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 265-288 of 395 results
Jet Ski Rentals in Osprey

Jet Ski Rentals in Osprey

Ride a 110 hp jet ski with safety instruction, fuel, and life jackets included

4.6 • 117 reviews
$136/ jetski
8-Hour Stand Up Paddle Board Rental in Osprey

8-Hour Stand Up Paddle Board Rental in Osprey

Paddle Sarasota-area waterways at your own pace with included gear

4.6 • 117 reviews
$40/ paddle board
Sunset Jet Ski Tour in Osprey

Sunset Jet Ski Tour in Osprey

Guided sunset jet skiing with room for your group

4.6 • 117 reviews
$325
Anna Maria Island Boat Rental With Captain Option
Up to 6

Anna Maria Island Boat Rental With Captain Option

Cruise the Gulf Coast on a spacious Sea Hunt center console, with a captain option available

5.0 • 4 reviews
$525/ boat
Sunset Cruise in Palmetto

Sunset Cruise in Palmetto

See the sunset over Tampa Bay, then cruise past Bradenton's city lights

4.6 • 85 reviews
$51/ person
Morning Guided Cruise on the Manatee River

Morning Guided Cruise on the Manatee River

Cruise the Manatee River before midday heat with narration from your crew

4.6 • 85 reviews
$54/ person
Manatee River 2-Hour Cruise

Manatee River 2-Hour Cruise

Narrated river cruise blending local history, ecology, and native wildlife

4.6 • 85 reviews
$54/ person
Explore Sarasota Bay on a 4- or 8-Hour Tritoon Rental
Up to 12

Explore Sarasota Bay on a 4- or 8-Hour Tritoon Rental

Rent a tritoon for up to 12 and cruise Sarasota Bay for 4 or 8 hours

4.5 • 771 reviews
$542& up
Morning Jet Ski Dolphin Excursion In Sarasota

Morning Jet Ski Dolphin Excursion In Sarasota

Ride a Jet Ski through Phillippi Creek and toward Siesta Key

4.5 • 234 reviews
$220/ jet-ski
Ride a Sunset Jet Ski in Sarasota

Ride a Sunset Jet Ski in Sarasota

Sunset jet ski ride with fast Gulf access from Siesta Key

4.5 • 234 reviews
$259/ jet-ski
23' Pontoon Rental in Bradenton Beach
Up to 10

23' Pontoon Rental in Bradenton Beach

Cruise Sarasota Bay for beach stops, fishing, and wildlife viewing

4.5 • 771 reviews
$514/ boat
Private 42' Sandbar Boat Charter Around Anna Maria Island

Private 42' Sandbar Boat Charter Around Anna Maria Island

Customize a private cruise for sandbars, islands, and waterfront stops

4.5 • 771 reviews
$1,356& up
Sarasota Jet Ski Rental

Sarasota Jet Ski Rental

Ride professionally maintained jet skis with Gulf access in Sarasota

4.5 • 234 reviews
$112/ jet ski
2-Hour Guided Jet Ski Tour in Sarasota

2-Hour Guided Jet Ski Tour in Sarasota

Ride the waters around Siesta Key with a guide, a sandbar stop, and island views

$281/ jet ski
Dolphin Jet Ski Tour in Bradenton

Dolphin Jet Ski Tour in Bradenton

Ride a 2025 Sea-Doo jet ski to Bradenton's dolphin hot spots

$436/ jet ski
Jet Ski Tour Under Sunshine Skyway Bridge

Jet Ski Tour Under Sunshine Skyway Bridge

Ride a jet ski beneath the Sunshine Skyway Bridge

$469
Jet Ski Snorkel Tour to Egmont Key

Jet Ski Snorkel Tour to Egmont Key

Ride a 2025 Sea-Doo to Egmont Key and snorkel its reefs

$873
3-Hour Point of Rocks Snorkeling Cruise

3-Hour Point of Rocks Snorkeling Cruise

Explore boat-access-only reaches of Point of Rocks with captain support and snorkeling gear

$159/ person
Bradenton Inshore Fishing Charter

Bradenton Inshore Fishing Charter

Fish Tampa Bay and Sarasota Bay grass flats with light tackle, live bait, and lures

$636& up
Siesta Key 4-Hour Snorkel Charter

Siesta Key 4-Hour Snorkel Charter

Explore Siesta Key's shallow waters on a private captain-led snorkel outing

$636& up
Sarasota Sunset Cruise

Sarasota Sunset Cruise

Spot dolphins, manatees, and coastal birds on a private Sarasota Bay cruise

$530
Siesta Key 4-Hour Sandbar Charter

Siesta Key 4-Hour Sandbar Charter

Relax, swim, and float on Sarasota's shallow sandbars aboard a private boat

$795
Sunset Fishing Charter in Sarasota

Sunset Fishing Charter in Sarasota

Cast a line as the sun sets over the Gulf of Mexico

$511
Jet Ski Rental on Sarasota Waterways & Sandbars

Jet Ski Rental on Sarasota Waterways & Sandbars

Ride at your own pace, with time to stop on a sandbar

$123/ jet-ski
1…111213…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