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Longboat Key, Florida Boat Rentals

Page 1 of 124 listings

Captained 25' Regency Tritoon with Fuel Included
Powerboats in Longboat Key · 10 guests

Captained 25' Regency Tritoon with Fuel Included

5.0
$89+/hour
Super Comfy 22’ Pontoon in Bradenton/ fuel included
Powerboats in Bradenton Beach · 10 guests

Super Comfy 22’ Pontoon in Bradenton/ fuel included

4.9
$57+/hour
Cruise in style with this beautiful Center Console boat
Powerboats in Cortez · 12 guests

Cruise in style with this beautiful Center Console boat

New
$190/hour
Fun and Adventure Await on a Brand-New Switch Sport!
Powerboats in Bradenton Beach · 8 guests

Fun and Adventure Await on a Brand-New Switch Sport!

3.0
$150/hour
Embark on a fishing trip with SeaHunt 22ft CC as you reel in the big one!!
Fishing in Bradenton · 4 guests

Embark on a fishing trip with SeaHunt 22ft CC as you reel in the big one!!

New
$125+/hour
Sarasota Luxury Cruise on 38ft Silverton Yacht with a USCG Licensed Captain
Events in Longboat Key · 6 guests

Sarasota Luxury Cruise on 38ft Silverton Yacht with a USCG Licensed Captain

New
Snoozed - Active 02 Jan 2025
Snorkeling, Sandbar Island Hopping, Manatees & Dolphins Tours
Tours in Holmes Beach · 6 guests

Snorkeling, Sandbar Island Hopping, Manatees & Dolphins Tours

5.0
Superowner
$595/day
24' Tritoon Bennington with new 175 Hp Suzuki Outboard for rent in Holmes Beach!
Powerboats in Holmes Beach · 12 guests

24' Tritoon Bennington with new 175 Hp Suzuki Outboard for rent in Holmes Beach!

4.8
$85/hour
Bayliner Trophy T22 Center Console Rental in Holmes Beach, Florida
Powerboats in Holmes Beach · 10 guests

Bayliner Trophy T22 Center Console Rental in Holmes Beach, Florida

5.0
$92+/hour
BOOK TODAY FOR FUTURE RENTAL! 21ft SeaDoo Switch Sport. Fun w/family & friends.
Powerboats in Holmes Beach · 9 guests

BOOK TODAY FOR FUTURE RENTAL! 21ft SeaDoo Switch Sport. Fun w/family & friends.

5.0
$75+/hour
Amazing 2017 Sportsman 232 Open Center Console
Powerboats in Holmes Beach · 10 guests

Amazing 2017 Sportsman 232 Open Center Console

5.0
$80/hour
2021 New Cypress Cay 23ft Tritoon Boat for Rent in Holmes Beach!!
Powerboats in Holmes Beach · 13 guests

2021 New Cypress Cay 23ft Tritoon Boat for Rent in Holmes Beach!!

5.0
$425+/day
Beautiful 25 foot Tritoon in Anna Maria, Fl available to book now
Powerboats in Holmes Beach · 10 guests

Beautiful 25 foot Tritoon in Anna Maria, Fl available to book now

5.0
$375/day
Beautiful Bayliner DX2200 | Perfect for a day exploring AMI!
Powerboats in Holmes Beach · 12 guests

Beautiful Bayliner DX2200 | Perfect for a day exploring AMI!

5.0
$429+/day
2021 Cypress Cay tritoon, seats up to 13ppl
Powerboats in Holmes Beach · 13 guests

2021 Cypress Cay tritoon, seats up to 13ppl

5.0
$450/day
Big Grey, our Gorgeous 23' Bayliner Deck Boat with sports tower!
Powerboats in Holmes Beach · 12 guests

Big Grey, our Gorgeous 23' Bayliner Deck Boat with sports tower!

5.0
$82+/hour
"ALLEGRIA' is a 24,2" Hurricane with bimini and plenty of seating.
Powerboats in Holmes Beach · 6 guests

"ALLEGRIA' is a 24,2" Hurricane with bimini and plenty of seating.

