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Things To Do

VRBO: "STARS" Downtown Location (highly recommend)

This was for a large group of us to celebrate 3 of our birthdays, so this Airbnb would be perfect for large parties/bachelor/bachelorette trips and birthdays. There is a pool out back that you share with the above unit, which we never had an issue with. There was only one spot and if the people renting the top unit got there first, they would get it, so you have to park down the street and around the corner in a pay-to-park parking lot. We actually booked this stay through VRBO versus Airbnb and it was a lot cheaper on that site.

Iconic Spots

  • 7 Mile Bridge

    • This is the bridge that you will cross over as you make your way into Key West

  • US Mile Marker 0

  • Southernmost Point

    • This can get a crowd quickly so be prepared to stand in line to snap this picture​

  • The Southernmost House

Museums & Tours

  • Ernest Hemingway Home and Museum

    • This is known for having the six-toed cats roaming around​

  • Pirate Museum

  • Key West Shipwreck Museum​​

  • Dry Tortugas National Park

    • You can take a tour that will take you here and you can choose between exploring Fort Jefferson, snorkeling, visiting the beaches and more​

Outdoor Activities

  • Sunset Watersports (link to their site below)

    • Rise and Reef Morning Snorkel​ (this is the one that we did)

      • This was a 3 hour day with unlimited mimosas and breakfast​

      • It was $40/person if you wanted to snorkel and $25/person if you only wanted to ride

    • Dinner Cruise

    • Parasailing

    • Jetski Tour

    • Sunset Sail and Snorkel

  • Lobster Diving

  • Fishing on a charter boat/ Inshore or Offshore

  • Glass bottom Kayaking

  • Rent bikes to cruise around

  • Beaches

    • Smathers Beach

    • Fort Zachary Taylor Beach

    • Simonton Beach

    • Higgs Beach

  • Dante's Pool Bar and Restaurant

    • No reservations, so if you want the poolside umbrella/chairs you need to arrive as close to opening as possible​

    • No cover required, but you need to actively be eating and drinking

    • Perfect for large parties

Where to Watch the Sunset

  • Sunset Pier

    • This gets super crowded so try and make a reservation if you can, but if not I would go very early to secure a spot​

  • Sunset Watersports Sunset Sail

  • Mallory Square Key West Sunset Celebration

    • Tons of people are out here watching the sunset on the water, getting fruity drinks and watching street performers​


  • Robbie's on Marathon​​

    • Their Bloody Mary's and feeding the tarpon are a must

  • Seaside Cafe at the Southernmost House Mansion

    • Rock Candy Mojitos​

  • Sunset Pier

    • Grab a drink and watch the sunset here​

  • Dante's Pool Bar and Restaurant

    • Perfect for drinking by the pool​

  • Duval Street

    • Willie T's

    • Durty Harry's​

    • Irish Kevin's

    • Garden of Eden

    • Green Parrot Bar

    • Flying Monkeys

    • Sloppy Joe's

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