Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /All experiences
    3. /Water Activities

    Best results for Water Activities in Key West, FL

    Showing 409-432 of 589 results
    Key West Custom Boat Charter for Up to 6
    Boat Tours

    Key West Custom Boat Charter for Up to 6

    Design a private Key West day on the water with your captain

    Design a private Key West day on the water with your captain
    4.8 • 284 reviews
    $540& up
    Key West 26' Deck Boat Rental
    Boat RentalsUp to 9

    Key West 26' Deck Boat Rental

    Set your own course on a Yamaha-powered Key West deck boat

    Set your own course on a Yamaha-powered Key West deck boat
    4.8 • 284 reviews
    $578/ boat
    Key West Double-Decker Slide Boat Charter
    Boat Tours

    Key West Double-Decker Slide Boat Charter

    Slide, lounge, and explore Key West waters from a double-decker pontoon

    Slide, lounge, and explore Key West waters from a double-decker pontoon
    4.8 • 284 reviews
    $759& up
    Key West 22' Bay Boat Rental
    Boat RentalsUp to 6

    Key West 22' Bay Boat Rental

    Take the helm of a well-equipped bay boat for your Key West day on the water

    Take the helm of a well-equipped bay boat for your Key West day on the water
    4.8 • 284 reviews
    $525/ boat
    Key West 4-Hour Pontoon Boat Rental
    Boat RentalsUp to 8

    Key West 4-Hour Pontoon Boat Rental

    Take the helm of a well-equipped pontoon for your Key West day on the water

    Take the helm of a well-equipped pontoon for your Key West day on the water
    4.8 • 284 reviews
    $578/ boat
    Private 3-Hour Sailing Cruise in Key West
    Sailing

    Private 3-Hour Sailing Cruise in Key West

    Sail the Florida Keys privately aboard a classic sailboat

    Sail the Florida Keys privately aboard a classic sailboat
    $635
    Customize a Private Boat Charter in Key West
    Yacht Charters

    Customize a Private Boat Charter in Key West

    Private Key West luxury activity boat charter for up to 13

    Private Key West luxury activity boat charter for up to 13
    4.8 • 93 reviews
    $907& up
    10-Hour Dry Tortugas National Park Fishing Charter
    Fishing Charters

    10-Hour Dry Tortugas National Park Fishing Charter

    Fish and explore Dry Tortugas National Park on a 10-hour family-friendly charter

    Fish and explore Dry Tortugas National Park on a 10-hour family-friendly charter
    4.7 • 3 reviews
    $3,180
    Key West 8-Hour Fishing Charter
    Fishing Charters

    Key West 8-Hour Fishing Charter

    Fish Key West backcountry and Marquesas Keys for tarpon, permit, and more

    Fish Key West backcountry and Marquesas Keys for tarpon, permit, and more
    4.7 • 3 reviews
    $1,272
    Fish Key West on a Full-Day Charter
    Private Fishing Charters

    Fish Key West on a Full-Day Charter

    Spend 8 hours fishing the waters west of Key West for tuna, reef fish, and more

    Spend 8 hours fishing the waters west of Key West for tuna, reef fish, and more
    4.7 • 3 reviews
    $2,438
    6-Hour Key West Fishing Charter
    Fishing Charters

    6-Hour Key West Fishing Charter

    Fish near Key West with a relaxed charter for families and first-time anglers

    Fish near Key West with a relaxed charter for families and first-time anglers
    4.7 • 3 reviews
    $1,802
    Key West 4-Hour Fishing Charter
    Fishing Charters

    Key West 4-Hour Fishing Charter

    Stay close to Key West for a family-friendly fishing outing

    Stay close to Key West for a family-friendly fishing outing
    4.7 • 3 reviews
    $1,272
    Gulf Shrimp Boat & Wreck Fishing Charter in Key West
    Fishing Charters

