Pilot House Key West

Pilot House

Main House Faces Simonton Cabana Suite Queen Private In Room Jacuzzi Pilot Poolside Lodging Grotto Style Jacuzzi Spa View from Hotel Suite Guesthouse Living Room Double Queen Beds Sleep Four Full Kitchen with Appliances Standard King Guestroom Inn Style with Double Historic Room with Kitchenette Standard Economy in Mansion
Luxurious accommodations in the historic capital Otto Mansion and new poolside Spanish Cabanas. Suites contain fully equipped kitchen. Cabanas offer King-size bed, wet bar, private entrance, and Jacuzzi tub. Pool, lush gardens, and spa surround the property. Clothing optional. In Old Town just 1/2 block off of famous Duval street. All rooms are NON SMOKING, but ashtrays have been provided for our smoking guest on all verandahs, balconies, porches, and decks. All rooms have A/C, Color cable TV, private line phones, paddle ceiling fans, private baths and beautiful tropical grounds.


What a fantastic location, the Pilot House Guesthouse is just one block from popular Duval and is located near many restaurants of all different cuisines, bars, and island attractions. You can rent a host of bikes like bicycles or scooters right at the front desk, we found them a great way to scoot everywhere in Key West. We booked our stay in the "Attic Suite" and would be fine with that room again, it was small but very unique. When talking to other guests at the guesthouse whom were staying in the other rooms they seemed very happy with their accommodations. Our room had a romantic private Jacuzzi and our deck. Sometimes it is also good to meet and talk to other people, so you my want to choose the large shared hot tub on the property. The communal Jacuzzi is very comfortable, we considered it the feature we loved most about the Pilot House. The ambiance was heightened by the surrounding wooden lattice wall that gave it a really great intimate appeal. We found that the tub was clothing optional, but thankfully everyone we met was wearing something. The large pool area was also clothing optional, we did find people swimming or sunning by it in the buff. You should be made aware of this before you go and decide if it is important to you. Normally we wouldn't search out such a place however we found the freedom and acceptance of such an adult atmosphere wonderful and really made our trip all the better. It wasn't creepy in the least, it was exciting and a vacation of a lifetime. You are asked to cover up when you're simply walking and exploring around the property. I hope this doesn't cause you to feel uneasy, just relax, go with an open mind, and have a great time, you may surprise yourself. Everyone we encountered was easy-going, very respectful, and a load of fun to get to know. The pool is sunny and well situated. We had a wonderful time at the Pilot House in Key West. It was the perfect place to experience all that the island had to offer. We will be back in the future.

This hotel absolutely made my Key West vacation so much better! The staff overtly friendly and wonderfully accommodating. They never shied away from any task I asked of them. I got exactly what I was hoping for and at an amazing room for a low price. I booked a room on the second floor with my own private balcony. The kitchenette was great but the marble bathroom was just superior. The location on the island was tremendous, I was right next to Duval Street and utilized the convenient store Walgreen's more than once on my trip. Being that it was so close the store made it easy to stock our kitchenette with water, alcohol, and snacks. I would most definitely return to the Pilot House for its hospitality, it's location and great deals on room rates!

My wife and I have just gotten back from week long stay at the Pilot House. We were in one of the Cabana Rooms that the guesthouse offers. My wife and I found the room to be extremely nice. The entire staff was more than just accommodating, they were down right pleasing to be around. The Pilot House is only steps from Duval Street. We plan to stay again and again here for all of our trips to Key West.

We made the mistake of not going directly to Key West for our last vacation. We spent a rather disappointing night in Miami before we hit Mile Marker Zero. When we actually started having fun was the moment we entered our accommodations at the Pilot House. It is so clean, extremely tasteful and offers a lovely balcony and kitchenette, great private pool and hot tub areas topped our list of perks. The crème de la crème was how near Duval St. was to our room. And it wasn't noisy at all! The price had to be the next great aspect of this place. This is not a Bed and Breakfast in the traditional sense, your only a short walk to any restaurant your heart could possibly want.

This hotel was more than I could have ever hoped for. The Pilot House opened it's arms and created the foundation that the rest of my vacation was based on. Unfortunately we only booked a two night stay. The beautiful rooms and spectacular grounds were unbelievably clean and colorful. The shear amount of character that this place had should win them an award or something. It was my first experience in a guesthouse, and quite frankly I only reserved it because we were getting such a good rate on our room. Lucky for us they had some availability or I might never had tried something other than the traditional hotels. Our room was a quaint standard queen size guestroom, the added room from the porch made it much more spacious. My morning coffee tasted better on that porch more than anywhere else I have ever had it! Our precious porch was perfectly private with lush tropical vegetation. The whole place exuded tranquility and relaxation, even though we had to vacation in the middle of high season. The entire guesthouse had no vacancies, yet it was almost as if we were the only ones staying there. Our well equipped room had a kitchenette with a microwave and fridge which we used a lot for the leftovers. We could walk to everything, so we didn't need a car at all. Next time we travel to Key West we will fly directly in. The hot tub was truly brilliant, the quietness and relaxation it allowed was worth its weight in gold. We felt completely comfortable being at the clothing-optional pool area. We will be coming back, and it is highly recommended that you join us!

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    414 Simonton Street
    Key West, Fl 33040


    • Adults Only
    • In Room Jacuzzi
    • Grotto Whirlpool Spa
    • Clothing Optional Pool
    • Full Kitchen
    • Classic Decor
    • Kitchenette
    • Bicycle Rental
    • Historic Downtown Location
    • 1/2 Block Off Duval Street
    • Full Concierge Service


  • Distance = (Walking)

  • Public Library
    .1 mi (3 min)
  • Fausto's Grocery
    .1 mi (2 min)
  • Margaritaville Cafe
    .2 mi (3 min)
  • Red Barn Theatre
    .2 mi (4 min)
  • Kermit's Key Lime Pie
    .3 mi (6 Min)
  • A&B Lobster House
    .4 mi (7 min)
  • Conch Tour Train
    .5 mi (9 min)
  • Emeralds International
    .4 mi (8 min)
  • Chamber of Commerce
    .6 mi (10 min)