Pilot House Key West

The Mansion at the Pilot House

Front Porch of the Otto Mansion King Cabana Suite In Room Jacuzzi Poolside Cabana Building Spa is Covered View of Simonton Street Livingroom Opens to Deck Double Queen Beds Full Kitchen with Microwave Standard King Room 1A with Kitchenette Queen with Balcony Standard in Main Building
The Pilot House in Key West combines a Victorian era mansion and poolside cabana suites to create luxury in an upscale tropical atmosphere . Offering guests an adults only atmosphere with a pool and spa, this is a luxurious accommodation that delivers when looking for a high level of quality just a short walk from Duval and Mallory Square festivities.

The details like hardwood floors and in room Jacuzzis set this guesthouse apart from the average hotel room. Most of the hotels in the area are priced much higher and don't offer the convenience of amenities like a full kitchen or kitchenette. We've been accommodating guests for their first vacation to Key West for years with the majority staying with us every time they visit. Long stays or just weekend getaways are all welcome so please check our availability for your next upcoming venture to paradise.


My husband and I chose the fabulous Pilot House bed and breakfast during our recent romantic getaway to Key West, Florida. As a time we wanted to be special, the folks there went above and beyond to ensure that all of our needs were met. Since the hotel caters to adults we did not have to worry about children running around or causing noise. In fact, this is the most relaxing hotel that I have ever stayed, where everything seem to just roll with a grain of salt.

Some of the world's nicest hotel staff work here, and we were both pleasantly surprised with the smiling faces and helpful and genuine people that always took care of our needs. We stayed in a great cabana in the back for a week, and loved every minute of it! It was decorated so beautiful, and very spacious and welcoming. We were right next door to the pool and spa and took advantage of both of these as well. Things got a little risque in the swimming area because we didn't feel like anyone was around, we knew there wouldn't be any kids running around the coner for the shock of thier life, and the atmosphere is so laid back no one would have cared anyway. It's just a different kind of vibe and atmosphere than other places.

Another significant benefit is that it is located within walking distance of nearly everything! Duval Street is one block away, as are many attractions super great restaurants, and of course bars galore. Good times!

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Off Season:


(Rates subject to change. Holidays and special events may be higher.)


Pilot House Map

    414 Simonton Street
    Key West, Fl 33040


    • Adults Only
    • In Room Jacuzzi
    • Whirlpool Spa
    • Pool
    • Kitchen

Driving Distance

  • Fl City / Miles (Hours)

  • Bahia Honda Key
    36.1 Mi ( 46 Min)
  • North Perry
    175 Mi (3 Hrs 26 Min)
  • Riviera Beach
    239 Mi (4 Hrs 28 Min)
  • Fort Myers Beach
    294 Mi (5 Hrs 30 Min)
  • Wauchula
    335 Mi (6 Hrs 16 Min)
  • Lakeland
    373 Mi (7 Hrs 03 Min)
  • Leesburg
    428 Mi (7 Hrs 32 Min)
  • Middleburg
    500 Mi (8 Hrs 50 Min)
  • Live Oak
    556 Mi (9 Hrs 28 Min)
  • Crawfordville
    628 Mi (10 Hrs 56 Min)
  • Carrabelle
    662 Mi (11 Hrs 30 Min)