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All listings in Clearwater

Great sailboat rentals near Clearwater, Florida.

Page 1 of 110 listings

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
$49/hour
Luxury Bali 4.2 Catamaran | Private Charters in St. Pete
Sailing in Saint Petersburg · 6 guests

Luxury Bali 4.2 Catamaran | Private Charters in St. Pete

5.0
$170+/hour
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
$206+/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
45' Luxury Sailing Catamaran Charter
Sailing in Saint Petersburg · 6 guests

45' Luxury Sailing Catamaran Charter

5.0
$300+/hour
Beautiful 45’ Sailboat - Private Charter
Sailing in Madeira Beach · 6 guests

Beautiful 45’ Sailboat - Private Charter

New
$225/hour
Day Sails & Sunset Cruises – Downtown St. Petersburg, FL – 36’ Catalina Yacht
Sailing in Saint Petersburg · 6 guests

Day Sails & Sunset Cruises – Downtown St. Petersburg, FL – 36’ Catalina Yacht

New
$206+/hour
40’ Fountaine Pajot Sailing Catamaran - Explore the Beauty of Tampa Bay
Sailing in Saint Petersburg · 12 guests

40’ Fountaine Pajot Sailing Catamaran - Explore the Beauty of Tampa Bay

New
$350+/hour
Beautiful 45’ Sailboat - Private Charter
Sailing in Madeira Beach · 6 guests

Beautiful 45’ Sailboat - Private Charter

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

St. Pete Sunset Sails - 34ft Sailboat

New
$160/hour

Sailing Reviews in Clearwater

  1. SL

    Samantha

    Luxury Bali 4.2 Catamaran | Private Charters in St. Pete

    Words can’t explain how phenomenal our trip was on the boat and with Jonas and his captain Carlos. Professional when setting/booking and organizing the plans, timely with responses and boat from heaven!!! I will book with Jonas everytime and if you don’t you will surely miss out on a lifelong memory and experience in a clean, warm and friendly environment. Can’t wait to book again with you guys. They were also flexible with any requests.

  2. Emma

    Emma

    Luxury Bali 4.2 Catamaran | Private Charters in St. Pete

    Sure! Here’s a more concise version of the review: --- Our catamaran rental was wonderful! The boat had all the amenities, with clean restrooms and a spacious salon that made our experience comfortable. The quality music system added to the fun, letting us enjoy our favorite tunes while cruising. Jonas was amazing. He tailored the trip to our desires, ensuring we had the best possible time on the water. Highly recommend this experience for anyone looking to enjoy a fantastic day at sea!

  3. Andrea

    Andrea

    Luxury Bali 4.2 Catamaran | Private Charters in St. Pete

    Don’t hesitate, book now! We had an incredible day on Jonas’ boat and what a gorgeous boat. “Wow” was our first reaction. Tons of space and immaculate! We had everything we needed and more. We were very thankful for the nice towels provided and the huge fridge to keep our food and drinks. Wonderful crew, super friendly, knowledgeable and made us feel at home! Incredible boat! Incredible team! Incredible experience! Thank you again Jonas and crew! Can’t wait to book again ! 100/10 and 6 stars!

  4. stephen

    stephen

    Luxury Bali 4.2 Catamaran | Private Charters in St. Pete

    We had the BEST time. First off, Jonas is just an all around nice and polite and respectful and solid guy…As is captain Craig. I’ve rented several 60ft plus yachts before but this was by far the best experience. The catamaran is large and seemed like a home. There were multiple washrooms which were very clean. It’s obvious that Jonas takes a deep level of pride in the service he offers. While I only had a party of 2, the catamaran is probably capable of holding 2 dozen people. The boat is utterly amazing and offers spectacular views from anywhere. I thought that Jonas and captain Craig (captain make it happin' )were the best! we honestly had the most fun...truly one of the best days ever and they clearly went out of their way to make sure we had a great day. Everything they did was 10/10. Jonas is doing everything right and I will definitely come back! one day on the catamaran was by far well worth the drive down from Canada! 🇨🇦 Thank you for the time and experience! :)

  5. PA

    Poorna

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

    We had an amazing time on the pontoon boat, and it was a perfect experience for our family. The boat was clean, comfortable, and very well maintained. Richard was extremely friendly and took the time to explain everything clearly about the boat and the surroundings, which made us feel confident and relaxed. Life vests were available for everyone, which was especially reassuring for families with kids. The ride was smooth, enjoyable, and safe, allowing us to fully enjoy our time together. Overall, it was a fantastic family experience, and we truly appreciated Richard’s professionalism and kindness. Highly recommended for families looking for a fun and stress-free outing on the water!

  6. 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.