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Pilot House Guest House

Certificate of Excellence
414 Simonton Street, Key West, FL 33040
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Pilot House Guest House
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337 Reviews from our TripAdvisor Community

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Traveler rating
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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 (116)
Date | Rating
  • English first
  • French first
  • Italian first
  • Any
English first
  • All months
    (337)
  • Mar-May only
    (98)
  • Jun-Aug only
    (105)
  • Sep-Nov only
    (68)
  • Dec-Feb only
    (66)
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Orlando, Florida
Level Contributor
56 reviews
39 hotel reviews
common_n_hotel_reviews_1bd8 166 helpful votes
5 of 5 stars Reviewed 1 week ago

We had been repeat offenders at Marrero's in the past but chose Pilot House for this year's vacation. What a great choice. Virginia and Daniel are gracious hosts and we found the location to be ideal for the things we like to do on Duval Street. The pool and spa were great. We found the other guests to be a... More 

Was this review helpful? Yes 1
lynnkephart, Manager at Pilot House Guest House, responded to this review

Over the last 20 years Key West has grown from a funky little town to a super vacation destination Home grown guest houses with shared bathrooms down the hall to Beautiful restored Historic homes where all the rooms have private bathrooms and the amenities of a hotel. The Pilot House offers a romantic get away with the best of both... More 

Central Kentucky
Level Contributor
42 reviews
10 hotel reviews
common_n_hotel_reviews_1bd8 19 helpful votes
5 of 5 stars Reviewed 2 weeks ago

We just got home from a vacation to Key West, staying at the Pilot House. We had plans to stay at Marrero's, but once they changed their clothing optional pool policy, we were fortunate enough to get a room here. Sadly, The Pilot House is changing their policy too in the next few months. I cannot imagine how this can... More 

Was this review helpful? Yes 2
lynnkephart, Manager at Pilot House Guest House, responded to this review

HOT HOT HOT. That's the weather right now. The Pilot house Pool is definitely the place to be. Stay cool relax meet friendly people find out about secret places to dine or romantic trips for sunset. . Mostly just relax. Good to hear you enjoyed your stay As an adults venue close to Duval its easy to get the most... More 

ORWIGSBURG
Level Contributor
3 reviews
5 of 5 stars Reviewed 3 weeks ago

This place was fantastic from the word go. The staff and the guest house were great. The room was clean and the pool and spa were delightful! The location of the Pilot House is also a major plus .. very close to everything!

Was this review helpful? Yes
lynnkephart, Manager at Pilot House Guest House, responded to this review

Ok "Simply Fantastic" thank you. That's an endorsement! There's lots to choose from when you visit Key West and We are glad you chose to stay with us. Even better to hear you enjoyed your stay. So thank you for your succinct review of the Pilot house Look forward to seeing you again soon Virginia Manager Pilot House More 

Atlanta, Georgia
Level Contributor
5 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
4 of 5 stars Reviewed 3 weeks ago

Very nice hotel great location. I usually wouldn't stay in the same place twice but this location is very conveniently located and great staff. we stayed here 3 nights and 4 days. The rooms and shower are really big.

Was this review helpful? Yes 1
lynnkephart, Manager at Pilot House Guest House, responded to this review

Hi Thanks for the review . Glad you enjoyed the visit. We really are conveniently located Having Faustos grocery store on the corner is a bonus and all the Restaurants and Bars on Duval 1/2 block away makes it so easy to get out to everything. Sounds like you had a Cabana room they are great I do have to... More 

1 review
5 of 5 stars Reviewed 3 weeks ago

Five stars and good news! We are Pilot House regulars. The location, the front veranda on room #1, and most of all Virginia, Daniel and the staff, have made our twice yearly visits to Key West for the past 10 years the best!! We were fortunate to book some time in November, before the scheduled closing for renovations. NEWS FLASH... More 

Was this review helpful? Yes
lynnkephart, Manager at Pilot House Guest House, responded to this review

