Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Siesta Key…
    3. /Water Activities
    4. /Boat Rentals
    5. /Siesta Key 27' Pontoon Boat Rental
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Destinations
    • Categories
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Gallery image

    Siesta Key 27' Pontoon Boat Rental

    Cruise Sarasota Bay and the Intracoastal with room for up to 14

    4.8 stars• 1.2K reviews

    Duration

    9 hrs

    Ideal For

    Up to 14 people

    Includes

    Boat, cooler, safety equipment

    Highlights

    Explore Sarasota Bay and Intracoastal waterways aboard a spacious 27-foot Berkshire pontoon boat. Cruise with friends or family, relax in the shade, and watch for dolphins and manatees.

    • Explore Sarasota Bay and Intracoastal waterways
    • Relax beneath the bimini top for shade
    • Bring your pet onboard
    • Store your gear in onboard compartments
    • Plan a fishing trip or a leisurely cruise

    What's Included

    • Bimini top
    • Coast Guard equipment and nautical charts
    • Storage compartments
    • Cooler

    Important details

    • Ages 26+ to rent
    • Requires at least two years of experience operating a similar vessel within 10 feet of this boat’s size
    • No marine losses in the past 10 years, violations or suspensions in the past 5 years, or criminal convictions or no-contest pleas
    • Bring a valid driver’s license at check-in
    • Renters born after January 1, 1988 require a boater’s license by law
    • All passengers must sign a release waiver
    • Navigation is limited to the Intracoastal and Sarasota Bay; Gulf of Mexico use is not permitted
    • Stay no farther north than the south end of Longboat Key or farther south than the Venice Jetties
    • Renters are responsible for property damage and liable for injuries to themselves and passengers
    Split the cost with your group

    This booking is for the whole experience, which fits up to 14 guests.

    From$48per person
    Split with

    Cancellation Policy

    Receive a full refund with at least 48 hours' notice of cancellation. Full refund if the operator cancels due to weather. No-shows are charged the full price.

    Product ID: TVDWX9

    FAQs

    Bring a fishing hat, sunscreen, polarized sunglasses, and boat shoes or sneakers with light-colored soles. You may also want a phone or camera.

    Use the onsite parking spots or free valet at Daiquiri Deck Restaurant. Do not park in the paid lot next to CB's.

    Renters born after January 1, 1988 need a boater's license. If you do not have one, you can take a free test using the link in your confirmation email.

    Meeting details

    CB's Saltwater Outfitters, 1249 Stickney Point Rd., Siesta Key, FL 34242

    Experience provided by CB's Saltwater Outfitters

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Full Day Rental

    $676.87

    This boat fits up to 14 guests · 9 hrs

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    What people are saying

    Review 1 of 3
    5/5

    ETHAN was amazing and helped spool my new extra heavy rod. I hope i can catch some bluegill on it!

    Photo of Harrison Kennedy

    Harrison Kennedy

    August 23, 2026

    Review 1 of 1
    5/5

    ETHAN was amazing and helped spool my new extra heavy rod. I hope i can catch some bluegill on it!

    Photo of Harrison Kennedy

    Harrison Kennedy

    August 23, 2026

    Nearby activities

    Sunset Tiki Boat Tour in Siesta Key
    Boat Tours

    Sunset Tiki Boat Tour in Siesta Key

    Enjoy a relaxed evening cruise along Siesta Key with music, LED lights and possible dolphin sightings.

    5.0 • 10.3K reviews
    $73/ person
    Guided Kayak Tour to Midnight Pass Beach in Siesta Key
    Kayaking Tours

    Guided Kayak Tour to Midnight Pass Beach in Siesta Key

    Paddle Jim Neville Marine Preserve to water-only Midnight Pass Beach

    4.9 • 3.2K reviews
    $61/ kayak
    Dolphin Watching Sunset Cruise in Siesta Key
    Dolphin Watching

    Dolphin Watching Sunset Cruise in Siesta Key

    Watch playful dolphins and a vibrant Gulf sunset while enjoying complimentary beer and wine.

    4.9 • 9.2K reviews
    $90/ person
    Lido Key Mangrove Kayak & Paddleboard Rental
    Stand Up Paddle Boarding

    Lido Key Mangrove Kayak & Paddleboard Rental

    Explore Lido Key’s mangrove tunnels with included gear, map, and a brief lesson

    5.0 • 658 reviews
    $51/ kayak
    Beach Horseback Ride & Swim in Palma Sola Bay, Bradenton
    Horseback Riding

    Beach Horseback Ride & Swim in Palma Sola Bay, Bradenton

    Ride a gentle horse along the sand, then cool off with a unique swim in Palma Sola Bay.

    4.9 • 470 reviews
    $164/ person
    Siesta Key Tiki Boat Tour with Music & Drinks
    Boat Tours

    Siesta Key Tiki Boat Tour with Music & Drinks

    Cruise Siesta Key’s waterways on a 2024 tiki boat with music, drinks and coastal wildlife views.

    5.0 • 10.3K reviews
    $53/ person