Florida Keys Kayak And Paddleboard Rentals
Explore the stunning waterways of the Florida Keys with our kayak and stand-up paddleboard rentals. Perfect for all ages and skill levels, this self-guided adventure allows you to navigate through beautiful mangrove tunnels and trails at your own pace. Enjoy a 2-hour rental with the option to extend and receive all necessary safety equipment, paddle instruction, and a satellite view map of the area.
- Choose from single kayaks, tandem kayaks, or paddleboards
- Discover the unique ecosystem of the Florida Keys
- Perfect for both beginners and experienced paddlers
- All rentals include safety equipment and instructional guidance
Cudjoe Key, Florida Boat Rental Services
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.
Private Fishing Charter Florida Keys
Great for families. Customizable. Not a crusty old fishing charter by any means! Lots of sea life in the Florida keys! We can pull stone crab traps (Oct 15-May 1st). Or get in and go for a swim or stop in at a sandbar! Captain has almost 20 years fishing experience. Take your catch to a restaurant to be cooked! Snorkel gear is available. Lobster diving charters are available in season (Aug 6-March 31). Pets are welcome
Hula Hank's Key West Tipsy Tiki Sunset Cruise
Imagine gliding over gentle waves aboard the Lazy Lady, a 53-foot, one of a kind tiki boat. Soak in the vibrant colors of an iconic Key West sunset - hues of orange, pink and purple.
Sip on ice-cold beverages prepared by your friendly crew while the warm sea breeze carries the sounds of island music and laughter. The atmosphere is relaxed and festive, perfect for making new friends or sharing moments with loved ones. Expect a laid-back and enjoyable trip while unwinding with a refreshing beverage from the bar.
As the last sliver of sun disappears below the water, watch for the green flash, an enchanting touch of magic. Sail back to Key West Harbor under the star-filled sky, creating a Key West memory to last a lifetime.
Key West After Dark, Ghost, Santeria & Voodoo Pedicab Tour
Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll through the narrow, historic streets, you'll hear chilling tales of ghostly encounters, from restless spirits who never left to eerie legends passed down through generations. We’ll pass by the famous haunted landmarks, including the Key West Cemetery, where some say the dead still walk at night, and the eerie corners of Old Town, known for their strange, unexplainable occurrences. With the breeze in your hair and the moonlight casting long shadows, prepare for a spine-tingling ride into the heart of Key West’s most mysterious and supernatural stories. Buckle up, it's going to be a night you won't forget!
Florida Keys Jet Ski Rental
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 Keys at Golden Hour Ultimate Private Sunset Tiki Cruise
Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the sky transforms into a vibrant canvas of colors, providing an unforgettable backdrop for your evening. Bring your favorite beverages to toast the day's end in a romantic and relaxing atmosphere. Capture unique photo opportunities with breathtaking reflections in the water, making this experience perfect for couples or anyone looking to unwind after a day of exploration.
- Enjoy a serene 2-hour cruise on the tranquil waters of the Florida Keys
- Front-row seat to a spectacular sunset with unobstructed views
- Bring your own beverages for a personal touch during the cruise
- Perfect for couples or those seeking a relaxing escape after sightseeing
Key West Christmas Cruise with Live Band and Drinks
Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in Key West. Enjoy a festive hot cocoa and holiday treats as we glide along with water for a fun night in Key West. Our beautiful 105-foot Schooner America 2.0 in full holiday decor that's sure to get you into the Christmas spirit in Key West harbor.
Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY
Experience an Unforgettable Fishing Adventure in Key West!
Join us for an exhilarating private deep-sea fishing adventure on the vibrant waters of Key West. Led by a skilled and experienced captain, our charters cater to both seasoned anglers and first-timers, ensuring an unforgettable experience.
Reel in magnificent mahi, wahoo, sailfish, and more. Our knowledgeable crew will guide you to prime fishing spots, employing techniques like trolling, reef, or wreck fishing and many more to maximize your chances of landing a trophy catch. Choose from flexible charter options: 1/2-day, 3/4-day, full-day, or extended 10-12 hour trips tailored to your preferences.
Our 36-foot Hatteras "Cowboy" offers comfort and safety with clean facilities, restrooms, , a flybridge, and state-of-the-art equipment. Book now and discover why our private charters are the ultimate choice for a thrilling day on the water in Key West.
Private Afternoon Snorkel with Sunset Sail in Key West
Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's amazing natural wildlife with up to five others, before sailing back to shore at sunset.
Experience Florida Keys Boat Charter Private Tour
Cruise the beautiful waters of the Florida Keys on an authentic tiki bar boat during this 1.5-hour Tiki Fun Cruise. Sip your favorite beverage while soaking in the sun and taking in stunning views of luxurious homes and coastal landscapes. Keep your eyes peeled for dolphins, sea turtles, and tropical seabirds as you glide over the crystal-clear waters. You can choose between a scenic harbor cruise or an island swim stop at a sandy beach for a refreshing dip in the turquoise sea. This is the perfect way to create unforgettable memories in paradise.
- Enjoy a leisurely 1.5-hour cruise on a tiki bar boat
- Spot local wildlife, including dolphins and sea turtles
- Customize your cruise with a scenic harbor tour or beach swim
- Knowledgeable Captain shares local history and fun facts
Private Vacation Photoshoot with Photographer in Key West
⭐ Top-Rated Vacation Photoshoots 2025
We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing travellers around the world, our small team specialises in authentic, natural photography that truly reflects your trip.
In Key West, we combine creativity with local knowledge to show you hidden gems, secret angles, and the best light. You’ll not only get beautiful, professional photos but also insider tips to make the most of your time here.
