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Best results for

Water Activities in Summerland Key, FL

Showing 145-168 of 834 results
Key West Reef Snorkeling Charter

Key West Reef Snorkeling Charter

Snorkel coral reefs and relax at a Key West sandbar

5.0 • 59 reviews
$169/ person
Private Sunset Cruise in Key West

Private Sunset Cruise in Key West

Cruise Key West harbor at sunset with your group and captain

4.9 • 5.9K reviews
$427
3-Hour Morning Snorkel Cruise in Key West

3-Hour Morning Snorkel Cruise in Key West

Morning catamaran snorkel trip with gear and drinks

4.9 • 12.7K reviews
$46/ person
Sand Dollar Swim Cruise in Marathon

Sand Dollar Swim Cruise in Marathon

Start the day with a family-friendly Florida Keys morning on the water

4.9 • 218 reviews
$107/ person
Champagne Sunset Sailing Cruise in Key West

Champagne Sunset Sailing Cruise in Key West

Private sunset sailing with bubbly, wines and a gourmet cheese buffet

4.9 • 635 reviews
$1,016
Cruise to the Key West Sandbar on a Private Charter
Up to 12

Cruise to the Key West Sandbar on a Private Charter

Private 25 ft tritoon sandbar charter for up to 12 guests

5.0 • 54 reviews
$795& up
Guided 2-Tank Reef Dive in Key West

Guided 2-Tank Reef Dive in Key West

Do two guided reef dives with an in-water divemaster

4.9 • 330 reviews
$226/ person
4-Hour Light Tackle Fishing Charter in Key West

4-Hour Light Tackle Fishing Charter in Key West

Cast light tackle from Stella Blue in calm nearshore waters

4.9 • 287 reviews
$1,080/ boat
23' Boat Rental in Cudjoe Key
Up to 8

23' Boat Rental in Cudjoe Key

Cruise or fish the Keys with GPS-guided local routes

5.0 • 58 reviews
$596/ boat
Sandbar & Snorkel Boat Charter in Key West

Sandbar & Snorkel Boat Charter in Key West

Cruise Key West backcountry, snorkel reefs, and relax at a sandbar on a private charter

5.0 • 55 reviews
$1,361/ boat
Key West Memorial Ash-Scattering Charter

Key West Memorial Ash-Scattering Charter

Hold a private, personalized farewell at sea with a caring local captain

5.0 • 74 reviews
$1,055
Key West Tiki Boat Sunset Cruise Past Mallory Square

Key West Tiki Boat Sunset Cruise Past Mallory Square

Cruise Key West Harbor on a tiki boat at sunset

4.9 • 192 reviews
$91/ person
Private Sandbar Charter in Key West

Private Sandbar Charter in Key West

Customize a private Key West boat day with room for your dog

4.9 • 187 reviews
$747& up
Private Sandbar & Sunset Cruise in Key West

Private Sandbar & Sunset Cruise in Key West

Private 5-hour sandbar and sunset cruise with snorkel gear and music

5.0 • 51 reviews
$795
Snorkel & Sunset Sail Cruise in Key West

Snorkel & Sunset Sail Cruise in Key West

Snorkel the living coral reef, then sail into the Key West sunset with included drinks

4.9 • 12.7K reviews
$57/ person
Key West Sandbar Tour

Key West Sandbar Tour

Explore mangrove backcountry and spend the day at Florida Keys sandbars

5.0 • 49 reviews
$533& up
Full-Day Fort Jefferson & Dry Tortugas Charter

Full-Day Fort Jefferson & Dry Tortugas Charter

Cruise privately to Fort Jefferson for flexible exploring, snorkeling, and beach time

4.9 • 154 reviews
$3,074
Private Mangrove Eco Paddle Tour Near Key West

Private Mangrove Eco Paddle Tour Near Key West

Set your own pace through Key West’s mangrove waterways

4.9 • 140 reviews
$461
Private 4-Hour Wreck Dive Charter

Private 4-Hour Wreck Dive Charter

Dive the USNS General Hoyt S Vandenberg on a private 2-tank wreck trip

4.9 • 330 reviews
$1,192
Key West Private Fishing Charter

Key West Private Fishing Charter

A crewed private charter shaped around your preferences

4.9 • 287 reviews
$1,080/ boat
20' Deck Boat Rental in Cudjoe Key
Up to 10

20' Deck Boat Rental in Cudjoe Key

Cruise local waters with GPS guidance and convenient delivery

5.0 • 58 reviews
$568/ boat
4-Hour Sandbar Cruise in Key West

4-Hour Sandbar Cruise in Key West

Share a laid-back Key West sandbar outing with fellow travelers

5.0 • 55 reviews
$284/ person
Key West 3.5-Hour Sandbar Kayak & Paddleboard Tour

Key West 3.5-Hour Sandbar Kayak & Paddleboard Tour

Cruise to a Key West sandbar with kayaking, paddleboards, lunch, and drinks

4.9 • 12.7K reviews
$110/ person
Private 2-Tank Reef Dive Charter in Key West

Private 2-Tank Reef Dive Charter in Key West

Book a private reef dive with an in-water divemaster for up to 6 guests

4.9 • 330 reviews
$1,192
1…678…35

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 Charters212Boat Tours111Snorkeling96Boat 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