There are three big decisions to make when coming to Key West. First: when to come? The arrival of autumn means the heat starts to relax, and Fantasy Fest* at the end of October and New Year’s Eve are some of the biggest events of the year. Second: how to get there? You can fly into Key West’s newly expanded airport, you can take a ferry from Fort Myers (appx 3 1/2 hour trip), or you can drive, although traffic at peak times on US-1 can be bumper-to-bumper slow, so beware.
Third, and perhaps the vital question: where to stay? Luxurious resorts, quaint guesthouses, and scandalous clothing optional hotels offer unique options for visiting Key West, and after all of the excitement of Duval St., going for a post-party float in the pool is always lovely.
Here are some of our favorite pools in Key West:
Pier House and Spa
Stand on the pool deck at Pier House (photo, above), and you have a clear view of the hotel’s little private beach, which leads to the beautiful Gulf of Mexico. Pier House is a favorite destination for travelers looking for waterfront luxury, and the views of the Gulf make it a popular spot for weddings. The pool and beach face west, which give a perfect view of those famous Key West sunsets!
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Island House
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Island House is all about the pool scene. This clothing-optional, all-male hotel has one of the most popular pools in Key West, where hotel guests mix with day-pass visitors at the poolside bar and float around. As a bonus, the restaurant at Island House is also quite good, and Island House guests enjoy free daily open-bar happy hour every day.
Marquesa Hotel
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Marquesa Hotel is on two separate properties, down the street from each other, and all hotel guests have access to all of the amenities in both locations. This pool, in the original property, has beautiful landscaping with brickwork and aesthetic waterfalls around the pool deck. Also of note, Cafe Marquesa, in the main building’s lobby, is renowned as one of the best restaurants on the island.
Equator Resort
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This all-male, clothing optional hotel has tropical-inspired rooms with balconies overlooking the pool and poolside bar, giving guests a bird’s eye view of the shenanigans in the water. On busy holiday weekends, the Equator Resort guests and day pass visitors can put on quite a show! The hotel’s staff is also well-known for providing polite, professional service.
*Fun Fact about Key West: Frank Romano and Joe Liszka, two of the founders of Fantasy Fest, were life partners for over 50 years, and helped raise vital money for many charities in Key West. The fountain at North Roosevelt Boulevard and Jose Marti Drive in Key West is dedicated to their love for each other, and their love for the island. How sweet!
Do you have a fun travel tip or recommendation for a great destination? Email danrenzi@gaycities.com
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