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Pensacola, Florida Boat Rentals & Yacht Charters

Page 1 of 6143 listings

Private Crab Island and Boat Tours: 4 hour, 6 hour, 8 hour trips available
Powerboats in Shalimar · 6 guests

Private Crab Island and Boat Tours: 4 hour, 6 hour, 8 hour trips available

5.0
$90/hour
Limited Availability
BEST OF 2025 Double Decker Tritoon! Crab Island/Destin
Powerboats in Fort Walton Beach · 13 guests

BEST OF 2025 Double Decker Tritoon! Crab Island/Destin

5.0
Superowner
Best of 2026
$125/hour
Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin
Sailing in Shalimar · 6 guests

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

5.0
$150/hour
Limited Availability
Harris Pontoon to cruise to Crab Island, the Destin Harbor and surrounding areas
Powerboats in Fort Walton Beach · 10 guests

Harris Pontoon to cruise to Crab Island, the Destin Harbor and surrounding areas

5.0
$80/hour
25' Tahoe Pontoon Rental In Fort Walton Beach, FL
Powerboats in Fort Walton Beach · 12 guests

25' Tahoe Pontoon Rental In Fort Walton Beach, FL

5.0
$63/hour
High Demand
Fast Luxury Barletta Tritoon! Perfect for Destin! 13 passenger, free amenities!
Powerboats in Okaloosa Island · 13 guests

Fast Luxury Barletta Tritoon! Perfect for Destin! 13 passenger, free amenities!

5.0
Superowner
Best of 2026
$125/hour
25' Power Speed and Luxury on the Emerald Coast 13 guests! Free Amenities
Powerboats in Fort Walton Beach · 13 guests

25' Power Speed and Luxury on the Emerald Coast 13 guests! Free Amenities

5.0
Superowner
Best of 2026
$125/hour
Suncatcher G3 Pontoon 24ft in Orange Beach, Alabama
Powerboats in Orange Beach · 6 guests

Suncatcher G3 Pontoon 24ft in Orange Beach, Alabama

5.0
$125/hour
High Demand
Avalon 24ft Fun Pontoon Boat in Fort Walton Beach
Powerboats in Fort Walton Beach · 12 guests

Avalon 24ft Fun Pontoon Boat in Fort Walton Beach

4.3
$75/hour
Limited Availability
24' Bentley Pontoon to cruise Crab Island, Destin Harbor and surrounding areas
Powerboats in Fort Walton Beach · 13 guests

24' Bentley Pontoon to cruise Crab Island, Destin Harbor and surrounding areas

3.7
$90/hour
High Demand
Large Pontoon Boat! Made in the Shade
Powerboats in Fort Walton Beach · 12 guests

Large Pontoon Boat! Made in the Shade

4.9
$75/hour
Limited Availability
30' Double Decker Tritoon Slide Boat for Destin Florida - Enjoy Crab Island!
Powerboats in Fort Walton Beach · 13 guests

30' Double Decker Tritoon Slide Boat for Destin Florida - Enjoy Crab Island!

5.0
$125/hour
Center Console in Destin, Fort Walton Beach, Navarre, Pensacola
Powerboats in Fort Walton Beach · 8 guests

Center Console in Destin, Fort Walton Beach, Navarre, Pensacola

5.0
$75+/hour
Morgan 382 Sailboat for charter in Pensacola, Florida
Sailing in Pensacola · 6 guests

Morgan 382 Sailboat for charter in Pensacola, Florida

5.0
$75/hour
24' Bentley Pontoon and Clear Kayaks for Family Fun!
Powerboats in Fort Walton Beach · 6 guests

24' Bentley Pontoon and Clear Kayaks for Family Fun!

