Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    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
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /All experiences
    3. /Water Activities

    Best results for Water Activities in Siesta Key, FL

    Showing 169-192 of 381 results
    Rent a 21' Chaparral Deck Boat in Sarasota
    Boat RentalsUp to 10

    Rent a 21' Chaparral Deck Boat in Sarasota

    Cruise Sarasota on a 21 ft Chaparral with Bluetooth stereo and swim ladder

    Cruise Sarasota on a 21 ft Chaparral with Bluetooth stereo and swim ladder
    5.0 • 78 reviews
    $451/ boat
    23.5' Mako Center Console Boat Rental In Sarasota
    Boat RentalsUp to ten

    23.5' Mako Center Console Boat Rental In Sarasota

    Rent a 23.5 ft Mako center console for cruising or fishing in Sarasota

    Rent a 23.5 ft Mako center console for cruising or fishing in Sarasota
    5.0 • 78 reviews
    $429/ boat
    Sunset Kayak Tour in Osprey
    Kayaking Tours

    Sunset Kayak Tour in Osprey

    Paddle mangroves after sunset with LED-lit views beneath your kayak

    Paddle mangroves after sunset with LED-lit views beneath your kayak
    5.0 • 8 reviews
    $69/ person
    3-Hour Clear Kayak Rental in Osprey
    Kayaking Tours

    3-Hour Clear Kayak Rental in Osprey

    Explore the water at your own pace in a clear kayak

    Explore the water at your own pace in a clear kayak
    5.0 • 8 reviews
    $53/ person
    Osprey 22' Pontoon Boat Rental
    Boat RentalsUp to 10

    Osprey 22' Pontoon Boat Rental

    Cruise Sarasota Bay with your family or group on a fuel-included pontoon boat

    Cruise Sarasota Bay with your family or group on a fuel-included pontoon boat
    4.6 • 117 reviews
    $364/ boat
    Single Kayak Rental in Osprey
    Kayaking Tours

    Single Kayak Rental in Osprey

    Paddle southwest Florida waterways at your own pace

    Paddle southwest Florida waterways at your own pace
    4.6 • 117 reviews
    $32/ kayak
    Osprey Tandem Kayak Rental
    Kayaking Tours

    Osprey Tandem Kayak Rental

    Explore southwest Florida waterways by kayak with included paddles and life jackets

    Explore southwest Florida waterways by kayak with included paddles and life jackets
    4.6 • 117 reviews
    $46/ kayak
    Jet Ski Rentals in Osprey
    Jet Skiing

    Jet Ski Rentals in Osprey

    Ride a 110 hp jet ski with safety instruction, fuel, and life jackets included

    Ride a 110 hp jet ski with safety instruction, fuel, and life jackets included
    4.6 • 117 reviews
    $136/ jetski
    8-Hour Stand Up Paddle Board Rental in Osprey
    Stand Up Paddle Boarding

    8-Hour Stand Up Paddle Board Rental in Osprey

    Paddle Sarasota-area waterways at your own pace with included gear

    Paddle Sarasota-area waterways at your own pace with included gear
    4.6 • 117 reviews
    $40/ paddle board
    Sunset Jet Ski Tour in Osprey
    Jet Skiing

    Sunset Jet Ski Tour in Osprey

    Guided sunset jet skiing with room for your group

    Guided sunset jet skiing with room for your group
    4.6 • 117 reviews
    $325
    4.5-Hour Siesta Key Sandbar Charter
    Yacht Charters

    4.5-Hour Siesta Key Sandbar Charter

    Cruise Siesta Key’s western coast with time for dolphins, a sandbar stop, and a swim

    Cruise Siesta Key’s western coast with time for dolphins, a sandbar stop, and a swim
    4.9 • 691 reviews
    $114
    Cruise Siesta Key & Sarasota Sandbar on a 4.5-Hour Charter
    Boat Tours

    Cruise Siesta Key & Sarasota Sandbar on a 4.5-Hour Charter

    Spend 4.5 hours cruising, snorkeling stops, and sandbar time off Siesta Key

    Spend 4.5 hours cruising, snorkeling stops, and sandbar time off Siesta Key
    4.9 • 691 reviews
    $114
    Cruise Sarasota on a Private 2-Hour Charter
    Yacht Charters

