Top Key West Self-guided Tours

Make the most of your Key West vacation by exploring the island with Fury’s golf cart rentals. Forget the long walks and drive straight into the adventure! Cruise through the Conch Republic like a local with our gas-powered golf cart rentals. Feel the refreshing sea breeze as you effortlessly navigate Key West’s charming streets in our high-quality street-legal golf cart rentals. Experience the thrill of driving down Duval Street with friends or family in our comfortable four- to six-passenger golf carts. Our top priority is your safety and enjoyment, so each golf cart rental is carefully maintained to ensure a smooth ride. Experience Key West in a fun, convenient and unforgettable way with Fury’s golf cart rentals!

Key West is a small island with a big personality, and the only way to truly experience it is on your own terms. Island Safari Rentals Rentals gives you a reliable, comfortable two-passenger scooter, a full tank of gas, and the freedom to write your own itinerary. A well-maintained fleet and seamless pickup process. Two convenient locations mean you're never far from getting started. Unlike a guided tour, there's no bus to wait for and no group to keep up with. Want to circle the island twice? Linger over lunch at a waterfront spot? Ride to the Southernmost Point at sunrise? It's entirely your call. Rentals flex from a quick 3-hour spin to a full month, and same-day bookings are welcome. Ride like a local. Explore like it's yours.

Explore the vibrant island of Key West with ease through our golf cart rentals. Perfect for couples, families & small groups, our 4 person golf carts are the ideal way to navigate the island's scenic roads without any hassles. Enjoy the convenience of gas included with your rental and flexible hourly or daily options, ensuring you can set your own pace for adventure. With a convenient downtown location and a fleet of new carts, your island exploration is just a ride away. - Key West's official golf cart rental company - Gas included to keep you cruising without extra costs - Convenient hourly and daily rental options available - Explore Key West's attractions like Duval Street, Southernmost Point and Smathers Beach easily

Explore the clear, calm waters of Key West at your own pace with a single or double kayak rental. Choose a morning or afternoon session, and after a brief introductory lesson, head out on the water. Glide over seagrass and through mangrove tunnels, keeping your eyes open for fish, birds, sharks, rays, and manatees.

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!

Enjoy the freedom and flexibility we offer—whether you want to paddle for just an hour or spend a full four hours exploring, you can do it all at your own pace. Our launch site gives you direct access to some of Key West’s most stunning and secluded mangrove tunnels, so you're in the heart of the adventure within minutes. No guided schedule, no rushing—just you, the water, and the wildlife. With high-quality gear, easy-to-follow route maps, and a laid-back local vibe, we make it simple to experience the best of Key West’s natural beauty, on your own terms.

The whole family can learn more about sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast to try your luck spotting dolphins, stingrays, turtles, and birds while you learn more about Key West’s waters than you ever would sailing along. Then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat.

Our 6-passenger golf cart rental offers a fun, private, and convenient way for families and groups to explore Key West together. Instead of splitting up or relying on crowded tours, everyone can ride comfortably in one street-legal cart while discovering the island at their own pace. With easy navigation through Old Town and quick access to popular spots like Duval Street, Mallory Square, and the Southernmost Point Buoy, it’s one of the most enjoyable and flexible ways to see the island. Spacious seating, reliable performance, and the freedom to stop wherever you like make this a truly memorable Key West adventure!

Eat your way around Key West on a food tour of “mom and pop” eateries in the Old Town historic district. Taste seafood, Cuban cuisine, and delicious key lime pie. The walking tour route takes you off typical touristy streets so you can see Key West like a local, listening to insights about the city's food, architecture, and history along the way. Tastings are enough for a hearty lunch.

Go parasailing above the emerald waters of Key West for a thrilling 1-hour tour that provides sweeping views of Florida’s southernmost city and its surroundings. Head out in a 12-passenger state-of-the-art parasailing boat out to the ocean, then your guide secures you into a double or triple-person parasailing device for a ride that gently lifts off and glides above the water, all without getting wet.

Unleash your adventurous spirit with a jet ski rental from Seahorse Water Adventures in Marathon, Florida. Explore stunning coastal views and encounter native wildlife at your own pace, whether you’re seeking excitement or relaxation. With both half-day and full-day rental options available, you can conveniently tailor your experience to fit your schedule. Enjoy the freedom of the open water while we ensure a smooth rental process, including safety gear. - Explore the beautiful waters of the Florida Keys at your leisure - Encounter native wildlife and stunning coastal views - Safety gear included for a worry-free adventure

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.

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.

Take in rare birds–eye views of Key West on a parasailing adventure over Smathers Beach. With a range of departure times offered throughout the day, this tour is a popular, flexible choice for families. Your guide, who ensures that the small group has a personalized experience, takes photos and videos available for purchase after the trip.

Head out into the calm waters between Stock Island and Key West for a 2-hour stand-up paddleboard adventure. Paddle through the mangroves and see native wildlife such as fish, birds, small sharks, rays, and maybe even a manatee swimming around in the crystal clear waters. This rental also comes with a brief lesson for beginners.

Explore Key West through the eyes of a local on a craft cocktail tour that stops at six off–the–beaten–path establishments for drinks and food tastings, from a historic mansion to a boutique hotel that was once a hospital. In addition to navigating for you, your guide uses the city’s bar scene to give you an overview of its history and culture. The tour includes five craft cocktails and two gourmet food tastings.

Discover the art of Tiki cocktails during a private, 2-hour class in Key West. Begin with a rum tasting, then learn how to prepare four different drinks, including a Mai Tai. Each cocktail is yours to enjoy, of course. You even learn how to safely light drinks on fire. Class includes: one rum tasting and four cocktails!

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.

Explore Key West in a unique way through this interactive and creative scavenger hunt. Walk or drive around to different checkpoints and creatively interpret clues on art, culture, and history, and complete wacky challenges for points, while competing against other teams for a spot on the leaderboard. Along the way, uncover hidden gems and local secrets.

What makes our e-bike rental truly unique is the combination of easy-to-ride electric bikes and a built-in GPS guided tour experience. While most rentals simply give you an e- bike, our e-bikes can guide you through Key West with an interactive talking GPS tour that leads you to more than 30 historic landmarks and must-see locations around the island. As you ride, the e-bike shares entertaining stories and history through its Bluetooth speaker, turning your ride into a fun and informative adventure. On top of that, our local team provides insider recommendations on the best scenic routes, photo spots, beaches, and hidden gems around the island. Instead of just renting an e-bike, you’ll get a complete Key West exploration experience designed to help you see more, learn more, and have more fun during your visit.

Enjoy an amazing day out on the water in Florida’s Key West with this ultimate adventure tour aboard a catamaran. Spend the day partaking in water sports such as parasailing, jet skiing, snorkeling, and riding on a Banana Boat. Sunbathe on the boat’s spacious deck, or just take in the sights of the Key West area. Drinks are included with your tour.

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.

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.

Discover the ultimate way to explore the Florida Keys on a fully customizable luxury boat charter. Cruise crystal-clear waters with a local captain and design your own itinerary—snorkel vibrant coral reefs, sip drinks on a sandbar, or head out to the legendary Dry Tortugas. Whether it’s a 2-hour cruise or a full-day escape, this private experience is tailored for relaxation, adventure, or both.