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Siesta Key Boating

Islands and boating go hand in hand, so we’d really be doing you a disservice by not sharing all of our tips when it comes to boating in Siesta Key. Experiencing the water from the beach is always a blast, but there’s so much more when it comes exploring the Florida Keys when you stay in our rentals. From waterways and canals to the entire Gulf of Mexico, the possibilities for Siesta Key boating are endless.

Where to Boat

In the 1950-60s, the U.S. Army dredged what would become the Intracoastal Waterway (ICW). In doing so, boaters now have access to deep waters in the bay and between the barrier islands, creating a plethora of opportunity for all levels of boaters.

Cruise the canals for a unique perspective of the varying mansions, giving yourself a tour of some of the most coveted high-end homes in the world. Cruising these waterways while boating in Siesta Key is also a great way to birdwatch and some even enjoy metal detecting adventures. There’s sure to be a treasure in those blue tropical waters! This is also a great way to explore the island towns and cities – stopping in for a meal at the waterfront restaurants or exploring the exciting urban amenities of these coastal towns.

Siesta Key Boating Siesta Key Boating

See Our Siesta Key Vacation Homes Here!

Embark on your very own seagrass snorkeling adventure by taking advantage of the quiet pockets where the water is less than 10 ft, escaping the hustle and bustle of the crowds for an unobstructed view of what’s going on under water.

Rent a kayak, paddle board, or jet ski for the perfect mode of transportation for your own exploration. Find an elusive sandbar, a private beach, or a mangrove tunnel for the perfect escape from all the crowds.

And naturally, nothing beats fishing from a boat out on the open water. Rent a boat of your own or embark on a guided charter in pursuit of spotted seatrout, redfish, pompano, bluefish, snook and cobia while staying in our rentals.

Where to Rent for Siesta Key Boating Adventures

  • Land, Sea & Air Rentals: Enjoy a captained boat day out on the emerald waters of Siesta Key and surrounding areas. Knowledgeable US Coast Guard Certified captains curate an unforgettable day including dolphin watching, sight seeing, sand bar hopping, with stops at waterfront dining and bars. For more information and bookings visit rentsiestakey.com/boat-charter

boat anchored just off shore of a beach with calm waters

  • Sip N’ Slip Tours offers an unparalleled boat tour experience, blending the thrill of a scenic cruise with the indulgence of a top-tier booze cruise. Embark on a journey of opulence as our expert crew navigates stunning waterways, providing a backdrop for unforgettable moments. Immerse yourself in the lap of luxury, enjoying curated experiences that redefine the art of relaxation or a party on the waves. Sip N’ Slip can be reached at 941-313-4349.

pontoon boat with slide from a arial view


  • Safe Harbor Siesta Key is located at 1265 Old Stickney Point Rd, Sarasota, FL and can be reached at 941-349-1970. They specialize in half and full day rentals of pontoons and deckboats.


  • Black Pearl of Siesta Key is located in the Nora Patterson Bay Island Park at 946 Siesta Dr, Sarasota FL. They can be reached at 941-735-9460. Rent a pontoon for 1, 3, or 6 days (for boating within the canal systems and waterway/inshore areas (not allowed on the Gulf of Mexico). You can also rent paddle boards, beach packages, or a guided pontoon tour with a USCG licensed captain.


  • Blue Wave Boat Rental LLC can be reached at 813-BLU-WAVE. They’re happy to bring the boat to you and provide a little bit more flexibility when it comes to your adventures (boats can be rented overnight, even on a weekly or monthly basis and can also be brought out into the gulf). Whether you’re looking for a party barge or a speedboat, they’ve got it. They also offer charters that are customizable to your group. Whether it’s a special occasion, a romantic getaway, or a sightseeing adventure – you can rest easy with a captain on board with a vast knowledge base of the area.


  • Siesta Key Aqua Tours is your one stop shop for the fun of boating in Siesta Key. Whether you need to stop in to their surf shop for supplies, want to schedule a guided adventure (like a banana boat ride, a water tube ride, or a dolphin cruise) or want to rent your own gear (jet skis and kayaks are always a favorite) – this is the place! They’re also happy to bring you on a sunset cruise, schedule a private island party, or custom tailor a charter for whatever you desire. Give them a call at 941-359-AQUA or visit their shop at 5253 S. Tamiami Trail Sarasota, FL 34239.