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Pilot House Guest House

Certificate of Excellence
414 Simonton Street, Key West, FL 33040
Pilot House Guest House
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323 reviews from our community

Traveler rating
    248
    48
    9
    7
    11
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4
248
10
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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Boynton Beach, Florida
1 review
5 of 5 stars Reviewed 2 days ago NEW

Just booked our next trip to Key West staying at The Pilot House - which is by far the best place to stay on the island. Been staying there for almost 8 years and is they only place we stay when we go. Location is fantastic, rooms are clean and comfortable, staff is extremely friendly. We can't wait to get... More 

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

Hi Christy, Great to see you coming back for your vacation with us, look forward to seeing you. November is an exciting time with the Parrotheads visiting and then the Powerboat Races so easy to join in when your close to Duval Street as we are here at the Pilot House. Thanks for taking the time to review us we... More 

Big Pine Key, Florida
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago

We were fortunate to have had the opportunity to stay at this delightful guest house to celebrate our 16th year anniversary. The tranquil setting, beautifully appointed room and attentive personnel went above and beyond what we had anticipated. Enjoying morning coffee on our porch, tucked beneath this mammoth Gumbo Limbo tree, overlooking a tropical oasis while listening to the birds... More 

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

Well congratulations on the anniversary. Very Cool Glad you were able to grab some time to treat yourselves with a night in Key West Happy to have a local with all the places to stay, choose to stay with us. Thank you Happy Anniversary Sincerely Virginia Manager Pilot house More 

St. Louis
Reviewer
5 reviews 5 reviews
3 hotel reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed 5 weeks ago

Many trips to Key West, but first time staying at the Pilot House - we'll be back! Location can't be beat, right around the corner from Duvall and Faust's grocery. Our cabana room (#11) was nice and clean and opened right up to the CO pool. Bed was very comfortable. Very friendly guests mostly our age so there was a... More 

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

You always have fun in Key West and you always have fun at the Pilot house. Being 1/2 block off Duval makes it so easy to enjoy everything. Great Restaurants, Clubs, Bars a little Shopping The Beach: Fort Zachary is beautiful and close. A great group of guests to meet at the pool and beautiful rooms to stay in. We're... More 

2 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed April 16, 2015

Pilot house has it all Great location Nice rooms Very clean We really enjoyed our visit and the guests there were terrific! We spent lots of time chatting around the pool There is a cute grocery store backers and wine shop right around the corner We rented bikes and rode to dinner most nights Would go back in a heartbeat!

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

Great location, Beautiful rooms and Awesome guests. what's not to love? The Pilot house is at the center of everything!! Thank you for the review I also want to say thank you from the other guests they thought you were great too.! We are family here and are thrilled you enjoyed your stay Look forward to seeing you again in... More 

Annapolis, Maryland
Senior Reviewer
8 reviews 8 reviews
4 hotel reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed April 11, 2015

Pilot House is lovely- rooms clean and airy, pool great and guests very friendly. The location cannot be beat. We rented bikes through the Pilot House and tooled around the island, even went to dinner on them! Grocery , bakery and Duval street right around the corner. Highly recommend this spot! Will definitely stay again

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

That's what I'm talkin' about. Get out on a couple of bikes, find your own hidden spot in Key West, explore. Ride to Roostica for Pizza on stock Island or visit the Rusty Anchor a conch favorite. But stay with us At The Pilot House close to Duval for an easy stroll to dinner Sunset the Bars and Clubs nothing... More 

Fort Lauderdale, Florida
Reviewer
4 reviews 4 reviews
4 hotel reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed April 6, 2015 via mobile

What more can you say about this hidden gem in Key West. We have stayed here many times and they never disappoint. It seems like every time we stay we make new friends. Our group has now grown to 5 couples and we all enjoy an annual reunion at the Pilot House. Daniel and Virginia are always great with dinner... More 

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

Great to hear about your experience with us at the Pilot House. When you find something that works for you, you stick with it. And meeting and making friends has become a theme here with us. The friendly atmosphere is made by guests such as yourselves. Our location makes it easy to get out and enjoy all of Duval and... More 

New York
2 reviews
5 of 5 stars Reviewed April 3, 2015

Have been going to Key West pretty much twice a year for 10 years and love staying here. Virginia and Daniel are very courteous and helpful with and towards the guest. On our last visit, our arrival was a little later then expected, we called Daniel to let him know, and he offered to make us a dinner reservation at... More 

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

Thank you for the review . We are very glad you enjoy staying with us at The Pilot house. Yes we are an adults only guest house. Close to Duval with all its great restaurants and Bars. Perfect for fun and relaxing Happy to help you find things to do, new places to dine, snorkeling trips or just a great... More 

Mesa, Arizona
Contributor
11 reviews 11 reviews
8 hotel reviews
16 helpful votes 16 helpful votes
5 of 5 stars Reviewed March 31, 2015

We have traveled to Key West many times, but this was our first stay at Pilot House and we loved it! The location can not be beat! It is just steps off of Duval at the perfect location & steps away from the grocery store. The hosts Daniel & Virginia were great and made the stay even better. They helped... More 

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

It's all about the company you keep and your great company. Thank you for the review and your description of your stay with us. It will help others get a feel for what we have to offer. Great mix of guests that week. and you certainly made everyone feel welcome at the pool.! A vacation should be for fun and... More 

1 review
5 of 5 stars Reviewed March 11, 2015

This was our first time visiting Key West and doing the clothing optional style vacation, staying at the Pilot house made this experience a very enjoyable one. The staff was excellent and welcoming; the resort is kept spotless and the location is perfect you can walk to every destination. This will be our place to go for my wife and... More 

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

Glad to hear you enjoyed what the Pilot House has to offer. Comfort and Convenience pretty much sum us up. A simple place, we offer a relaxed and intimate atmosphere for adult couples to relax. A secluded Pool and Jacuzzi A variety of rooms kept spotlessly clean all a short walk form Duval and best of all we have a... More 

2 reviews
5 of 5 stars Reviewed March 7, 2015

From the moment we booked this vacation till the moment we left was a great experience. Virginia made great suggestions on amenities, restaurants and any other random questions we had. Our room was quaint and in a very romantic setting. All the Key West "must do's" were within walking distance. We just left today and are already planning our next... More 

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

Thanks for the great review we are thrilled your visit to Key West was such a success. The Pilot house prides itself on its hospitality. We offer a unique vacation experience for adults only. Our focus is on maintaining a relaxing and friendly environment and we are always happy to share our favorite tips on dining and day trips. Of... More 

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