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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 433-456 of 1,234 results
    Paddle Board, Kayak & Hobie Cat Rentals at Smathers Beach

    Paddle Board, Kayak & Hobie Cat Rentals at Smathers Beach

    Your beach rental, ready and waiting at Smathers Beach

    4.8 • 24.1K reviews
    $28/ rental
    Lily Pad Floating Mat Add-On for Boats in Key West

    Lily Pad Floating Mat Add-On for Boats in Key West

    Add a floating mat to your boat day

    4.8 • 24.1K reviews
    $57/ mat
    Key West 6-Hour Reef Fishing Trip

    Key West 6-Hour Reef Fishing Trip

    Reef fishing with tackle, bait, a license, and crew assistance

    4.8 • 1.7K reviews
    $88/ person
    3-Hour Dolphin Watching & Snorkeling Cruise in the Keys

    3-Hour Dolphin Watching & Snorkeling Cruise in the Keys

    Cruise the Keys waters and watch dolphins, with time to snorkel

    5.0 • 29 reviews
    $158/ person
    Private Party Boat Fishing Charter in Key West

    Private Party Boat Fishing Charter in Key West

    Private fishing for your Key West group, with gear and fish cleaning included

    4.8 • 1.7K reviews
    $2,290
    3-Hour Key West Sandbar Charter

    3-Hour Key West Sandbar Charter

    Cruise to shallow sandbars and glide through mangroves in the Florida Keys

    5.0 • 29 reviews
    $112/ person
    Florida Keys Sunset Charter

    Florida Keys Sunset Charter

    Watch the Florida Keys sunset from the Gulf of Mexico

    5.0 • 29 reviews
    $146/ person
    Private Charter or Rental in San Jose

    Private Charter or Rental in San Jose

    Customize a private outing for up to 9 people

    5.0 • 29 reviews
    $737& up
    3-Hour Dolphin Watching Charter in San Jose

    3-Hour Dolphin Watching Charter in San Jose

    Customize a private boat outing around dolphin watching and sandbar time

    5.0 • 29 reviews
    $169/ person
    Florida Keys Sunset Charter

    Florida Keys Sunset Charter

    Watch the Florida Keys sunset from Gulf waters

    5.0 • 29 reviews
    $623
    Full-Day Private Yacht Charter & Reef Snorkeling in Key West

    Full-Day Private Yacht Charter & Reef Snorkeling in Key West

    Charter a private sailing catamaran or power yacht for 8 hours of snorkeling and island stops

    4.9 • 56 reviews
    $6,867
    Private Sunset Yacht Cruise & Snorkel in Key West

    Private Sunset Yacht Cruise & Snorkel in Key West

    Sail, snorkel, and toast the sunset on your own Key West yacht

    4.9 • 56 reviews
    $2,088& up
    Private Half-Day Yacht Charter & Snorkeling in Key West

    Private Half-Day Yacht Charter & Snorkeling in Key West

    Charter a private yacht for 4 hours with snorkeling or sailing options

    4.9 • 56 reviews
    $4,029
    Private Luxury Yacht Charter & Snorkeling in Key West

    Private Luxury Yacht Charter & Snorkeling in Key West

    Shape your private yacht day around swimming, harbor views, and time to unwind

    4.9 • 56 reviews
    $2,860/ boat
    Kayak Through Mangroves & Spot Marine Life

    Kayak Through Mangroves & Spot Marine Life

    Paddle serene mangrove waterways with an expert guide and spot vibrant marine life.

    4.8 • 996 reviews
    $70/ person
    Key West Mangrove Maze Kayak Rental

    Key West Mangrove Maze Kayak Rental

    Paddle at your own pace through serene mangroves and discover Key West’s vibrant marine life.

    4.8 • 996 reviews
    $46& up
    Key West Deep Sea Fishing Charter

    Key West Deep Sea Fishing Charter

    Fish Key West’s offshore waters from a stable 45-foot sportfishing boat

    4.8 • 1K reviews
    $1,305& up
    Private 34' Light Tackle Fishing Charter in Key West

    Private 34' Light Tackle Fishing Charter in Key West

    Fish reefs, shallows, and offshore edges aboard a fast 34-foot center console

    4.8 • 1K reviews
    $1,325& up
    34' Marquesas Islands Fishing Charter, Key West

    34' Marquesas Islands Fishing Charter, Key West

    Chase offshore species in the remote waters of the Marquesas

    4.8 • 1K reviews
    $1,855
    4-Hour Private Boat Charter in Key West Backcountry

    4-Hour Private Boat Charter in Key West Backcountry

    Customize a 4-hour private tri-toon cruise with a licensed captain in Key West’s backcountry

    4.8 • 996 reviews
    $523
    Private Full-Day Key West Backcountry Boat Charter

    Private Full-Day Key West Backcountry Boat Charter

    Customize your Key West backcountry day on a captained tri-toon with a swim deck

    4.8 • 996 reviews
    $1,161
    Private Key West Backcountry Tri-Toon Boat Charter
    Up to 10

    Private Key West Backcountry Tri-Toon Boat Charter

    Customize a 6-hour captained Manitou tri-toon cruise for up to 10 in Key West

    4.8 • 996 reviews
    $784
    Private Key West Sunset Pontoon Cruise

    Private Key West Sunset Pontoon Cruise

    Private 2-hour Key West sunset cruise on a Manitou pontoon for up to 10

    4.8 • 996 reviews
    $348
    Sunset Jet Ski Tour in Key West

    Sunset Jet Ski Tour in Key West

    Ride a small-group jet ski at sunset and escape the Mallory Square crowds

    4.8 • 996 reviews
    $197
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    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