Top Key West Rentals - page 2

Become the captain of your vacation when you rent this pontoon boat for a half-day adventure. As long as you can pass a Florida Boaters Safety Test, you can rent this premier 22ft pontoon boat and sail up to 9 of your friends and family into the waters surrounding Key West. Find a sandbar to explore or take to the open water with the radio blasting.

Discover a side of Key West some visitors miss, and immerse yourself in its beautiful scenery, on a half-day sailing tour. Board your catamaran and head to North America's only living coral barrier reef. Pass some of Key West’s top attractions on the way, then dive in to see hundreds of species of colorful fish, coral, and other sea life. This cruise includes snorkeling gear, plus beer, wine, and soft drinks.

Fun Rentals Key West bicycle rentals stand out because we combine high-quality bikes, local expertise, and a hassle-free rental experience designed specifically for exploring the island. We offer a large fleet of comfortable beach cruisers and multi-speed hybrid bicycles in men’s, women’s, and children’s sizes, making it easy for couples, families, and groups to ride together and enjoy Key West at a relaxed pace. What really makes the experience special is our local knowledge. Our team will provide a map and insider recommendations for the best scenic routes, waterfront rides, historic neighborhoods, and hidden local spots many visitors never discover. Ride through Old Town, cruise along the island streets, and visit iconic landmarks like Duval Street, Mallory Square, and the Southernmost Point Buoy at your own pace. With easy-riding bikes and tips from locals, exploring Key West becomes effortless, fun, and unforgettable.

Fun Rentals Key West bicycle rentals stand out because we combine high-quality bikes, local expertise, and a hassle-free rental experience designed specifically for exploring the island. We offer a large fleet of comfortable beach cruisers and multi-speed hybrid bicycles in men’s, women’s, and children’s sizes, making it easy for couples, families, and groups to ride together and enjoy Key West at a relaxed pace. What really makes the experience special is our local knowledge. Our team will provide a map and insider recommendations for the best scenic routes, waterfront rides, historic neighborhoods, and hidden local spots many visitors never discover. Ride through Old Town, cruise along the island streets, and visit iconic landmarks like Duval Street, Mallory Square, and the Southernmost Point Buoy at your own pace. With easy-riding bikes and tips from locals, exploring Key West becomes effortless, fun, and unforgettable.

Our 4-passenger golf cart rentals are the perfect blend of convenience, fun, and flexibility for exploring Key West. With a smaller footprint than larger carts, these vehicles are easy to maneuver through Old Town’s charming streets and tight parking areas, making them ideal for couples or small groups who want to move around the island quickly and effortlessly. What truly sets Fun Rentals apart is our focus on quality equipment and local expertise. Our modern, street-legal carts are comfortable, reliable, and designed for smooth island cruising. Our friendly team also provides insider tips on the best scenic routes, hidden local gems, and must-see attractions so you can make the most of your Key West adventure. You’ll be able to cruise famous spots like Duval Street, visit the sunset celebration at Mallory Square, and stop for photos at the Southernmost Point Buoy — relaxed, all at your own pace!

Set sail for adventure with our Tiki Party Boat rental, cruising the breathtaking waters! Whether you're soaking up the sun, spotting local marine life, or enjoying refreshing drinks on deck, our 14-passenger tiki boat is the perfect way to experience paradise. Complete with bar top and chairs, take your party to the sea! Want a stress-free day? Hire a captain and let them handle the navigation while you focus on fun. Book now and turn your day on the water into a true paradise escape!

We are Key West's largest boat rental service and have been helping travelers explore our local waterways for over 39 years. Our boats are located at a full service marina with ice, gas, snacks, drinks, beer, fishing equipment, bait and so much more. We are your one stop shop for everything you need to enjoy your time on the water. Our expert staff will guide you through the boat and give directions to local hotspots. Book with Sunset Watersports and see the difference.

The 24' Hurricane Sundeck stands out as the ultimate choice for families and groups looking for comfort and versatility on the water. Its spacious design and thoughtful features make every outing enjoyable and stress-free. Why You’ll Love It: Perfect Balance: Combines generous space with easy maneuverability for smooth cruising. Room for Everything: Plenty of space for coolers, gear, and unforgettable memories. Premium Features: Wraparound seating, built-in cooler space, Bimini shade top, stereo system, swim ladder, and a wide deck area for lounging. Ideal for Any Occasion: Great for family outings, sandbar trips, sightseeing, or celebrating with friends. Capacity: Comfortably accommodates up to 12 passengers.

