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Best results for

Water Activities in Osprey, FL

Showing 337-360 of 395 results
Jet Ski Rental on Anna Maria Island

Jet Ski Rental on Anna Maria Island

Speed, sightseeing, and flexible time on the water

5.0 • 243 reviews
$158/ jet ski
Private Mangrove Tunnel Kayak Tour in Sarasota

Private Mangrove Tunnel Kayak Tour in Sarasota

Paddle private mangrove tunnels with a guide and look for Sarasota Bay wildlife

5.0 • 1.5K reviews
$101/ kayak
Half-Day Kayak & Paddleboard Rental on Longboat Key

Half-Day Kayak & Paddleboard Rental on Longboat Key

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

5.0 • 658 reviews
$62/ kayak
Bradenton Pirate Treasure Hunt Cruise

Bradenton Pirate Treasure Hunt Cruise

Set sail on an interactive pirate cruise with a treasure hunt

5.0 • 640 reviews
$39/ person
Private Pirate Cruise in Bradenton

Private Pirate Cruise in Bradenton

Set sail on an interactive private treasure hunt for your crew

5.0 • 640 reviews
$1,134
SUP Yoga Class on Holmes Beach Waters

SUP Yoga Class on Holmes Beach Waters

Practice yoga on a paddleboard and connect with nature in a tranquil setting.

5.0 • 625 reviews
$75/ person
Paddle Pristine Mangrove Tunnels in Neal Preserve

Paddle Pristine Mangrove Tunnels in Neal Preserve

Explore mangrove tunnels by kayak or paddleboard with experienced guides in Neal Preserve.

5.0 • 625 reviews
$55/ tour
2-3 Hour Guided Jet Ski Tour of Anna Maria Island

2-3 Hour Guided Jet Ski Tour of Anna Maria Island

Guided island cruising with photo stops and group-paced riding

5.0 • 243 reviews
$429& up
24' Pontoon Boat Rental in Palmetto with Sandbar Access
Up to 13

24' Pontoon Boat Rental in Palmetto with Sandbar Access

Cruise with up to 13 friends on a spacious pontoon equipped for sandbar hopping

5.0 • 168 reviews
$599& up
Captained Tritoon Cruise in Anna Maria Island

Captained Tritoon Cruise in Anna Maria Island

Cruise Anna Maria Island by captained tritoon with room for up to 6

5.0 • 168 reviews
$396& up
Sunset Dolphin Cruise in Bradenton Beach

Sunset Dolphin Cruise in Bradenton Beach

Private Gulf cruise with sunset views and chances to spot marine life

5.0 • 122 reviews
$452
Siesta Key Private Catamaran Charter
Up to 49

Siesta Key Private Catamaran Charter

Customize your day exploring sandbars, islands, and marine life on a private catamaran.

4.9 • 9.2K reviews
$1,248& up
Kayak & Paddleboard Rental at Turtle Beach

Kayak & Paddleboard Rental at Turtle Beach

Rent a kayak or paddleboard and explore Turtle Beach waterways with a provided map

4.9 • 3.2K reviews
$51/ kayak
21' Tritoon Boat Rental in Sarasota
Up to 10

21' Tritoon Boat Rental in Sarasota

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

5.0 • 78 reviews
$480/ boat
2.5-Hour Sandbar Cruise in Holmes Beach

2.5-Hour Sandbar Cruise in Holmes Beach

Cruise to a local sandbar and swim or snorkel

4.9 • 1.8K reviews
$78/ person
24' Pontoon Boat Rental in Holmes Beach
Up to 10

24' Pontoon Boat Rental in Holmes Beach

Set your own course for sandbars, swims, and open-water exploring

4.9 • 1.8K reviews
$588/ boat
Private Tiki Boat Cruise in Holmes Beach

Private Tiki Boat Cruise in Holmes Beach

Slide and explore sandbars aboard a private two-story tiki boat

4.9 • 1.8K reviews
$766& up
Private Island Snorkeling Charter in Holmes Beach

Private Island Snorkeling Charter in Holmes Beach

Island hopping, snorkeling and shelling for your private group

4.9 • 1.8K reviews
$684& up
Bachelorette Boat Charter Anna Maria Island

Bachelorette Boat Charter Anna Maria Island

Private island boat party for your bachelorette celebration

4.9 • 1.8K reviews
$766
Sea Ray SDX 250 Boat Rental in Sarasota
Up to 12

Sea Ray SDX 250 Boat Rental in Sarasota

Rent a Sea Ray SDX 250 for 6 hours with seating for up to 12

4.9 • 950 reviews
$1,002
Jet Ski Rental in Sarasota

Jet Ski Rental in Sarasota

Ride a jet ski on Sarasota's waters

4.9 • 950 reviews
$202/ jet ski
Englewood 3-Hour Single Kayak Rental

Englewood 3-Hour Single Kayak Rental

Paddle Lemon Bay independently in a stable sit-on-top kayak

4.9 • 892 reviews
$45/ kayak
Sarasota Sunset Charter

Sarasota Sunset Charter

Private Yellowfin cruise with sandbar swimming and sunset views

4.9 • 517 reviews
$1,547
Offshore Fishing Charter on Kai Fin

Offshore Fishing Charter on Kai Fin

Fish offshore with a USCG-licensed captain, mate, bait, and standard fuel included

4.9 • 517 reviews
$5,102
1…1314151617
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