The Best Boat Rentals in Siesta Key

Most self-operated pontoons, deck boats, and center consoles in Siesta Key typically run about $60–$150 per hour, with half-day outings often landing between $350–$600 and full days starting around $700. Captained leisure cruises usually range from roughly $150–$250 per hour depending on group size and itinerary, while larger motor yachts can be $300–$500+ per hour and up for premium vessels. Prices usually include safety gear, basic orientation, a bimini or shaded area, Bluetooth audio, and often a cooler; taxes, fuel, captain’s fee or gratuity, and add‑ons like floating mats can be extra. Booking longer blocks or weekday trips commonly brings better value.

You’ll find easygoing pontoon and deck boats for sandbar stops and swimming, center consoles for cruising and nearshore fishing, bowriders for family sightseeing, and a range of captained options from small cruisers to mid-size yachts for celebrations. Sailboat charters are available in the Sarasota area as well if you prefer time under canvas. If you want a set-it-and-relax day, choose a captained charter; if you’re comfortable handling a boat, self-operated pontoons and deck boats are popular on the Intracoastal and Sarasota Bay.

Pick a captained trip if you want a stress-free day with local route planning, expert sandbar timing, and help with anchoring and docking. A captain is also a smart call if you’re unfamiliar with Sarasota Bay’s shallows, seagrass flats, and the shifting shoals near New Pass and Big Sarasota Pass. Confident boaters often enjoy self-operated pontoons or center consoles inside the protected Intracoastal Waterway, but many visitors still go captained so everyone can relax and enjoy the day.

Common meeting points include Safe Harbor Siesta Key (often called Siesta Key Marina) on Old Stickney Point Road, the public boat ramps at Turtle Beach on the south end of the island, Marina Jack at the Sarasota Bayfront downtown, and the Ken Thompson Park/City Island boat ramp near New Pass. Your captain or owner will confirm the most convenient pickup spot based on your itinerary, parking, and wind and tide on the day.

Expect postcard views of Siesta Beach’s bright white shoreline, the Sarasota skyline and Ringling Bridge, and the barrier islands around Big Sarasota Pass and New Pass. It’s common to spot bottlenose dolphins and seasonal manatees in Sarasota Bay along with ospreys, pelicans, and herons over the flats. Many cruises add a sandbar stop for swimming in clear, shallow water and time to relax off the boat.

Florida does not issue a traditional “boating license,” but if you were born on or after January 1, 1988 and plan to operate a boat of 10 horsepower or more, you must complete approved boater education and carry the Florida Boating Safety Education ID Card or a Florida temporary certificate with your photo ID. Visitors can take the quick online exam for a 90‑day temporary certificate before their trip. If you book a captained charter, the captain handles the operation and no card is required for guests.

Yes—families are welcome. Every legal boat rental provides U.S. Coast Guard–approved life jackets sized for the group, and most hosts can supply infant and child sizes on request. Florida law requires children under 6 to wear a life jacket while a vessel under 26 feet is underway, and it’s always wise for young boaters to keep theirs on even when anchored. Pack sun protection, snacks, and towels, and let your host know if you need a shade-forward setup for naptime.

Nearly all rentals allow you to bring your own snacks, picnic spreads, and beverages. Many boats provide a cooler and ice or can add them on request. For safety and to keep decks tidy, glass is often discouraged and red-stain drinks may be restricted. If you’re operating the boat yourself, designate a sober skipper. Captains can also suggest dock‑and‑dine stops if you’d like to tie up for lunch mid‑cruise.

Many boats welcome well‑behaved dogs with prior approval, though size limits and cleaning fees can apply. Bring a nonslip towel, a collapsible water bowl, and a leash for busy docks and sandbars. If your pup is new to boating, consider a canine life jacket for extra peace of mind and choose a shaded vessel with easier boarding.

Summer in Florida often brings calmer mornings and pop‑up afternoon thunderstorms, so earlier departures are usually smoothest. Captains watch radar, wind, and tide to plan safe, comfortable routes and anchorages, and they’ll advise if conditions like small‑craft advisories or temporary red tide reports make rescheduling wise. Most listings include clear weather policies with flexible options to move your trip or receive a refund if unsafe conditions arise.

Absolutely. Pontoon party cruises and mid‑size yachts are popular for celebrations, and many hosts can accommodate playlists, simple decorations, and photo stops at sandbars or skyline backdrops. Share your exact headcount early—including infants—since capacity is set by the specific vessel and captain. If you’re coordinating multiple pickups, your captain can recommend the easiest launch and parking plan to keep the day effortless.

Boating is year‑round, but March through August brings warm water and long beach days, with holiday weekends like Memorial Day, July 4th, and Labor Day being especially busy on the water. Late spring and fall shoulder months often pair great weather with lighter crowds. April typically features the Suncoast Boat Show at Marina Jack, which can make the Bayfront lively. In 2025 the Sarasota Powerboat Grand Prix is on pause; if it returns in a future year, expect extra boat traffic around Lido Beach during race weekend. For calmer water and easier parking, choose weekdays and morning departures; sunsets are gorgeous too if the forecast is clear.

Yes—sandbar days are a local favorite. Captains commonly time tides for the New Pass sandbar close to the city skyline and, on longer charters, can cruise up the bay toward the spacious Jewfish Key sandbar and nearby Beer Can Island, or tuck into the quiet boat‑accessible shoreline at Palmer Point near the south end of Siesta Key. Your captain will pick the best spots for the day’s wind and tide and build in swim time, floating, and dolphin‑watching along the way.