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Best results for

Water Activities in Summerland Key, FL

Showing 313-336 of 835 results
Key West Child Snorkel Gear Rental

Key West Child Snorkel Gear Rental

Child-sized snorkeling gear for exploring the water

5.0 • 28 reviews
$14/ set
Key West Snorkeling Vest Rental

Key West Snorkeling Vest Rental

Stay comfortably afloat while snorkeling with a vest sized for juniors and adults

5.0 • 28 reviews
$11/ vest
Private Fishing Charter in Key West on a 43' Boat

Private Fishing Charter in Key West on a 43' Boat

Fish Key West waters from a private 43-foot sport-fishing boat

4.9 • 53 reviews
$1,060& up
Private 3-Hour Sailing Lesson in Key West

Private 3-Hour Sailing Lesson in Key West

Choose your boat and learn to sail with a private instructor in Key West

4.9 • 51 reviews
$143& up
Private Sailing Lesson in Key West for All Levels

Private Sailing Lesson in Key West for All Levels

Learn at your own pace with private instruction on the water

4.9 • 51 reviews
$95& up
2-Hour Beginner Sailing Lesson in Key West

2-Hour Beginner Sailing Lesson in Key West

Learn sailing fundamentals aboard Hobie Wave catamarans

4.9 • 51 reviews
$48/ person
Private Dolphin Watch & Snorkel Sail in Key West

Private Dolphin Watch & Snorkel Sail in Key West

Sail Key West and snorkel the backcountry on your own private boat

4.8 • 376 reviews
$959
Private Key West Sailing Charter with Giant Lily Pad Float

Private Key West Sailing Charter with Giant Lily Pad Float

Private sail to a shallow-water anchorage with time to lounge on a Lilypad float

4.8 • 376 reviews
$789
Sail a Private Key West Harbor Sunset Charter

Sail a Private Key West Harbor Sunset Charter

Private 2-hour Key West sunset sail with captain and mate

4.8 • 376 reviews
$732
Private 1939 Patton Schooner Day Sail in Key West

Private 1939 Patton Schooner Day Sail in Key West

Sail a 1939 wooden schooner and take a turn at the helm

4.8 • 376 reviews
$1,345
Sail Key West Harbor on a 90-Minute Private Charter

Sail Key West Harbor on a 90-Minute Private Charter

Private Key West harbor sail with time at the helm

4.8 • 376 reviews
$448
Private Snorkel, Boca Grande & Sunset Charter in Key West

Private Snorkel, Boca Grande & Sunset Charter in Key West

Private 4-hour snorkel and Boca Grande cruise with sunset finish

5.0 • 26 reviews
$1,108
Private Sunset Catamaran Sail in Key West

Private Sunset Catamaran Sail in Key West

Sail past Key West landmarks and relax on a private catamaran cruise at sunset

5.0 • 26 reviews
$907
Key West 4-Hour Lunch Cruise & Sandbar Stop

Key West 4-Hour Lunch Cruise & Sandbar Stop

Cruise Key West, grab dockside lunch, and cool off at a nearby sandbar

5.0 • 26 reviews
$874
Snorkel & Sunset Cruise in Key West

Snorkel & Sunset Cruise in Key West

Private 3–4 hour snorkel charter with two stops and a sunset finish

5.0 • 26 reviews
$757
Private Key West Boat Charter with Tiki Bar & Sandbar Stop

Private Key West Boat Charter with Tiki Bar & Sandbar Stop

Private Key West cruise with a Tiki Bar stop and sandbar swim

5.0 • 26 reviews
$875
Private Coral Reef Snorkeling Charter in Key West

Private Coral Reef Snorkeling Charter in Key West

Explore two living coral reefs with snorkeling gear included

5.0 • 26 reviews
$583
Key West Snorkeling & Dolphin Watching Charter

Key West Snorkeling & Dolphin Watching Charter

Explore a live reef, relax on Boca Grand sandbar, and look for dolphins

5.0 • 26 reviews
$933
Private Half-Day Sail & Snorkel Charter in Key West

Private Half-Day Sail & Snorkel Charter in Key West

Sail Key West waters your way with snorkeling, kayaking, fishing, and time to unwind

5.0 • 26 reviews
$1,134& up
Key West Full-Day Private Sailing Charter

Key West Full-Day Private Sailing Charter

Sail beyond Key West for snorkeling, kayaking, fishing and lunch

5.0 • 26 reviews
$1,815& up
Key West Sandbar Private Charter

Key West Sandbar Private Charter

Swim, paddle, and relax at a secluded Key West island or sandbar

5.0 • 26 reviews
$758
Key West Sunset Sandbar Charter

Key West Sunset Sandbar Charter

Explore a secluded sandbar, paddleboard, and end the day with sunset views

5.0 • 26 reviews
$933
Key West Sunset Sandbar Private Charter

Key West Sunset Sandbar Private Charter

Set out for sandbar time, island sightseeing, and sunset views on a private Key West boat trip

5.0 • 26 reviews
$1,750
Private Backcountry Sandbar Boat Tour in Key West

Private Backcountry Sandbar Boat Tour in Key West

Cruise to Key West sandbars on a private charter for up to 6 guests

4.8 • 284 reviews
$540& 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