We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
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
  • Overview
  • Reviews (276)
  • Photos (171)
  • Amenities
  • Q&A
  • Room tips (92)
  • Location
  • More
Pilot House Guest House
Ranked #21 of 98 Key West B&B and Inns
Certificate of Excellence 2014
We can't find prices for this accommodation
Our online travel partners don't provide prices for this accommodation, but we can search other options in Key West
Check In Check Out
Write a Review

276 people have reviewed this hotel

Traveler rating
    207
    45
    8
    5
    11
See reviews for
2
210
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
Traveler tips help you choose the right room.   Room tips (92)
Date | Rating
  • English first
  • French first
  • Any
English first
Ft. Lauderdale
1 review
5 of 5 stars Reviewed yesterday NEW

We enjoyed being in the heart of Key West during our two-night stay at the Pilot House. The room was ideally furnished with all the necessities (even had the hair dryer), the pool was breathtaking and sparkling clean (we enjoyed the clothing optional adult option as well!), and the onsite bicycle rental is a must! This is THE way to... More

Was this review helpful? Yes
Wayne, Pennsylvania
Senior Contributor
38 reviews 38 reviews
5 hotel reviews
19 helpful votes 19 helpful votes
5 of 5 stars Reviewed 2 days ago NEW

It was our first visit to the Pilot House Guest House and would couldn't have been more pleased. This guest house is located in the heart of all the action, just a block and a half from Duvall Street. We typically rent scooters while in Key West, but opted for the rental bikes offered by the Pilot house folks. It... More

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

Well, when you have to go you have to go. Sorry we couldn't extend your stay. Looking forward to your next visit. As you mentioned the advantages of the Pilot house are its location and atmosphere. There's a growing set of travelers who met here over the years and plan future stays together sounds like you fit right in. Relaxing... More

Reviewer
3 reviews 3 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 1 week ago NEW

I love this place. Great pool, great hot tub, great rooms, great staff. Stayed in a poolside cabana room that was clean, modern, well appointed. The other guests and I had a great time. It was like hanging out with old friends. I will be back... Soon.

Was this review helpful? Yes 1
Contributor
15 reviews 15 reviews
6 hotel reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed 1 week ago

This was our first time to pilot house. We would surely return. It was so pleasant, welcoming and friendly. The poolside rooms were great. Clean, amazing a/c and huge shower! The amenities were very nice as well. We met so many nice people. It was close to everything and even had bikes to rent on the property. We hope to... More

Was this review helpful? Yes
Odessa, Florida
Reviewer
3 reviews 3 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago

I just booked our third annual visit to the Pilot House in Key West. We were looking for a place to get away in KW two years ago and decided on The Pilot House because of the Clothing Optional Pool and the other amenities listed on the website. Our first year we stayed on the lower level of the Main... More

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

Wow, Thanks for the endorsement we will work hard to live up to your expectations. A vacation is a step out of the everyday where you reward yourself with a little R&R. Glad you found the Pilot house in Key West to relax and recharge. Our regular guests are our greatest asset and we appreciate your continued business and of... More

Canton, Ohio
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago

My husband and I have been to Key West the past four years. Each time we have stayed at Pilot House. We have stayed in Room #1 and the attic. The rooms are spotless and very well maintained. The staff is very helpful and friendly. Stay at The Pilot House, you won't be disappointed.

Was this review helpful? Yes 1
1 review
5 of 5 stars Reviewed 3 weeks ago

We enjoyed a fabulous stay and cannot wait to get back to the Pilot House again. Quiet friendly adult atmosphere just off Duval close to all that Key West has to offer. Have a question regarding dining, entertainment or excursions the Pilot House staff can point you in the right direction.

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

Any time I travel I want to stay where I can get to all the things I'm interested In. We are lucky at the Pilot House to be in the middle of all the action . We love to share the locals perspective on fun things to do. The Guests who stay with us are often another great source of... More

Senior Reviewer
7 reviews 7 reviews
4 hotel reviews
9 helpful votes 9 helpful votes
4 of 5 stars Reviewed 3 weeks ago

We had a lovely pool-side room, which you might want to avoid if you want a quiet night. Loved floating around in the pool with palm trees overhead. The hot tub is nice. This hotel is very conveniently located, a short walk away from Duval St. Our room was pretty and immaculate and included a small kitchen.

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

Thank you for your review. Glad you were able to find the Pilot House the perfect place to relax. Our Guests are a warm and friendly crowd who enjoy relaxing poolside. The Cabana rooms are popular right by the pool. Sounds like someone was a bit noisy poolside during your stay but you didn't let it spoil your time with... More

Senior Reviewer
9 reviews 9 reviews
9 helpful votes 9 helpful votes
5 of 5 stars Reviewed 3 weeks ago

My wife and I have stayed here before and love it. When the kids went away for three weeks we took a vacation. Room number 1 is always our choice. There is something about waking up and having one's morning coffee on the front porch. The staff is fantastic and the property is still very well maintained. In addition, after... More

Was this review helpful? Yes 2
Huntsville, Alabama
Top Contributor
99 reviews 99 reviews
25 hotel reviews
41 helpful votes 41 helpful votes
4 of 5 stars Reviewed 4 weeks ago

Pilot House has one of the very best locations to enjoy all that Duval Street and Old Town Key West has to offer. We chose the Cabana rather than the main house as we prefer the feel of staying in an historic Inn rather that in a B&B. The rooms were comfortable and while not having a full kitchen, they... More

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

Thank you for your review of the Pilot House . We' re glad you enjoyed your stay and appreciate the points you made describing your experience with us. You are so right about the location being 1/2 block from Duval makes it easy to enjoy everything either its dinning, night life, or shopping, you can walk everywhere. The Pilot house... More

Owners: What's your side of the story?
If you own or manage Pilot House Guest House, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.
Manage your listing

Been to Pilot House Guest House? Share your experiences!

Write a Review Add Photos & Videos

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

171 photos of this hotel

Traveler photos: See what travelers like you saw

Viewed
All traveler photos (98)
Viewed
Room/suite (25)
Viewed
Hotel & grounds (30)
Viewed
View from room (2)
Viewed
Bathroom (3)
Viewed
Pool/beach area (6)
Viewed
Dining (1)
Viewed
Other (31)

Management photos: Courtesy of the property manager

Viewed
All management photos (74)
Viewed
Hotel & grounds (10)
Viewed
View from room (7)
Viewed
Family/play areas (2)
Viewed
Pool/beach area (8)
Viewed
Room/suite (14)
Viewed
Bathroom (2)
Viewed
Other (31)

Amenities

Free High Speed Internet ( WiFi ) Kitchenette Suites Swimming Pool Wheelchair access
Hotel Class
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 
Number of rooms
14

Questions & Answers

Enter your question for this accommodation's staff to answer. Other travelers may answer as well.
    Posting guidelines

    See which rooms travelers prefer

    Bookmark for later
    Save Saved
    You added Pilot House Guest House to your Saves list