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Black Pearl of Siesta Key

Your Siesta Key / Sarasota Pontoon Boat Rentals

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Captain's Guided Tour

BRAND NEW! 4 Hours • $495 all inclusive

Don’t want to explore Siesta Key alone? Let our USCG licensed captain take you on a tour through the canals of the Key!

Captain Guided Tour Image 1

Siesta Key Best Pontoon Boat Rentals & Tours

Awaiting you when you arrive in Siesta Key is an absolute blast of fun. Now you can arrange to have the Black Pearl pontoon boats at your disposal if staying at any of the Cottages Vacation Homes. For all properties, you can reserve the boat for one day, or for waterfront properties, we also offer three or six consecutive days at your dock (Please note: Longer pontoon rentals on your dock require a Sunday or Wednesday start day).

All Siesta Key pontoon rentals begin around 9 a.m. on boat delivery and end at 5:00 p.m. on the last day of your selected dates. You are free to use the Black Pearls anywhere in the canal systems and waterway/inshore areas (not allowed in Gulf of Mexico). USCG licensed Captain available for your Siesta Key adventure.

Rave Customer Reviews

“We had a great experience renting from Black pearl. Larry is very helpful and can tell you a the great spots to check out in the area. Can’t wait to come back and see more of siesta key and the surrounding area from one of black pearls boats.”

-Paul C.

“Rented on of the Black Pearls for a day on Sunday. After a cruise up the waterway, we anchored on one of the sandbars and spent the day enjoying the water and friends. Great day, great time, great boat. Look forward to doing it again real soon. You just don’t get to see Siesta Key fully until you see it from the water. FIVE STAR deal.”


“Larry was very accommodating and very helpful throughout the process. He delivered the boat, gave very helpful recommendations, and went above and beyond to make our experience the best. The boat was beautiful, comfortable and impeccably kept. I definitely wouldn’t hesitate to do this again!”

-Hutchins Family

We booked a guided tour with Larry to celebrate family birthdays. The boat was beautiful, clean, and had plenty of room to accommodate our group with our coolers and bags. We stopped at a beach, a tiki bar, and a shaded picnic spot for lunch. We saw manatees, dolphins, birds, waterfront homes and landmarks. Larry was personable, knowledgeable, and accommodating. We could not have asked for a better day on the water! Thanks to Larry for making our family’s birthdays special!! I highly recommend the Black Pearl and can’t wait to book our next trip!

Brandy W.

Larry is THE BEST! We had the most amazing fun time on his pontoon boat! We were in Siesta for a bachelorette party! Larry drove us around the water. We had an amazing time on his boat. the boat was nice, new, and well kept. Larry was such a great host! He was knowledgeable and accommodating for all of us. I highly recommend!!


Hi Capt. Larry, We appreciate you for showing us some southern hospitality. I remember you mentioned that you were fully booked until next week but was still able to accommodate us yesterday. We love the pontoon boat we rented from you. The quality of the boat, the leather seating, the electric cockpit with gps and depth finder made our excursion comfortable and safe. The boat trip was the highlight of our vacation in siesta keys. We enjoyed all the places that you recommended for us to see. If we ever head back your way, we will definitely use your service again and will for sure recommend your company to others. Thank you so much, Will from Folsom, California


Rented from THE Black Pearl – all I can say what a day. We rented a pontoon boat for the day. Capt. Larry was very helpful and through going over the operations of the boat with an emphasis on safety. He will put you at ease if you have not driven a Pontoon boat before. Capt Larry gives great advice on places to stop along the Siesta Key inter-costal. Boat was in great conditions – no issues at all. If you are looking for something to do for a day – this is the way to go!!! Thanks Capt. Larry The Fox Family – Chicago GO HAWKS GO!!!

J Fox

We were a group of crazy Canadian’s staying at the Cottages on the Key and spend an unforgettable day with Captain Larry. The boat was super clean and Larry went above and beyond to make us feel welcome. We all agreed it was a highlight of our vacation and seeing the area from the water provides a whole new experience. We have been to Siesta Keys before and this was our first boat tour. Would highly recommend Black Pearl and using Larry to provide a guided tour. Thank you again “Uncle” Larry for making our day on the water so special! (Your Nova Scotia Kid’s)

Darlene Stevensen