The Best Boat Rentals in Key West

Expect most private charters to range from about $600–$1,200 for a half day and $1,000–$2,000 for a full day, depending on boat size, season, and what’s included. Short sunset trips of 2–3 hours commonly run $300–$800. Hourly rates for standard powerboats or sailboats often start around $100–$250 per hour, while larger yachts can be $300–$500+ per hour or $2,500–$6,000+ per day. Many captained sightseeing trips include a USCG-licensed captain, basic fuel, ice and water, and snorkel gear; taxes, marina fees, premium fuel usage, and gratuity are typically extra. Self-operated rentals usually exclude fuel and require a refundable security deposit. Always review the listing details so there are no surprises on the dock.

You’ll find a wide mix, from easygoing pontoons and center consoles for sandbar-hopping, to deck boats and fishing rigs for reef or backcountry trips, plus sailing monohulls and catamarans for day sails and sunset cruises. If you’re celebrating or traveling with a larger group, there are mid-size motor yachts and sailing cats with spacious lounging areas and shaded decks.

If you want a stress-free day with local know-how, book a captained charter—your captain handles navigation, weather calls, and the best routes to reefs and sandbars. Confident boaters can choose a self-operated rental; just know the backcountry has shallow flats and shifting channels, so local knowledge is valuable. If anyone in your party was born on or after January 1, 1988 and plans to operate a motorboat of 10 horsepower or more, Florida requires proof of boating safety education; visitors can take a quick online exam for a temporary certificate valid in Florida.

Common meeting points include the Key West Historic Seaport and Key West Bight Marina near 201 William Street in Old Town, City Marina at Garrison Bight along North Roosevelt Boulevard, and Stock Island Marina Village on Shrimp Road just across the bridge from Key West. Your exact pickup spot will be confirmed in your booking message; arrive a few minutes early for parking and boarding.

Typical routes cruise past Sunset Key and the Historic Seaport, the clear-water beaches by Fort Zachary Taylor, and the open waters toward the reef. Many trips stop at shallow backcountry flats and sandbars where you might spot dolphins, rays, sea turtles, and seabirds. On calmer days offshore, captains may point out Sand Key Lighthouse and nearby reef zones with good visibility for snorkeling.

Florida does not issue a traditional “boating license,” but anyone born on or after January 1, 1988 who will operate a motorboat of 10 hp or more must carry a Boating Safety Education ID Card or an approved temporary certificate, along with photo ID. Out-of-state boaters who have completed a NASBLA-approved course are generally covered. If you book a captained charter, your captain handles the operation and no card is needed for guests.

Yes—families are welcome on most boats. Every vessel must carry a U.S. Coast Guard–approved life jacket for each person on board, and children under age six must wear a life jacket while underway on boats under 26 feet. Captains provide a safety briefing before departure, and many boats also stock snorkel vests and shaded areas. If you’re bringing infants or toddlers, tell the owner so they can confirm sizing and space for a stroller or diaper bag.

BYO is common. Most charters allow snacks, picnic spreads, canned beverages, and reusable bottles; many provide a cooler with ice and bottled water. Glass is often discouraged on deck for safety. If you prefer hands-off planning, ask about catered platters or a stop at the marina market before boarding. Please pack reef-safe sunscreen and plan to carry out any trash.

Many captains welcome well-behaved dogs, especially on sandbar trips—just mention the breed and size in your inquiry. Bring a leash, a small towel, water bowl, and doggy waste bags. Some protected beaches and islands west of Key West do not allow pets ashore, so your captain will steer you to pet-friendly sandbars where wading and swimming are fine.

Captains watch marine forecasts closely. Summer and early fall bring warm water and occasional brief showers, while the official Atlantic hurricane season runs from June 1 to November 30. If conditions are unsafe, the captain will typically reschedule or cancel per the listing’s policy; many offer a refund or credit when weather makes it impossible to go. Morning departures are usually the smoothest, and flexible travelers can often shift to a calmer time window on the same day.

Absolutely—private boats make stress-free celebrations. Share your headcount and vibe—chill sandbar day, upbeat sunset cruise, or snorkeling and music—and your captain will tailor the route and pace. Most small private boats carry up to six guests, while larger inspected vessels can host bigger groups. You can bring decorations and a playlist; just keep it tidy and plan for a customary gratuity at the end.

Boating happens year-round. December through April is the dry season with clear skies and cooler water, while May through October brings warmer seas that are great for snorkeling but also more humidity and pop-up showers. Memorial Day, July 4th, and Labor Day weekends are popular on the water, so book early. Late October’s Fantasy Fest week and early November’s offshore powerboat championship also fill marinas and charters quickly. Weekdays and morning departures are your best bet for lighter crowds and calmer conditions.

Captains often run to the shallow flats and sandbars in the backcountry, including Mud Keys to the northeast and, farther west, Woman Key, Boca Grande, and Marvin Key. Depending on the day’s tides and wind, closer sandbars can be 25–45 minutes from the dock, while more remote spots may take an hour or so. Your captain will choose the clearest water and least-crowded bar for the conditions, with time to swim, float, and relax before an easy cruise back.