Cookies!
We use cookies to improve your browsing experience. And dolphins make us happy. Find out more about our cookies policy here.
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
$260-$1,540
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$50-$565
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$70-$290
Fishing Charters
Let a captain do the driving while you do the fishing
$50-$265
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$50-$270
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
Rafting
A high-energy adventure for the whole family
$120
Kayaks
Who says you need a motor to have fun on the water?
$120
Top Sailboat Rental Locations Near Siesta Key
Recent Reviews in Siesta Key
TO
Tripp
Palm Beach FL: Private sailing, sighting-seeing and swimming with Capt Eric
Eric and his boat were outstanding! This was a highlight of our Newport vacation. My family (wife, daughters in their 20s) went sailing for 3-4 hours. Eric pointed out lots of famous sites and told us the history of Newport harbor. He let my daughter sail most of time (she's an experienced sailor). I highly recommend Eric!
Leah
Sunset Sails: Explore the Open Waters of Tampa, Florida
Such an amazing experience! From the day I inquired to the moment we got off the boat , Arlo was a great person and made the experience unforgettable! Highly recommend, you won’t regret it and you’ll have the best memories to hold on to. Thank you again!
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.
Lesley
New 2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!
Our experience renting from Meghan was excellent! The boat was great; clean and delivered on time with a full tank of gas. Meghan responded quickly to our initial request and communication was great throughout. We would definitely rent again from Meghan.
Christopher
New 2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!
Thanks again to Meghan and Martin for making our boat rental experience amazing from start to finish. The new boat was awesome and everything went exactly as planned. We will be using them again in the future and recommend them for a top notch experience as well.
KH
Kolleen
New 2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!
Meghan and Martin were absolutely wonderful. Their boat is beautiful and well equipped with everything you need for an outing. Martin gave us suggestions on where to go and honey holes for fishing. We appreciate everything and will definitely be back for a full day rental!
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!
Dive into Our Journal
August 01, 2023
10 Boating Adventures of a Lifetime
Read Article
October 03, 2022
Getmyboat's Guides to the World of Boating
Read Article
August 12, 2021
Caribbean Flavors on the Water in NYC - Book an Anchored & Chef'd Catered Cruise with Getmyboat!
Read Article
July 19, 2021
Sailing Charters on Lake Tahoe | Getmyboat
Read Article
December 30, 2019
South Africa Boating & Watersports Guide - Getmyboat
Read Article
December 26, 2019
Complete Fishing Guide to Southern California - GetMyBoat
Read Article
Real reviews from happy Getmyboaters.
4.9 out of 5! 500,000+ reviews
