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Best 1099

things to do in Summerland Key, FL

Showing 457-480 of 1,099 results
Key West 26' Deck Boat Rental
Up to 9

Key West 26' Deck Boat Rental

Set your own course on a Yamaha-powered Key West deck boat

4.8 • 284 reviews
$578/ boat
Double-Decker Waterslide Boat Charter in Key West

Double-Decker Waterslide Boat Charter in Key West

Slide, lounge, and explore Key West waters from a double-decker pontoon

4.8 • 284 reviews
$759& up
Key West 3-Hour Boat Bar Crawl

Key West 3-Hour Boat Bar Crawl

Cruise Key West’s waterfront bars while your captain handles the boat

4.8 • 284 reviews
$540
Offshore Fishing Charter in Key West

Offshore Fishing Charter in Key West

Cast offshore from Key West with fishing gear and licenses included

4.8 • 278 reviews
$1,166& up
Key West 22' Bay Boat Rental
Up to 6

Key West 22' Bay Boat Rental

Take the helm of a well-equipped bay boat for your Key West day on the water

4.8 • 284 reviews
$525/ boat
Key West 4-Hour Pontoon Boat Rental
Up to 8

Key West 4-Hour Pontoon Boat Rental

Take the helm of a well-equipped pontoon for your Key West day on the water

4.8 • 284 reviews
$578/ boat
Private Sandbar, Snorkel & Dolphin Charter in Key West

Private Sandbar, Snorkel & Dolphin Charter in Key West

Choose sandbar time, snorkeling, or dolphin watching on a 4-hour private charter

5.0 • 25 reviews
$1,484
Florida Keys Sunset Charter

Florida Keys Sunset Charter

Watch the Florida Keys sunset from the water with Captain Tom

5.0 • 25 reviews
$371
Looe Key Snorkel & Picnic Island Trip from Big Pine Key

Looe Key Snorkel & Picnic Island Trip from Big Pine Key

Snorkel Looe Key’s protected reef with an optional Picnic Island beach stop

5.0 • 25 reviews
$529
Big Pine Key Sunset Sandbar & Snorkel Charter

Big Pine Key Sunset Sandbar & Snorkel Charter

Explore sandbars, snorkel the backcountry, and end with a Keys sunset

5.0 • 25 reviews
$794
6-Hour Sandbar, Fishing & Snorkel Charter in Big Pine Key

6-Hour Sandbar, Fishing & Snorkel Charter in Big Pine Key

Combine sandbar time, coral-head snorkeling, and inshore snapper fishing

5.0 • 25 reviews
$822
Reef & Wreck Fishing Charter in Key West

Reef & Wreck Fishing Charter in Key West

Private Key West fishing with gear, licenses, and crew guidance included

5.0 • 25 reviews
$1,484& up
Key West Sunset Private Charter

Key West Sunset Private Charter

Harbor cruising and sunset views aboard a private boat

5.0 • 25 reviews
$1,007
Private Offshore Big Game Fishing Charter in Key West

Private Offshore Big Game Fishing Charter in Key West

Big-game fishing from a 39-foot boat with a private bathroom and shower

5.0 • 25 reviews
$1,696& up
Shark Fishing Charter in Key West

Shark Fishing Charter in Key West

Hands-on shark fishing with gear, bait and local guidance

5.0 • 25 reviews
$1,484& up
Fort Jefferson Full-Day Fishing Charter

Fort Jefferson Full-Day Fishing Charter

Fish Dry Tortugas grounds aboard a private, fully equipped charter boat

5.0 • 25 reviews
$3,816
Dry Tortugas Full-Day Private Charter

Dry Tortugas Full-Day Private Charter

Explore Fort Jefferson and Key West reefs by private boat

5.0 • 25 reviews
$3,392
Big Pine Key Sandbar Charter

Big Pine Key Sandbar Charter

Customize a Lower Keys outing with snorkeling, sandbars, and paddle boarding

5.0 • 25 reviews
$583
Full-Day Private Sandbar & Snorkel Charter in Big Pine Key

Full-Day Private Sandbar & Snorkel Charter in Big Pine Key

Design a Lower Keys charter with sandbars, reefs, snorkeling, or bar stops

5.0 • 25 reviews
$900
Sandbar Hopping & Snorkel Boat Tour from Big Pine Key

Sandbar Hopping & Snorkel Boat Tour from Big Pine Key

Customize a day of Florida Keys sandbars, reefs, and snorkeling

5.0 • 25 reviews
$741
Full-Day Snapper & Grouper Fishing Charter in Big Pine Key

Full-Day Snapper & Grouper Fishing Charter in Big Pine Key

Fish reef and Gulf waters for snapper and grouper

5.0 • 25 reviews
$1,006
6-Hour Offshore Fishing Charter in Big Pine Key

6-Hour Offshore Fishing Charter in Big Pine Key

Fish offshore with trolling and electric-reel deep dropping

5.0 • 25 reviews
$1,166
Full-Day Offshore Fishing Charter in Big Pine Key

Full-Day Offshore Fishing Charter in Big Pine Key

Try multiple fishing styles while targeting prized Florida Keys species

5.0 • 25 reviews
$1,324
Big Pine Key Lobster & Fishing Charter

Big Pine Key Lobster & Fishing Charter

Fish for snapper and grouper, catch lobster, then unwind at a Keys sandbar

5.0 • 25 reviews
$1,166
1…192021…46
Fishing Charters217Boat Tours114Snorkeling96Boat Rentals95Yacht Charters92
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  • 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