We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Pilot House Guest House – reviews, photos

2.0 of 5
414 Simonton Street, Key West, FL 33040
Hotel amenities
Pilot House Guest House
Ranked #42 of 101 Key West B&B and Inns
4.5 of 5 stars 109 Reviews
Which Key West hotels are on sale?
See hotels
Write a Review

109 reviews from our community

What travellers say about this B&B/inn
  • Pilot House(9)
  • Duval street(5)
  • Cabana room(4)
  • Hot tub(4)
  • Clothing optional pool(3)
Traveller rating
    67
    22
    6
    3
    11
Only show reviews for Family (1) | Couples (79) | Business (0)
Date Rating
Philadelphia, Pennsylvania
Reviewer
5 reviews 5 reviews
1 helpful vote 1 helpful vote
“Our best trip thus far”
5 of 5 stars Reviewed 29 January 2012
1
person found this review helpful

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 sun deck and now it's where I spend my time. There is only four lounges there but it works for me. The hot tub is well maintained and a great place to start and end the day. I have tried to book this place during Fantasy Fest but have never been successful. This year I booked another clothing optional facility in town and was shocked that it was beat and dirty. A walk through wouldn't uncover this if you don't go in the rooms. I had the pool room and it was terrible. To their credit, when I told them of my fellings they reluctantly gave me my money back but made it clear they were not pleased and it was a very uncomfortable time until we left. I learned a difficult lesson and will remain loyal to Pilot House regardless of not being able to book for FF.

Room Tip: Cabana rooms were great
See more room tips
  • Stayed January 2012, travelled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 4 of 5 stars Service
Was this review helpful? Yes
See 4 more reviews by Ed M for Key West
Ask Ed M about Pilot House Guest House
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
2 reviews
Reviews in 2 cities Reviews in 2 cities
2 helpful votes 2 helpful votes
“Lobster festival at the pilot house in key west”
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 and the Sunday lobster brunch is to die for. Now the good stuff. The nude sun bathing is nice but we could not even travel the 5 feet from our room to the pool with out a towel the staff is very strict about this. You can only be naked in the pool or laying on a chair. The staff leaves around 6 pm and that rule goes out of the window. There is a neighbor that can see down into the pool but they seemed discreet. Over all it was a great trip. Hope you do as well. Also if you go at lobster fest there is a group of nice people we met that all go every year and enjoy staying there together and are nice people.

  • Stayed August 2011
    • 5 of 5 stars Value
    • 4 of 5 stars Location
    • 3 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 3 of 5 stars Service
Was this review helpful? Yes
Ask Bill2bhappy about Pilot House Guest House
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Northwestern Indiana
Senior Reviewer
10 reviews 10 reviews
Reviews in 6 cities Reviews in 6 cities
25 helpful votes 25 helpful votes
“Relaxing Stay”
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 website, the hotel is just as nice as is shown on the website.

  • Stayed December 2011, travelled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
See 2 more reviews by JohnTheBiker for Key West
Ask JohnTheBiker about Pilot House Guest House
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Ft Lauderdale, FL
Senior Contributor
40 reviews 40 reviews
Reviews in 23 cities Reviews in 23 cities
15 helpful votes 15 helpful votes
“Tried and true”
4 of 5 stars Reviewed 6 November 2011 via mobile
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.

  • Stayed November 2011
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 4 of 5 stars Service
Was this review helpful? Yes
See 4 more reviews by Nvizble for Key West
Ask Nvizble about Pilot House Guest House
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
London, United Kingdom
2 reviews
1 helpful vote 1 helpful vote
“Loved this place”
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 bite to take back to your room. One thing that wasn't the best was trying to book from overseas beforehand, they didn't seem every helpful. But were perfectly nice when we arrived so perhaps crossed wires

  • Stayed November 2010, travelled as a couple
    • 3 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 3 of 5 stars Service
Was this review helpful? Yes
Ask in2thewind about Pilot House Guest House
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC

Travellers who viewed Pilot House Guest House also viewed

Eden House
4.5 of 5 stars 704 Reviews
Key West, Florida Keys
CHECK RATES! ABS:HotelCheckRates-d224519?&src=ShowUserReviewsHotels&fromServlet=ShowUserReviews&Action=QC_AlsoViewed
Ambrosia Key West Tropical Lodging
5 of 5 stars 753 Reviews
Key West, Florida Keys
CHECK RATES! ABS:HotelCheckRates-d251933?&src=ShowUserReviewsHotels&fromServlet=ShowUserReviews&Action=QC_AlsoViewed
Knowles House B&B
5 of 5 stars 258 Reviews
Key West, Florida Keys
CHECK RATES! ABS:HotelCheckRates-d611236?&src=ShowUserReviewsHotels&fromServlet=ShowUserReviews&Action=QC_AlsoViewed
View all 41 hotels in Key West, ranked by popularity »

Been to Pilot House Guest House? Share your experiences!

Write a Review Add Photos Add Videos

Additional Information about Pilot House Guest House

414 Simonton Street, Key West, FL 33040
Price range (per night):* INR6,441 - 14,843

Owners: What's your side of the story?

If you own or manage Pilot House Guest House, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.

  • Manage your listing