Enjoy the waters of the Florida Keys, don't have experience on the waters around Cudjoe Key? We have separate colored tracks to spots on the water on the 9" GPS.

Create your own adventure: fish, snorkel, paddleboard, or just cruise in style! The newest fleet in town! Our spacious pontoons provide plenty of space and shade while you make your way through our beautiful local waterways! What’s Included: 12 Passenger Pontoon Boat Rental (Children and babies count as passengers) Safe, reliable, and well-maintained equipment Includes a 70qt cooler (purchase ice at check-in) Life vests for all passengers Guests are welcome to bring their own snack and drinks, or purchase upon arrival at our fully stocked Marina Store! Alcohol permitted for guests 21+ Optional Add Ons: Paddleboards- A fun and suitable activity for people of all ages and abilities. Lily Pad- This floating foam island allows you to rest, kick-back, tan, run, and play on.

Double Decker Pontoon Boat with slides for up to 14 passenger Rental in sunny Key West, Florida. Want a stress-free day? Hire a captain and let them handle the navigation while you focus on fun. Book now and turn your day on the water into a true paradise escape!

Experience the ultimate adventure aboard our 25' Cobia Center Console with twin engines, designed for power, stability, and comfort. Perfect for fishing trips, sandbar cruising, or exploring offshore waters, this vessel offers unmatched versatility. Highlights A safe, comfortable ride that handles well in all conditions, making it a favorite for those who want flexibility on the water. • Length: 25 feet • Capacity: Up to 9 passengers • Features: T-top shade, live well, rod holders, swim ladder, spacious deck, and premium seating • Best For: Fishing enthusiasts, families wanting versatility, or groups looking for comfort and style

Discover the unparalleled joy of exploring Key West waters aboard this center console! Our fleet boasts the newest, most luxurious vessels, fully equipped with top-tier upgrades for your comfort and convenience. Nestled within our full-service marina, we've proudly served our community for 39 years, earning our reputation as the go-to destination for boat rentals in Key West. Join us and embark on an adventure of a lifetime – where every wave carries the promise of unforgettable memories!

Turn your trip into something unforgettable with a Polaris Slingshot rental from Keys Vacation Supply Rentals. This open-air ride lets you feel the ocean breeze, soak in panoramic views, and enjoy the road like never before—all while being easy to drive with a standard license. With built-in navigation, premium sound, and flexible rental options, you can explore at your own pace and make every mile part of the adventure. It’s more than just transportation—it’s the highlight of your vacation waiting to be booked.

Private 2-Hour Key West Sunset Cruise | Luxury Manitou Pontoon | Up to 10 Guests Leave the crowds behind and experience the magic of a Key West sunset from the water on your own private 2-hour cruise aboard a brand-new Manitou luxury pontoon. Departing from the tranquil Cow Key Channel, you'll enjoy a relaxed and intimate journey through hidden backchannels and open waters — all with a front-row seat to one of nature’s most unforgettable shows. Cruise in comfort with up to 10 guests, guided by a licensed local captain, and take in stunning views of the sunset-drenched coastline, including iconic sights near Mallory Square — without ever getting caught in the crowd. Whether you're planning a romantic evening, a family outing, or a fun get-together with friends, this cruise offers the perfect mix of laid-back luxury and scenic beauty. Reserve your sunset escape now — and experience Key West the way locals love it: peaceful, personal, and absolutely stunning.

Explore the beautiful mangrove tunnels and seagrass beds of Key West with convenient kayak rentals. Perfect for adventure seekers, you can set your own pace while paddling through serene waters. Choose from 2-hour or 3-hour rental options to fit your schedule. Phone cases are available for your convenience, ensuring your belongings stay safe while you enjoy your adventure. - Rent a kayak and discover the unique ecosystem of Key West - Customize your experience with flexible rental durations - Paddle through scenic mangrove tunnels at your leisure - Conveniently located at Cow Key Marina, available daily from 9 AM to 5 PM