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Explore Greetwell

Explore extraordinary experiences in 500+ destinations

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

    Water Activities in Siesta Key, FL

    Showing 97-120 of 532 results
    Self-Guided Kayak & Paddleboard Rental on Sarasota Bay

    Self-Guided Kayak & Paddleboard Rental on Sarasota Bay

    Paddle independently with guidance before you launch

    4.9 • 963 reviews
    $62/ rental
    Sarasota Sunset Tiki Boat Cruise

    Sarasota Sunset Tiki Boat Cruise

    Watch the Sarasota sunset from a private tiki boat

    5.0 • 71 reviews
    $934
    North Jetty Self-Guided Paddleboard Rental

    North Jetty Self-Guided Paddleboard Rental

    Set your own pace on a self-guided coastal paddle

    5.0 • 196 reviews
    $47/ paddleboard
    Private Mangrove Tunnel Kayak & Paddleboard Tour in Sarasota

    Private Mangrove Tunnel Kayak & Paddleboard Tour in Sarasota

    Paddle Lido Key mangrove tunnels with a private guide

    4.9 • 3.3K reviews
    $91/ kayak
    21' Bowrider Boat Rental in Sarasota
    Up to 9

    21' Bowrider Boat Rental in Sarasota

    Cruise Southwest Florida waterways with room to relax, swim, and sunbathe

    5.0 • 78 reviews
    $451& up
    Evening Mangrove Tunnel Kayak Tour at Emerson Point Preserve

    Evening Mangrove Tunnel Kayak Tour at Emerson Point Preserve

    Follow mangrove tunnels to the bay in search of manatees and dolphins

    5.0 • 88 reviews
    $58& up
    4.5-Hour Siesta Key Sandbar Charter

    4.5-Hour Siesta Key Sandbar Charter

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

    4.9 • 691 reviews
    $114
    Anna Maria Single Kayak Rental

    Anna Maria Single Kayak Rental

    Paddle Anna Maria canals or venture into Tampa Bay

    4.9 • 773 reviews
    $28/ kayak
    8-Hour Boat Charter in Bradenton Beach

    8-Hour Boat Charter in Bradenton Beach

    Design a private day of snorkeling, sandbars and island cruising

    5.0 • 122 reviews
    $1,045
    8-Hour Offshore Fishing Charter Anna Maria Island

    8-Hour Offshore Fishing Charter Anna Maria Island

    Private reef fishing for seasonal offshore catches

    5.0 • 100 reviews
    $1,166
    Yamaha Jet Ski Rental in Siesta Key

    Yamaha Jet Ski Rental in Siesta Key

    Ride new Yamaha jet skis across Florida's largest riding area at your own pace

    4.9 • 9.3K reviews
    $134& up
    Private 42' Sailing Catamaran Charter in Sarasota

    Private 42' Sailing Catamaran Charter in Sarasota

    Private 6–8 hour Bali 4.2 catamaran charter on Sarasota Bay

    4.9 • 517 reviews
    $3,522
    Full-Day Kayak & Paddleboard Rental in Sarasota

    Full-Day Kayak & Paddleboard Rental in Sarasota

    Paddle independently with a detailed itinerary and launch-site instruction

    4.9 • 963 reviews
    $73/ rental
    Sunset Tiki Boat Cruise in Sarasota

    Sunset Tiki Boat Cruise in Sarasota

    Cruise Sarasota’s Gulf Coast as the sun sets from a tiki boat

    5.0 • 71 reviews
    $88/ person
    Nokomis Double Kayak Rental

    Nokomis Double Kayak Rental

    Paddle Gulf Coast waters and explore nearby islands at your own pace

    5.0 • 196 reviews
    $59/ kayak
    Private Kayak or Paddleboard Tour in Siesta Key

    Private Kayak or Paddleboard Tour in Siesta Key

    Paddle Midnight Pass on a private Siesta Key kayak or paddleboard tour

    4.9 • 3.3K reviews
    $91/ person
    Private Inshore Fishing Charter in Holmes Beach

    Private Inshore Fishing Charter in Holmes Beach

    Explore inshore waters with fish cleaning included for your keeper catch

    5.0 • 67 reviews
    $622& up
    Mangrove Fishing Kayak Rental at Emerson Point Preserve

    Mangrove Fishing Kayak Rental at Emerson Point Preserve

    Paddle beneath mangroves and watch for coastal wildlife

    5.0 • 88 reviews
    $85/ kayak
    Cruise Siesta Key & Sarasota Sandbar on a 4.5-Hour Charter

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

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

    4.9 • 691 reviews
    $114
    Private Sunset Boat Tour on Anna Maria Island

    Private Sunset Boat Tour on Anna Maria Island

    Slow down on the water with a private sunset escape

    5.0 • 66 reviews
    $359
    Private Dolphin Tour & Snorkeling in Bradenton Beach

    Private Dolphin Tour & Snorkeling in Bradenton Beach

    Private sandbar snorkeling with chances to spot dolphins and marine life

    5.0 • 122 reviews
    $537
    4-Hour Fishing Charter From Holmes Beach

    4-Hour Fishing Charter From Holmes Beach

    Fish Tampa Bay or nearby reefs for a wide variety of local species

    5.0 • 100 reviews
    $741
    15-Minute Banana Boat Ride in Siesta Key

    15-Minute Banana Boat Ride in Siesta Key

    Cruise Siesta Key’s shoreline from a beachfront pickup point

    4.9 • 9.3K reviews
    $40
    Private 42' Sailing Catamaran Charter in Sarasota
    2 to 3

    Private 42' Sailing Catamaran Charter in Sarasota

    Enjoy a customizable luxury sail with captain and mate aboard a spacious 42-ft catamaran.

    4.9 • 517 reviews
    $2,489
    1…456…23
    Siesta Key Things To Do
    Boat Tours126Kayaking Tours91Boat Rentals88Yacht Charters64Fishing Charters58
    More
    • Jet Skiing40
    • Dolphin Watching32
    • Bike Rentals27
    • Car Rentals19
    • Snorkeling17
    • Sunrise and Sunset Tours17
    • Equipment Rental14

    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.

    Train Tours
    12
  • Paddleboarding10
  • Parasailing9
  • Scuba Diving9
  • Food Tours8
  • Ferries7
  • Helicopter Tours7
  • Stand Up Paddle Boarding7
  • Trolley Tours7
  • Bar and Pub Crawl6
  • Bike Tours5
  • Ghost and Haunted5
  • Historical Tours5