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Best results for

Water Activities in Osprey, FL

Showing 97-120 of 395 results
Boca Grande Shark Fishing Charter

Boca Grande Shark Fishing Charter

Target sharks off Boca Grande with Captain Steve

5.0 • 56 reviews
$742& up
Private Island & Sandbar Hopping Tour on Anna Maria Island

Private Island & Sandbar Hopping Tour on Anna Maria Island

Design your own Gulf Coast island escape

5.0 • 55 reviews
$530& up
Pedal Kayak Mangrove Tunnel Eco Tour in Sarasota

Pedal Kayak Mangrove Tunnel Eco Tour in Sarasota

Pedal kayak Sarasota Bay to seagrass beds and mangrove tunnels

4.9 • 196 reviews
$78/ kayak
Sunset Kayak Tour on Anna Maria Island

Sunset Kayak Tour on Anna Maria Island

Paddle to sandbars and a secluded beach for Gulf sunset views

4.9 • 169 reviews
$69/ kayak
2-Hour Private Boat Charter Anna Maria Island
Up to 10

2-Hour Private Boat Charter Anna Maria Island

Explore sandbars, islands and coastal waters on a private outing

5.0 • 65 reviews
$339& up
Cruise Sarasota Bay on a 6-Hour Private Yacht Charter

Cruise Sarasota Bay on a 6-Hour Private Yacht Charter

Charter a 38-foot Sea Ray for 6 hours of Sarasota Bay cruising

4.9 • 517 reviews
$2,527
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 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
2-Hour Private Cruise in Siesta Key

2-Hour Private Cruise in Siesta Key

Cruise Siesta Key’s western coast with your private group

4.9 • 691 reviews
$57/ person
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
Guided Clear Kayak Tour of Anna Maria Island Sound

Guided Clear Kayak Tour of Anna Maria Island Sound

Morning paddle through mangroves in a clear tandem kayak

5.0 • 43 reviews
$73/ person
Private Venice FL Fishing Charter up to 9 Miles Offshore

Private Venice FL Fishing Charter up to 9 Miles Offshore

Private fishing trips with gear, bait, licenses and catch filleting included

5.0 • 41 reviews
$423& up
Boca Grande Tarpon Fishing Charter

Boca Grande Tarpon Fishing Charter

Target tarpon in Boca Grande’s Gulf Coast waters

5.0 • 56 reviews
$1,060& up
Private Dolphin, Sunset & Tiki Bar Cruise Anna Maria Island

Private Dolphin, Sunset & Tiki Bar Cruise Anna Maria Island

Design your ideal day on the water

5.0 • 55 reviews
$530& up
Emerson Point Preserve Pedal Kayak Tour

Emerson Point Preserve Pedal Kayak Tour

Pedal kayak 2 miles through mangrove tunnels at Emerson Point

4.9 • 196 reviews
$78/ kayak
Bradenton Mangrove Kayak Tour

Bradenton Mangrove Kayak Tour

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

4.9 • 169 reviews
$58/ kayak
Englewood 22' Tritoon Boat Rental
Up to 10

Englewood 22' Tritoon Boat Rental

Cruise, anchor, and relax aboard a 2024 tritoon

4.9 • 99 reviews
$459/ boat
Sarasota 4-Hour Private Yacht Charter

Sarasota 4-Hour Private Yacht Charter

Cruise Sarasota Bay with space to swim, socialize and relax

4.9 • 517 reviews
$1,810
Single Kayak Rental in Siesta Key

Single Kayak Rental in Siesta Key

Explore Midnight Pass independently by kayak

5.0 • 196 reviews
$47/ kayak
1-Hour Jet Ski Rental in Bradenton

1-Hour Jet Ski Rental in Bradenton

Take the controls for an independent jet ski ride in a designated area

5.0 • 37 reviews
$147/ jetski
Private 2-Hour Cruise in Siesta Key

Private 2-Hour Cruise in Siesta Key

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

4.9 • 691 reviews
$57
Evening Offshore Fishing Charter in Bradenton

Evening Offshore Fishing Charter in Bradenton

Cast for bay and nearshore reef species on a private evening trip

5.0 • 100 reviews
$741
Sunset to Night Glow Kayak Tour in Bradenton

Sunset to Night Glow Kayak Tour in Bradenton

See Florida sunset colors from a clear tandem kayak

5.0 • 43 reviews
$79/ person
Private Sandbar Cruise with Waterslide in Venice, FL

Private Sandbar Cruise with Waterslide in Venice, FL

Slide, snorkel, and swim on a private double-decker charter

5.0 • 41 reviews
$317& up
1…456…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