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Pilot House Guest House

Certificate of Excellence
414 Simonton Street, Key West, FL 33040
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340 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
    (340)
  • Mar-May only
    (98)
  • Jun-Aug only
    (108)
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    (68)
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    (66)
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Dillon Beach, California
Level Contributor
16 reviews
9 hotel reviews
common_n_hotel_reviews_1bd8 8 helpful votes
5 of 5 stars Reviewed 1 week ago

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 

Was this review helpful? Yes
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 7 helpful votes
3 of 5 stars Reviewed 2 weeks ago

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 

Was this review helpful? Yes 3
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 

Davenport, Florida
Level Contributor
14 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
5 of 5 stars Reviewed 3 weeks ago

This was my second stay here at the Pilot House and I must say that it was again a great place to stay. The location of this resort with it being so close to everything is perfect. Virgina and Daniel were extremely helpful both times I was there. I did spend a lot less time there at the resort socializing... More 

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

Glad to hear you enjoyed you second visit with us as much as your first. The Pilot house is an adults only guest house for relaxation and fun. So close to everything its easy to get the most out of even the shortest visit. Duval Street is 1/2 block from us Fausto's grocery is around the corner. There's bikes for... More 

Orlando, Florida
Level Contributor
55 reviews
38 hotel reviews
common_n_hotel_reviews_1bd8 164 helpful votes
5 of 5 stars Reviewed July 26, 2015

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 3
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
43 reviews
11 hotel reviews
common_n_hotel_reviews_1bd8 14 helpful votes
5 of 5 stars Reviewed July 19, 2015

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
5 reviews
5 of 5 stars Reviewed July 14, 2015

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 July 13, 2015

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 July 10, 2015

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
89 reviews
18 hotel reviews
common_n_hotel_reviews_1bd8 39 helpful votes
4 of 5 stars Reviewed July 7, 2015

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 

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Amenities