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    1. Local experiences
    2. /All experiences
    3. /Water Activities

    Best results for Water Activities in Osprey, FL

    Showing 193-216 of 349 results
    Private Sandbar Charter in Sarasota
    Boat Tours

    Private Sandbar Charter in Sarasota

    Cruise Sarasota Bay your way, with time to unwind on a sandbar

    Cruise Sarasota Bay your way, with time to unwind on a sandbar
    5.0 • 55 reviews
    $1,314& up
    Cruise Sarasota on a 22' Pontoon Boat Rental
    Boat RentalsUp to 13

    Cruise Sarasota on a 22' Pontoon Boat Rental

    Rent a 22' Bentley pontoon and cruise Sarasota’s Intracoastal waterways

    Rent a 22' Bentley pontoon and cruise Sarasota’s Intracoastal waterways
    5.0 • 78 reviews
    $480/ boat
    21' Tritoon Boat Rental in Sarasota
    Boat RentalsUp to 10

    21' Tritoon Boat Rental in Sarasota

    Cruise Sarasota’s intracoastal waterways on a 21' Bennington tritoon for up to 10

    Cruise Sarasota’s intracoastal waterways on a 21' Bennington tritoon for up to 10
    5.0 • 78 reviews
    $480/ boat
    24' Sea Ray Sundeck Boat Rental in Sarasota
    Boat RentalsUp to 9

    24' Sea Ray Sundeck Boat Rental in Sarasota

    Rent a 24' Sea Ray SunDeck to explore Sarasota waterways and sandbars

    Rent a 24' Sea Ray SunDeck to explore Sarasota waterways and sandbars
    5.0 • 78 reviews
    $537/ boat
    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
    $463/ 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
    $509/ boat
    Guided Kayak & Food Tour in Sarasota
    Kayaking Tours

    Guided Kayak & Food Tour in Sarasota

    Paddle Sarasota Bay, then taste your way through downtown

    Paddle Sarasota Bay, then taste your way through downtown
    4.9 • 63 reviews
    $203/ person
    Lakewood Ranch 12-Person Pontoon Boat Rental
    Boat RentalsUp to 12

    Lakewood Ranch 12-Person Pontoon Boat Rental

    Cruise with Bluetooth audio, a swim ladder, and fishing-ready features

    Cruise with Bluetooth audio, a swim ladder, and fishing-ready features
    5.0 • 16 reviews
    $280/ boat
    Sunset Kayak Tour on Anna Maria Island
    Kayaking Tours

    Sunset Kayak Tour on Anna Maria Island

    Paddle to sandbars and a secluded beach for Gulf sunset views

    Paddle to sandbars and a secluded beach for Gulf sunset views
    4.9 • 167 reviews
    $69/ kayak
    Bradenton Mangrove Kayak Tour
    Kayaking Tours

    Bradenton Mangrove Kayak Tour

    Paddle Sarasota Bay’s mangrove tunnels and look for seasonal birdlife

    Paddle Sarasota Bay’s mangrove tunnels and look for seasonal birdlife
    4.9 • 167 reviews
    $58/ kayak
    Guided Kayak Tour of Emerson Point Mangroves
    Kayaking Tours

    Guided Kayak Tour of Emerson Point Mangroves

    Paddle mangrove tunnels and explore sandbars in Terra Ceia Bay

    Paddle mangrove tunnels and explore sandbars in Terra Ceia Bay
    4.9 • 167 reviews
    $58/ kayak
    Englewood Fishing Charter
    Fishing Charters

    Englewood Fishing Charter

    Cast for snapper, grouper, sharks and more on a private fishing trip

    Cast for snapper, grouper, sharks and more on a private fishing trip
    4.7 • 54 reviews
    $1,308& up
    4-8 Hour Pontoon Rental in Holmes Beach
    Boat RentalsUp to 12

    4-8 Hour Pontoon Rental in Holmes Beach

    Cruise sandbars and island stops on your own schedule

    Cruise sandbars and island stops on your own schedule
    5.0 • 225 reviews
    $452/ boat
    Holmes Beach Pontoon Boat Rental
    Boat RentalsUp to 12

    Holmes Beach Pontoon Boat Rental

    Cruise, swim, and island hop on a fully loaded pontoon

    Cruise, swim, and island hop on a fully loaded pontoon
    5.0 • 225 reviews
    $452/ boat
    Jet Ski Rental on Anna Maria Island
    Jet Skiing

    Jet Ski Rental on Anna Maria Island

    Speed, sightseeing, and flexible time on the water

    Speed, sightseeing, and flexible time on the water
    5.0 • 225 reviews
    $177/ jet ski
    Parasailing Flight in Englewood
    Parasailing

    Parasailing Flight in Englewood

    Fly solo, double, or triple on a parasail flight

    Fly solo, double, or triple on a parasail flight
    5.0 • 914 reviews
    $112/ person
    Englewood 90HP Pontoon Rental
    Boat RentalsUp to 11

    Englewood 90HP Pontoon Rental

    Cruise, fish, shell, or picnic aboard a 90HP pontoon

    Cruise, fish, shell, or picnic aboard a 90HP pontoon
    4.8 • 31 reviews
    $367/ boat
    Englewood 90HP Pontoon Boat Rental
    Boat RentalsUp to 9

    Englewood 90HP Pontoon Boat Rental

    Cruise Lemon Bay and stop at Stump Pass on a family-friendly pontoon

    Cruise Lemon Bay and stop at Stump Pass on a family-friendly pontoon
    4.8 • 31 reviews
    $367/ boat
    Lemon Bay Skiff Rental
    Boat RentalsUp to 6

    Lemon Bay Skiff Rental

    Fish and cruise Lemon Bay’s backwaters aboard a 50HP skiff

    Fish and cruise Lemon Bay’s backwaters aboard a 50HP skiff
    4.8 • 31 reviews
    $257/ boat
    Englewood 21' Fishing Boat Rental
    Boat RentalsUp to 6

    Englewood 21' Fishing Boat Rental

    A fishing-ready center console for bridges and beaches around Manasota Key

    A fishing-ready center console for bridges and beaches around Manasota Key
    4.8 • 31 reviews
    $385/ boat
    Manasota Key Bayliner Deck Boat Rental
    Boat RentalsUp to 8

    Manasota Key Bayliner Deck Boat Rental

    Cruise Manasota Key with shade, storage and Bluetooth sound

    Cruise Manasota Key with shade, storage and Bluetooth sound
    4.8 • 31 reviews
    $367/ boat
    Kayak & Paddleboard Rental on Longboat Key
    Paddleboarding

    Kayak & Paddleboard Rental on Longboat Key

    Rent a kayak or paddleboard for 4 hours with gear, route map, and lesson

    Rent a kayak or paddleboard for 4 hours with gear, route map, and lesson
    5.0 • 926 reviews
    $62/ kayak
    3-Hour Guided Wildlife Kayak Tour on Longboat Key
    Kayaking Tours

    3-Hour Guided Wildlife Kayak Tour on Longboat Key

    Paddle between Anna Maria Island and Longboat Key with a guided wildlife-focused route

    Paddle between Anna Maria Island and Longboat Key with a guided wildlife-focused route
    5.0 • 926 reviews
    $73/ kayak
    4-Hour Kayak & Paddleboard Rental on Longboat Pass
    Kayaking Tours

    4-Hour Kayak & Paddleboard Rental on Longboat Pass

    Paddle Longboat Pass for 4 hours with a map and basic lesson

    Paddle Longboat Pass for 4 hours with a map and basic lesson
    5.0 • 926 reviews
    $51/ kayak
    1…8910…15

    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.