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All listings in Clearwater

Great sailboat rentals near Clearwater, Florida.

Page 1 of 15 listings

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat
Sailing in Saint Pete Beach · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

5.0
$110/hour
Instant Book
Set Sail aboard the Most Photographed Boat in the Tampa Bay Region!
Sailing in Treasure Island · 28 guests

Set Sail aboard the Most Photographed Boat in the Tampa Bay Region!

New
$695/hour
Set Sail on a Suncoast Escapade!
Sailing in Treasure Island · 6 guests

Set Sail on a Suncoast Escapade!

New
$225/hour
St. Pete Sunset Sails - 34ft Sailboat
Sailing in Saint Petersburg · 4 guests

St. Pete Sunset Sails - 34ft Sailboat

New
$160/hour
22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!
Powerboats in Bay Pines · 10 guests

22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

4.7
Snoozed - Active 02 Jan 2026

Sailing Reviews in Clearwater

  1. LP

    Leeann

    Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

    Oleg was an awesome captain! He went above and beyond to accommodate us!

  2. CC

    Christine

    22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

    Richard was prompt and affordable. We really enjoyed our day out. There should be mention of the wear and tear on the boat and the fact that the depth finder was broken. Kind of an issue when navigation in such shallow water. Luckily we have experience with that but those who do not may have an issue.

  3. CB

    Christine

    22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

    Great value and very efficient communication. The day we rented a boat was very windy. Richard provided a pontoon with a higher horsepower motor - it made our day much more enjoyable. We will definitely reach out to rent from Richard next time we are in FLA!

  4. LS

    Leighanna

    22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

    My family and I had a blast! we celebrated my birthday and this was an awesome time. Richard was quick to respond, fantastic price point, made drop off and pick up so easy, and all around amazing great guy. Don't hesitate to book as you will be thrilled that you did! **Remember an aux cord to hook up your device to listen to music**

  5. DA

    Diana

    22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

    As advertised and better. Perfect experience all around. We saw dolphins, spent time on sand bars and drove around sunny waters. The two shades were a lifesaver. The boat is surprisingly fast and comfortable. Highly recommend!

  6. Jeremy

    Jeremy

    22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

    Everything worked out great. Very easy process leaving the boat ramp and coming back. Lots of shade which really helps. We anchored at the sandbar on our trip. Max speed is around 13mph with full capacity.