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Best results for

Water Activities in Osprey, FL

Showing 241-264 of 395 results
Lemon Bay Skiff Rental
Up to 6

Lemon Bay Skiff Rental

Fish and cruise Lemon Bay’s backwaters aboard a 50HP skiff

4.8 • 33 reviews
$241/ boat
Englewood 21' Fishing Boat Rental
Up to 6

Englewood 21' Fishing Boat Rental

A fishing-ready center console for bridges and beaches around Manasota Key

4.8 • 33 reviews
$385/ boat
Manasota Key Bayliner Deck Boat Rental
Up to 8

Manasota Key Bayliner Deck Boat Rental

Cruise Manasota Key with shade, storage and Bluetooth sound

4.8 • 33 reviews
$367/ boat
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
Englewood Fishing Charter

Englewood Fishing Charter

Cast for snapper, grouper, sharks and more on a private fishing trip

4.7 • 54 reviews
$1,308& up
Sunset Kayak Tour in Osprey

Sunset Kayak Tour in Osprey

Paddle mangroves after sunset with LED-lit views beneath your kayak

5.0 • 8 reviews
$69/ person
3-Hour Clear Kayak Rental in Osprey

3-Hour Clear Kayak Rental in Osprey

Explore the water at your own pace in a clear kayak

5.0 • 8 reviews
$53/ person
2-Hour Sarasota Bay Sightseeing Cruise

2-Hour Sarasota Bay Sightseeing Cruise

Take in Sarasota Bay views, local history and waterfront wildlife from the water

4.6 • 956 reviews
$51/ person
Double Kayak Rental in Anna Maria Island

Double Kayak Rental in Anna Maria Island

Paddle together with free local beach delivery and pickup

4.6 • 275 reviews
$62/ kayak
Paddle Board Rental on Anna Maria Island

Paddle Board Rental on Anna Maria Island

Flexible paddle board rentals with free local beach delivery and pickup

4.6 • 275 reviews
$62/ board
Single Kayak Rental on Anna Maria Island

Single Kayak Rental on Anna Maria Island

Flexible rental periods with free local beach delivery and pickup

4.6 • 275 reviews
$40/ kayak
Osprey 22' Pontoon Boat Rental
Up to 10

Osprey 22' Pontoon Boat Rental

Cruise Sarasota Bay with your family or group on a fuel-included pontoon boat

4.6 • 117 reviews
$364/ boat
Single Kayak Rental in Osprey

Single Kayak Rental in Osprey

Paddle southwest Florida waterways at your own pace

4.6 • 117 reviews
$32/ kayak
Osprey Tandem Kayak Rental

Osprey Tandem Kayak Rental

Explore southwest Florida waterways by kayak with included paddles and life jackets

4.6 • 117 reviews
$46/ kayak
1…101112…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