Best results for Holmes Beach Florida

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

Rent a street-legal 6-passenger golf cart and explore Siesta Key

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.

Get kayaks or paddleboards delivered straight to your Siesta Key resort

Cruise Siesta Key with a Class 1 or Class 2 electric bike

Explore Sarasota at your own pace on a fully equipped Aventon Pace 500.3 e-bike

Family bike options with kid sizes and child seats

Cruise the Legacy Trail on a comfortable bike with included essentials

Comfortable Jamis hybrid bike rental for Legacy Trail rides

Choose an easygoing or sporty ride for the Legacy Trail

Smooth pedal-assist rides for exploring more of the Legacy Trail

Choose a bike style that fits your plans for a full day on Siesta Key

Ride Siesta Key and reach the Legacy Trail with an e-bike rental

Ride paved trail miles from Sarasota toward Venice

Cruise Tampa Bay with a private skylounge, spacious decks, and water toys

Cruise sandbars and coves aboard a 43-foot Tiara with fuel included

Cruise Tampa Bay with water toys, indoor comfort, and spacious decks

Private 2-hour sunset sail with downtown St. Petersburg views

Relax on a 3-hour sail with a U.S. Coast Guard–licensed captain from downtown St. Pete

Start the day aboard a classic yacht with optional sailing instruction