Hey Guys thanks for the review, yup were still rockin'. If you haven't been to Key West or if you want to try a new place you've still got time. the Pilot house is always a great place to be when you visit Paradise. Close to everything great group of Guests it's really a no brainer. Room 1 has that... More 

Wayne, Pennsylvania
Level Contributor
82 reviews
15 hotel reviews
common_n_hotel_reviews_1bd8 42 helpful votes
4 of 5 stars Reviewed 4 weeks ago

The Pilot House is our favorite getaway in the Keys. We were very sad to hear that the Pilot House as we know it will be closing in November. From what we understand they will be closing and undergoing renovations with new corporate ownership. We were happy to have visited one last time prior to the changes. As usual, Virginia... More 

Was this review helpful? Yes 3
lynnkephart, Manager at Pilot House Guest House, responded to this review

With over 20 years in the Hospitality Industry here in Key West the Pilot house has grown with the island and been a destination for vacationers throughout that time. We love that our guests come as visitors and leave as family and we appreciate all the support we have had over the years. It is true we are changing hands.... More 

Miami, Florida
1 review
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed June 27, 2015

Very nice, completely comfortable and other visitors friendly and nice. I write to ask whether presently, almost July 2015, the construction on site and next door are completed ? Did not really travel Aug 2014. It was several years ago, but pulldown menu gave no choices pre 2014

Was this review helpful? Yes 2
lynnkephart, Manager at Pilot House Guest House, responded to this review

We are thrilled to report The Historic home next to the Pilot house has been restored to its original grandeur and has made our block of Simonton even more beautiful. The Pilot house is not undergoing and construction at the time of this post. As far as our immediate neighbors there isn't any work going on that impacts our visitors... More 

Boston
Level Contributor
3 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 24 helpful votes
4 of 5 stars Reviewed June 19, 2015

Great location in terms of being right around the corner from the main drag. Virginia is a wonderful host, with her attitude, accent, and height adding an aura of formal dignity to the place. We love our annual trips to Key West as the perfect 3-4 day escape from the rat race to relax, walk, people watch, eat and drink.... More 

Was this review helpful? Yes 4
lynnkephart, Manager at Pilot House Guest House, responded to this review

We don't do breakfast but we have kitchenettes in all rooms in fact 3 rooms in the mansion have full kitchens and 1 poolside has a full kitchen. Key West is a friendly live and let live place and it attracts like minded people. The Pilot house prides itself on being a part of that Tradition. Attracting a friendly yet... More 

Tampa, Florida
Level Contributor
3 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed June 17, 2015

Getting ready to head back to Key West and we are looking forward to staying at the Pilot House Key West again. This is the best place to stay in Key West. The location are perfect - only a block from Duval. We love the owners, Virginia and Daniel.

Was this review helpful? Yes 1
lynnkephart, Manager at Pilot House Guest House, responded to this review

Hi guys , see you soon. Thanks for sharing your experience with us, here on Trip Advisor. The Location of the Pilot house is a huge advantage when you vacation in Key West. Reason enough to choose us. The experience with the other guests is another great part of what makes us work. A real key west vibe curtsey of... More 

Baltimore, Maryland
Level Contributor
15 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed June 14, 2015

We thoroughly enjoyed our stay in Key West. It was our first time in Key West and were very glad we picked Pilot House. They were wonderful to deal with when making the reservation, taking the time to be sure I knew the pool and spa areas were clothing optional (I knew that already, it was why I picked the... More 

Was this review helpful? Yes
lynnkephart, Manager at Pilot House Guest House, responded to this review

Good to hear your first visit to the Pilot house was fun. The pool and Spa are clothing optional however many guests who stay with us have mentioned, as you did, that the friendly atmosphere was comfortable weather you took advantage of that or not. We have a loyal following who just want to take advantage of the closeness to... More 

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Amenities