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Best results for

Water Activities in Summerland Key, FL

Showing 169-192 of 834 results
17' Center Console Boat Rental in Cudjoe Key
Up to 6

17' Center Console Boat Rental in Cudjoe Key

Take the helm of a GPS-equipped center console for daytime Keys boating

5.0 • 58 reviews
$568/ boat
Key West Custom Boat Charter

Key West Custom Boat Charter

Build a private Key West day around snorkeling, fishing, sandbars, or Dry Tortugas

5.0 • 55 reviews
$1,020/ boat
Swim Stop Cruise in Key West

Swim Stop Cruise in Key West

Cruise from Key West to a Gulf swim stop with a captain-led tiki boat ride

4.9 • 192 reviews
$96/ person
Private Sandbar Charter in Key West

Private Sandbar Charter in Key West

Customize a private Key West cruise with sandbar and island exploration

4.9 • 187 reviews
$908/ boat
5-Hour Key West Sandbar & Snorkel Private Charter

5-Hour Key West Sandbar & Snorkel Private Charter

Snorkel the reef, then cruise to a remote Key West sandbar

5.0 • 51 reviews
$795
Private Waterfront Bar Hop Boat Cruise Near Key West

Private Waterfront Bar Hop Boat Cruise Near Key West

Pair Stock Island’s waterfront scenery with marina bars, seafood, and tacos

5.0 • 49 reviews
$722
Florida Keys Night Fishing Charter

Florida Keys Night Fishing Charter

Fish Florida Keys waters after dark aboard a private, fully equipped boat

4.9 • 154 reviews
$1,484& up
90-Minute Guided Jet Ski Tour in Key West

90-Minute Guided Jet Ski Tour in Key West

Ride a 28-mile guided jet ski loop around Key West from Opal Key Marina

4.9 • 12.7K reviews
$142/ jet-ski
Guided 2-Tank Wreck & Reef Dive in Key West

Guided 2-Tank Wreck & Reef Dive in Key West

Dive a guided wreck and shallow reef combo in Key West

4.9 • 330 reviews
$226/ person
22' Deck Boat Rental with Dock Delivery in Cudjoe Key
Up to 12

22' Deck Boat Rental with Dock Delivery in Cudjoe Key

GPS-guided cruising and fishing around Cudjoe Key

5.0 • 58 reviews
$596/ boat
Key West Sunset Cruise

Key West Sunset Cruise

Set out on a shaded boat for a Key West sunset

5.0 • 55 reviews
$681& up
Private Night Dive Charter From Finz Dive Center

Private Night Dive Charter From Finz Dive Center

Dive after dark on a private 2-tank scuba charter with an in-water dive master

4.9 • 330 reviews
$1,225
18' Pontoon Boat Rental in Cudjoe Key

18' Pontoon Boat Rental in Cudjoe Key

GPS-equipped pontoon rental with boat delivery

5.0 • 58 reviews
$511/ boat
Key West Light Tackle Fishing Charter

Key West Light Tackle Fishing Charter

Set out for Key West fishing with shade, coolers, and optional tackle

5.0 • 55 reviews
$1,270& up
Key West Tiki Cruise

Key West Tiki Cruise

Cruise Key West's Historic Seaport past Sunset Pier and Mallory Square

4.9 • 192 reviews
$68/ person
Key West Sandbar Charter

Key West Sandbar Charter

Explore Key West waters on a customizable private boat trip

4.9 • 187 reviews
$1,022& up
Snorkel & Sunset Cruise In Key West

Snorkel & Sunset Cruise In Key West

Private 5-hour snorkel and sunset cruise for all ages

5.0 • 51 reviews
$795
Cruise Dry Tortugas On A Private Charter From Key West

Cruise Dry Tortugas On A Private Charter From Key West

Private Dry Tortugas charter with breakfast, picnic lunch, and snacks included

5.0 • 51 reviews
$3,859
Private Captain for Your Own Boat in the Florida Keys

Private Captain for Your Own Boat in the Florida Keys

Put a licensed captain at the helm of your Florida Keys boat

4.9 • 154 reviews
$848& up
Deep-Drop Swordfish Fishing Charter in Cudjoe Key

Deep-Drop Swordfish Fishing Charter in Cudjoe Key

Target daytime swordfish and deepwater species on a private Florida Keys charter

4.9 • 154 reviews
$2,544& up
Dive Key West on a Private Full-Day 4-Tank Charter

Dive Key West on a Private Full-Day 4-Tank Charter

Private 8-hour Key West charter with up to 4 dives

4.9 • 330 reviews
$2,100
3.5-Hour Scuba Skills Refresher Course

3.5-Hour Scuba Skills Refresher Course

Refresh your scuba skills with guided practice in essential procedures

4.9 • 330 reviews
$170/ person
Private Sandbar & Mangrove Island Boat Charter in Key West

Private Sandbar & Mangrove Island Boat Charter in Key West

Private access to Key West sandbars, beaches, and mangroves

5.0 • 51 reviews
$681
3-Tank Dive Charter in Key West

3-Tank Dive Charter in Key West

Build a Private Dive Day Around Your Favorite Water Activities

4.9 • 330 reviews
$1,656/ boat
1…789…35
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
  • 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.