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Best results for

Water Activities in Summerland Key, FL

Showing 289-312 of 835 results
Key West Mangrove Maze Kayak Rental

Key West Mangrove Maze Kayak Rental

Paddle at your own pace through serene mangroves and discover Key West’s vibrant marine life.

4.8 • 996 reviews
$46& up
34' Marquesas Islands Fishing Charter, Key West

34' Marquesas Islands Fishing Charter, Key West

Chase offshore species in the remote waters of the Marquesas

4.8 • 1K reviews
$1,855
4-Hour Private Boat Charter in Key West Backcountry

4-Hour Private Boat Charter in Key West Backcountry

Customize a 4-hour private tri-toon cruise with a licensed captain in Key West’s backcountry

4.8 • 996 reviews
$523
Private Full-Day Key West Backcountry Boat Charter

Private Full-Day Key West Backcountry Boat Charter

Customize your Key West backcountry day on a captained tri-toon with a swim deck

4.8 • 996 reviews
$1,161
Private Key West Backcountry Tri-Toon Boat Charter
Up to 10

Private Key West Backcountry Tri-Toon Boat Charter

Customize a 6-hour captained Manitou tri-toon cruise for up to 10 in Key West

4.8 • 996 reviews
$784
Sunset Jet Ski Tour in Key West

Sunset Jet Ski Tour in Key West

Ride a small-group jet ski at sunset and escape the Mallory Square crowds

4.8 • 996 reviews
$197
Key West Guided Jet Ski Tour Around the Island, 27 Miles

Key West Guided Jet Ski Tour Around the Island, 27 Miles

Ride a jet ski around Key West with scenic stops along the way

4.8 • 996 reviews
$209
Guided 2-Hour Paddleboard Eco Tour in Key West

Guided 2-Hour Paddleboard Eco Tour in Key West

Paddle through Key West mangroves with a guide on this 2-hour eco tour

4.8 • 996 reviews
$70/ person
Self-Guided Paddleboard Rental in Key West, 2-Hour

Self-Guided Paddleboard Rental in Key West, 2-Hour

Paddle at your own pace with a 2-hour self-guided paddleboard rental

4.8 • 996 reviews
$46/ person
Ride a Jet Ski on a 1-Hour Freestyle Tour in Key West

Ride a Jet Ski on a 1-Hour Freestyle Tour in Key West

Pilot a jet ski in a supervised open-water area, ideal for beginners

4.8 • 996 reviews
$197/ jet ski
Private Deep Sea Fishing Charter in Key West

Private Deep Sea Fishing Charter in Key West

Private offshore fishing for up to 6 on a fast, shaded 36-foot Hatteras

4.8 • 1K reviews
$1,087& up
3-Hour Shark Fishing Charter in Key West

3-Hour Shark Fishing Charter in Key West

Hands-on shark fishing in Key West for all ages

4.8 • 1K reviews
$708
Private Key West Deep Sea Fishing Charter on 47' Hatteras

Private Key West Deep Sea Fishing Charter on 47' Hatteras

Fish offshore with a knowledgeable crew on a 47-foot Hatteras

4.8 • 1K reviews
$1,415& up
Full-Day Shared Deep Sea Fishing Charter in Key West

Full-Day Shared Deep Sea Fishing Charter in Key West

Shared offshore fishing in Key West with a pro crew, max 6 passengers

4.8 • 1K reviews
$381/ person
Private Deep Sea Fishing Charter in Key West

Private Deep Sea Fishing Charter in Key West

Fish offshore for mahi, tuna, sailfish, and marlin on a private charter

4.8 • 1K reviews
$1,251& up
Marquesas Islands Full-Day Fishing Charter

Marquesas Islands Full-Day Fishing Charter

Private light-tackle fishing in the remote Marquesas

4.8 • 1K reviews
$1,797
Private 40' Deep Sea Fishing Charter in Key West

Private 40' Deep Sea Fishing Charter in Key West

Private offshore fishing with a family-friendly crew in Key West

4.8 • 1K reviews
$1,196& up
6-Hour Deep Sea Fishing Charter in Key West

6-Hour Deep Sea Fishing Charter in Key West

Target offshore game fish with a professional crew, bait and tackle included

4.8 • 1K reviews
$315/ person
Key West 4-Hour Deep Sea Fishing Charter

Key West 4-Hour Deep Sea Fishing Charter

Shared offshore fishing with bait, tackle, and fishing license included

4.8 • 1K reviews
$250/ person
Private Key West Sandbar & Snorkel Charter on 26' Tritoon
Up to 6

Private Key West Sandbar & Snorkel Charter on 26' Tritoon

Enjoy a customizable cruise through Florida Keys sandbars with snorkel gear and coolers included.

4.8 • 782 reviews
$911& up
Key West Dolphin Watch & Snorkel Tour

Key West Dolphin Watch & Snorkel Tour

Spot playful dolphins and snorkel vibrant reefs on a small-group Key West cruise

4.8 • 782 reviews
$120/ person
Key West Snorkel Gear Rental

Key West Snorkel Gear Rental

Mask, snorkel and fins for exploring Key West waters

5.0 • 28 reviews
$14/ set
Key West Adult Small Snorkel Gear Rental

Key West Adult Small Snorkel Gear Rental

Get a complete mask, snorkel, and fins set for your time in the water

5.0 • 28 reviews
$14& up
Child Large Snorkel Gear Rental In Key West

Child Large Snorkel Gear Rental In Key West

Get a child large snorkel set for exploring beneath the surface

5.0 • 28 reviews
$14/ set
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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