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Best results for

Water Activities in Summerland Key, FL

Showing 193-216 of 834 results
3-Tank Dive Charter in Key West

3-Tank Dive Charter in Key West

Build a Private Dive Day Around Your Favorite Water Activities

4.9 • 330 reviews
$1,656/ boat
Dry Tortugas Snorkel & Dive Charter

Dry Tortugas Snorkel & Dive Charter

Explore Dry Tortugas reefs and Fort Jefferson in one full day

4.9 • 330 reviews
$952/ person
Private Sandbar & Mangrove Island Boat Charter in Key West

Private Sandbar & Mangrove Island Boat Charter in Key West

Private boat time for sandbars, mangroves, and beach picnics

5.0 • 51 reviews
$795
Offshore & Deep Drop Fishing Charter in the Florida Keys

Offshore & Deep Drop Fishing Charter in the Florida Keys

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

4.9 • 154 reviews
$1,802& up
Private Sandbar & Mangrove Island Boat Charter in Key West

Private Sandbar & Mangrove Island Boat Charter in Key West

Explore secluded sandbars, mangroves, and private beaches by boat

5.0 • 51 reviews
$908
4-Hour Snorkel Charter in Key West

4-Hour Snorkel Charter in Key West

Reef or sandbar snorkeling with your private group

5.0 • 51 reviews
$681
Florida Keys Freedive Spearfishing Charter

Florida Keys Freedive Spearfishing Charter

Target reef fish on a private Florida Keys freedive hunt

4.9 • 154 reviews
$1,484& up
Reef & Wreck Fishing Charter in Cudjoe Key & Key West

Reef & Wreck Fishing Charter in Cudjoe Key & Key West

Fish coral reefs and historic wrecks with gear and guidance included

4.9 • 154 reviews
$1,272& up
Key West Shallow Reef Snorkeling Charter

Key West Shallow Reef Snorkeling Charter

Private snorkeling tailored to your day in Key West’s shallow waters

4.9 • 137 reviews
$742& up
Stock Island Private Boat Charter

Stock Island Private Boat Charter

Create a private day on the water tailored to your interests

4.9 • 137 reviews
$742& up
Private Sandbar Charter in Stock Island

Private Sandbar Charter in Stock Island

Plan your own day of sandbars, beaches and calm-water cruising

4.9 • 137 reviews
$636& up
Snorkeling Charter in Key West

Snorkeling Charter in Key West

Explore a coral reef just 7 miles from Key West by private boat

5.0 • 46 reviews
$742& up
Key West Sandbar Charter

Key West Sandbar Charter

Explore Key West sandbars with music, snorkeling, and time on the water

5.0 • 46 reviews
$742& up
Key West Light Tackle Fishing Charter

Key West Light Tackle Fishing Charter

Fish light tackle with bait, gear, licensing, and catch filleting included

5.0 • 46 reviews
$742
Custom Key West Charter

Custom Key West Charter

Shape a private Key West outing around the activities you want to do

5.0 • 46 reviews
$742& up
Deep Sea Fishing Charter

Deep Sea Fishing Charter

Spend 8 hours fishing deep water, wrecks, and snapper or mahi action

5.0 • 44 reviews
$1,590
Key West Snorkel & Sandbar Charter

Key West Snorkel & Sandbar Charter

Reef snorkeling, sandbar time, or both on a private Key West charter

5.0 • 44 reviews
$477& up
Key West 4-Hour Fishing Charter

Key West 4-Hour Fishing Charter

Target reef, shark, tarpon, or pelagic fish on a private Key West outing

5.0 • 44 reviews
$848
6-Hour Key West Fishing Charter

6-Hour Key West Fishing Charter

Troll offshore or fish reefs and wrecks for a range of species

5.0 • 44 reviews
$1,166
Sandbar Charter in the Florida Keys

Sandbar Charter in the Florida Keys

Cruise to Florida Keys sandbars with water, ice, and cooler space included

4.9 • 113 reviews
$681& up
Guided Spearfishing Charter in Key West

Guided Spearfishing Charter in Key West

Explore reefs and blue water on a guided spearfishing trip

4.9 • 113 reviews
$908& up
Key West Guided Freediving Charter

Key West Guided Freediving Charter

Explore Florida Keys wrecks and reefs with an experienced underwater guide

4.9 • 113 reviews
$681& up
23' Tri-Hull Deck Boat Rental in Cudjoe Key
Up to 8

23' Tri-Hull Deck Boat Rental in Cudjoe Key

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

4.9 • 109 reviews
$562/ boat
19' Bay Boat Rental in Cudjoe Key

19' Bay Boat Rental in Cudjoe Key

A roomy bay boat with GPS, livewells and swim access

4.9 • 109 reviews
$460/ boat
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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 Charters212Boat Tours111Snorkeling96Boat 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