    Gulf Shrimp Boat & Wreck Fishing Charter in Key West

    Fish Key West shrimp boats and wrecks without heading far offshore

    Fish Key West shrimp boats and wrecks without heading far offshore
    4.7 • 3 reviews
    $2,756
    Private Sandbar Charter in Key West
    Boat Tours

    Private Sandbar Charter in Key West

    Cruise mangroves, swim a local sandbar, and set your own pace

    Cruise mangroves, swim a local sandbar, and set your own pace
    5.0 • 39 reviews
    $313& up
    Reef Fishing Charter in Key West
    Fishing Charters

    Reef Fishing Charter in Key West

    Cast for snapper on a private Key West reef trip

    Cast for snapper on a private Key West reef trip
    5.0 • 39 reviews
    $949& up
    Lobster Snorkeling Charter in Key West
    Snorkeling

    Lobster Snorkeling Charter in Key West

    Find lobster hideouts and learn how to catch them

    Find lobster hideouts and learn how to catch them
    5.0 • 39 reviews
    $949& up
    Customize a 4-Hour Private Charter in Key West
    Yacht Charters

    Customize a 4-Hour Private Charter in Key West

    Choose sandbar time, snorkeling, or dolphin watching on a 4-hour private charter

    Choose sandbar time, snorkeling, or dolphin watching on a 4-hour private charter
    5.0 • 25 reviews
    $1,484
    Custom Boat Charter in Key West
    Yacht Charters

    Custom Boat Charter in Key West

    Build your ideal day with snorkeling, fishing and time on the water

    Build your ideal day with snorkeling, fishing and time on the water
    5.0 • 39 reviews
    $1,267& up
    Key West Boat Wedding Charter
    Yacht Charters

    Key West Boat Wedding Charter

    Exchange vows on the waters of Key West

    Exchange vows on the waters of Key West
    5.0 • 39 reviews
    $737& up
    Reef & Wreck Fishing Charter in Key West
    Fishing Charters

    Reef & Wreck Fishing Charter in Key West

    Private Key West fishing with gear, licenses, and crew guidance included

    Private Key West fishing with gear, licenses, and crew guidance included
    5.0 • 25 reviews
    $1,484& up
    Key West Sunset Private Charter
    Yacht Charters

    Key West Sunset Private Charter

    Harbor cruising and sunset views aboard a private boat

    Harbor cruising and sunset views aboard a private boat
    5.0 • 25 reviews
    $1,007
    Key West Deep Sea Fishing Charter
    Fishing Charters

    Key West Deep Sea Fishing Charter

    Big-game fishing from a 39-foot boat with a private bathroom and shower

    Big-game fishing from a 39-foot boat with a private bathroom and shower
    5.0 • 25 reviews
    $1,696& up
    Shark Fishing Charter in Key West
    Fishing Charters

    Shark Fishing Charter in Key West

    Hands-on shark fishing with gear, bait and local guidance

    Hands-on shark fishing with gear, bait and local guidance
    5.0 • 25 reviews
    $1,484& up
    Fort Jefferson Full-Day Fishing Charter
    Fishing Charters

    Fort Jefferson Full-Day Fishing Charter

    Fish Dry Tortugas grounds aboard a private, fully equipped charter boat

    Fish Dry Tortugas grounds aboard a private, fully equipped charter boat
    5.0 • 25 reviews
    $3,816
    1…171819…25

    Travel guides for Water Activities

    13 Stunning Beaches in Florida With Clear Water You Need to Visit
    Best of Florida • 2026

    13 Stunning Beaches in Florida With Clear Water You Need to Visit

    Clarity is geology, not luck: quartz sand, seagrass filtration, and how close the Gulf Stream runs. Thirteen beaches, and the trade-off each one asks of you.

    Do You Need a License to Rent a Boat in Florida? Your Complete Guide
    Best of Florida • 2026

    Do You Need a License to Rent a Boat in Florida? Your Complete Guide

    Florida issues no boating license at all. What the marina checks is a safety education card, and whether you need one comes down to one date: January 1, 1988.