Top Key West Self-guided Tours

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.

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!

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 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!

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!

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.

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.

Get ready for fun in the sun—and leave all the planning to someone else—on this half-day sailing, kayaking, and snorkeling adventure off the coast of Key West. Kayak through a maze of mangrove-canopied canals and streams, home to a tropical array of birds, rays, sharks, sport fish and more. Then jump into the water for a snorkeling session above a coral reef teeming with marine life. Snacks, beer, wine, and soft drinks are included.

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.

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!

Experience Key West’s tropical blue waterways on this Jet Ski tour along the Atlantic Ocean and/or the Gulf of Mexico. Enjoy panoramic island views and watch for dolphins, stingrays, sea turtles, manatees, and more while gliding over warm ocean water. Bring a waterproof camera to capture this southernmost point in the continental United States.

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.

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.

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.

Explore the waters of Key West in style with a customizable boat charter. You'll sail out in a luxury vessel that has a mix of shaded and open outdoor seating and an air-conditioned cab in case the temperatures get too hot. You'll also have access to snorkeling equipment if you want to get in the water or a spear gun if you want to do a little fishing.

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!

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

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 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.

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.

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.

Step into vibrant Key West for a scavenger hunt like no other! Guided by Tara, your upbeat game show host, you’ll embark on an interactive adventure filled with creative challenges, playful clues, and memorable moments. Connect with your group and the colorful island spirit as you solve tasks, capture fun photos, interact with locals, and discover hidden stories of Key West. This is an imaginative, lighthearted experience—perfect for all ages and backgrounds, whether you’re an explorer or an artist at heart. No bars or drinking stops, just teamwork, laughter, and discovery. Celebrate your unique journey together after the hunt! Bring your curiosity, and let Key West surprise you.