5.0
$90/hour
Private Bareboat Pontoon Charter Near Crab Island & Destin Harbor
Powerboats in Fort Walton Beach · 12 guests

Private Bareboat Pontoon Charter Near Crab Island & Destin Harbor

5.0
$63/hour
Party in Crab Island!!! For all occasions (Paddleboard, Lily Pad & More)
Powerboats in Fort Walton Beach · 12 guests

Party in Crab Island!!! For all occasions (Paddleboard, Lily Pad & More)

5.0
$75/hour
2013 Captained Bennington 26ft Pontoon Rental in Fort Walton Beach
Powerboats in Fort Walton Beach · 10 guests

2013 Captained Bennington 26ft Pontoon Rental in Fort Walton Beach

4.9
$120/hour
Crab Island Fun! Slide, Paddleboard, Lily Pad, Inflatables & More
Powerboats in Fort Walton Beach · 12 guests

Crab Island Fun! Slide, Paddleboard, Lily Pad, Inflatables & More

4.8
$140/hour
Limited Availability
Relax on a 22-ft Bentley Pontoon in Fort Walton Beach for 10 People
Powerboats in Fort Walton Beach · 10 guests

Relax on a 22-ft Bentley Pontoon in Fort Walton Beach for 10 People

5.0
$54+/hour
Limited Availability
24ft Crest Double Decker Pontoon with Slide
Powerboats in Fort Walton Beach · 12 guests

24ft Crest Double Decker Pontoon with Slide

5.0
$100/hour
Most Badass Party Pontoon in Pensacola ! FREE Amenities !
Powerboats in Pensacola · 13 guests

Most Badass Party Pontoon in Pensacola ! FREE Amenities !

5.0
$125/hour
The Pink Pearl Tiki, up to 18 passengers!
Powerboats in Orange Beach · 18 guests

The Pink Pearl Tiki, up to 18 passengers!

5.0
$225/hour
Instant Book
2020 Bennington TriToon for Bachelorette Parties, Cruising, Private Island, more
Powerboats in Fort Walton Beach · 11 guests

2020 Bennington TriToon for Bachelorette Parties, Cruising, Private Island, more

5.0
$120/hour

Pensacola Reviews

  1. CD

    Cortnie

    BEST OF 2025 Double Decker Tritoon! Crab Island/Destin

    We visited Crab Island for my bachelorette trip, and it was truly the BEST DAY EVER! From start to finish, everything was absolutely perfect. The boat was amazing, and the double slides off the back were such a fun feature—having the water assist made them even more exciting! A huge thank you to Louis, our captain, who made the entire experience unforgettable. He was incredibly friendly, helpful, and made sure our group had everything we needed to enjoy the day. His positive attitude and attention to detail really took the trip to the next level. If you're considering a charter for Crab Island, look no further—we cannot recommend this boat and crew enough! Thank you for helping make my bachelorette celebration so special. We are already looking forward to coming back and doing it all again!

  2. KM

    Keith

    25' Tahoe Pontoon Rental In Fort Walton Beach, FL

    Chris was absolutely amazing to work with. Easy process and made the rental experience a breeze. If looking for a great afternoon trip to Crab Island I highly recommend Chris and his team. Thanks again for the great day!

  3. AM

    Amanda

    BEST OF 2025 Double Decker Tritoon! Crab Island/Destin

    There were a few folks in our group who had never been to Crab Island, so of course, I had to ensure they had a good time. We booked Rod’s vessel and boy was it FUN!!! It was the perfect size for a large group, the captain was amazing, the process was smooth from start to finish, and overall it truly was the perfect crab island experience!! Thank you!!!

  4. NL

    Nate

    Private Crab Island and Boat Tours: 4 hour, 6 hour, 8 hour trips available

    We had the best day out on the crab island. The boat was beautiful, the views were amazing, and Captain Shelly made the whole experience unforgettable. She was incredible with our children — patient, fun, and made them feel completely safe and included. Truly a perfect family day. We highly recommend Shelly!

  5. EP

    Erin

    Harris Pontoon to cruise to Crab Island, the Destin Harbor and surrounding areas

    Everything went smooth from the booking to the trip itself. My group had a great experience on the boat! Our captain for the day was Jakob. He was very friendly and his service was top tier!!! I would definitely recommend booking with Liz and requesting Jakob as a captain!

  6. KG

    Kyna

    BEST OF 2025 Double Decker Tritoon! Crab Island/Destin

    Trip was great! The boat was very nice and the floating equipment was perfect for our family! The kids loved the slides! Our captain maneuvered around crab island like a pro making us feel very comfortable! Highly recommend!