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All listings in Clearwater

Great sailboat rentals near Clearwater, Florida.

Page 1 of 110 listings

Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete
Sailing in Saint Petersburg · 6 guests

Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

5.0
$238+/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
$59/hour
Day Sails and Sunset Cruises in Downtown St. Petersburg,  44' Morgan Sailboat
Sailing in Saint Petersburg · 6 guests

Day Sails and Sunset Cruises in Downtown St. Petersburg, 44' Morgan Sailboat

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
Beautiful 45’ Sailboat - Private Charter
Sailing in Madeira Beach · 6 guests

Beautiful 45’ Sailboat - Private Charter

5.0
$225/hour
45' Luxury Sailing Catamaran Charter
Sailing in Saint Petersburg · 6 guests

45' Luxury Sailing Catamaran Charter

5.0
$300+/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. AL

    Amy

    Beautiful 45’ Sailboat - Private Charter

    Loved how beautiful the boat is, and the opportunity to learn more about sailing, and other adventures that they offer like yoga on an island, night adventures out into the Gulf to see celestial events, sailing school and more.

  2. CG

    Casey

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

    Richard was great and was very quick with getting back to us! Made our first experience on this site wonderful! Had a great time and the boat and price were perfect.

  3. KG

    Kelly

    Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

    This was a wonderful experience! Full run of the boat! Jonas was great with a lot of little extra touches from snacks to a full stocked fridge of non alcoholic beverages! I highly recommend! Made my birthday a great day!

  4. MO

    Milena

    Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

    Had an amazing time on this charter today! The crew was incredibly nice, communicated everything clearly, and made the whole experience easy and enjoyable from start to finish!! The trip itself was fantastic, and you can tell they really care about their guests having a great time. I would absolutely recommend this boat to anyone looking for a fun and stress-free experience on the water!

  5. TE

    Tate

    Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

    Jonas and Captain Carlos took top care of my family and I! I was so impressed with the amenities and cleanliness of the boat. They were both extremely knowledgeable about the area and sailing in whole. My nephew had a blast and they showed him patience and earned the respect of an 8 year old in addition to all of the "adults". Thank you so much, Jonas and Captain Carlos!

  6. SL

    Samantha

    Luxury Bali 4.2 Catamaran | All-Inclusive 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.