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Explore Greetwell

Explore extraordinary experiences in 500+ destinations

What's trending

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Rentals & Charters

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Questions? We're here to help.Real people, 7 days a week.

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  • 13 Stunning Beaches in Florida With Clear Water You Need to Visit
  • Best results for

    Water Activities in Longboat Key, FL

    Showing 481-504 of 762 results
    Sunset Boat Rental in Tierra Verde

    Sunset Boat Rental in Tierra Verde

    Private evening boating with beach views and Skyway Bridge access

    4.7 • 435 reviews
    $403/ boat
    22' Center Console Boat Rental in St. Pete Beach
    4 to 5

    22' Center Console Boat Rental in St. Pete Beach

    Fish or cruise with a 225 HP center console and onboard navigation

    4.7 • 435 reviews
    $45/ boat
    Bring-Your-Own-Drinks Tiki Boat Tour in Treasure Island

    Bring-Your-Own-Drinks Tiki Boat Tour in Treasure Island

    Relax on the Gulf with your own drinks and coolers ready on board

    4.7 • 232 reviews
    $69/ person
    Corvette-Inspired Jetcar Rental in Bradenton

    Corvette-Inspired Jetcar Rental in Bradenton

    Cruise Palma Sola Bay in a Corvette-inspired watercraft that handles like a jet ski

    5.0 • 11 reviews
    $202/ jetcar
    20' Deck Boat Rental in Venice, FL for Gulf & ICW
    Up to 10

    20' Deck Boat Rental in Venice, FL for Gulf & ICW

    Rent a 20' deck boat with Bluetooth stereo for up to 10 passengers

    4.7 • 153 reviews
    $434/ boat
    21' Deck Boat Rental in Venice, Florida
    Up to 10

    21' Deck Boat Rental in Venice, Florida

    Rent a 21' deck boat for up to 10 and cruise the Intracoastal Waterway or Gulf

    4.7 • 153 reviews
    $434/ boat
    22' Pontoon Boat Rental in Venice, FL
    Up to 12

    22' Pontoon Boat Rental in Venice, FL

    Cruise the Intracoastal Waterway on a 22' pontoon, up to 12 passengers

    4.7 • 153 reviews
    $463/ boat
    26' Panga Fishing & Dive Boat Rental in Venice, FL
    Up to 6

    26' Panga Fishing & Dive Boat Rental in Venice, FL

    Rent a 26' Panga for fishing or diving, up to 6 passengers

    4.7 • 153 reviews
    $434/ boat
    Explore Venice, FL by Kayak Rental

    Explore Venice, FL by Kayak Rental

    Rent a single or double kayak for 4 or 8 hours

    4.7 • 153 reviews
    $52/ kayak
    20' Deck Boat Rental in Venice, FL for Gulf & Intracoastal
    Up to 10

    20' Deck Boat Rental in Venice, FL for Gulf & Intracoastal

    Rent a 20' deck boat for up to 10 passengers on the Intracoastal Waterway or Gulf

    4.7 • 153 reviews
    $434/ boat
    Deckboat Rental in Venice, FL
    Up to 10

    Deckboat Rental in Venice, FL

    Rent a 22’ deckboat for up to 10 and cruise the Intracoastal Waterway or Gulf

    4.7 • 153 reviews
    $463/ boat
    Pontoon Boat Rental in Venice, FL (ICW Only)
    Up to 12

    Pontoon Boat Rental in Venice, FL (ICW Only)

    Rent a 22’ pontoon for up to 12 on the Intracoastal Waterway

    4.7 • 153 reviews
    $463/ boat
    22' Pontoon Boat Rental on the Intracoastal in Venice
    Up to 12

    22' Pontoon Boat Rental on the Intracoastal in Venice

    Rent a 22’ pontoon for up to 12 on the Intracoastal Waterway

    4.7 • 153 reviews
    $463/ boat
    22' Pontoon Boat Rental in Venice
    Up to 12

    22' Pontoon Boat Rental in Venice

    Rent a 22’ pontoon for up to 12 on the Intracoastal Waterway

    4.7 • 153 reviews
    $463/ boat
    Private Sandbar & Shelling Boat Charter in Gulfport

    Private Sandbar & Shelling Boat Charter in Gulfport

    Enjoy the Gulf with your own group, not a shared tour boat

    5.0 • 11 reviews
    $689
    Private Sunset Catamaran Cruise in Gulfport

    Private Sunset Catamaran Cruise in Gulfport

    Enjoy a Gulf sunset with the whole boat to yourselves

    5.0 • 11 reviews
    $477
    Private Family-Friendly Fishing Charter in Gulfport

    Private Family-Friendly Fishing Charter in Gulfport

    Cast a line with the family, with fishing gear included

    5.0 • 11 reviews
    $1,802
    Private Sunset & Sunshine Skyway Bridge Cruise in Gulfport

    Private Sunset & Sunshine Skyway Bridge Cruise in Gulfport

    Watch the Gulf sunset, then cruise beneath the Skyway's accent lights

    5.0 • 11 reviews
    $689
    Private Full-Day Offshore Fishing Charter in Gulfport

    Private Full-Day Offshore Fishing Charter in Gulfport

    Enjoy a twin-hull ride to Florida's offshore fishing grounds

    5.0 • 11 reviews
    $2,650
    Private Full-Day Nearshore Fishing Charter in Gulfport

    Private Full-Day Nearshore Fishing Charter in Gulfport

    Head straight into the Gulf for fishing up to 30 miles offshore

    5.0 • 11 reviews
    $2,014
    Jet Ski Rental on Roberts Bay & the Gulf in Venice, FL

    Jet Ski Rental on Roberts Bay & the Gulf in Venice, FL

    Choose a faster ride or a scenic cruise on the water

    4.7 • 153 reviews
    $136/ jet-ski
    Private Family-Friendly Fishing Charter in St. Petersburg

    Private Family-Friendly Fishing Charter in St. Petersburg

    Share a fishing outing for all ages

    5.0 • 10 reviews
    $795& up
    Private Family-Friendly Fishing Charter in St. Petersburg

    Private Family-Friendly Fishing Charter in St. Petersburg

    Share a fishing outing with the whole family

    5.0 • 10 reviews
    $583& up
    Private Boat Charter in St. Petersburg

    Private Boat Charter in St. Petersburg

    Cruise St. Pete waterways with sandbar stops, swimming, and island exploring

    5.0 • 9 reviews
    $226& up
    1…202122…32
    Longboat Key Things To Do
    Boat Tours205Fishing Charters108Kayaking Tours107Boat Rentals100Yacht Charters90
    More
    • Dolphin Watching47
    • Jet Skiing46
    • Bike Rentals36
    • Snorkeling29
    • Sunrise and Sunset Tours21
    • Car Rentals20
    • Sailing18

    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.

    Paddleboarding
    16
  • Equipment Rental14
  • Train Tours12
  • Bike Tours10
  • Food Tours9
  • Parasailing9
  • Scuba Diving8
  • Stand Up Paddle Boarding8
  • Ferries7
  • Helicopter Tours7
  • Scooter Rentals7
  • Trolley Tours7
  • Bar and Pub Crawl6