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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 #23 of 94 Key West B&B and Inns
Certificate of Excellence 2014
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305 reviews from our community

Traveler rating
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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 (103)
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Miami, Florida, United States
1 review
5 of 5 stars Reviewed 3 days ago NEW

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 4 days ago NEW

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 1 week ago

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 3 weeks ago 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 3 weeks ago

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 4 weeks ago

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 4 weeks ago

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 

Fort Lauderdale, Florida
Reviewer
3 reviews 3 reviews
3 hotel reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed 4 weeks ago via mobile

The Pilot House continues to be our go to place in KW. Located one block from Duval. The Pilot House is a quiet boutique hotel that provides a great quiet location but close to all the action on Duval. The poolside cabana rooms are very large with king bed, kitchen area, large bathroom, whirlpool tub, and huge shower. The rooms... More 

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

Happy Holidays. Thanks for making us your go to place in Key West. Location Location Location not only true for real estate but on holiday as well. Proximity to all the fun is a high priority . The Pilot House is 1/2 block off Duval Street, a walk or ride to Ft Taylor beach. As you mentioned Bikes available to... More 

Reviewer
3 reviews 3 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 4 weeks ago

Visited Key West the weekend before Christmas to see the Christmas light displays on the homes. We chose to stay at the Pilot House because it is centrally located in old town and it was easy to get to new town. This was the third time we stayed at the Pilot House this year and have enjoyed every moment of... More 

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

Isn't Christmas fabulous. Here in Key West we love an excuse to put some sparkle on and all the homes and businesses get in the act. The Pilot House is no exception. For visitors taking a Conch train tour around is a fun way to see all over the island and the Christmas evening tours are very popular with the... More 

ohio
Contributor
12 reviews 12 reviews
5 hotel reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed 5 weeks ago

We stayed at Pilot House in October. It was a very laid back, and relaxing vibe. Our room in the Cabana suites was right next to the pool. Every morning I could drink my coffee, and read while sitting at our little table right outside our room poolside. We were also close enough to everything we needed. A short walk... More 

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

Thanks for the review. Glad you enjoyed your stay. Happy the Pilot house was able to make your visit to Key West so enjoyable. Sounds like you were able to take full advantage of the modest amenities we have here. The tables out side your room serve many purposes and morning coffee is just a start. We also see friends... 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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