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All listings in Florida

Incredible sailboat rentals in Florida, United States.

4.8

(636 Reviews)

Page 1 of 5 • 105 listings

Sailing in Miami · 9 guests

23’ Bayliner Beautiful Boat In Miami

5.0

$90/hour

Sailing in Key West · 6 guests

Captained 42' Sailing Catamaran with 3 cabins and all the toys

5.0

$320/hour

Limited Availability

Sailing in Saint Petersburg · 12 guests

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

5.0

Superowner

$300+/hour

Sailing in Shalimar · 6 guests

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

5.0

$150/hour

Powerboats in Cape Coral · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat

5.0

$100+/hour

Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat 50' (49-Person)

5.0

Superowner

$700+/hour

Limited Availability

Sailing in Saint Petersburg · 6 guests

Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

5.0

$238+/hour

Sailing in Fort Lauderdale · 12 guests

60ft Fountaine Pajot Motor Yacht Charter in Fort Lauderdale

5.0

Superowner

Best of 2026

$425+/hour

Events in Miami · 49 guests

⛵️ Ultimate Catamaran Party Boat | Up to 49 Passengers!

4.9

Superowner

$700+/hour

Sailing in Miami · 12 guests

Luxury Leopard 38 Catamaran located in Downtown Miami

5.0

$219+/hour

Sailing in West Palm Beach · 12 guests

Hunter Passage 456 Yacht - Sailing From West Palm Beach, FL

4.3

Superowner

$125+/hour

Sailing in Pensacola · 6 guests

Morgan 382 Sailboat for charter in Pensacola, Florida

5.0

$75/hour

Sailing in Saint Petersburg · 6 guests

Day Sails and Sunset Cruises in Downtown St. Petersburg, 44' Morgan Sailboat

5.0

$206+/hour

Sailing in Miami Beach · 49 guests

⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender

5.0

Superowner

$700+/hour

Events in Miami · 13 guests

47ft Sea Ray Yacht Rental | Miami Luxury Experience

New

$200/hour

Sailing in Fort Lauderdale · 6 guests

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

5.0

Superowner

$119+/hour

High Demand

Sailing in Deerfield Beach · 12 guests

50ft Catamaran Charter with Water Toys -Boca Raton, FL

5.0

$350/hour

Sailing in Miami Beach · 49 guests

⛵️ MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)

5.0

Superowner

$700+/hour

Events in Miami · 13 guests

60ft AIcon Yacht – Perfect for Luxury Day Trips

4.8

$350/hour

High Demand

Events in Miami · 13 guests

“Exclusive Escape, Unlimited Adventure on our Yacht”

4.8

$250/hour

Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.6

Superowner

$125+/hour

Sailing in Miami Beach · 42 guests

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

4.8

Superowner

$700+/hour

Sailing in Miami · 6 guests

Let's go Sailing in Miami!

5.0

$45+/hour

Sailing in Fort Lauderdale · 6 guests

Marlowe Hunter 33’ Sailing In Fort Lauderdale

5.0

$90+/hour

Top Destinations Nearby

Sailing Reviews in Florida

Sharai

23’ Bayliner Beautiful Boat In Miami
SUCH an amazing time! I did so much research on private boats to get for my sister’s bachelorette and this truly exceeded my expectations! This is 10000% legit, great price, lots of room, amazing response time from Catalina, incredible fun time on the boat and such an amazing experience overall. I read so many reviews so please believe me when I say I’m a real person and this was such a great time so book it!!
TE
Tate

Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete
Jonas and Captain Carlos took top care of my family and I! I was so impressed with the amenities and cleanliness of the boat. They were both extremely knowledgeable about the area and sailing in whole. My nephew had a blast and they showed him patience and earned the respect of an 8 year old in addition to all of the "adults". Thank you so much, Jonas and Captain Carlos!
SS
Serah

23’ Bayliner Beautiful Boat In Miami
Antonio was our captain and he was very polite and professional! This is my second time in Miami and I will definitely book with him again! Best experience, peaceful, and he lets you connect to Bluetooth for your own music, free water and drinks! Best experience ever!
Sarah

Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete
Jonas and Carlos were super friendly and ran the boat smoothly. The boat was exactly as advertised and we had a great time! Thank you so much for a fun experience!
GK
Grace

23’ Bayliner Beautiful Boat In Miami
Antonio was a great captain! We had the best time on the boat and recommend doing the experience with the sandbar. Also, the Bluetooth surround sound on the boat really elevated the experience!
Daniel

23’ Bayliner Beautiful Boat In Miami
10/10 boat and service. Catalina was super responsive, we had a great experience. The captain was amazing and made the experience even better. The boat was nice and clean and a perfect size for our group. Will definitely book again!