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Best results for

Water Activities in Summerland Key, FL

Showing 49-72 of 834 results
6-Hour Key West Private Charter With Snorkeling

6-Hour Key West Private Charter With Snorkeling

Customize your 6-hour Key West private boat charter for snorkeling, beach time, and more

5.0 • 278 reviews
$1,087
Key West Day Sail with Snorkel & Kayak Lunch

Key West Day Sail with Snorkel & Kayak Lunch

Sail Key West's clear waters, kayak mangrove islands, snorkel vibrant reefs, and refuel with a buffet lunch—all in one day.

4.9 • 5.9K reviews
$165/ person
Glass Bottom Boat Reef Eco Tour in Key West

Glass Bottom Boat Reef Eco Tour in Key West

See Key West’s reef through glass viewing panels on an air-conditioned catamaran

4.9 • 12.7K reviews
$64/ person
Key West Mangrove Paddleboard Eco Tour

Key West Mangrove Paddleboard Eco Tour

Relaxed paddling and a lesson through Key West's mangrove creeks

4.9 • 8K reviews
$79/ person
Private Full-Day Sandbar & Snorkel Boat Trip in Key West

Private Full-Day Sandbar & Snorkel Boat Trip in Key West

Cruise the Florida Keys for snorkel time and a sandbar stop on a 32' Belzona

5.0 • 188 reviews
$1,590
Sandbar & Lunch Boat Charter, 6-Hour

Sandbar & Lunch Boat Charter, 6-Hour

Private 6-hour sandbar cruise with lunch for up to 6 guests

5.0 • 183 reviews
$953
6-Hour Shared Fishing Charter in Key West

6-Hour Shared Fishing Charter in Key West

A social fishing trip with extra time on the water

5.0 • 101 reviews
$292/ person
Private Sailing Charter in Key West

Private Sailing Charter in Key West

Charter the 54-foot Schooner Valora for a private sail in Key West

4.9 • 3K reviews
$1,340
Snorkel & Sandbar Sunset Sail in Key West

Snorkel & Sandbar Sunset Sail in Key West

Snorkel the reef, visit a sandbar, and sail into sunset on a spacious catamaran

5.0 • 1.7K reviews
$124/ person
Private Backcountry Sandbar Boat Tour in Key West

Private Backcountry Sandbar Boat Tour in Key West

Explore Key West backcountry sandbars on a private charter for up to 6

5.0 • 76 reviews
$875
Custom Charter in Key West

Custom Charter in Key West

Build a private Key West day around sandbars, snorkeling, dolphins, and more

5.0 • 74 reviews
$1,479& up
10-Hour Dry Tortugas Snorkeling Cruise

10-Hour Dry Tortugas Snorkeling Cruise

Snorkel the Dry Tortugas and explore Fort Jefferson on Garden Key

5.0 • 101 reviews
$795/ person
Stock Island Inshore Fishing Charter

Stock Island Inshore Fishing Charter

Cast for reef and wreck fish with guidance for every skill level

5.0 • 278 reviews
$795& up
Private Sandbar & Snorkel Boat Charter in Key West
Up to 6

Private Sandbar & Snorkel Boat Charter in Key West

Customize your Key West day on a private boat with snorkeling gear and sandbar stops included

4.9 • 5.9K reviews
$695
Parasailing, Jet Ski & Ocean Waterpark Combo in Key West

Parasailing, Jet Ski & Ocean Waterpark Combo in Key West

Parasail, ride a Jet Ski, and play on Key West’s ocean waterpark in 3.5 or 6–6.5 hours

4.9 • 12.7K reviews
$146/ person
2-Hour Kayak Rental in Key West

2-Hour Kayak Rental in Key West

Paddle mangrove creeks and calm coastal waters at your own pace

4.9 • 8K reviews
$45/ person
Luxury Center Console Boat Rental in Key West
Up to 12

Luxury Center Console Boat Rental in Key West

Shape your Key West day around sandbars, snorkeling, and time on the water

5.0 • 188 reviews
$1,272& up
Cruise on a 4-Hour Private Boston Whaler Charter

Cruise on a 4-Hour Private Boston Whaler Charter

Private 4-hour Boston Whaler charter with captain for up to 6 guests

5.0 • 183 reviews
$688
4-Hour Fishing Charter in Key West

4-Hour Fishing Charter in Key West

Share a social fishing trip with gear, bait and licenses included

5.0 • 101 reviews
$265/ person
Sail a Key West Champagne Sunset Cruise

Sail a Key West Champagne Sunset Cruise

Sail a Key West schooner at sunset with drinks, appetizers, and cocktails included

4.9 • 3K reviews
$134/ person
Adults-Only Snipes Key Sandbar Cruise from Key West

Adults-Only Snipes Key Sandbar Cruise from Key West

An adults-only sandbar outing with lunch, drinks and water toys

4.9 • 1K reviews
$138/ person
4-Hour Key West Light Tackle Fishing Charter

4-Hour Key West Light Tackle Fishing Charter

Private 4-hour light tackle fishing charter for up to 4 guests

5.0 • 76 reviews
$689
Key West Private Sunset Cruise

Key West Private Sunset Cruise

A private evening on the water for toasts, music and horizon views

5.0 • 74 reviews
$1,055
Lobster Mini Season Charter in Key West

Lobster Mini Season Charter in Key West

Catch lobsters during Key West's July Mini Season

5.0 • 101 reviews
$1,060& up
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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

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.

  • 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