our time worth while. I definitely recommend for any occasion. Both Captains Dave and Joes made sure we were equipped with everything and comfortable during our sailing. My favorite part was swimming and lounging on the floatable pools.. oh, and seeing dolphins! Overall 10/10 experience!