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Pilot House Guest House

Certificate of Excellence
2.0 of 5
Hotel website
414 Simonton Street, Key West, FL 33040
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348 Reviews from our TripAdvisor Community

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Chicago, Illinois
1 review
5 of 5 stars Reviewed January 9, 2016

We have been traveling to Key West for many years and have found the Pilot House to be our favorite place to stay. Co-managers Virginia and Daniel do everything to make sure you are completely satisfied during you visit! The rooms, pool, and hot tub are always very clean. The remodeled guest house is very charming and comfortable. Both Virginia... More 

Helpful?
Thank Keith H
lynnkephart, Manager at Pilot House Guest House, responded to this review

Thanks for staying with us on your recent visit to Key West. After more than 20 Years the Pilot House is Finally closing its doors. Lots of great memories for all of us. Our guests have been the best in the world and Daniel and I want to extend a huge thank you for making our jobs so much fun.... More 

Fort Lauderdale, Florida
Level Contributor
14 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 13 helpful votes
4 of 5 stars Reviewed December 28, 2015

I have stayed here many, many times over the past 10+ year. Always ground floor cabana room. Love that you can walk right out your door to the clothing optional pool and Jacuzzi. Virginia has been the Inn keeper for at least as long as I have been going there. She was kind enough to wait for us on Christmas... More 

Helpful?
1 Thank kathi c
lynnkephart, Manager at Pilot House Guest House, responded to this review

Thank you for your review of your visit and the Pilot House Guest house. So sorry to hear your stay was disrupted by the guests in the room above you. Christmas is a busy time and the whole Island was full of celebrating maybe the people above just didn't realize how sound carries. Thank you for your understanding we appreciate... More 

Cincinnati, Ohio
Level Contributor
8 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed November 23, 2015

This was our first visit to the Pilot House. We stayed in the main house in a standard queen room. The room was old but very clean and neat. It was exactly what we expected from the age of the house. Virginia and Daniel were very nice and helpful. The rest of the staff was extremely accommodating on when they... More 

Helpful?
Thank Mark S
lynnkephart, Manager at Pilot House Guest House, responded to this review

Mark, Happy thanksgiving! Glad you had a good time with us during your recent visit to Key West. Looks like we will hold the door for another month now and stay open till the first of February. We really appreciate your generous review and while so many of you have expressed your disappointment at the coming closure remember we will... More 

Level Contributor
16 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed November 17, 2015

I enjoyed my stay here. The hotel room was clean, cold, and had a lot of amenities I wanted! We stayed in the pool cabana. The pool was on the smaller size and if you want to tan, you have to do it early because it's not in a very sunny spot. I didn't like that the house next door... More 

Helpful?
Thank iLoveFood352
lynnkephart, Manager at Pilot House Guest House, responded to this review

Key West is a beautiful historic town. In our neighborhood the streets a lined with cypress trees and Victorian homes. The Pilot House itself is one of the houses on the National Registry of Historic Homes. Our neighbor's houses are similar, mostly 2 story Victorians so yes we have privacy to a point.... for the pool. Glad you enjoyed your... More 

Boynton Beach
2 reviews
5 of 5 stars Reviewed November 13, 2015 via mobile

We have been traveling to KW for many years. Married at ft Zachary 15 yrs ago. Our favorite place to stay is the Pilot House guest house. Over the years, if we can't get in there, we have tried many other B&B's on the island. While all were nice, they didn't compare to the Pilot House hospitality. Virginia and Daniel... More 

Helpful?
Thank Ruth A
lynnkephart, Manager at Pilot House Guest House, responded to this review

Thank's for the review. Also for being such a loyal and fun guest. The Pilot house has been blessed with so many great visitors over the years and I say it all the time, it is the guests who have made it such a wonderful place to stay with friendly welcomes and cool vibes . And for both Daniel and... More 

Berryville, Virginia
1 review
4 of 5 stars Reviewed October 28, 2015

The views, rooms, pool & sauna were great; however, being woken up at 8:30 am, due to nearby construction (no fault to PH tho), was a real bummer when your night ends at 3:30-4:00 am. Daniel & Virginia were fabulous. Sad that we can't return here on our next trip to Key West.

