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“We were hoping that we weren't going to be disappointed and we weren't” 5 of 5 stars
Review of Pilot House Guest House

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Pilot House Guest House
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2.0 of 5 Bed and Breakfast   |   414 Simonton Street, Key West, FL 33040   |  
Hotel amenities
Ranked #18 of 97 Key West B&B and Inns
New Jersey
Senior Reviewer
9 reviews 9 reviews
6 hotel reviews
Reviews in 5 cities Reviews in 5 cities
10 helpful votes 10 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
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283 people have reviewed this hotel

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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
    4.5 of 5 stars
  • Cleanliness
    4.5 of 5 stars
Traveler tips help you choose the right room.   Room tips (95)
Date | Rating
  • English first
  • French first
  • Any
English first
Plainfield, Illinois
2 reviews
Reviews in 2 cities Reviews in 2 cities
2 helpful votes 2 helpful votes
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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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
South Jersey
Senior Reviewer
7 reviews 7 reviews
3 hotel reviews
Reviews in 3 cities Reviews in 3 cities
11 helpful votes 11 helpful votes
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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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
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
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Chicago, IL
2 reviews
2 helpful votes 2 helpful votes
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
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Overland Park, Kansas
Reviewer
5 reviews 5 reviews
4 hotel reviews
Reviews in 2 cities Reviews in 2 cities
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed October 26, 2010

Our experience was excellent. Room was comfortable, large and clean. The staff was polite, professional and helpful. The pool was very nice. Spa was outstanding. we were only a few blocks off Duval, and always felt safe.
The pool and Spa area were clothing optional. A little awkward at first but we felt very comfortable in a short period. We had a cabana room, which was very close to the pool. The room was very roomy with all the amenities we wanted. We have been to Key West several times and will be sure to stay at Pilot house again.
Thanks to the staff for an excellent stay.

  • Stayed September 2010, traveled as a couple
    • 4 of 5 stars Value
    • 4 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
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Winston Salem, North Carolina
1 review
2 helpful votes 2 helpful votes
4 of 5 stars Reviewed September 27, 2010

My wife and I just returned from a three day trip, we stayed at the pilot house the whole time. We were probably the youngest couple to stay there but we enjoyed the company of the other guests and loved the nude pool and hot tub. Nothing better then laying out under the sun by the pool completely naked! Very laid back place, nice people...will come back for sure!

  • Stayed September 2010, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 3 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 2
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

Address: 414 Simonton Street, Key West, FL 33040
Location: United States > Florida > Florida Keys > Key West
Amenities:
Free High Speed Internet ( WiFi ) Kitchenette Suites Swimming Pool Wheelchair access
Hotel Style:
Ranked #18 of 97 B&Bs / Inns in Key West
Price Range (Based on Average Rates): $$
Hotel Class:2 star — Pilot House Guest House 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 
Also Known As:
Pilot House Guest House Hotel Key West

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