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
    • 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 Summerland Key, FL

    Showing 1-24 of 611 results
    Deep-Drop Swordfish Fishing Charter in Cudjoe Key
    Fishing Charters

    Deep-Drop Swordfish Fishing Charter in Cudjoe Key

    Target daytime swordfish and deepwater species on a private Florida Keys charter

    Target daytime swordfish and deepwater species on a private Florida Keys charter
    4.9 • 149 reviews
    $2,226& up
    Florida Keys Spiny Lobster Hunting Charter
    Fishing Charters

    Florida Keys Spiny Lobster Hunting Charter

    Snorkel shallow Florida Keys reefs for spiny lobster with local guidance

    Snorkel shallow Florida Keys reefs for spiny lobster with local guidance
    4.9 • 149 reviews
    $901
    Florida Keys Deep Sea Fishing Charter
    Fishing Charters

    Florida Keys Deep Sea Fishing Charter

    Chase pelagic fish and deep-water species aboard a private Florida Keys charter

    Chase pelagic fish and deep-water species aboard a private Florida Keys charter
    4.9 • 149 reviews
    $1,749& up
    Florida Keys Freedive Spearfishing Charter
    Fishing Charters

    Florida Keys Freedive Spearfishing Charter

    Target reef fish on a private Florida Keys freedive hunt

    Target reef fish on a private Florida Keys freedive hunt
    4.9 • 149 reviews
    $1,431& up
    Reef & Wreck Fishing Charter in Florida Keys
    Fishing Charters

    Reef & Wreck Fishing Charter in Florida Keys

    Fish coral reefs and historic wrecks with gear and guidance included

    Fish coral reefs and historic wrecks with gear and guidance included
    4.9 • 149 reviews
    $1,219& up
    4-Hour Looe Key Snorkel & Dive Tour
    Snorkeling

    4-Hour Looe Key Snorkel & Dive Tour

    Explore Looe Key’s protected reef by snorkel or certified dive

    Explore Looe Key’s protected reef by snorkel or certified dive
    4.1 • 764 reviews
    $113/ person
    Night Dive & Snorkel Trip in Ramrod Key
    Scuba Diving

    Night Dive & Snorkel Trip in Ramrod Key

    Explore a protected reef after dark by snorkel or dive

    Explore a protected reef after dark by snorkel or dive
    4.1 • 764 reviews
    $125/ person
    Private Half-Day Boat Charter in Ramrod Key
    Yacht Charters

    Private Half-Day Boat Charter in Ramrod Key

    Shape a private reef, wreck, or sandbar outing for your group

    Shape a private reef, wreck, or sandbar outing for your group
    4.1 • 764 reviews
    $2,694
    Adolphus Busch Wreck Dive in Ramrod Key
    Scuba Diving

    Adolphus Busch Wreck Dive in Ramrod Key

    Explore an artificial-reef cargo ship on an advanced two-tank wreck dive

    Explore an artificial-reef cargo ship on an advanced two-tank wreck dive
    4.1 • 764 reviews
    $136/ person
    24' Boat Rental in Big Pine Key
    Boat RentalsUp to 8

    24' Boat Rental in Big Pine Key

    Explore on a 250 HP, fishing-ready boat with delivery and pickup included

    Explore on a 250 HP, fishing-ready boat with delivery and pickup included
    4.9 • 71 reviews
    $3,120/ boat
    24' Pontoon Rental in Marathon
    Boat RentalsUp to 10

    24' Pontoon Rental in Marathon

    Bring your group aboard for fishing, snorkeling, or a day on the water

    Bring your group aboard for fishing, snorkeling, or a day on the water
    4.9 • 71 reviews
    $1,231/ boat
    Backcountry Fishing Boat Rental in Big Pine Key
    Boat RentalsUp to 5

    Backcountry Fishing Boat Rental in Big Pine Key

    Navigate bays and backcountry with fishing-ready Garmin technology

    Navigate bays and backcountry with fishing-ready Garmin technology
    4.9 • 71 reviews
    $2,605/ boat
    23' Tritoon Boat Rental in Cudjoe Key
    Boat RentalsUp to 12

