Free Concierge Service
Text or call 1-877-GREET-WELL
Ask AIAI
Ask AIAI
Why travelers choose Greetwell

Curated by our team

Every experience is hand selected and approved by Greetwell.

Personal concierge

Real humans available to help before, during, and after your booking.

Intimate & authentic

Including unique in-home experiences you won't find anywhere else.

Easy booking & cancellation

Reserve in minutes with free cancellation on most experiences.

Greetwell

Experiences that stay with you long after the trip

Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

About

  • Our Story
  • For Experience Providers
  • For Hospitality Partners
  • For Developers

Resources

  • Travel Guides
  • Experience Gift Cards
  • Help Center
[email protected]1-877-GREET-WELL

Safe & Secure Payments

© 2026 Greetwell, Inc. All rights reserved.
Privacy PolicyTerms
Free Concierge Service
Text or call 1-877-GREET-WELL
Ask AIAI
Ask AIAI
Best results for

Water Activities in Osprey, FL

Showing 361-384 of 395 results
Sarasota 4-Hour Private Boat Charter

Sarasota 4-Hour Private Boat Charter

Cruise, swim, and unwind on a private Yellowfin center console

4.9 • 517 reviews
$2,065
Sarasota Full-Day Private Boat Charter
Up to 13

Sarasota Full-Day Private Boat Charter

Cruise, swim, and unwind aboard a private Yellowfin charter

4.9 • 517 reviews
$3,643
Pedal Kayak Rental at Bird Key Park Sarasota

Pedal Kayak Rental at Bird Key Park Sarasota

Rent a pedal kayak and explore Sarasota Bay with all gear and safety equipment included.

4.9 • 196 reviews
$45/ kayak
Sandbar & Snorkel Charter in Palmetto

Sandbar & Snorkel Charter in Palmetto

Design a private day of fishing, snorkeling, and sandbar stops

5.0 • 52 reviews
$424& up
Stand Up Paddle Board Rental in Bradenton FL

Stand Up Paddle Board Rental in Bradenton FL

Enjoy a self-guided paddle adventure with a versatile inflatable board.

4.9 • 134 reviews
$35/ hour
Bradenton Jet Ski Rental: 3-Seater Skis

Bradenton Jet Ski Rental: 3-Seater Skis

Ride the latest 3-seater jet skis and enjoy hassle-free fun on the water.

4.9 • 134 reviews
$120/ hour
Dolphin Sightings Jet Ski Rental in Sarasota

Dolphin Sightings Jet Ski Rental in Sarasota

Scan Sarasota's coastal waters for dolphin sightings by jet ski

5.0 • 37 reviews
$198/ jet ski
2-Hour Egmont Key Jet Ski Rental

2-Hour Egmont Key Jet Ski Rental

Explore Egmont Key from the water by jet ski

5.0 • 37 reviews
$283/ jetski
3-Hour Jet Ski Rental to Egmont & Passage Key

3-Hour Jet Ski Rental to Egmont & Passage Key

Explore Egmont and Passage Key by guided jet ski

5.0 • 37 reviews
$452/ jet ski
Sarasota Bay 2-Jet Ski Rental

Sarasota Bay 2-Jet Ski Rental

Ride side by side on two jet skis in Sarasota Bay

4.9 • 73 reviews
$254& up
Sarasota 3-Jet Ski Rental

Sarasota 3-Jet Ski Rental

Ride Sarasota Bay together on three jet skis

4.9 • 73 reviews
$382/ rental
4-Jet Ski Rental in Sarasota

4-Jet Ski Rental in Sarasota

Bring your crew together on four jet skis in Sarasota Bay

4.9 • 73 reviews
$509& up
Solo Jet Ski Rental in Sarasota

Solo Jet Ski Rental in Sarasota

Take the controls on a high-performance jet ski built for one rider

4.9 • 73 reviews
$120& up
Guided Kayak & Food Tour in Sarasota

Guided Kayak & Food Tour in Sarasota

Paddle Sarasota Bay, then taste your way through downtown

4.9 • 64 reviews
$203/ person
Anna Maria Island 24' Pontoon Boat Rental
Up to 15

Anna Maria Island 24' Pontoon Boat Rental

Cruise Anna Maria Island waters with a paddleboard and kids kayak included

4.8 • 794 reviews
$411/ boat
Private Boat Tour from Nokomis with Snorkeling
Up to 6

Private Boat Tour from Nokomis with Snorkeling

Customize a 4-hour private cruise with snorkeling, paddleboarding, dolphin watching, and more.

4.8 • 466 reviews
$899
4-Hour Holmes Beach Sandbar & Island Private Charter

4-Hour Holmes Beach Sandbar & Island Private Charter

Private 4-hour sandbar and island hop with morning or afternoon departures

4.8 • 382 reviews
$770& up
6-Hour Private Water Charter in Holmes Beach

6-Hour Private Water Charter in Holmes Beach

Design your day around snorkeling, sandbars, paddling, and time on the water

4.8 • 382 reviews
$1,150& up
Holmes Beach Christmas Light Canal Cruise

Holmes Beach Christmas Light Canal Cruise

Watch Gulf sunsets and waterfront Christmas lights from a private, captain-led boat

4.8 • 382 reviews
$523
3-Hour Guided Fishing Charter in Bradenton Beach

3-Hour Guided Fishing Charter in Bradenton Beach

Cast the backcountry flats with gear, bait, and your fishing license included

5.0 • 13 reviews
$429
Bradenton Beach 4-Person Fishing Charter

Bradenton Beach 4-Person Fishing Charter

Cast, troll, or jig with bait, tackle, and a fishing license included

5.0 • 13 reviews
$1,145
4-Hour Fishing Charter in Bradenton Beach

4-Hour Fishing Charter in Bradenton Beach

Fish local waters with provided gear, bait, and a captain

5.0 • 13 reviews
$572
Catch & Release Fishing Charter in Bradenton Beach

Catch & Release Fishing Charter in Bradenton Beach

Cast a line on a relaxed, captain-led trip with gear and fishing license included

5.0 • 13 reviews
$286
Guided Snorkeling Charter at Egmont Key

Guided Snorkeling Charter at Egmont Key

Cruise to historic fort ruins for snorkeling and island exploration

5.0 • 13 reviews
$565& up
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