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Pilot House Guest House: Traveler Reviews

2.0 of 5
414 Simonton Street, Key West, FL 33040
Hotel amenities
Pilot House Guest House
Ranked #25 of 98 Key West B&B and Inns
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198 reviews from our community

Traveler rating
    141
    35
    6
    4
    12
See reviews for
Families
2
 
Couples
153
 
Solo
5
 
Business
1
 
Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    4.5 of 5 stars
  • Rooms
    4.5 of 5 stars
  • Service
    4.5 of 5 stars
  • Value
    4 of 5 stars
  • Cleanliness
    4.5 of 5 stars
Date Rating
New Jersey
Reviewer
3 reviews 3 reviews
3 hotel reviews
Reviews in 2 cities Reviews in 2 cities
2 helpful votes 2 helpful votes
“We were hoping that we weren't going to be disappointed and we weren't”
5 of 5 stars Reviewed March 8, 2011

This is the first trip that my wife and I have been on without any guests in several years, and we were hoping that we weren't going to be disappointed and we weren't. We had been to Key West twice before staying in chain hotels (Marriott etc) and this was the first time at a B and B in Key West. We had a great time, it had the Bed but no Breakfast but that was half the fun, just lounging around and not having to be "at" breakfast at a certain time.

We arrived after making the trip down from Ft. Lauderdale which we had done in the past. What a great ride on the way down but not so much on the way up when you are leaving! When we arrived the staff we very nice and immediatley gave us some hints about parking, dinner etc. My wife liked the security of the property with its high wall and locked gate. Very nicely done. The landscaping was very nice and at night it was even prettier with the indirect lighting. The room was better than was expected (we have stayed in B and Bs in New England before) with its own private entrance, bathroom etc. Ours had a non working fireplace but it added to the room's feel and the mantle made a great shelf for our IPod music player. Small refrig, sink and cabinets were just enough for us to buy some wine, cheese, water and other small supplies. We also had a small table and chairs on the covered porch where we did have our breakfast a couple of mornings. Water pressure and hot water in the shower were very good and that is a huge plus for me.

Being so close to Duval was also great. Walked there all the time which took all of about 5 minutes. If you didn't know the Pilot House was there you would not even know it. That part was great, felt like we had our own place in Key West just off Duval!

The Pool was very nice, shaded at times which was fine with us. If you wanted sun you had it and if you wanted shade you had that too. After the first day I wanted shade. The pool was fun in that it was never "crowded" like a resort pool would be, trying to get your towel on your chair to reserve it early in the day. The most people we saw at the pool at any one time was 8, which is when we all started singing Sweet Caroline with Virginia who checked us in earlier in the day.

The hot tub as you can see from the pictures on the Pilot House website is interesting in that it has a tree growing through the roof. It was clean in and around the spa everytime we used it which was at least once a day. The hot tub was one of the best features of the Pilot House.

Lastly, we liked it so much that we have already booked the place again for later in the year. Can't wait to go back.

  • Stayed February 2011, traveled as a couple
    • 5 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 1
Ask SteveandWendy53 about Pilot House Guest House
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Plainfield, Illinois
1 review
“Pilot house was perfect in every way.”
5 of 5 stars Reviewed March 8, 2011

We called Pilot House at the last minute on our way to Key West to make a reservation. Virginia was very helpful and when we arrived she greeted us and showed us the property. What a beautiful guest house! Our rooms were very large and clean. The clothing optional pool was tasteful and the hot tub divine. I would definitely recommend a stay at Pilot House.

  • Stayed February 2011, traveled 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
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Ask Mollycat_11 about Pilot House Guest House
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
South Jersey
Reviewer
3 reviews 3 reviews
Reviews in 3 cities Reviews in 3 cities
8 helpful votes 8 helpful votes
“Another wonderful stay in poaradise”
5 of 5 stars Reviewed February 22, 2011

Just returned from another wonderful stay at the Pilot House. We have stayed there many times and every time has been excellent. This Guest House really does put the Guest first. Virginia and Daniel are there to make sure your stay is as enjoyable as possible. Their location is excellent and their amenities are fantastic, possibly the greatest hot tub in the world. Thank-you for another wonderful stay

  • Stayed January 2011, traveled as a couple
    • 5 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
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Ask mtnest52 about Pilot House Guest House
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Wilmington, North Carolina
1 review
1 helpful vote 1 helpful vote
“Great Place, Great Staff, Great Time”
5 of 5 stars Reviewed January 18, 2011

This is our second stay at Pilot House and we will definitely be back.We have stayed in two different room in the mansion. They have beautifully melded the feel of an old mansion with modern conveniences. You really get the charm and history of Key West at the Pilot House. The one room/suite had a fully equipped kitchen and we were able to cook while staying in this room. The other room was very nice and we could do breakfast and lunch with the frig, coffeemaker, toaster, and microwave.Eating out on the decks surrounded by palms was pure luxury. The hotel is centrally located in a quiet area off of Duval Street, steps away from great restaurants and entertainment. The pool area is great and clothing optional. All the guests were very social during both of our stays, and it didn't seem to matter if they had a suit on or not., everyone seemed comfortable. The spa/hot tub area has been recently redone and has a very "tropical" feel. The staff, Scott, Daniel, and Virginia were very welcoming, and you immediately felt their warmth and professionalism. They were very helpful in recommending restaurants and other points of interest., and their knowledge of the island added to the enjoyment of our stay. If you enjoy the feel and friendliness of a small inn, this is the place to stay.

  • Stayed October 2010, traveled as a couple
    • 5 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 1
Ask kandl4keys about Pilot House Guest House
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Chicago, IL
Reviewer
3 reviews 3 reviews
3 hotel reviews
Reviews in 2 cities Reviews in 2 cities
2 helpful votes 2 helpful votes
“A great place to have a great time....”
4 of 5 stars Reviewed December 1, 2010

Being a key West regular, this was the first time we have stayed at the Pilot House. We stayed in the Cabana rooms by the pool and found them to be unique in their layout and comfortable. Scott, your host, was more than accomadating and worked hard to keep the whole place in order. The place is more geared to people that want to tan in the nude and everyone was friendly and fun to be around. Laying out in the Key West sun without a suit on is a pleasure that everyone should experience. We have found that staying in ANY of the old mansions (B & B's) is the way to experience Key West. If you are looking for the fine hotel feel or the Cancun "resort" feel. This is not it. These buildings are 100 years old so dont expect the Ritz. They are charming, relaxed, clean and majestic. Its also the way most of the island is. If this isnt what you want, try Hawaii, but I'll take this any day of the week !!!!

  • Stayed September 2010, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 2
Ask alncath about Pilot House Guest House
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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Additional Information about Pilot House Guest House

Also Known As:
Pilot House Guest House Hotel Key West
Pilot House Guest House Hotel
Address: 414 Simonton Street, Key West, FL 33040
Region: United States > Florida > Florida Keys > Key West
Amenities:
Free High-Speed Internet Kitchenette Suites Swimming Pool Wheelchair access
Hotel Style:
Ranked #25 of 98 B&Bs / Inns in Key West
Price Range: $$
Hotel Class:2 star (2*)
Official Description (provided by the hotel):
Luxurious accommodations in the historic Otto Mansion and pool side Cabana rooms. Full kitchens and kitchenettes available. Pool, spa and lush gardens surround the property tucked away in downtown Key West. ... more   less 

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