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Explore Greetwell

Explore extraordinary experiences in 500+ destinations

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Rentals & Charters

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  • Yacht Charters

Questions? We're here to help.Real people, 7 days a week.

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  • How to Budget for Yacht Charter Costs
  • Best 1234

    things to do in Sugarloaf Key, FL

    Showing 1,153-1,176 of 1,234 results
    Key West Reef & Offshore Fishing Charter

    Key West Reef & Offshore Fishing Charter

    Cast for reef and blue-water species with a professional crew

    5.0 • 15 reviews
    $954/ boat
    4.5-Hour Key West Sandbar Cruise

    4.5-Hour Key West Sandbar Cruise

    Float, wade, and unwind at Key West’s shallow-water sandbars

    4.7 • 8.1K reviews
    $202/ person
    2-Seater Scooter Rental in Key West for Experienced Riders

    2-Seater Scooter Rental in Key West for Experienced Riders

    Explore the island at your own pace

    4.7 • 432 reviews
    $62/ scooter
    Single-Seat Scooter Rental in Key West

    Single-Seat Scooter Rental in Key West

    See Key West at your own pace

    4.7 • 432 reviews
    $45/ scooter
    4-Seater Gas Golf Cart Rental in Key West

    4-Seater Gas Golf Cart Rental in Key West

    Discover Key West at your own pace

    4.7 • 432 reviews
    $114/ cart
    6-Seater Gas Golf Cart Rental in Key West

    6-Seater Gas Golf Cart Rental in Key West

    Explore Key West at your own pace

    4.7 • 432 reviews
    $182/ cart
    Private Backcountry & Flats Fishing Charter in Key West

    Private Backcountry & Flats Fishing Charter in Key West

    Head out with Captain Karl for a private day of fishing

    5.0 • 12 reviews
    $583& up
    Private Boat Tour Around Key West & Southernmost Buoy

    Private Boat Tour Around Key West & Southernmost Buoy

    See Key West's landmarks from the water without getting wet

    5.0 • 12 reviews
    $511
    Private Sunset Boat Tour Around Key West

    Private Sunset Boat Tour Around Key West

    See Key West's landmarks from the water and catch the sunset with friends or family

    5.0 • 12 reviews
    $624
    Private Custom Boat Charter in Key West

    Private Custom Boat Charter in Key West

    Shape your own private outing on the water

    5.0 • 12 reviews
    $908
    Private Sandbar Boat Charter Near Key West

    Private Sandbar Boat Charter Near Key West

    Enjoy a sandbar escape with your favorite food and drinks

    5.0 • 12 reviews
    $908
    Fishing Charter in Key West Aboard a 63' Vessel

    Fishing Charter in Key West Aboard a 63' Vessel

    Roomy sport-fishing charter with space for large day-trip groups

    4.7 • 50 reviews
    $2,440& up
    Private Island-Hopping Catamaran Charter in Key West

    Private Island-Hopping Catamaran Charter in Key West

    Stretch out on spacious decks between island stops

    5.0 • 6 reviews
    $1,816& up
    Key West Adult Drag Show

    Key West Adult Drag Show

    Enjoy live songs from stage, screen, and radio with Miss Bouvee's adult-humor performance

    4.6 • 1.7K reviews
    $40/ person
    Explore the Tennessee Williams Museum in Key West

    Explore the Tennessee Williams Museum in Key West

    Visit the Tennessee Williams Museum during daily open hours

    4.6 • 508 reviews
    $8/ person
    Private Sunset Viewing at Key West Lighthouse

    Private Sunset Viewing at Key West Lighthouse

    Watch the sunset with private access to the Key West Lighthouse

    4.6 • 508 reviews
    $355& up
    Sunset & Night Scuba Dive for Certified Divers in Key West

    Sunset & Night Scuba Dive for Certified Divers in Key West

    Explore Key West’s underwater world after sunset with lights and gear included

    4.6 • 349 reviews
    $199/ person
    Coral Restoration Dive in Key West

    Coral Restoration Dive in Key West

    Join hands-on coral nursery care and reef restoration work in Key West

    4.6 • 349 reviews
    $186/ person
    Discover Scuba Resort Course in Key West

    Discover Scuba Resort Course in Key West

    Learn scuba basics and make two guided reef dives in one day

    4.6 • 314 reviews
    $284/ person
    Private Full-Day Tuna Fishing Charter Near Key West

    Private Full-Day Tuna Fishing Charter Near Key West

    Chase Blackfin tuna around the Gulf's shrimp boats

    4.7 • 10 reviews
    $2,650
    Private Deep Drop Grouper Fishing Charter on Stock Island

    Private Deep Drop Grouper Fishing Charter on Stock Island

    Reach federal Gulf fishing grounds on a private offshore charter

    4.7 • 10 reviews
    $2,544
    Private Guided Sandbar Trip in Key West
    Up to 10

    Private Guided Sandbar Trip in Key West

    Swim and snorkel at Key West sandbars with a licensed captain and included gear

    5.0 • 2 reviews
    $597& up
    Captained Sandbar Boat Rental in Key West
    Up to 10

    Captained Sandbar Boat Rental in Key West

    Cruise Key West sandbars with a local captain; includes snorkel gear, floats, and room for up to 10

    5.0 • 2 reviews
    $851
    Sandbar & Snorkel Tritoon Charter in Key West

    Sandbar & Snorkel Tritoon Charter in Key West

    Customize your Downtime on a tritoon charter for just 6 guests

    5.0 • 1 reviews
    $158/ person
    1…484950…52
    Fishing Charters226Boat Tours178Boat Rentals108Yacht Charters100Snorkeling99
    More
    • Sailing83
    • Scuba Diving74
    • Car Rentals52
    • Sunrise and Sunset Tours45
    • Bike Rentals34
    • Private Fishing Charters25
    • Dolphin Watching24
    • Kayaking Tours18
    • Jet Skiing17
    • Scooter Rentals12
    • Ghost and Haunted9
    • Scavenger Hunts8
    • Dinner Cruises7
    • Scenic Flights7
    • Bar and Pub Crawl6
    • Parasailing6
    • Private Boat Charters6
    • Helicopter Tours5
    • Historical Tours5
    • Paddleboarding5