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All listings in Clearwater

Great sailboat rentals near Clearwater, Florida.

Page 1 of 16 listings

Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht
Sailing in Saint Petersburg · 6 guests

Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

5.0
$205+/hour
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. Robert

    Robert

    Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

    If you're looking for a professional to take you sailing but you don't want it to feel like a tour boat, take a ride on Nick's personal boat. Bring along something cold to drink and enjoy the peace and quiet of being out on the water. My only regret is I should have made it a full day

  3. GM

    Gary

    Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

    Nick was a very experienced and knowledgeable skipper who truly welcomed us aboard. This is a beautiful sailing vessel that provides a fun, safe and comfortable ride for everyone aboard. We had a super trip with Nick and would love to book a whole day with him next time we are in town.

  4. 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.

  5. 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!

  6. 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**