We’re proud to be recognised among the top-rated photography tours of 2025, trusted by travellers worldwide for our relaxed style and stunning results
Morning Mimosa and Swim 2hr Luxury Cruise in Marathon FL
Experience a relaxing start to your day on a spacious 53’ luxury catamaran as you cruise through the clear waters surrounding Marathon. Enjoy a complimentary morning mimosa as the crew guides you along scenic coastlines with views of the Atlantic Ocean, Boot Key, and the iconic Seven Mile Bridge.
Take a refreshing swim in calm, shallow waters and explore the sandy bottom for shells and sea life. With plenty of space on board, comfortable seating, and friendly local crew, this tour offers a peaceful and memorable way to experience the beauty of the Florida Keys.
Half Day Luxury Boat Tour in Key West with Snorkeling
Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your group exploring with stops like Fort Zachary Taylor Historic State Park, U.S. Coast Guard Cutter Ingham Maritime Museum, Smathers Beach, Southernmost Point of your list.
2 Hour Mangrove Maze Kayak Tour in Key West
Navigate through the stunning Mangrove Tunnels on this engaging 2-hour kayak tour in Key West. Ideal for all ages and skill levels, this adventure allows you to explore diverse ecosystems while searching for fascinating wildlife like manatees, nurse sharks, and playful dolphins. Led by knowledgeable guides, every excursion provides a unique experience filled with insights about the local flora and fauna. With single and double kayaks available, gather your family or friends for an unforgettable journey through the mangroves.
- Tour duration: 2 hours, suitable for ages 6 and up
- Max group size of 35, ensuring a personalized experience
- Spot wildlife including manatees, sea stars, and birds
- Essential gear: sunscreen, water, and waterproof items recommended
Sandbar Excursions with Snorkeling and Sunset Cruises in Key West
Explore the beautiful waters of Key West with us, where the adventure includes snorkeling in crystal blue waters, lounging on secluded beaches, and witnessing stunning sunsets. This intimate charter accommodates up to 6 guests, ensuring a personalized experience. Choose from hourly, half-day, or full-day trips to tailor your Florida Keys getaway. Unwind and create unforgettable memories in paradise with a guided tour that showcases the essence of the Keys.
- Snorkel in the clear waters of Key West with small group settings
- Relax on secluded beaches away from the crowds
- Enjoy breathtaking sunsets on the water
- Flexible trip duration options: hourly, half-day, or full-day
Six Fins Key West Sandbar Charter – Swim, Snorkel & Island Escape
Discover the “backyard” of Key West locals with our Secret Sandbars Charter—hidden gems few visitors ever see. Unlike crowded party boats, this is your private slice of paradise. Imagine stepping off your boat into ankle-deep water, surrounded by endless blue sky and shimmering ocean, with no other boats in sight. Explore uninhabited islands, search for starfish and conch in the tide pools, or relax on a floating mat as the captain takes care of everything.
This isn’t just a boat ride—it’s the ultimate Key West daydream, brought to life.
Key West Center Console Boat Rental With Sound and Seat Upgrade
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.
Parasailing Experience in Key West
Soar up to 300ft above Key West for stunning panoramic views
Enjoying a thrilling 10-15 minute parasailing experience
Parasail with friends with the double, or triple flight options
Safe and fun for ages 6 and up.
Choose between two departure locations in Key West
PRIVATE Guided Mangrove Eco-Tour Adventure
Paddle through the serene waters of Geiger Key at your own pace, with a private guided kayak/Paddleboard tour that immerses you in the natural beauty of the Florida Keys. Paddle through tranquil mangroves where your expert guide highlights local wildlife and ecological wonders, from tropical bird habitats to vibrant sea turtles. This eco-friendly adventure is suitable for all skill levels, ensuring a relaxing time as you navigate the peaceful waterways. Discover hidden gems and soak in the lush surroundings, all while enjoying small group sizes for a personalized experience.
Key West Jet Ski Tour: 1-hour Freestyle w/Sub Pits
Most Key West jet ski trips lock you into a fixed route and a big group. This one doesn't — it's a private, freestyle hour where the ride is yours to shape.
✅ A private, flexible alternative to large guided group tours
✅ No set route — open the throttle, cruise, or stop to swim, your call
✅ A short guided escort out, then the open-water zone is yours
✅ Ideal for repeat riders, thrill-seekers, or anyone short on time
If you want speed, sightseeing, or just space to play on your own terms, the freestyle ride gives you the freedom a guided tour can't.
Private Sandbar Charter & Island Escape in Key West
Explore the crystal-clear waters and pristine sandbar islands that surround the Florida Keys. This private sandbar charter is fully customizable—whether you’re looking to relax with a drink in hand, explore the local marine sanctuary, or simply enjoy a laid-back day on the water.
Your captain will tailor the experience to your preferences, taking you to the best sandbar spots and providing everything you need for a carefree day in paradise. Enjoy sunshine, calm waters, and unforgettable views of Key West’s natural beauty.
This is the ultimate way to experience the islands—your day, your way, in the heart of the Florida Keys.
2 HR Key West Clear Kayak Rental – Discover Mangroves & Wildlife!
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.
38' Private Luxury Sunset Charter w. Music & Drinks, up to 13 ppl
Ready to explore Sunset Charter with drinks and Music? aboard a luxurious private boat charter, accommodating up to 13 guests. Sailing aboard a 38’ private charter a smoother ride with plenty of deck space, and you’ll see 20s of things do from boat can do photography and get a explanation from caption cum guide