5.0
Superowner
$135/hour
Bentley Pontoon on Anna Maria Island,  Florida
Powerboats in Holmes Beach · 13 guests

Bentley Pontoon on Anna Maria Island, Florida

5.0
$70/hour
Beautiful Deck Boat to Explore, Swim, Tube and more in AMI!
Powerboats in Holmes Beach · 9 guests

Beautiful Deck Boat to Explore, Swim, Tube and more in AMI!

4.9
$379+/day
 Starcraft 23ft Deck Boat for groups of up to 12! Enjoy Anna Maria in style!
Powerboats in Holmes Beach · 12 guests

Starcraft 23ft Deck Boat for groups of up to 12! Enjoy Anna Maria in style!

4.9
$113/hour
Brand New 10 Person Hurricane Deck Boat
Powerboats in Holmes Beach · 10 guests

Brand New 10 Person Hurricane Deck Boat

5.0
$63+/hour
Captained, Anna Maria sandbars from Jewfish to clothing optional Passage Key
Powerboats in Holmes Beach · 6 guests

Captained, Anna Maria sandbars from Jewfish to clothing optional Passage Key

New
$125+/hour
Instant Book
New 2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!
Powerboats in Holmes Beach · 8 guests

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

4.9
$372+/day
22' Bennington Pontoon in Holmes Beach
Powerboats in Holmes Beach · 12 guests

22' Bennington Pontoon in Holmes Beach

5.0
$80/hour

Longboat Key Reviews

  1. LM

    Lesley

    Captained 25' Regency Tritoon with Fuel Included

    Truly awesome day on the water with Shawn. Great communication. Easy directions for where to meet him. Impeccable boat that was so comfortable. Cooler with ice. Comfy floats. And great recommendations for our itinerary. Definitely booking with him again next year!

  2. JB

    Jennifer

    Captained 25' Regency Tritoon with Fuel Included

    Everything from the boat to the itinerary to Captain Shawn himself were more perfect than you could possibly imagine! He had the perfect day planned based on what we said we were looking for and he hit every mark. He made sure the kids had a day to remember and the adults got to relax! He even made sure we always had a drink in hand from the cooler we stuffed full of drinks and snacks. I cannot say enough wonderful things about Captain Shawn. He’s part of the family now and we’ll never book with anyone else. Thank you for the perfect day on the water! ❤️

  3. KL

    Kevin

    Super Comfy 22’ Pontoon in Bradenton/ fuel included

    Boat owner arrived early, was very friendly and answered all questions. Once we were underway, had a great day. We were somewhat limited on where we could go due to weather, but still plenty of great options. We would definitely take this boat out again!

  4. EM

    Elise

    Snorkeling, Sandbar Island Hopping, Manatees & Dolphins Tours

    We had the best day! Got to do a little if everything! Fishing, swimming, boat tour around the whole island! Mix up with departure time, totally no fault of Crystins Boat rental, but they honored my time anyway!! I would totally recommend this company to anyone! Clay the Captain was great!

  5. CM

    Clara

    Snorkeling, Sandbar Island Hopping, Manatees & Dolphins Tours

    Don’t hesitate! Our boat day was the highlight of our girls’ trip. Captain Marc was attentive to our needs and took care of every last detail. We learned so much about the area and he took us to see some really cool spots. Beyond happy with his service, communication and eagerness to make it a great day for us. We are already planning another boat day with him!

  6. EA

    Elizabeth

    Snorkeling, Sandbar Island Hopping, Manatees & Dolphins Tours

    I recently had the pleasure of going on a boat tour with Crysten's Boat Rentals and Private Tours, and I have to say it was an absolutely incredible experience. From start to finish, this boat company and captain(!) exceeded my expectations and provided a truly unforgettable adventure. One of the highlights of the trip was the stunning scenery we were able to take in from the boat. Captain Marc took us to some of the most beautiful spots along the coast, and we were able to see everything from stunning natural landmarks to picturesque coastal views. Captain Marc was knowledgeable, friendly, and went out of his way to make sure everyone on board was comfortable and having a great time. Overall, I would highly recommend Crysten's Boat Rentals and Private Tours to anyone looking for a memorable and exciting boat tour. The stunning scenery, and top-notch service make for an unforgettable experience that is sure to be a highlight of any vacation. Whether you're a seasoned boater or a first-time traveler, this boat company is definitely worth checking out!