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All 97 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 97 Key West B&B and Inns
Certificate of Excellence 2014
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287 reviews from our community

Traveler rating
    217
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    11
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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 (98)
Date | Rating
  • English first
  • French first
  • Any
English first
Brea, California, United States
1 review
4 of 5 stars Reviewed 5 days ago NEW

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

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wallingford
2 reviews
5 of 5 stars Reviewed 1 week ago NEW

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

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Colorado
Reviewer
3 reviews 3 reviews
5 of 5 stars Reviewed 2 weeks ago

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

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Christmas, Florida
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago

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

OLATHE KANSAS
Senior Reviewer
8 reviews 8 reviews
6 hotel reviews
22 helpful votes 22 helpful votes
5 of 5 stars Reviewed August 14, 2014

this is going to be a review and a trip report combo: for the past 5 years my wife and i had a week that we split between miami southbeach and key west kidless. this year we decided just to stay in key west for the whole week based on key west's crime rate and the pace of the place... More

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

Miami and Key West are both awesome places to vacation. They are quit different in what they offer. Key west is a more relaxed recharging kind of place, an island destination. The pilot house is perfect for what ever type of holiday you want Central to everything on Duval no need for a car. Private inviting pool to chill out... More

North Carolina
Senior Reviewer
10 reviews 10 reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed August 12, 2014 via mobile

This was our first visit to the Pilot House. Attic suite was great- loved the private deck. Enjoyed all of the amenities ! Daniel and Virginia were so helpful. All of their recommendations were excellent. We will be back!

Was this review helpful? Yes 1
Horsham, Pennsylvania
Top Contributor
75 reviews 75 reviews
15 hotel reviews
27 helpful votes 27 helpful votes
5 of 5 stars Reviewed August 11, 2014

As the title says, this was our third visit and it was another fantastic stay! Virginia and Daniel made sure our stay was great. The closeness to duval street makes it easy to pop out and visit a bar or two come back for a break and then head out again. Guests are friendly as well.

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

Third visit, fantastic! We really appreciate all the guests who have tried the Pilot House and decided to stick with us. We are a small guest house and lucky to be situated in the heart of Old Town Key West. The property has 14 rooms all with private bathrooms and kitchens or kitchenettes. Depending on the weekend and the guests,... More

Arcadia, Florida
Reviewer
3 reviews 3 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed August 10, 2014

We love staying at the pilot house. It is peaceful and relaxing. A great place to get away from children. lol You meet awesome friends and keep coming back every year for meet up. Staff is outstanding as well. Virginia is great. Rooms very clean and housekeeping keeps your rooms neat. Can't wait till next years trip

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1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed August 9, 2014

We went to the pilothouse for our honeymoon, it was great. For an older property it is well kept. we stayed in the attic suite and found it to be a great choice. its a climb, so if your not able to climb stairs, not good. the clothing optional pool was a first for me and my wife, it was... More

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

Go up the stairs till you can't go any further. It feels like being in the tree tops looking out over the Island You see the Light house and the Old Customs House roof. If a cruise ship is docked you look straight across at it resting in Mallory Square. This is your private getaway. Your own jaccuzzi and sundeck.... More

Farmington, New Hampshire
1 review
5 of 5 stars Reviewed August 9, 2014

This was our second year at Key West. 1st at The Pilot House. We stayed in the Cabana and couldn't have been happier. The room was clean, cool, and comfortable. Huge walk in shower, kitchenette with coffee pot - microwave- and sink. The staff was excellent from checking in to housekeeping. They were knowledgeable about the island and places to... More

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

Our Cabana rooms Rock!. The Huge showers, the Jacuzzi bath tubs. Having a kitchenette is a bonus but with so many great restaurants a 1/2 block away on Duval and in the surrounding neighborhood most guests just stock up on drinks. As a guest house we don't provide any food or beverage totally un necessary so close to all the... 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*
Also Known As:
Pilot House Guest House Hotel Key West

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