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All 98 Key West B&Bs / inns

Pilot House Guest House

2.0 of 5 Bed and Breakfast   |   414 Simonton Street, Key West, FL 33040
Hotel amenities
Pilot House Guest House
Ranked #20 of 98 Key West B&B and Inns
Certificate of Excellence 2013
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255 people have reviewed this hotel

Traveler rating
    188
    43
    7
    5
    12
See reviews for
2
198
9
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 (86)
Date | Rating
  • English first
  • French first
  • Any
English first
Atlanta, Georgia
Reviewer
4 reviews 4 reviews
3 helpful votes 3 helpful votes
4 of 5 stars Reviewed 6 days ago NEW

We stayed April the 3rd - 7th at the Pilot House. We stayed in the pool side Cabana #13. The room was very nice and comfortable. The wife and I loved the 5X5 shower. The staff was very nice and took the time to stop and say hi to us when we were out at the pool. This was our... More

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

Glad your Key West visit was a success and that you found the Pilot house to your liking. The Cabana rooms are huge and very popular with king beds kitchenettes and Jacuzzi bath tubs. Key West is a place to have fun and enjoy yourself and the Pilot House is ideally located to take advantage of all the amazing activities... More

Greene, Iowa
1 review
5 of 5 stars Reviewed 1 week ago NEW

Kermit's key lime pie is the best of Key West - a perfect combo of sweet and tart, not too fancy but very pleasing. The Pilot House Guest House is best of Key West in its own way - nothing too fancy but clean and comfortable, a nice blend of relaxation and a little decadent fun. The clothing optional pool... More

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

The people you meet while here are friends waiting to happen. The Pilot House Clientele behave in a way respectful to all. As a small property this means a little give and take. We are grateful to our guests for creating a welcoming and fun atmosphere while maintaining the boundaries established that allow the MOST people to enjoy our slice... More

Rochester, New York
Senior Reviewer
9 reviews 9 reviews
4 hotel reviews
10 helpful votes 10 helpful votes
5 of 5 stars Reviewed 1 week ago

We had the oppurtunity to stay at The Pilot House when we visited KW for a wedding. This guest house has the perfect blend of quaint and quiet, but is just steps away from the bustle of Duval st. I believe we had room #3. The accommodations were clean and tasteful, the in room fridge was a godsend as there... More

Was this review helpful? Yes 1
Saint Paul, Minnesota
Contributor
18 reviews 18 reviews
2 helpful votes 2 helpful votes
3 of 5 stars Reviewed 2 weeks ago

Loved our room and location at the Pilot House Guest House but the quirky pool and poolside rules were a little much. "Stand up, cover up" was the mantra of the property managers as apparently one neighboring property could see into the enclosed pool area. We had a poolside room that had a little table and chair set where we... More

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

Thank you for your review we appreciate all the points you made about the Guest House and what it has to offer. Proximity to Duval Street, Fausto’s grocery, Bars, Restaurants and Beaches. Quoted from the tentative and confirmation letters all guests receive: “The Pilot House is an Adults only Guest House, while we are happy to offer a clothing optional... More

Saint Augustine Beach, Florida
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago

Pilot House has true Key West character unlike corporate chain motels. It's only a block from Duval but far enough away for peace and quiet and a good night sleep. They provide bikes and it's a very short ride to the harbor front or Mallory Square and close to enough to walk if you want. Spa is great after a... More

Was this review helpful? Yes 1
Palm Harbor, Florida
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 4 weeks ago

We've stayed here 4 times now and have 2 more reservations coming up. It's a block from Duval where all the bars & restaurants are. The CO pool is great but our favorite is the covered Spa! We've met some of the most fun people there.

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

We stayed here for a week and it was hard for us to leave to sightsee. Daniel made us feel so welcome and made sure us and all the other guests were happy as he walked by. If we needed ANYTHING, Daniel was on top of it. We didn't have much interaction with Virginia, but the one time we did,... More

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

The Cabana rooms are very popular, King Beds, Jacuzzi bath tubs, kitchenettes, right by the pool. The Pilot House is ideally situated to enjoy all the Island Paradise can offer. Close to everything and still Peaceful and Private. We keep busy making sure the Guest House is at its best. You had a split stay with us meaning in the... More

Chicago
1 review
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed March 11, 2014

We were 4 girls in our 30's not looking to have the college experience of Spring Break but wanted a place with character and flair - we got both at the Pilot House! We shared Room #7 and it was this beautiful and large room in pristine condition with a sweet little balcony and a kitchen, not to mention the... More

Was this review helpful? Yes 2
Tampa, Florida
1 review
5 of 5 stars Reviewed March 11, 2014

We just returned from a 3-night stay at the Pilot House and couldn't have been happier with our accommodations. Daniel and Virginia were great in providing a tour of the property and giving suggestions for dining and entertainment. We stayed in the main house and loved the king bed and the kitchenette. We love staying close to Duval and this... More

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

Glad you enjoyed your stay at the Pilot House. Your room is one of my favorites with the balcony overlooking Simonton Street. The 4 poster king bed and the handy kitchenette for any snacks you bring back from dinning out on Duval. The Pilot house while NOT a clothing Optional property per say is happy to allow nude sunning and... More

Kennesaw, Georgia
Contributor
19 reviews 19 reviews
10 hotel reviews
19 helpful votes 19 helpful votes
4 of 5 stars Reviewed February 14, 2014

My wife and I stayed in an upstairs room in the Cabana at The Pilot House (TPH) four nights in early February. As advertised The Pilot House is a guest house, it is not a B&B. A well-meaning friend gave us some BedandBreakfast.com gift certificates, which TPH accepts. I can’t imagine somebody stumbling in and not understanding that there might... More

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

Thank you for your refreshing insightful review. From the perspective of someone who normally stays at big chain hotels your observations have captured the charm and quirkiness of the Pilot House. The pool, the jaccuzzi,.... the tanning. The descriptions of your experience are wonderful. Yes, it is rude to stare. However Our Guests are laid back and here to relax... 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
Amenities:
Free High Speed Internet ( WiFi ) Kitchenette Suites Swimming Pool Wheelchair access
Hotel Style:
Ranked #20 of 98 B&Bs / Inns in Key West
Price Range (Based on Average Rates): $$
Hotel Class:2 star — Pilot House Guest House 2*
Official Description (provided by the hotel):
Luxurious accommodations in the historic Otto Mansion and pool side Cabana rooms. Full kitchens and kitchenettes available. Pool, spa and lush gardens surround the property tucked away in downtown Key West. ... more   less 
Also Known As:
Pilot House Guest House Hotel
Pilot House Guest House Hotel Key West

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