    Cruise Sarasota on a Private 2-Hour Charter

    Leisurely 2-hour private cruise from Lido/Longboat Key with coolers and ice onboard

    Leisurely 2-hour private cruise from Lido/Longboat Key with coolers and ice onboard
    4.9 • 691 reviews
    $57
    2-Hour Private Cruise in Siesta Key
    Boat Tours

    2-Hour Private Cruise in Siesta Key

    Cruise Siesta Key’s western coast with your private group

    Cruise Siesta Key’s western coast with your private group
    4.9 • 691 reviews
    $57/ person
    Private 2-Hour Cruise in Siesta Key
    Boat Tours

    Private 2-Hour Cruise in Siesta Key

    Cruise Siesta Key’s western coast on a private 2-hour daytime or sunset boat ride

    Cruise Siesta Key’s western coast on a private 2-hour daytime or sunset boat ride
    4.9 • 691 reviews
    $57
    2-Hour Sunset Cruise in Sarasota
    Boat Tours

    2-Hour Sunset Cruise in Sarasota

    Plan a private coastal cruise with your own food and drinks

    Plan a private coastal cruise with your own food and drinks
    4.9 • 691 reviews
    $57/ person
    4.5-Hour Cruise in Bradenton Beach
    Boat Tours

    4.5-Hour Cruise in Bradenton Beach

    Customize a Gulf Coast cruise with sandbar swims and waterfront stops

    Customize a Gulf Coast cruise with sandbar swims and waterfront stops
    4.9 • 691 reviews
    $684
    Sarasota Private Cruise
    Boat Tours

    Sarasota Private Cruise

    Customize a private cruise along Florida's western coast

    Customize a private cruise along Florida's western coast
    4.9 • 691 reviews
    $114/ person
    2-Hour Cruise in Venice
    Boat Tours

    2-Hour Cruise in Venice

    Private coastal cruising with flexible routes and sunset options

    Private coastal cruising with flexible routes and sunset options
    4.9 • 691 reviews
    $57/ person
    Venice Sandbar Cruise
    Boat Tours

    Venice Sandbar Cruise

    Cruise Venice’s coast with time for dolphin searching, swimming, and waterfront stops

    Cruise Venice’s coast with time for dolphin searching, swimming, and waterfront stops
    4.9 • 691 reviews
    $114/ person
    Sarasota 4.5-Hour Sandbar Cruise
    Boat Tours

    Sarasota 4.5-Hour Sandbar Cruise

    Cruise coastal waters with time for a sandbar swim, waterfront stops, or an eco-focused outing

    Cruise coastal waters with time for a sandbar swim, waterfront stops, or an eco-focused outing
    4.9 • 691 reviews
    $114/ person
    Venice Shark Tooth Snorkel & Dive Tour
    Snorkeling

    Venice Shark Tooth Snorkel & Dive Tour

    Find prehistoric shark teeth while exploring Venice’s Boneyard

    Find prehistoric shark teeth while exploring Venice’s Boneyard
    4.8 • 466 reviews
    $112/ person
    Venice 4-Hour Scuba Refresher Course
    Scuba Diving

    Venice 4-Hour Scuba Refresher Course

    Rebuild scuba confidence with a skills refresher tailored to you

    Rebuild scuba confidence with a skills refresher tailored to you
    4.8 • 466 reviews
    $338/ person
    Guided Megalodon Fossil Shore Dive in Venice
    Scuba Diving

    Guided Megalodon Fossil Shore Dive in Venice

    Guided beach dive to search for Megalodon fossils

    Guided beach dive to search for Megalodon fossils
    4.8 • 466 reviews
    $191/ person
    1…789…16

    Travel guides for Water Activities

    13 Stunning Beaches in Florida With Clear Water You Need to Visit
    Best of Florida • 2026

    13 Stunning Beaches in Florida With Clear Water You Need to Visit

    Clarity is geology, not luck: quartz sand, seagrass filtration, and how close the Gulf Stream runs. Thirteen beaches, and the trade-off each one asks of you.

    Do You Need a License to Rent a Boat in Florida? Your Complete Guide
    Best of Florida • 2026

    Do You Need a License to Rent a Boat in Florida? Your Complete Guide

    Florida issues no boating license at all. What the marina checks is a safety education card, and whether you need one comes down to one date: January 1, 1988.