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Best results for

Water Activities in Summerland Key, FL

Showing 505-528 of 834 results
Paddleboard Rental in Marathon

Paddleboard Rental in Marathon

Glide across the Florida Keys and explore the marine ecosystem

4.5 • 95 reviews
$69/ paddleboard
Lily Pad Float Rental in Marathon

Lily Pad Float Rental in Marathon

Enjoy a durable floating water mat for family time on the water

4.5 • 95 reviews
$89
Single Kayak Rental in Marathon

Single Kayak Rental in Marathon

Paddle calm coastal waters and look for local wildlife

4.5 • 95 reviews
$37/ kayak
Upper Keys 3-Hour Fishing Charter

Upper Keys 3-Hour Fishing Charter

Fish Upper Keys waters with gear, bait and water included

4.5 • 1.4K reviews
$444
Private 3/4-Day Offshore Fishing Charter in Marathon

Private 3/4-Day Offshore Fishing Charter in Marathon

Private offshore fishing with trolling and live-bait techniques

4.5 • 1.4K reviews
$1,267
6-Hour Wreck Fishing Charter in Marathon

6-Hour Wreck Fishing Charter in Marathon

Private reef, bay & wreck fishing with gear and licenses included

4.5 • 1.4K reviews
$1,479
Private 3/4-Day Reef & Wreck Fishing Charter in Marathon

Private 3/4-Day Reef & Wreck Fishing Charter in Marathon

Private bottom fishing across reefs, bays and wrecks

4.5 • 1.4K reviews
$1,479
Offshore Fishing Charter in Duck Key for 6 Hours

Offshore Fishing Charter in Duck Key for 6 Hours

Private offshore fishing with gear, fuel and fishing licenses included

4.5 • 1.4K reviews
$1,267
Private 3/4-Day Reef & Wreck Fishing Charter in Duck Key

Private 3/4-Day Reef & Wreck Fishing Charter in Duck Key

Private reef and wreck fishing with gear, licenses and a captain included

4.5 • 1.4K reviews
$1,479
Duck Key 6-Hour Reef Fishing Charter

Duck Key 6-Hour Reef Fishing Charter

Bottom-fish reefs, bays, and wrecks with a captain and gear included

4.5 • 1.4K reviews
$1,479
Private 3/4-Day Offshore Fishing Charter in Marathon

Private 3/4-Day Offshore Fishing Charter in Marathon

Private offshore fishing with trolling and live-bait techniques

4.5 • 1.4K reviews
$1,267
Private 3/4-Day Wreck & Reef Fishing Charter in Marathon

Private 3/4-Day Wreck & Reef Fishing Charter in Marathon

Private wreck fishing with captain, gear, and fishing license included

4.5 • 1.4K reviews
$1,479
Private Sandbar Boat Charter in Key West on a 28' Jetboat

Private Sandbar Boat Charter in Key West on a 28' Jetboat

Private charter with local captains and flexible sandbar stops

$689& up
Private Fishing Charter in Marathon

Private Fishing Charter in Marathon

Reef, offshore, tarpon, or island adventures with gear and licenses included

4.5 • 1.4K reviews
$949
Private 3-Hour Sailing Cruise in Key West

Private 3-Hour Sailing Cruise in Key West

Sail the Florida Keys privately aboard a classic sailboat

$635
Private Tarpon & Shark Fishing Charter in Marathon

Private Tarpon & Shark Fishing Charter in Marathon

Fish backcountry bridges and shallow waters for tarpon, sharks, snook and more

$689& up
Private Fishing Charter in Marathon

Private Fishing Charter in Marathon

Fish reefs, wrecks or offshore waters with gear, fuel and fishing licenses included

4.5 • 1.4K reviews
$1,055& up
Private Fishing Charter From Marathon

Private Fishing Charter From Marathon

Choose fishing or island adventures with a captain and gear included

4.5 • 1.4K reviews
$1,118& up
Fishing Charter in Marathon Aboard a 39' Yellowfin

Fishing Charter in Marathon Aboard a 39' Yellowfin

Private charter options for reef, offshore, island, and long-range fishing

4.5 • 1.4K reviews
$1,267& up
Private Fishing Charter in Marathon

Private Fishing Charter in Marathon

Fish reefs, wrecks, bays, or offshore waters with a captain and gear included

4.5 • 1.4K reviews
$981& up
Private Fishing Charter in Marathon

Private Fishing Charter in Marathon

Choose your ideal private fishing or island adventure with a captain

4.5 • 1.4K reviews
$981& up
Private Fishing Charter in Marathon

Private Fishing Charter in Marathon

Choose your fishing adventure aboard a 43' Freeman with a captain

4.5 • 1.4K reviews
$1,585& up
Marathon Private Fishing Charter

Marathon Private Fishing Charter

Fish reefs, flats, wrecks and more with a private captain

4.5 • 1.4K reviews
$822& up
32' Fishing Charter in Marathon

32' Fishing Charter in Marathon

Private fishing and island adventures with a captain, gear, fuel, and licenses included

4.5 • 1.4K reviews
$949& up
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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.

Summerland Key Things To Do
Fishing Charters214Boat Tours112Snorkeling96Boat Rentals92Yacht Charters92
More
  • Sailing72
  • Scuba Diving68
  • Car Rentals49
  • Sunrise and Sunset Tours44
  • Private Fishing Charters27
  • Bike Rentals25
  • Dolphin Watching22
  • Kayaking Tours19
  • Jet Skiing17
  • Scenic Flights9
  • Scavenger Hunts8
  • Dinner Cruises7
  • Ghost and Haunted7
  • Scooter Rentals7
  • Bar and Pub Crawl6
  • Paddleboarding6
  • Parasailing6
  • Private Boat Charters6
  • Helicopter Tours5
  • Historical Tours5