Free Concierge Service
Text or call 1-877-GREET-WELL
Ask AIAI
Ask AIAI
Why travelers choose Greetwell

Curated by our team

Every experience is hand selected and approved by Greetwell.

Personal concierge

Real humans available to help before, during, and after your booking.

Intimate & authentic

Including unique in-home experiences you won't find anywhere else.

Easy booking & cancellation

Reserve in minutes with free cancellation on most experiences.

Greetwell

Experiences that stay with you long after the trip

Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

About

  • Our Story
  • For Experience Providers
  • For Hospitality Partners
  • For Developers

Resources

  • Travel Guides
  • Experience Gift Cards
  • Help Center
[email protected]1-877-GREET-WELL

Safe & Secure Payments

© 2026 Greetwell, Inc. All rights reserved.
Privacy PolicyTerms
Free Concierge Service
Text or call 1-877-GREET-WELL
Ask AIAI
Ask AIAI
Best results for

Water Activities in Summerland Key, FL

Showing 601-624 of 834 results
23' Center Console Fishing Boat Rental in Key West
Up to 6

23' Center Console Fishing Boat Rental in Key West

Rent a 23' center console and fish Key West your way

4.1 • 134 reviews
$568/ boat
21' Backcountry Fishing Boat Rental in Key West
2 to 8

21' Backcountry Fishing Boat Rental in Key West

Self-guided shallow-water fishing, snorkeling, and sandbar exploring

4.1 • 134 reviews
$568/ boat
Key West Sandbar Boat Rental
2 to 8

Key West Sandbar Boat Rental

Explore Key West waters with onboard navigation and sandbar-ready comforts

4.1 • 134 reviews
$568/ boat
Key West 23' Fishing Boat Rental
2 to 8

Key West 23' Fishing Boat Rental

Set your own course for fishing, snorkeling, and sandbars

4.1 • 134 reviews
$568/ boat
4-Hour Looe Key Snorkel & Dive Tour

4-Hour Looe Key Snorkel & Dive Tour

Explore Looe Key’s protected reef by snorkel or certified dive

4.1 • 767 reviews
$113/ person
Night Dive & Snorkel Trip in Ramrod Key

Night Dive & Snorkel Trip in Ramrod Key

Explore a protected reef after dark by snorkel or dive

4.1 • 767 reviews
$125/ person
Private Half-Day Boat Charter in Ramrod Key

Private Half-Day Boat Charter in Ramrod Key

Shape a private reef, wreck, or sandbar outing for your group

4.1 • 767 reviews
$2,694
Adolphus Busch Wreck Dive in Ramrod Key

Adolphus Busch Wreck Dive in Ramrod Key

Explore an artificial-reef cargo ship on an advanced two-tank wreck dive

4.1 • 767 reviews
$136/ person
Pontoon Boat Rental in Key West
Up to 12

Pontoon Boat Rental in Key West

Cruise Key West waterways on a 25' pontoon boat for up to 12 passengers

$460/ boat
Cruise Key West on a 25' Double-Decker Pontoon Rental
Up to 13

Cruise Key West on a 25' Double-Decker Pontoon Rental

Rent a 25' double-decker pontoon with two slides for up to 13 passengers

$596/ boat
30' Double Decker Pontoon Rental with Slides in Key West
Up to 13

30' Double Decker Pontoon Rental with Slides in Key West

Rent a 13-passenger double-decker pontoon and cruise the Keys your way

$596& up
30' Double Decker Pontoon Rental with Slides in Key West
Up to 13

30' Double Decker Pontoon Rental with Slides in Key West

Rent a 30' double-decker pontoon with 3 slides for up to 13

$704/ boat
Half-Day Tarpon & Snapper Fishing Charter in Key West

Half-Day Tarpon & Snapper Fishing Charter in Key West

Fish nearshore in the Florida Keys on a 4-hour bay boat trip

$848
Dry Tortugas Private Cruise From Key West

Dry Tortugas Private Cruise From Key West

Explore Fort Jefferson and vibrant reefs by private yacht

$2,120
Private Backcountry Sandbar & Snorkel Charter in Key West

Private Backcountry Sandbar & Snorkel Charter in Key West

Snorkel reefs, watch for dolphins, and relax on a private sandbar for up to 6

$742& up
Private Morning Tiki Boat Cruise in Key West

Private Morning Tiki Boat Cruise in Key West

Bring your own drinks for a private morning tiki boat cruise

$426
Happy Hour Tiki Boat Cruise in Key West

Happy Hour Tiki Boat Cruise in Key West

Cruise Key West on a private tiki bar boat with a captain

$341
Cruise the Key West Sandbar on an 8-Hour Charter

Cruise the Key West Sandbar on an 8-Hour Charter

Private 8-hour sandbar charter for up to 6, with stops at Marvin Key and Snipes Key

$1,362
4-Hour Private Deep-Sea Fishing Charter in Key West

4-Hour Private Deep-Sea Fishing Charter in Key West

Fish offshore on a private, air-conditioned Key West charter

$1,166
Key West Private Boat Charter

Key West Private Boat Charter

Swim, snorkel, or relax on a private Key West boat

$323& up
Night Bully Net Fishing Charter in Key West

Night Bully Net Fishing Charter in Key West

Fish for lobsters by bully net on a small-group Key West night charter

$636
Full-Day Key West Bay Boat Fishing Charter

Full-Day Key West Bay Boat Fishing Charter

Spend 8 hours fishing the Florida Keys from a Pathfinder bay boat

$1,378/ boat
Key West 3-Hour Boat Charter

Key West 3-Hour Boat Charter

Speed across Key West waters for sandbars, swings and wildlife watching

$1,375
Key West Sandbar Boat Charter

Key West Sandbar Boat Charter

Charter a 4-hour trip to Key West sandbars for swimming and snorkeling

$795
1…252627…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