My Top Ten Key West Accommodations

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Top Ten Key West Accommodations places to stay.

March 28 2020 – Key West has no shortage of places to stay. You just need to decide on what amenities you want and what type of property you prefer. Chain hotel, vacation rental, boutique hotel, B&B guest house or intimate inn? Key West has it all. This is my Top Ten favorite properties based on the feedback I receive from all of the people I help put together their Key West vacations.

First – Choose A Location

You may also consider on what part of the island you want to stay. So I have separated my Key West top ten accommodations geographically. While only 2 x 4 miles, people have definite preferences. Some people want to be in the middle of all the action while others want more peace and quiet.

Stock Island Accommodations

Before arriving on Key West proper, you will find Stock Island. Not far from downtown Key West and my favorite accommodations offer free shuttle services. You will find rates slightly less here because of the short distance to Key West. It is also a great option if a Key West fishing charter is on your list of Key West activities. The best fishing charters of Key West are on Stock Island. Our pick:

  • Ocean’s Edge – 6 pools, bar, restaurant, gym, marina, bike rentals, kayak rentals, shuttle service, parking, pet friendly.

Upon entering Key West, you will be in what we call New Town. Here you will find many options, and because they are again a short distance to downtown Key West, rates are slightly lower. Our picks:

  • Marriott Beachside – restaurant, bar, gym, beach, pool, parking, shuttle service
  • 24 North – pool, library, hotel shuttle, 2 bars, Starbucks, outdoor concert area

The Historic Seaport is home to bars, boutiques, and the harbor walk where one can gaze at several historic ships. Our picks:

Duval Street is our version of Bourbon Street. It is basically the main drag on the island and so while it can be noisy, you are in the heart of all of the action here. Our picks:

If you enjoy nightly celebrations and views of cruise ships, then Mallory Square is a perfect location for you to stay. Our pick:

Smathers Beach is the largest beach on the island and has Watersports activities to boot. Our pick:

Casa Marina neighborhood is a gorgeous area near Higgs Beach. It is named thus for the Casa Marina, build by Flagler as a hotel for his railroad from the mainland to Key West. Our pick is of course:

  • Casa Marina – 2 pools, beach, gym, spa, restaurant, bar, valet parking

We have many visitors that come through my doors when they are enjoying the Key West fishing Charters that I have put together for them. I get to hear about all the places that they stay and this is the Top Ten Key West Accommodations from the latest first hand experiences of real folks who stayed there.