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“Another Great Stay at the Pilot House” 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
Sandusky, Ohio
Top Contributor
53 reviews 53 reviews
3 hotel reviews
Reviews in 6 cities Reviews in 6 cities
24 helpful votes 24 helpful votes
“Another Great Stay at the Pilot House”
5 of 5 stars Reviewed May 4, 2013

This was out second time at the Pilot House. Daniel and Virginia were great, very welcoming and took care of whatever we needed. The room was comfortable and the fridge and wet bar area are great for making boat drinks! The clothing optional pool and spa are a awesome and we met great people again this year. Planning to go back again next year!

  • Stayed April 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 4 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.
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287 reviews from our community

Traveler rating
    217
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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 (98)
Date | Rating
  • English first
  • French first
  • Any
English first
Treasure Island, Florida
1 review
5 of 5 stars Reviewed April 30, 2013

My better half and I just returned from Key West. We LOVE the PILOT HOUSE and I am sure you will too! As owners of a small Mom and Pop style retreat in Treasure Island Florida-called BUNGALOWS(bungalowsflorida.com) we are aware of the amount of work it takes to run a property like the PILOT HOUSE. Not just the effort but the LOVE that goes along with the work that makes you know you are very special. Virginia and Daniel do a great job and so do all the other employees. The owner is very blessed to have such an honest caring group taking care of his investment.
We will be back again and again and again...PEACE and LOVE Jane and Peter

Room Tip: They all have their own special charm!
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  • Stayed April 2013, traveled on business
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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lynnkephart, Manager at Pilot House Guest House, responded to this review, May 9, 2013
Thanks for the glowing review. We are glad you felt at home and enjoyed your stay with us here at the Pilot house. Coming from someone in the guest house business that is a great complement. We know you have lots to choose from visiting Key West and we are grateful you chose us.

Our Guests are like family (so welcome to the family) and we look forward to your next visit
sincerely virginia Manager Pilot House Guest house
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Youngstown, Ohio
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
1 helpful vote 1 helpful vote
4 of 5 stars Reviewed April 29, 2013

We have been to Key West many times - However, this is the first time we've stayed at the Pilot House. In fact the first time we've stayed anywhere in Old Town. We have always stayed on the Atlantic side - beach front and were anxious about the change in location and from full blown resort to "inn". While beach side definitely has allot to offer we found our stay at the Pilot house an extremely welcome change, in fact we loved it! While we have never been to a clothing optional resort this time around we were specifically looking for clothing optional in Key West, this was the only place I could find. It couldn't have worked out better for our first experience. The other couples there helped to create a very friendly and comfortable environment. Conversation poolside was just the right amount = we got to know the other couples but it never felt over bearing and we had plenty of R&R time (much needed after late nights out!). We found the pool and spa excellent. Plenty of sunshine or shady spots. The spa was in a really cool little area. You really do feel like you were in a tropical oasis. In the early mornings by the pool it was extremely quite and restful. Mid morning the inn keepers turn on "Pirate Radio" and just the right sound level. As guests started to return from breakfast or morning outings the pool would fill up with about 6 to 8 couples. All couples were comfortable taking full advantage of the clothing optional. Virginia and Daniel were extremely nice and very very watchful over the hotel grounds to make sure everything was just right! Every day the pool area and gardens were clean by the staff.

  • Stayed April 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 3 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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Boca Raton, Florida
2 reviews
Reviews in 2 cities Reviews in 2 cities
5 of 5 stars Reviewed April 29, 2013

My wife and I wanted to get away for a few days and decided to try Key West. We then decided to stay at a B&B. We did our reviews and had a few referrals, and selected the Pilot House. We read about the clothing optional pool and felt we were on vacation and wanted to try something new. We fell in love with the Pilot House from the moment we saw our room (the attic). We had an amazing view as well as a full apartment with private deck and hot tub. Although we had our own deck and hot tub, we found the pool area to be so welcoming and the other guests to be so friendly that we hung around the pool every chance we had. Many of the other guests were there for their 8th or 9th times, a validation to the awesome place that this is. The staff is very friendly, the place was clean and the location can't be beat. We will be returning to Key West and will not even consider another place to stay. Absolutley off the charts on the scorecard. Alan and Nancy H.

Room Tip: If you want privacy and your own deck, reserve the attic.
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  • Stayed April 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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lynnkephart, Manager at Pilot House Guest House, responded to this review, May 1, 2013
The Attic is a unique space and Im glad it was so great for you. The view, the privacy, of course the jacuzzi under the stars.
When you want to find the "hidden treasures' of key west the guests here are an excellent source of information, the trips, fishing, snorkeling, parasailing, paddleboarding.... and don't forget the restaurants, bars shops,museums and galleries that surround the pilot house all within walking distance form our central location on here Simonton street.

