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Best results for

Water Activities in Summerland Key, FL

Showing 25-48 of 834 results
Private Half-Day Snorkel & Dolphin Boat Charter in Key West
Up to 6

Private Half-Day Snorkel & Dolphin Boat Charter in Key West

Create your perfect four-hour Key West boat charter with snorkeling, dolphins, fishing, or beach time.

5.0 • 278 reviews
$795
Private Key West Island Hopping & Snorkel Boat Charter

Private Key West Island Hopping & Snorkel Boat Charter

Customize your time on the water with snorkeling, fishing, island stops, or a sunset cruise

5.0 • 199 reviews
$738
Marathon Sandbar Cruise

Marathon Sandbar Cruise

Cruise Marathon’s waters, then float and paddle at a local sandbar

5.0 • 3.9K reviews
$102/ person
Lower Keys Sandbar Cruise

Lower Keys Sandbar Cruise

Cruise to a Lower Keys sandbar to swim, snorkel, and relax with your group

5.0 • 100 reviews
$774& up
6-Hour Sandbar Boat Charter in Key West

6-Hour Sandbar Boat Charter in Key West

Cruise on a 32' Belzona to relax and float at a Key West sandbar

5.0 • 188 reviews
$1,590
Private Half-Day Sandbar & Mangrove Boat Tour in Key West
Up to 6

Private Half-Day Sandbar & Mangrove Boat Tour in Key West

Discover mangrove islands and pristine sandbars on a comfortable 25-ft Sea Ray with captain and fuel included

5.0 • 183 reviews
$741
8-Hour Private Fishing Charter in Key West

8-Hour Private Fishing Charter in Key West

Spend 8 hours on a private Key West fishing charter tailored to your target species

5.0 • 101 reviews
$1,590
Marathon Reef, Wreck & Offshore Fishing Charter

Marathon Reef, Wreck & Offshore Fishing Charter

Choose reef, wreck, or offshore fishing based on the day’s conditions

5.0 • 150 reviews
$1,113
Private Kayak, Snorkel & Sail Charter in Key West

Private Kayak, Snorkel & Sail Charter in Key West

Private 4-hour kayak, snorkel, and sail trip for up to 6 in Key West

5.0 • 1.7K reviews
$847
Choose-Your-Activities Private Charter

Choose-Your-Activities Private Charter

Build your own private boat day with snorkeling, sandbar time, or sightseeing

5.0 • 115 reviews
$742& up
8-Hour Deep Sea Fishing Charter in Key West

8-Hour Deep Sea Fishing Charter in Key West

Private 8-hour fishing charter for up to 6, with captain, gear, and fuel included

5.0 • 379 reviews
$1,855
Key West 4-Hour Fishing Charter

Key West 4-Hour Fishing Charter

Fish Key West your way with a charter tailored to your preferred style

5.0 • 101 reviews
$954& up
3-Hour Key West Private Boat Charter

3-Hour Key West Private Boat Charter

Choose one Key West water activity on a private 3-hour express charter

5.0 • 278 reviews
$689
3-Hour Private Charter in Key West

3-Hour Private Charter in Key West

Customize a private boat outing with snorkeling, fishing, island stops, and sunset cruising

5.0 • 199 reviews
$624
Marathon Snorkel & Sandbar Cruise

Marathon Snorkel & Sandbar Cruise

Pair reef snorkeling with sandbar swimming, paddling, and a Seven Mile Bridge cruise

5.0 • 3.9K reviews
$116/ person
Key West Reef Snorkel Charter

Key West Reef Snorkel Charter

Learn snorkeling basics and explore Key West’s coral reef and sea life

5.0 • 100 reviews
$827& up
Private Half-Day Sandbar Boat Charter in Key West

Private Half-Day Sandbar Boat Charter in Key West

Cruise Key West on a 32' Belzona to relax at the sandbar

5.0 • 188 reviews
$1,272
Cruise a Sandbar for 5 Hours on a Boston Whaler

Cruise a Sandbar for 5 Hours on a Boston Whaler

Spend 5 hours hanging out at a sandbar with a captain and gear for up to 6 guests

5.0 • 183 reviews
$794
10-Hour Private Fishing Charter in Key West

10-Hour Private Fishing Charter in Key West

Fish for a full day on a private 10-hour Key West charter

5.0 • 101 reviews
$1,802
Marathon Reef & Wreck Fishing Charter

Marathon Reef & Wreck Fishing Charter

Fish calmer nearshore reefs, with wreck fishing possible when conditions allow

5.0 • 150 reviews
$901
Kayak, Guided Snorkel & Morning Sail in Key West

Kayak, Guided Snorkel & Morning Sail in Key West

Paddle the mangroves and snorkel with a small group in the Key West National Wildlife Refuge

5.0 • 1.7K reviews
$135/ person
Shared Sandbar Charter with Snorkeling in Key West

Shared Sandbar Charter with Snorkeling in Key West

Share a relaxed sandbar outing with water gear, shade, and ice-cold water included

5.0 • 115 reviews
$142/ person
Private Key West Snorkel, Fishing & Sandbar Boat Charter

Private Key West Snorkel, Fishing & Sandbar Boat Charter

Private 2-hour Key West charter with a captain and flexible itinerary options

5.0 • 379 reviews
$530
Key West Private Sandbar Cruise

Key West Private Sandbar Cruise

Cruise to a Key West sandbar for swimming, walking, and time in the sun

5.0 • 101 reviews
$1,007& 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