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All 93 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 #22 of 93 Key West B&B and Inns
Certificate of Excellence 2014
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308 reviews from our community

Traveler rating
    234
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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 (104)
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Bonita Springs, Florida
1 review
5 of 5 stars Reviewed 5 days ago NEW

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
Lafayette, Indiana
1 review
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed 3 weeks ago

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 4 weeks ago

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 

Charlotte, North Carolina
Senior Contributor
23 reviews 23 reviews
8 hotel reviews
21 helpful votes 21 helpful votes
4 of 5 stars Reviewed January 21, 2015

We decided to book a stay at the Pilot House for our recent trip to Key West. We stayed in the historic mansion in a queen bedroom. We were pleasantly surprised at how large our room was. Additionally, the step down shower was a nice treat. We have stayed in many guesthouses in Key West and are accustomed to small... More 

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

Glad you enjoyed your stay. Choosing a Guest house is a unique way to get the feel of a place and Key West has some wonderful B&B's We appreciate you decided to stay with us. Everything is a matter of Taste and the Pilot house has 2 distinct styles, the classic Victorian and the more modern Cabana building. Our regulars... More 

Seminole, Florida, United States
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed January 15, 2015

We have been staying at Pilot House for a few years now. We go three or four times a year. The stay is always enjoyable and the place is centrally located to Duval St. where everything is happening. Daniel and Virginia are always pleasant and willing to help you out whenever they can. They are like family to us. Virginia... More 

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

Rich, good to see you guys again this past New Year. What a great time it was. Stepping out to Duval street which was 1 long street party was awesome. I ended up in the crowd at Bourbon Street Bar watching Sushi being lowered in the ruby Hi Heal Shoe. Sloppy Joes had a great crowd too when I passed... More 

1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed January 3, 2015 via mobile

Hospitality is great! We just made reservations for this, our second year. We even have the same the same room as last year! We are looking forward to making this a yearly destination. The rooms are clean, service is great, and we love the pool and spa!!!

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

Thanks for taking the time to post a review of your experience with us here at The Pilot House . Happy to hear your returning for your next vacation. Our regular guests who have made the Pilot house their home away from home bring with them a special vibe that extends to first time visitors and we are grateful to... More 

1 review
1 helpful vote 1 helpful vote
2 of 5 stars Reviewed January 2, 2015

I should have known something was wrong when I only needed 2 nights, but they had a 4 night minimum. Suppose to have a poolside room, but got the room beside the hot tub which was the worst! Controls for hot tub clicked all night, could hear everything being said in hot tub. No wifi password provided. AC was warm.... More 

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

December Is not only a great time to visit but the dates of your stay (Christmas thru New Years) are second only to Fantasy Fest in popularity. There is actually a 5 night minimum and all rooms are booked up by the end of July, 5 months in advance. Looking up the details of your booking, I must note, that... More 

Fulton. Missouri
Contributor
15 reviews 15 reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed December 27, 2014

If you aren't into nudity, stay away from the pool. We loved the location of Pilot House and the atmosphere. We will definitely stay there again. Everyone was so friendly and we were within walking distance of all the hot spots in Key West.

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

Thank you for your review of the Pilot House. Again being so close to Duval street is a big advantage. The pool is a great place to unwind and guests discover the atmosphere here to be a pleasant intro, so to speak, to an all over tan. Others return because it is so comfortable weather you decide to wear a... More 

Dillon Beach, California
Senior Reviewer
6 reviews 6 reviews
3 hotel reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed December 27, 2014

What a wonderful place to stay the rooms were huge with a walk in shower and very large bathtub that could fit 2 so can the shower. The best part was the clothing optional pool and private spa very sexy and the other guests were respectful. The staff went out of their way to help we are locals and will... More 

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

Erin, Thank you very much for your review. We're glad you enjoyed your vacation with us at the Pilot house. The Cabana rooms are like studio apartments and the bathrooms are huge. glad you found us to your liking and hope we'll see you soon sincerely Virginia Manager Pilot house 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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