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Best results for

Water Activities in Summerland Key, FL

Showing 457-480 of 834 results
22' Sea Fox Boat Rental in Key West

22' Sea Fox Boat Rental in Key West

Take the helm for flexible Key West boating, from a half day to a week

4.7 • 21 reviews
$426/ boat
Key West 13-Person Pontoon Rental
Up to 13

Key West 13-Person Pontoon Rental

Cruise Key West waters with onboard GPS, shade, and a cooler

4.7 • 21 reviews
$460/ boat
2-Tank Vandenberg Wreck Dive in Key West

2-Tank Vandenberg Wreck Dive in Key West

Explore the USNS Vandenberg on a 2-tank morning wreck dive

4.6 • 349 reviews
$260/ person
Scuba Refresher Course for Certified Divers in Key West

Scuba Refresher Course for Certified Divers in Key West

Refresh your scuba skills with a pool session and a guided 2-tank reef dive

4.6 • 349 reviews
$132/ person
Afternoon 2-Tank Barrier Reef Dive in Key West

Afternoon 2-Tank Barrier Reef Dive in Key West

Explore two reef dives on the Florida Keys barrier reef with a conservation-focused PADI Eco Center

4.6 • 349 reviews
$203/ person
Sunset & Night Scuba Dive for Certified Divers in Key West

Sunset & Night Scuba Dive for Certified Divers in Key West

Explore Key West’s underwater world after sunset with lights and gear included

4.6 • 349 reviews
$199/ person
Beginner Scuba Diving in Key West

Beginner Scuba Diving in Key West

Learn scuba basics in a pool, then explore shallow reef areas with an instructor

4.6 • 349 reviews
$280/ person
Key West Reef Dive & Snorkel Trip

Key West Reef Dive & Snorkel Trip

Explore Key West’s barrier reef with diving or snorkeling options

4.6 • 311 reviews
$182/ person
Key West USS Vandenberg Wreck Dive

Key West USS Vandenberg Wreck Dive

Dive the 10-story Vandenberg artificial reef off Key West

4.6 • 311 reviews
$182/ person
Offshore & Reef Fishing Charter or Eco Tour in Marathon

Offshore & Reef Fishing Charter or Eco Tour in Marathon

Choose offshore fishing, reef and wreck fishing, or an ocean eco tour from Marathon

4.7 • 15 reviews
$1,873/ boat
Marathon Offshore Fishing Charter

Marathon Offshore Fishing Charter

Fish offshore, explore reefs and wrecks, or enjoy an eco tour from Marathon

4.7 • 15 reviews
$2,043
Key West Naturist Charter

Key West Naturist Charter

Private sandbar charter with dolphin and turtle watching

5.0 • 4 reviews
$1,219
8-Hour Private Sailing Catamaran Charter in Key West

8-Hour Private Sailing Catamaran Charter in Key West

Private sailing, ocean scenery, and a setting built around your comfort

5.0 • 4 reviews
$1,855
Sandbar Charter in Key West

Sandbar Charter in Key West

Cruise shallow waters with sandbar stops and onboard comforts

5.0 • 4 reviews
$1,219
4-Hour Charter in Key West

4-Hour Charter in Key West

Choose a sandbar or reef outing, weather permitting

5.0 • 4 reviews
$371/ person
Key West Sunrise or Sunset Catamaran Charter

Key West Sunrise or Sunset Catamaran Charter

Private catamaran sailing for sunrise or sunset ocean views

5.0 • 4 reviews
$1,007
4-Hour Sailing Catamaran Charter in Key West

4-Hour Sailing Catamaran Charter in Key West

Private sailing with an onboard bathroom and kitchen

5.0 • 4 reviews
$1,219
6-Hour Private Sailing Charter in Key West

6-Hour Private Sailing Charter in Key West

Private catamaran sailing with ocean serenity

5.0 • 4 reviews
$1,590
4-Hour Sandbar or Reef Charter in Key West

4-Hour Sandbar or Reef Charter in Key West

Bring your own drinks for a shared ocean charter to a weather-dependent sandbar or reef

5.0 • 4 reviews
$371/ person
Sunrise & Sunset Catamaran Charter in Key West

Sunrise & Sunset Catamaran Charter in Key West

Enjoy a private catamaran outing in a clothing-optional setting at your comfort level

5.0 • 4 reviews
$1,007
4-Hour Sailing Catamaran Charter in Key West

4-Hour Sailing Catamaran Charter in Key West

Private catamaran sailing with a full bathroom and kitchen

5.0 • 4 reviews
$1,219
Naturist Sailing Catamaran Charter in Key West

Naturist Sailing Catamaran Charter in Key West

Sail privately in a clothing-optional setting shaped around your comfort

5.0 • 4 reviews
$1,590
Naturist Catamaran Charter in Key West

Naturist Catamaran Charter in Key West

Spend a private day on a clothing-optional sailing catamaran

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

4-Hour Private Fishing Charter in Key West

Fish or relax on a private 4-hour charter with a local captain

5.0 • 2 reviews
$1,060
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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