The Best Boat Rentals in Islamorada

Expect most private charters to run about $100–$200 per hour for smaller center consoles and deck boats, $600–$900 for a half day, and $1,200–$1,800 for a full day. Larger premium vessels and offshore fishing charters can range from roughly $2,000 to $3,000+ for a full day. Inclusions vary by listing, but it’s common to have a licensed captain on captained trips, U.S. Coast Guard–approved safety gear, a Bluetooth sound system, coolers with ice, and snorkel masks. Fuel, taxes, and gratuity may be extra, so review your offer details before you book.

Islamorada fleets are built for Keys-style fun. You’ll find center consoles for reef and sandbar hopping, deck boats and pontoons for relaxed cruising, sportfishing boats for offshore runs, plus sailboats, catamarans, and party-style tiki or pontoon setups for celebrations. Pick the boat that fits your group size, comfort preferences, and plans for snorkeling, fishing, or a sandbar day.

If you want a carefree day, a captained charter is the easiest option—your captain handles navigation, anchoring at the sandbar, and local tips for reefs and wildlife. If you prefer to operate the boat yourself, you’ll need to be comfortable with local channels, tides, and shallow flats. Florida requires anyone born on or after January 1, 1988 to hold a Boating Safety Education ID Card or a 90‑day temporary certificate to operate a motorboat of 10 hp or more; captained trips do not require you to hold a card.

Common pickup points include Whale Harbor Marina near Mile Marker 83.5, Bud N’ Mary’s Marina at Mile Marker 79.8 (oceanside), Plantation Yacht Harbor Marina inside Founders Park on the bayside, and the marina at the Postcard Inn at Holiday Isle. Some trips also arrange custom pickup at nearby public ramps or resort docks—confirm your meet-up details when you book.

Highlights include the turquoise shallows of the famous Islamorada Sandbar just outside Whale Harbor Channel, the historic Alligator Reef Lighthouse offshore, and nearshore reefs like Cheeca Rocks with colorful coral and tropical fish. On the bayside, you can cruise Florida Bay’s mangrove fringes toward Everglades country, spotting dolphins, rays, and seabirds. Many captains combine reef snorkeling with a sandbar stop or sunset cruise.

Florida doesn’t issue a traditional “boating license,” but anyone born on or after January 1, 1988 must complete an approved course and carry a Florida Boating Safety Education ID Card to operate a motorboat of 10 hp or more. Visitors can take an approved online exam to get a temporary certificate that’s valid for up to 90 days. If you book a captained charter, no card is required for you as a passenger.

Yes—families are welcome on most private charters. Every vessel must carry a properly sized, U.S. Coast Guard–approved life jacket for each person aboard, and Florida law requires children under 6 to wear a life jacket while underway on vessels under 26 feet. Let your captain know the ages and sizes of any children so youth and infant vests are ready when you arrive.

Most private charters allow you to bring snacks, picnic lunches, and drinks, and many provide coolers with ice. Cans are preferred over glass, as glass is restricted or discouraged in many park and marina areas and is unsafe on deck. If alcohol is part of your plans, keep in mind that the operator must remain sober and boating under the influence is illegal; hiring a captain is the simplest way to relax responsibly.

Many private charters are pet‑friendly, especially for dogs that are calm and comfortable on the water. Always request a pet‑friendly boat in your inquiry. Bring a leash, fresh water, a towel, and consider booties for hot decks. Some public parks and beaches around Islamorada restrict dogs in certain areas, and glass is not permitted; follow your captain’s guidance to keep your pup—and wildlife—safe.

Captains monitor the marine forecast and may adjust routes, delay departure, or reschedule if conditions are unsafe—for example, thunderstorms, strong winds, or small‑craft advisories. Summer (June through October) is the Keys’ wet season with more frequent afternoon storms, while June 1–November 30 is Atlantic hurricane season. Check your listing’s cancellation terms before booking, and plan to be flexible if the forecast changes.

Absolutely. Private boats make it easy to customize a day—think reef snorkeling and cruising before anchoring at the sandbar, or a golden‑hour sunset ride with a playlist and a cake. Tell the captain your occasion, headcount, and any decor or catering plans. Boats that emphasize spacious seating, shade, and easy swim access are ideal for celebrations so everyone can move around and mingle comfortably.

Boating is year‑round here. For calmer air and drier weather, November through April is popular; summer delivers warm water and lively sandbar days, but expect midday heat and pop‑up storms. Major boating holidays—Memorial Day, July 4th, and Labor Day—are extremely busy, especially at the sandbar, so book early and aim for morning departures. Notable local events include the annual Swim for Alligator Lighthouse in early September and the Islamorada Sailfish Tournament in December; these weekends fill fast. Weekdays are typically less crowded and can be easier on the budget, and mornings often offer smoother seas and clearer snorkeling than late afternoons.

Yes—the sandbar off Whale Harbor Channel is a classic Islamorada experience with shallow, clear water perfect for floating and relaxing. It’s busiest on sunny weekends and holiday afternoons. For a more laid‑back vibe, go on a weekday, arrive early, and avoid peak holiday weekends. Your captain will know the best anchor spots, currents, and seagrass‑safe approaches so you can enjoy it without stress.