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All 94 Key West B&Bs / inns

Pilot House Guest House

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2.0 of 5 Bed and Breakfast   |   414 Simonton Street, Key West, FL 33040
Hotel amenities
Pilot House Guest House
Ranked #18 of 94 Key West B&B and Inns
Certificate of Excellence 2014
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294 reviews from our community

Traveler rating
    223
    47
    8
    5
    11
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2
226
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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
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Orlando
1 review
5 of 5 stars Reviewed yesterday NEW

We were married on the beach at Key West then had a small impromptu reception at the Pilot House where we spent the weekend. Virginia was AWESOME!, made our stay more than perfect. She and the staff went way beyond for us. The other guests were great, friendly and fun. Our room was the best! We are already looking forward... More

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1 review
5 of 5 stars Reviewed 5 days ago NEW

Stayed for four days in September and wished we had another four to stay.......had an wonderful time.......excellent hospitality in a very relaxing and welcoming environment....everything was clean and fresh....the clothing optional pool and Jacuzzi were great.....everyone we met were so friendly.......we have booked two returns......we intend to become regulars! Thank you Virginia and Daniel for a great time.

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Mount Laurel, New Jersey
2 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed 3 weeks ago

The Pilot house is my favorite hotel. Daniel and Virginia treat their guests like family. The rooms are home-like and cozy. The rooms are very clean. The clothing optional pool and Jacuzzi are beautiful.Typically, the guests are regulars and everyone is so friendly. The hotel is a block off of Duvall so you have a quieter environment to relax, but... More

Was this review helpful? Yes 2
Carleton, Michigan
1 review
5 of 5 stars Reviewed 4 weeks ago

I came to the Pilot house after I had already booked another room and was very disappointed once I got there...Virginia made my stay awesome she went above and beyond what she had to do to make sure I was happy with my room! The staff was very friendly, my room was super clean overall a great place to stay,... More

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NJ
Reviewer
3 reviews 3 reviews
3 hotel reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed 4 weeks ago via mobile

My wife and I had another excellent stay. Daniel and Virginia go out of their way to make us feel like family. It is just a block from Duval which is convenient for nightlife, yet far enough away for quiet time when desired. The clientele they have acquired here are all friendly. The Pilot House has acquired many regulars, some... More

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Bucharest
Senior Reviewer
10 reviews 10 reviews
4 hotel reviews
6 helpful votes 6 helpful votes
4 of 5 stars Reviewed September 27, 2014

Such a charming place, just a block away from the buzz of Duval! Rooms are of medium size, but nicely ornated to create a romantic atmosphere. Ant there is a coffee machine to help those like me to kick start the day - and get to the real Cuban coffee or the espresso in the cafes nearby. The place is... More

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lynnkephart, Manager at Pilot House Guest House, responded to this review

Key West is famous for it's live and let live attitude. We are lucky to be able to reflect that here at the Pilot House The Staff all enjoy meeting and taking care of our guests and we know it is these people that make the atmosphere here welcoming for everyone. With 2 distinct styles of accommodation either the Victorian... More

Brea, California, United States
1 review
1 helpful vote 1 helpful vote
4 of 5 stars Reviewed September 15, 2014

Our first trip to Key West was topped off with our stay at the Pilot House. The atmosphere was just what we were looking for, casual and comfortable. The central location to Duval Street, entertainment and shopping was very convenient. Virginia is very down to earth and made us feel welcome from the beginning of our stay. We stayed in... More

Was this review helpful? Yes 1
wallingford
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed September 13, 2014

We only discovered this gem this year and have already gotten their twice. We don't leave without booking our next vacation with Virginia and Daniel to insure we always have something to look forward to after returning to our northern climate in CT. We cannot imagine a more laid back place to stay with all the amenities we need for... More

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

Welcome to the Pilot house family glad your experience with us here in the heart of Old Town Key West was a success. We love it when we can share all the amazing things Key West has to offer. All the beautiful historic homes surrounding us on Simonton Street 1/2 block from Duval. Sunset Sails, snorkel trips to the tortugas,... More

Colorado
Contributor
11 reviews 11 reviews
3 hotel reviews
14 helpful votes 14 helpful votes
5 of 5 stars Reviewed September 4, 2014

I almost hate writing this review. This ended up being such a cool place I want to keep it to myself. This past weekend was our first stay here. In a turn of the (20th) century mansion, guest rooms have been created with tasteful decor. The Pilot House has a very laid back vibe and is totally unpretentious. If you... More

Was this review helpful? Yes 2
Christmas, Florida
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed September 3, 2014

My wife and I are long time guest of the Pilot House, and we are very delinquent in writing a review. Perhaps we didn't want to give away Key West's best kept secret. Virginia and Daniel (and now Vicki filling in) are the best Inn Keepers on the Island...and believe me we have stayed everywhere since 1994, and we know.... More

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

One of the best parts of this job is the people you meet from all over the world. And a real joy is getting to know them over the years of return visits Thanks for taking the time to review the Pilot house guest house. Your praise is appreciated and we will continue to work hard to deserve it. Look... More

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Hotel Summarization (Beta)

What travelers say

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

Additional Information about Pilot House Guest House

Address: 414 Simonton Street, Key West, FL 33040
Location: United States > Florida > Florida Keys > Key West
Price Range (Based on Average Rates): $$
Hotel Class:2 star — Pilot House Guest House 2*
Number of rooms: 14
Also Known As:
Pilot House Guest House Hotel Key West

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