It was great meeting you, see you again soon

virginia pilot house guest house manager
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Naples, Florida, United States
Reviewer
3 reviews 3 reviews
Reviews in 3 cities Reviews in 3 cities
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed April 29, 2013

My husband and I bicycled down the Keys and stayed at The Pilot House Inn in Key West as our final destination. I found the inn on bedandbreakfast.com and was attracted to it by its location and general appearance. We were thrilled to arrive at the place! The property consists of an old Victorian era house and a tucked away modern cabana style grouping of rooms by the pool.The whole property is lushly landscaped and you feel like you are in a secret garden the whole time you are there. The pool area is clothing optional, which was something new for us. We were pleased to discover that everyone was friendly, relaxed, quiet and laid back- whether they had clothes on or off. The whole place was so relaxed and beautiful that we ended up peeling our own clothes off and enjoying a relaxing skinny dip in the pool! Never thought we would, but glad we did! The staff there was wonderful- attentive but casual and friendly. Very Peaceful stay.

  • Stayed April 2013, 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.
lynnkephart, Manager at Pilot House Guest House, responded to this review, May 1, 2013
What a great way to see the Keys. Biking to Key West to stay at the Pilot house
We're glad your stay with us was such a success. Sounds like the Pilot House was a perfect fit for your vacation. We love your pictures in front of the house with your bikes.
And a brilliant Idea for the return trip , the Key West Express Ferry to FT Myers.
Hope to see you again soon thanks for the review
virginia manager pilot house Guest house
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Detroit, Michigan
2 reviews
Reviews in 2 cities Reviews in 2 cities
5 of 5 stars Reviewed April 25, 2013

We stayed at the Pilot House in April. Beautiful Historic Victorian House with new cabana rooms in the back by the pool so there is a room type for everybody. We will definity be back. Virginia and Daniel are the best managers. Very friendly environment. Guests are known to be outgoing and hospitable. The hotel is a guest house that is clean and excellently maintained with refrigerators & kitchenettes. The pool is great and we enjoyed the hot tub under the gazebo! We were tempted to not go out :) Pilot House is within walking distance of the nightlife and tours so no taxi needed. We were able to walk to Sloppy Joes & Margaritaville & Irish Kevins & Green Parrot. Lots of sight seeing with many historic buildings. We had a very special time and highly recommend this guest house.

Room Tip: Cabanas by pool have in room jacuzzi tubs!
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  • Stayed April 2013, 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
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
lynnkephart, Manager at Pilot House Guest House, responded to this review, April 26, 2013
Key west has the most beautiful Victorian architecture. Homes like the Pilot House converted to Guest houses over the years have made it easy to enjoy these beautiful structures up close and personal.

The Deluxe queen room ajacent to the garden jacuzzi is a favorite of several guests the privacy and proximity to the garden jacuzzi as well as the full kitchen mean a long stay is relaxing and comfortable, a home away from home.

Like so many who visit Key West being able to get out to the attractions without need of a car is a bonus.

Glad to have you back with us and hope to see you again very soon
virginia manager Pilot House key West
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New Orleans, Louisiana
Senior Reviewer
7 reviews 7 reviews
Reviews in 2 cities Reviews in 2 cities
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed April 17, 2013

My wife and I took advantage of the new direct SW flights to Key West from New Orleans. Picked the Pilot House because of location. When we checked in we dropped our stuff off and headed out exploring Key West. When we returned we noticed that the A/C was not cooling properly. The office was closed and it wasn't that hot out at night. So we opened the windows and turned up the ceiling fan. The next day we mentioned it to Virginia and we left to get some breakfast at Sarabeth's. When we returned the A/C was fixed and Virginia gave us a nice discount for our first night. We stayed in room #12, which was upstairs in the cabana's by the pool. The room was very clean and a good size. It has a large shower with a rain head and a jetted tub. The bathroom was roomy, plenty of counter space, but no seating. The kitchen had everything we needed, but we didn't use it much. We did get some snacks and drinks at a grocery store half a block away (Faustos?). The grocery store did have a decent wine selection. We walked everywhere, so we never rented the bikes the guest house had. Duval was a half a block away, the Pilot House is located near the 400 block of Duval. So 4 blocks from Mallary Square or 6 blocks away from Hemingway's house, in the other location. We had a relaxing and low stress stay. Virginia is a hard working lady that cares about her guests and we enjoyed her suggestions (food and activities).

Room Tip: Cabana area rooms are nice, but remember it's by a clothing optional pool. You get more privacy...
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  • Stayed April 2013, 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
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
lynnkephart, Manager at Pilot House Guest House, responded to this review, April 19, 2013
The SouthWest direct flights make visiting easy thats for sure. there is also one form New York too.
Thanks for giving us the chance to correct the AC breakdown your pacience and understanding was appreciated. Maintaince is a constant and obviously important part of running a guest house.

Sarabeths is a favorite of our guests, I wish they would deliver! Another breakfast treat is Blue Heaven.
Glad you enjoyed your Key West visit and your stay with us at the Pilot House
Hope to see you here again soon
virginia
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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 ( Wi-Fi ) 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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