Helpful?
Thank DaisyM219
lynnkephart, Manager at Pilot House Guest House, responded to this review

Glad you had such a good time with us. So many great places to enjoy from beaches to bar, restaurants to local bodegas. Hang by the pool meet friends. That's what the Pilot house is about . Sorry for the construction noise next door during the day. The local theatre was getting some work done. There's an awesome renaissance in... More 

Tucson, Arizona
Level Contributor
16 reviews
common_n_hotel_reviews_1bd8 5 helpful votes
5 of 5 stars Reviewed October 21, 2015

This was our fourth stay at the Pilot House, which my wife and I have come to equate with Key West. The location is exceptional, close to Duval but far enough to avoid the noise, and within walking distance to a grocery store and most of the great restaurants, bars, and the Seaport. The Cabana rooms are roomy and comfortable,... More 

Helpful?
1 Thank regradyjr
lynnkephart, Manager at Pilot House Guest House, responded to this review

Good to hear you enjoyed your stay. We had a great group this past weekend. Quit the social center at the pool. Your private slice of paradise was the attic. I love the views from up there. Key west Building codes means your able to see over the tops of the trees all around the island. Including the Old Customs... More 

Bath, United Kingdom
Level Contributor
44 reviews
17 hotel reviews
common_n_hotel_reviews_1bd8 19 helpful votes
5 of 5 stars Reviewed September 15, 2015

Lovely place with laid back atmosphere. My room by the Jacuzzi had wi-fi but it was near the router, but around the pool area is well covered by wi-fi. Well furnished and very comfortable but no real cooking facilities and no on-site restaurant. Microwave, fridge and coffee facilities in room. Local shop (2 minutes) supplies all needs but as loads... More 

Helpful?
1 Thank Macchu123
lynnkephart, Manager at Pilot House Guest House, responded to this review

Hi, thanks for the review you covered the most important parts of a visit to Key West and the advantages of the Pilot house.as a place to stay while here. We are 1/2 block off Duval so you are able to easily enjoy the night life weather you are a "foodie" out to discover a brilliant new restaurant or looking... More 

Dillon Beach, California
Level Contributor
36 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 8 helpful votes
5 of 5 stars Reviewed August 23, 2015 via mobile

This place was off the hook fell in love with it very very nice large rooms I just can't put the right words to do this place the actual justice it deserves. Romantic would be a good one. Two pools main one and private one which we had access to it was very cozy and just made you feel like... More 

Helpful?
1 Thank Erin V
lynnkephart, Manager at Pilot House Guest House, responded to this review

Erin, thanks for the glowing review. Thrilled you had a good time with us. The only thing I want to address here is the "2 pools" The secluded Jacuzzi is sometimes confused as a pool its spacious and definitely relaxing a great private spot but big enough for socializing and that's one of the awesome things about the Pilot house... More 

Louisville, Kentucky
Level Contributor
12 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 10 helpful votes
3 of 5 stars Reviewed August 17, 2015

First of all i want to say this was our 5th time to Key West staying at a C/O place. First time here. Daniel was very friendly and made us feel at home. The house keeper did a great job with our room and made it very nice. Then Virginia shows up and makes you feel very uncomfortable.She seems to... More 

Helpful?
3 Thank Vacation2501
lynnkephart, Manager at Pilot House Guest House, responded to this review

Thank you for taking the time to review the Pilot house. Key West is a great place to relax and the Pilot house strives to provide an atmosphere of welcome relaxation fun and respect with our guests and our neighbors. We are not, and never have been a Clothing Optional Resort. We offer a pool and jaccuzzi and the lawn... More 

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