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The Best Sailboat Rentals Near Siesta Key
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Siesta Key
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$250-$1,525
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$45-$580
Fishing Charters
Let a captain do the driving while you do the fishing
$45-$240
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$40-$245
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$75-$245
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$90-$100
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$1,690
Top Sailboat Rental Locations Near Siesta Key
Recent Reviews in Siesta Key
Madelyn
Sailing From West Palm Beach, FL - $200/Hour - $33.33/Person
Captain Mark was very welcoming and talkative! he kept us entertained with jokes and stories. it was slightly chill that day but they had an enclosure that kept us toasty!!!
Alana
50ft Catamaran Charter with Water Toys - Deerfield/Boca Raton, FL
We had the absolute best time with Kristen and Darren! They went above and beyond for our bachelorette experience, all the gals and I spent the entire car ride home raving about how great they were and how much fun we had. From the boat to the service to the water activities, could not recommend them more!
RB
Russell
Sailing From West Palm Beach, FL - $200/Hour - $33.33/Person
Captain Mark is very knowledgeable and personable. He tailored our itinerary to our requests. His boat is comfortable and sails well. Highly recommended.
PS
Paige
Cabbage Key, Captiva Day Trip 1-6 people Captained
Wonderful trip. Made for the perfect afternoon activity for three couples of varying ages, smooth ride and a great value for seeing the views around the fort myers/Cape Coral area. Joe was extremely responsive and prompt to any questions/requests and made sure we were comfortable throughout our travels. Would recommend to anyone!
DD
David
Hunter 336 Sailboat! Relaxing Sailing Palm Beach
Great way to get out on the water in PB.
TN
TUNG
New 2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!
Definitely recommend. We showed up almost an hour late because we ended up going to wrong Marina and he still waited for us and was not mad at us for having him wait. He explained how to operate and was there to assist us when we came back to Marina to help us dock. Super nice gentleman and will definitely book again.
Top Sailboat Rental Locations in the United States
How To Book on Getmyboat
Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
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