Best results for Water Activities in Osprey, FL

Explore Midnight Pass on a self-guided, all-ages paddle

Ride a Jet Ski through Phillippi Creek and toward Siesta Key

Sunset jet ski ride with fast Gulf access from Siesta Key

Ride professionally maintained jet skis with Gulf access in Sarasota

Get kayaks or paddleboards delivered straight to your Siesta Key resort

Cruise Siesta Key’s waterways on a 2024 tiki boat with music, drinks and coastal wildlife views.

Soar over Siesta Key’s coastline with an optional Gulf dip

Enjoy a relaxed evening cruise along Siesta Key with music, LED lights and possible dolphin sightings.

Rent a 26-foot tritoon with seating and shade for up to 12

Rent a 26' tritoon for a full day with seating for up to 12

Cruise Sarasota Bay with a 17-foot deck boat rental

Rent a 25-foot pontoon for up to 12 people for a full day on the water

Rent a 23-foot pontoon for up to 10 people

Cruise and anchor around Sarasota Bay by deck boat

Rent a 21' deck boat for up to 8 people on Siesta Key

Rent a 23-foot pontoon for up to 10 people

Rent a 21-foot deck boat and cruise the bay with up to 8 people

Cruise Sarasota Bay waterways with shade, storage, and room to fish or relax

Cruise Sarasota Bay’s mangroves, sandbars, and beaches by pontoon

Cruise Sarasota Bay and the Intracoastal on a roomy pontoon

Cruise Sarasota Bay and the Intracoastal with room for up to 14

Cruise Sarasota’s Intracoastal waterways on a shaded pontoon

Cruise Sarasota Bay and Intracoastal waterways aboard a shaded pontoon

Cruise Sarasota’s bays and waterways with fishing-ready gear