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All 101 Key West B&Bs / inns »

Pilot House Guest House

2.0 of 5
414 Simonton Street, Key West, FL 33040
Hotel amenities
Ranked #44 of 101 Key West B&B and Inns
4.5 of 5 stars 85 Reviews
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85 reviews from our community

What travellers say about this B&B/inn
  • Pilot House(9)
  • Duval street(5)
  • Hot tub(4)
  • Cabana room(4)
  • Clothing optional pool(3)
Traveller rating
    51
    17
    5
    3
    9
Only show reviews for Family (1) | Couples (59) | Business (0)
Date Rating
Ed M
Philadelphia, Pennsylvania
Reviewer
5 reviews
5 of 5 stars Reviewed 29 January 2012

My wife and I just returned from Pilot House and had the best trip of many. They continue to maintain the facility very well. I must mention Virginia and Daniel who were most gracious. We have been to the site seven times and they couldn't have been nicer or more helpful. For several visits I never realized they had a... More

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Bill2bhappy
2 reviews
2 helpful votes
4 of 5 stars Reviewed 12 January 2012
2
people found this review helpful

We stayed for a long weekend to enjoy lobster fest. We stayed at the bungalow rooms first floor by the pool. The room was comfortable the in room jacuzzi was a single person Jacuzzi tub and there was a separate shower. Friday night of lobster fest you have to do the bar crawl sat the street festival food is amazing... More

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JohnTheBiker
Northwestern Indiana
Senior Reviewer
10 reviews
25 helpful votes
5 of 5 stars Reviewed 6 January 2012
1
person found this review helpful

Wonderful hotel. One block off of Duval Street. Very peaceful pool and hot tub area. We had a cabana room just off of the pool. Very clean and well laid out with a kitchenette and a really neat large shower and jacuzzi. Daniel (the owner) was helpful and friendly. We would definitely stay here again. Take a look at their... More

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Nvizble
Ft Lauderdale, FL
Senior Contributor
29 reviews
9 helpful votes
4 of 5 stars Reviewed 6 November 2011
2
people found this review helpful

Great location, well cared for, know what they are doing. I have stayed here a few times. There are other places I like better but this is a go-to place. More

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in2thewind
London, United Kingdom
2 reviews
1 helpful vote
4 of 5 stars Reviewed 29 September 2011
1
person found this review helpful

Absolutely loved this place. Stayed in a Cabana Room and can't wait to go back and stay in the attic suite! A great balance between hotel style while still self catering. Nice and close to everything but just off the beaten track. Nice grocery shop right across the road which sold everything including warm food for a quick and cheap... More

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Charley J
Woodlawn, Tennessee
Senior Reviewer
6 reviews
5 of 5 stars Reviewed 26 September 2011

Too sum this up without writing a novel is for us to say that the Pilot House provided us with an excellent Key West vacation. The staff was extremely accomodating and the guesthouse was amazing. The room was very well kept and clean and the pool and spa were the same. The clothing optional part was a definate big plus... More

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Psstuff
2 reviews
1 helpful vote
4 of 5 stars Reviewed 31 August 2011

After a fairly exhaustive search to find a place that was a combination of Key West charm, location and attractiveness, we settled on the Pilot House. During our search, we were aware of some of the negative comments about this place, but we found they were prompt in answering our questions, we liked the looks of the room pictured on... More

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Dee P
Punta Gorda, Florida
1 review
5 of 5 stars Reviewed 27 August 2011

Our first trip to Key West was a fabulous one due to our great hotel and its staff. The rooms were extremely clean and comfortable. The pool and spa were just as clean and well kept. The hotel is located about a block off of Duval Street; we were close to everything and felt safe returning late at night. Our... More

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Snorkelman777
Ormond Beach
Reviewer
4 reviews
4 helpful votes
5 of 5 stars Reviewed 15 August 2011

My wife and I scheduled this trip at the last minute so we ended up with a room in the cabana section. It was more than I wanted to pay, but it turned out to be a really good vaule. The room was clean, modern and very roomy. I think a similar room at a hotel would have been substantially... More

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missouritraveler76
Neosho, Missouri
Senior Reviewer
6 reviews
20 helpful votes
5 of 5 stars Reviewed 3 August 2011
1
person found this review helpful

My wife and I stayed at the Pilot House the last week of July 2011 and were very pleased with the facility. I had read some differing reviews before we arrived so wasn't quite sure what to expect. The hotel was very nice and quiet and convenient to Old Key West. A couple of weeks before our arrival we got... More

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