Black Pearl of Siesta Key

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Captain's Guided Tour

BRAND NEW! 4 Hours • $425 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!

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The best Siesta Key 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 5:30 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