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 94 Key West B&Bs / inns

Pilot House Guest House

Save
You added Pilot House Guest House to your Saves list
2.0 of 5 Bed and Breakfast   |   414 Simonton Street, Key West, FL 33040
Hotel amenities
Pilot House Guest House
Ranked #21 of 94 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

298 reviews from our community

Traveler rating
    226
    47
    8
    6
    11
See reviews for
2
230
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 (100)
Date | Rating
  • English first
  • French first
  • Any
English first
  • All months
    (298)
  • Mar-May only
    (85)
  • Jun-Aug only
    (92)
  • Sep-Nov only
    (68)
  • Dec-Feb only
    (53)
All months
There are newer reviews for Pilot House Guest House
See the most recent reviews
West Palm Beach, Florida
Senior Contributor
22 reviews 22 reviews
3 hotel reviews
19 helpful votes 19 helpful votes
5 of 5 stars Reviewed October 8, 2012

This was our first time to Key West and first time to the Pilot House. We stayed at the end of Sept. Great place to stay, very well kept. Price is very reasonable compared to others in neighborhood. Parking is 20 dollars a day. We never moved the car...within walking distance of everything. We stayed in the house, on the... More 

Was this review helpful? Yes
Chicago, Illinois
2 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed October 4, 2012

My wife and I have visited Key West every year for the past 10 or so. By far, our favorite hotel to stay at is the Pilot House. Virginia and Daniel are great hosts and the location is perfect. Rooms: Our favorite are the cabana rooms (the top floor room in the mansion is also great). The cabana rooms are... More 

Was this review helpful? Yes
Miami Beach, Florida
Reviewer
5 reviews 5 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed October 1, 2012

We have been staying at the Pilot House for the past 15 years, coming from Miami for 5-6 long weekends a year!! The pool area is a tropical paradise , where guests can mingle, drink, relax and have a lot of fun. Prime location, walk to everything. The people are great and we have made several long term friendships over... More 

Was this review helpful? Yes
Gettysburg, Pennsylvania
Contributor
13 reviews 13 reviews
5 hotel reviews
10 helpful votes 10 helpful votes
4 of 5 stars Reviewed September 30, 2012

We spent a week at the Pilot house, our beds were comfortable, rooms were cleaned and freshened daily, and we thoroughly enjoyed our balcony and the property. The location is PRIME! It is so close to all the activities near Duval street, and Mallory Square,etc. But So nice and quiet where it is located. There is a little grocery store... More 

Was this review helpful? Yes
Santa Fe, New Mexico
Senior Reviewer
6 reviews 6 reviews
5 hotel reviews
1 helpful vote 1 helpful vote
4 of 5 stars Reviewed September 15, 2012

This was our second visit to Key West and the Pilot House, the first being in 2008 and just like the last time, we were not dissapointed. We arrived just after 'Isaac' had passed through the keys and the combination of being out of season and tourists having fled, we were the only guests the first night of our stay.... More 

Was this review helpful? Yes
Whitestone, New York
Senior Reviewer
7 reviews 7 reviews
5 of 5 stars Reviewed September 10, 2012

Just returned from another great time at the pilot house .it keeps getting better there ,we got there extremeley late and our key was exactley where it was suppose to be . the people we met at the pool were so much fun we all drank talked and laughed . the staff there can do enough for u they are... More 

Was this review helpful? Yes
Knoxville, Tennessee
1 review
5 of 5 stars Reviewed September 9, 2012

Pilot House has a very friendly staff and provides travelers with a clean comfortable stay. This hotel is located one block from Duval Street and even has a grocery store with a deli just behind it. The friendly staff and location are just a couple of reasons why we will be staying at the Pilot House again on our next... More 

Was this review helpful? Yes
Jacksonville, Florida USA
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed September 8, 2012

My wife and I have stayed at the Pilot House several times over the years, and have just reserved again for our anniversary. What first attracted us was the fact that it's an adults only establishment (due to the clothing optional pool and spa). What keeps us coming back is how well everything is kept up, and how friendly and... More 

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

Great seeing you this last weekend always good to have familiar and friendly faces here at the pilot house we look forward to your next visit More 

Horsham, Pennsylvania
Reviewer
5 reviews 5 reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed August 28, 2012

This was our first time at the pilot house and my wife and I really enjoyed our stay here. We stayed in the attic suite and we both loved it. We enjoyed the privacy and the view of the city. It was great at night to sit out in the hot tub and look at the stars. We also enjoyed... More 

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

Well I'm glad the Attic Suite worked out so well for you. 3 Flights of Stairs can be daunting for some but those who book the attic all love that view of the stars and the private hot tub. This is what makes it the most popular room in the house. Secluded romantic and a spectacular view over the tops... More 

dallastown
Contributor
15 reviews 15 reviews
3 hotel reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed August 21, 2012

just returned from 7th? stay at the Pilot House, is truly home away from home. we have rebooked for our 8th? (i lose track) stay for 2013 lobsterfest. already set the countdown for then. we always stay in the same room in the house, is so beautiful and peaceful on the balcony. Daniel, Virginia and Giovannia take such exceptional care... More 

Was this review helpful? Yes
Questions? Get answers from hotel staff and past guests. Ask a question
Owners: What's your side of the story?
Register now for free — and start getting automatic notification of new reviews, responding to traveler feedback, adding new photos to your listing and much more.
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)
  • Clothing optional pool(4)
  • Very nice(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

208 photos of this hotel

Traveler photos: See what travelers like you saw

Viewed
0:48
All traveler photos (135)
Viewed
0:48
Videos (2)
Viewed
Hotel & grounds (44)
Viewed
Pool/beach area (12)
Viewed
Room/suite (48)
Viewed
View from room (3)
Viewed
Bathroom (3)
Viewed
Dining (1)
Viewed
Other (22)

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)
Hotels you might also like...
Check In Check Out
Price Your Stay