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Pilot House Guest House

Certificate of Excellence
414 Simonton Street, Key West, FL 33040
Pilot House Guest House
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315 reviews from our community

Traveler rating
    240
    48
    9
    7
    11
See reviews for
4
240
10
1
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 (107)
Date | Rating
  • English first
  • French first
  • Italian first
  • Any
English first
  • All months
    (315)
  • Mar-May only
    (89)
  • Jun-Aug only
    (92)
  • Sep-Nov only
    (68)
  • Dec-Feb only
    (66)
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1 review
5 of 5 stars Reviewed 2 weeks ago

This was our first time visiting Key West and doing the clothing optional style vacation, staying at the Pilot house made this experience a very enjoyable one. The staff was excellent and welcoming; the resort is kept spotless and the location is perfect you can walk to every destination. This will be our place to go for my wife and... More 

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

Glad to hear you enjoyed what the Pilot House has to offer. Comfort and Convenience pretty much sum us up. A simple place, we offer a relaxed and intimate atmosphere for adult couples to relax. A secluded Pool and Jacuzzi A variety of rooms kept spotlessly clean all a short walk form Duval and best of all we have a... More 

2 reviews
5 of 5 stars Reviewed 3 weeks ago

From the moment we booked this vacation till the moment we left was a great experience. Virginia made great suggestions on amenities, restaurants and any other random questions we had. Our room was quaint and in a very romantic setting. All the Key West "must do's" were within walking distance. We just left today and are already planning our next... More 

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

Thanks for the great review we are thrilled your visit to Key West was such a success. The Pilot house prides itself on its hospitality. We offer a unique vacation experience for adults only. Our focus is on maintaining a relaxing and friendly environment and we are always happy to share our favorite tips on dining and day trips. Of... More 

Gainesville, Florida
1 review
5 of 5 stars Reviewed 3 weeks ago

The pilot house was by far the most accomodating, relaxed, and friendly hotel to stay in the keys. Upon arrival, daniel showed us all the accomodations and the room was super clean and spacious for two people to share. We stayed poolside and thoroughly enjoyed the Caribbean music they played during the day time. The location is a close enough... More 

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

The World is a crazy place but Key West is the best way to give yourself a break. The Pilot house IS the place to relax and Its so close to everything you want to do while your enjoying Paradise. The Cabana rooms are awesome but I suggest try the Main house as well. It is a beautiful Victorian all... More 

ogden
Contributor
14 reviews 14 reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed 4 weeks ago via mobile

this was our third time at Pilot House, last time having been in 2009. It hasn't changed !! Total peace and relaxation. The rooms are super clean, comfortable and have modern amenities. Virginia is accommodating and friendly. She has a great pride in the place and it shows. I would recommend Pilot House to anybody visiting the Keys.

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

Thank you for the recommendation I am a firm believer in Word of Mouth as a small Guest house we don't have all the bells and whistles of a large resort but I like to think it is to our advantage . A more intimate and friendly experience where you get to know other Guests and have a great social... More 

Jersey City, New Jersey
Contributor
13 reviews 13 reviews
4 hotel reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed 4 weeks ago

This is our fourth or fifth time staying at the Pilot House and we still love it. I won't repeat my reviews of the past since they still apply. But Virginia and Daniel are the perfect hosts--they keep the place running flawlessly and always do their best to accommodate their guests. I will, however, mention one thing that could make... More 

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

The Pool is the place to be. Cool off, relax, read a book meet new friends. Plan dinner and a night out this is where it all gets sorted. We are a small boutique venue with only 14 rooms. The Pilot house as you know was originally a private home and there is limited garden space. It is an intimate... More 

Chicago
Contributor
18 reviews 18 reviews
4 hotel reviews
8 helpful votes 8 helpful votes
5 of 5 stars Reviewed 4 weeks ago

The Pilot House is just a block off of Duval St. (far enough away from the noise but close to the restaurants and bars), and a half block from Fausto's (the best/only grocery store), making it one of the most convenient places in downtown. We made the mistake of getting a place on Truman Street our first time in Key... More 

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

Wow 12 years coming to the Pilot house . Thank you, glad to be your choice to stay in Key West. There are a lot of place to choose from and we are grateful you continue to stay with us. The Balcony with your room is a favorite spot for morning coffee or evening drinks and watching the world go... More 

Bonita Springs, Florida
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed February 23, 2015

My girlfriend and I have been staying at the Pilot House when in KW for over five years. The rooms are clean and well kept. The pool and hot tub are clean, inviting, and FUN! It is close to Duval Street and everything you would want to do in KW.

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

For adults only. Relax by the pool enjoy the hot tub The Pilot house is a small unique slice of Old Key West. Our Guests are mostly regulars such as your selves but always welcoming to new visitors with tips and suggestions for places to dine, snorkel trips, sunset sails, check out a show at La-Te-Da or see a band... More 

Lafayette, Indiana
1 review
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed February 6, 2015

Will be making our fourth trip to the Pilot House this summer. My wife & I wouldn't stay anywhere else! The rooms are clean, nicely furnished, and best of all the staff are very friendly & accomodating! Great pool area with jacuzzi. Also, the location is 1 block from Duval St. ..... close to bars & great restaurants. For a... More 

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

Thanks for taking the time to post a review. We are a small Boutique Guest House 1/2 a block off Duval street the main "Drag" in Key West. Central to all of the Bars and restaurants an easy walk to the beaches and don't forget we have bicycles for rent if you want to get over to Smathers Beach or... More 

Indianapolis, Indiana
1 review
5 of 5 stars Reviewed January 28, 2015

Have been coming here for many years and can't think of a better place to stay. 2-3 min walk to Fausto's for groceries and another 75 yds to Duval St. Doesn't get much better. Clean and large rooms, friendly staff, make for a great vacation. Daniel and Virginia are the wonderful and friendly managers. The best. They will go out... More 

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

Thanks for the great review glad you like staying with us and appreciate the high praise we'll continue to work hard to make the Pilot House the best it can be. And we really love helping out guests with insider tips on Key West. Our repeat clientele such as yourselves have also made the Pilot house the welcoming place it... More 

Miami, Florida, United States
1 review
5 of 5 stars Reviewed January 22, 2015

W#e have stayed at the Pilot House many times. It is very quaint and beautiful as well as peaceful. The location can't be beat as it is a block from Duval Street and three short blocks to the waterfront and numerous great restaurants, as well as tour boats. It has a spa and a heated pool kept very clean. Both... More 

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

Being in the middle of Old Town is the main reason travelers choose to try us. You also have your favorite room, your home away from home. Our guests really reflect the feel and spirit of Key West and make others welcome to the Pilot house with their own particular insights into the Island. Thanks for the review we appreciate... More 

Hotel Review Summarization

What travelers say

  • Hot tub(6)
  • Very nice(4)
  • Clothing optional pool(4)
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