Pilot House Guest House

414 Simonton St , Key West, FL 33040-6815 USA (Show map)


Luxurious accommodations in the historic Victorian Otto Mansion and new poolside Cabanas. Suites contain fully equipped kitchen. Cabanas offer king-size bed,wet bar, private entrance, jacuzzi tub. Pool, lush gardens and spa surround the property. Clothing optional. Located in Old Town just 1/2 block from Duval Street. Private and elegant...an exceptional value.

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Innkeepers: Virginia & Daniel



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  • Guest room5
  • Service4.7
  • Value4.3
  • Cleanliness5
  • Onsite Dining3.6

Heaven on Earth

4.4 on January 02, 2014

Was surprised with a trip to Key West for Thanksgiving by my girlfriend ..her first time...and she decided to stay at The Pilot House...WOW what an amazing experience..from the location (literally half a block from Duval St and no Duval noise) to the beautiful rooms and amazing pool and jacuzzi....I knew from the beginning that this place was a keeper when the locals would ask where we were staying and when we would tell them...the response was always..."oh that's an amazing place..make sure to tell them we said hi".. Only negative was the surprise of no breakfast...they were doing a bit of construction and relocating the office, so we assumed that was the reason the no breakfast was offered...other than that our experience was 5 stars

Excellent B&B

5 on March 24, 2012

Great rooms and value. Location is excellent. Only 1 block to Duval St. A super market is only a 1/2 block from the property. Enjoyed our stay and met great people. Would stay here again. We stayed in attic suite and enjoyed the privacy of the deck and private hot tub. This unit has a view of the city.

Paradise in Paradise

5 on May 13, 2009

The Pilot House is like staying in Paradise in Paradise. The pool is great, especially since it is now heated. The rooms have such a character all to themselves. Scott, Daniel, and Virginia are always available to answer questions and ensure the stay is the best.

Pilot house is ok

3.0 on March 11, 2009

The pilot house was a very romantic bed and breakfast, loved the atmosphere and the room did exceed my expectation. it had a full kitchen, very clean and romantic. I had no problem as far as the B and B itself, however you will NOT SLEEP. You can hear the other guest's comings and goings and their entire conversations at all hours of the nite, also the noise from Duval st , mostly the motorcycles. But i guess that is to be expected at a b and b. Also we were told that there would be parking, when we got there we were told there is an additional $10 perday to park in their lot. I feel that is unfair. WE were lied to about that . Ther is no continental breakfast offered eiher that you would get at other b and b's.

A Gem

4.6 on January 07, 2009

My fiance and I stayed here my second time to Key West. It was so relaxing, we stayed an extra day. The Cabana's rain shower head made us buy one at home. And the secluded spa was just amazing. Well worth it.


4.8 on March 09, 2008

My wife and I visited recently for our 25th Anniversay. The staff couldn't have been more attentive and helpful. Accomodations were very clean and well maintained. Romantic atmosphere added to the reason for our visit. Clothing optional at pool and hot tub was very discreet with an adult mentality, added to the ambiance, so much so that my very private wife joined right in. Already booked for next March and looking foward to it!


4.8 on July 30, 2007

We have stayed at the Pilot House several times and it has been outstanding each time. Convenient to everything. Take your pick, mansion or cabana, they are all great. Prefer not to stay anywhere else in Key West.

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Area Attractions

Antique Shopping, Aquarium, Art Galleries, Beach, Gourmet/Fine Dining, Historical interests, Live Music, Museum, National/State parks, Nature area, Ocean, Outlet Stores, Performing Theater, Religious Services

Inn Details

Establishment type

Historic Inn

On-site amenities

Fax Machine

Room amenities

Air conditioning, Alarm clock, Ceiling fans, Coffee/Tea facilities, Fridge, Hairdryer, Hot tub/whirlpool tub, Ironing Board, Microwave, Private entrance, Radio, Satellite/Cable TV, TV, Telephone, VCR, Wet bar

On-site activities

Bicycle rental, Boating, Fishing, Golfing, Sailing, Shopping, Sight-seeing, Swimming, Swimming pool, Tennis courts, Water sports

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  • Check In:: 3:00PM
  • Check Out:: 11:00AM
  • Open All Year Round: Yes
  • Smoking Allowed: Outside only Outside and common areas
  • Drinking Allowed: Yes
  • Suitable For Children: No
  • Childcare Provided: No
  • Guest Pets Allowed: No
  • Disabled Access Yes

Terms and Conditions

  • Minimum Stay: 3 nights on weekends
  • Accepted payments AMEX, VISA, Discover, Mastercard, Diners club, Personal checks, Travelers checks, Cash
  • Deposit Amount Required: 1 night room and tax except special events in which 50% is requested.
  • Cancellations: More than 14 days prior to arrival to receive deposit back. Less than 14 days nonrefundable.



Virginia & Daniel

Languages spoken


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