    23' Tritoon Boat Rental in Cudjoe Key

    GPS-guided tritoon cruising with walk-up water access

    GPS-guided tritoon cruising with walk-up water access
    5.0 • 54 reviews
    $624/ boat
    22' Tritoon Boat Rental in Cudjoe Key
    Boat RentalsUp to 12

    22' Tritoon Boat Rental in Cudjoe Key

    GPS-guided Tri Toon cruising with delivery to eligible properties

    GPS-guided Tri Toon cruising with delivery to eligible properties
    5.0 • 54 reviews
    $624/ boat
    23' Boat Rental in Cudjoe Key
    Boat RentalsUp to 8

    23' Boat Rental in Cudjoe Key

    Cruise or fish the Keys with GPS-guided local routes

    Cruise or fish the Keys with GPS-guided local routes
    5.0 • 54 reviews
    $596/ boat
    23' WorldCat Boat Rental in Cudjoe Key
    Boat Rentals

    23' WorldCat Boat Rental in Cudjoe Key

    Cruise the Keys on a 23-foot dual-hull World Cat for three days or more

    Cruise the Keys on a 23-foot dual-hull World Cat for three days or more
    5.0 • 54 reviews
    $3,405/ boat
    20' Deck Boat Rental in Cudjoe Key
    Boat RentalsUp to 10

    20' Deck Boat Rental in Cudjoe Key

    Cruise local waters with GPS guidance and convenient delivery

    Cruise local waters with GPS guidance and convenient delivery
    5.0 • 54 reviews
    $568/ boat
    17' Center Console Boat Rental in Cudjoe Key
    Boat RentalsUp to 6

    17' Center Console Boat Rental in Cudjoe Key

    Take the helm of a GPS-equipped center console for daytime Keys boating

    Take the helm of a GPS-equipped center console for daytime Keys boating
    5.0 • 54 reviews
    $568/ boat
    Cudjoe Key 24' Center Console Boat Rental
    Boat RentalsUp to 8

    Cudjoe Key 24' Center Console Boat Rental

    GPS-guided center console for Keys exploration

    GPS-guided center console for Keys exploration
    5.0 • 54 reviews
    $624/ boat
    22' Deck Boat Rental in Cudjoe Key
    Boat RentalsUp to 12

    22' Deck Boat Rental in Cudjoe Key

    GPS-guided cruising and fishing around Cudjoe Key

    GPS-guided cruising and fishing around Cudjoe Key
    5.0 • 54 reviews
    $596/ boat
    18' Pontoon Boat Rental in Cudjoe Key
    Boat Rentals

    18' Pontoon Boat Rental in Cudjoe Key

    GPS-equipped pontoon rental with boat delivery

    GPS-equipped pontoon rental with boat delivery
    5.0 • 54 reviews
    $494/ boat
    23' Deck Boat Rental in Cudjoe Key
    Boat RentalsUp to 8

    23' Deck Boat Rental in Cudjoe Key

    A 23-foot tri-hull boat for experienced navigation in Cudjoe Key waters

    A 23-foot tri-hull boat for experienced navigation in Cudjoe Key waters
    4.9 • 111 reviews
    $562/ boat
    19' Bay Boat Rental in Cudjoe Key
    Boat Rentals

    19' Bay Boat Rental in Cudjoe Key

    A roomy bay boat with GPS, livewells and swim access

    A roomy bay boat with GPS, livewells and swim access
    4.9 • 111 reviews
    $460/ boat
    18' Center Console Boat Rental in Cudjoe Key
    Boat Rentals

    18' Center Console Boat Rental in Cudjoe Key

    Navigate Cudjoe Key waters with GPS and a 150 hp Yamaha

    Navigate Cudjoe Key waters with GPS and a 150 hp Yamaha
    4.9 • 111 reviews
    $448/ boat
    12345…26

    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.