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Best results for

Water Activities in Osprey, FL

Showing 289-312 of 395 results
Jet Ski Rental with Bluetooth Audio in Bradenton

Jet Ski Rental with Bluetooth Audio in Bradenton

Ride to your own soundtrack with waterproof Bluetooth audio

$87/ watercraft
Sunrise Jet Ski Tour in Bradenton

Sunrise Jet Ski Tour in Bradenton

Head out at sunrise on your choice of two Sea-Doo models

$436/ ski
Sunset Jet Ski Tour in Bradenton

Sunset Jet Ski Tour in Bradenton

Take to the water on a 2025 Sea-Doo for an evening ride

$436/ jet-ski
Jet Ski Rental in Bradenton on a Sea-Doo Spark Trixx

Jet Ski Rental in Bradenton on a Sea-Doo Spark Trixx

Try water acrobatics with a jet ski built for tricks

$76/ watercraft
37' Luxury Boat Charter Near Bradenton

37' Luxury Boat Charter Near Bradenton

Customize a luxury day on the water for swimming, fishing, sightseeing, or celebrations

4.0 • 1 reviews
$907& up
Private Inshore Sport Fishing Charter

Private Inshore Sport Fishing Charter

Fish inshore with a US Coast Guard licensed captain on a private boat

$610& up
Tritoon Boat Rental in Holmes Beach
Up to 13

Tritoon Boat Rental in Holmes Beach

Cruise Holmes Beach waters on a 13-passenger tritoon with shade and wrap-around seating

$480& up
Pontoon Boat Rental in Holmes Beach
Up to 12

Pontoon Boat Rental in Holmes Beach

Rent a boat for 4 hours to 7 days, with space for up to 12 passengers

$509& up
Private Beach Cat Boat Tour

Private Beach Cat Boat Tour

Customize your route with snorkeling, sightseeing, and island stops on a private boat

$924& up
Private 3- to 6-Hour Anna Maria & Longboat Key Boat Tour

Private 3- to 6-Hour Anna Maria & Longboat Key Boat Tour

Customize a private Anna Maria & Long Boat Key boat tour for up to 6 people

$612& up
8-Hour Private Sailing Charter From Treasure Island

8-Hour Private Sailing Charter From Treasure Island

Sail for 8 hours and choose Egmont Key, Anna Maria, or Shell Key

$3,260
Cruise Sarasota on a 4-Hour Tritoon Rental
Up to 12

Cruise Sarasota on a 4-Hour Tritoon Rental

Rent a 26-foot tritoon with seating and shade for up to 12

$485
Full-Day 26' Tritoon Boat Rental in Siesta Key
Up to 12

Full-Day 26' Tritoon Boat Rental in Siesta Key

Rent a 26' tritoon for a full day with seating for up to 12

$626/ boat
Half-Day Deck Boat Rental in Sarasota
Up to 4

Half-Day Deck Boat Rental in Sarasota

Cruise Sarasota Bay with a 17-foot deck boat rental

$293/ boat
25' Pontoon Rental in Siesta Key
Up to 12

25' Pontoon Rental in Siesta Key

Lounge on plush seating and swim from the rear boarding ladder

$428/ boat
Full-Day 25' Pontoon Boat Rental in Siesta Key
Up to 12

Full-Day 25' Pontoon Boat Rental in Siesta Key

Rent a 25-foot pontoon for up to 12 people for a full day on the water

$570/ boat
Private Half-Day Sail & Shelling Trip to Shell Key

Private Half-Day Sail & Shelling Trip to Shell Key

Sail to Shell Key for swimming, snorkeling, and shelling

$1,621
Cruise Treasure Island On A 2-Hour Sunset Sail

Cruise Treasure Island On A 2-Hour Sunset Sail

Private 2-hour sunset sail with bay views and dolphin spotting

$1,060
Private Sightseeing & Sandbar Boat Charter in Sarasota

Private Sightseeing & Sandbar Boat Charter in Sarasota

Customize your private cruise with sandbar, beach, dining, and wildlife stops

$403& up
Full-Day Deck Boat Rental on Sarasota Bay
Up to 4

Full-Day Deck Boat Rental on Sarasota Bay

Cruise and anchor around Sarasota Bay by deck boat

$434/ boat
Half-Day 21' Deck Boat Rental in Siesta Key
Up to 8

Half-Day 21' Deck Boat Rental in Siesta Key

Rent a 21' deck boat for up to 8 people on Siesta Key

$372/ boat
Full-Day Pontoon Boat Rental in Sarasota
Up to 10

Full-Day Pontoon Boat Rental in Sarasota

Rent a 23-foot pontoon for up to 10 people

$524
Sarasota Bachelor & Bachelorette Party Charter

Sarasota Bachelor & Bachelorette Party Charter

Set sail on a private Sarasota party charter tailored to your celebration

$818
Full-Day Deck Boat Rental In Siesta Key
Up to 8

Full-Day Deck Boat Rental In Siesta Key

Rent a 21-foot deck boat and cruise the bay with up to 8 people

$513/ boat
1…121314…17
Osprey Things To Do
Boat Tours82Boat Rentals70Yacht Charters62Kayaking Tours58Fishing Charters37
More
  • Jet Skiing29
  • Dolphin Watching27
  • Bike Rentals21
  • Sunrise and Sunset Tours17
  • Snorkeling14
  • Car Rentals12
  • Train Tours12

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.

Horseback Riding
9
  • Parasailing9
  • Equipment Rental8
  • Food Tours8
  • Helicopter Tours7
  • Outdoor Picnics7
  • Paddleboarding7
  • Stand Up Paddle Boarding6
  • Trolley Tours6
  • Sailing5
  • Scooter Rentals5
  • Private Boat Charters4
  • Scuba Diving4