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.

“We could not have picked a better place to stay.....” 5 of 5 stars
Review of Pilot House Guest House

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 mm/dd/yyyy Check Out mm/dd/yyyy
Pilot House Guest House
Save Saved
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
Ranked #18 of 97 Key West B&B and Inns
Dunedin, Florida
Contributor
12 reviews 12 reviews
6 hotel reviews
Reviews in 4 cities Reviews in 4 cities
4 helpful votes 4 helpful votes
“We could not have picked a better place to stay.....”
5 of 5 stars Reviewed July 15, 2011

My wife and I come to Key West every year and this time we wanted to stay at an adult only guest house. We fell in love with the Pilot House the moment we check in and got to our room. We stayed in one of the cabana's #9 ( July 7 - 11 ) by the pool and I will tell you that will be our room of choice whenever we are back. The room was only a couple steps to the pool and lounge chairs. The charm of this place is that it is cozy and the staff and other guests are friendly, things that you just don't find at large hotels / resorts. We travel quite a bit and have stayed at many different type of places and they all have their good points depending on what you are looking for, the Pilot House though makes you feel like you are at home with friends. This was our first time at a clothing optional pool and I can tell you that it was fun and very relaxing. The secluded spa was great too. If you are looking for the Ritz Carlton you might be disappointed because this is a guest house, places like this is what Key West is famous for, but I will say that the next time we stay at a Ritz Carlton I might be a little disappointed because it will lack the charm of this gem. Thanks Virginia for a great stay, the Spanish Limes and for not having our room rented so we could extend our stay another day. M & S

Room Tip: We have only stayed in the cabana rooms and those will be our choice for future trips.
See more room tips
  • Stayed July 2011, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 2
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Write a Review

283 people have reviewed this hotel

Traveler rating
    214
    45
    8
    5
    11
See reviews for
2
217
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 (95)
Date | Rating
  • English first
  • French first
  • Any
English first
Fort Myers, Florida
2 reviews
Reviews in 2 cities Reviews in 2 cities
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed June 6, 2011

I just had a wonderful weekend at the Pilothouse, staying June 3rd and 4th 2011, the staff and the amenities were great. The rooms were awesome and the jacuzzi was very relaxing. Every single guest was so nice and enjoyed the laid back atmosphere. The only bad thing was, I couldnt have stayed longer. Thanks Virginia, and see you soon.
Dr. Brandon

  • Stayed June 2011, traveled with family
    • 4 of 5 stars Value
    • 4 of 5 stars Sleep Quality
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Monroe, Michigan
Reviewer
4 reviews 4 reviews
5 of 5 stars Reviewed June 2, 2011 via mobile

Virgina and Daniel are great hosts.... Great location, great property, great cute pool, and clothing optional pool makes a nice touch in Key West.

We will be back, thank you.

  • Stayed May 2011
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Monroe, Michigan
Reviewer
4 reviews 4 reviews
5 of 5 stars Reviewed June 2, 2011

Virgina and Daniel are the best guest house managers we have ever met... The rooms and gounds were always very clean.... the anoying rooster--- well you can't do anything about the early wake up call but laugh... you will learn that chickens are a protected bird in Key West. This is a great place for clothing optional and close to all the action without any of the noise and distractions. The pool is cute for Key West and well maintained. We will be going back.

  • Stayed May 2011, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Morristown, New Jersey
1 review
5 of 5 stars Reviewed June 2, 2011

We cannot wait to return next year, only for a longer stay. Rooms were great, spotless and comfortable. Reminded us of Cape May NJ. Daniel and Virginia were so helpful with anything we needed, it was like a family resort for adults.
The other guests we met were from all over the country and most had been comming back for years. We now understand why! Clothing optional around pool was not an issue and the sun felt great. We loved the pool and had wine, cheese with all guests who were there . Thanks for a great vacation Daniel and Virginia and your great staff. See you next May. Hope to see all our new friends also!!!!!!! Jim and Pauline

Room Tip: Old house room 1A great porch for people watching.
See more room tips
  • Stayed May 2011, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Alexandria, Virginia
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed May 12, 2011

We have stayed here twice so far and have just booked our third visit. The staff is the most accomodating, friendly staff we have met anywhere, and we travel at least one week a month somewhere! The inn is just the right size...perfect to meet other guests, if you like, or to be "on your own" if you prefer. We met many nice people and ended up having dinner with several a few nights! The location can't be beat...an easy walk to all the great restaurants, shops, bars, etc. - literally a few blocks away. We never feel guilty if we don't bring our workout clothes - we just walk off our meals, drinks, etc. Try the Pilot House~~you will not be disappointed.

  • Stayed April 2011, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Weston, Florida
1 review
1 helpful vote 1 helpful vote
3 of 5 stars Reviewed May 2, 2011

We stayed at the Pilot house for the 3rd in 8 years, this past April. Its a great location, good rate and guestes are awesome. Only nothing has been updated or changed in those 8 years. We have stayed in the Cabana room, the Attic and this last saty in the mantion front room. The mantion is noisy. Dont plan on sleepin in. The maid service sounds like they are doing construction in the room next to you. The bed felt as if it was going to collapse. Things are very dated. I know this is a historic building, but they could update aplicances and furntiure. Worst of all The staff person "Virginia" was very unpleasant. We arrived late to Key West and was unable to check in properly, getting our room key from a lock box. Knowing that parking is scarce in KW, I parked overnight in the loading zone. I quickly corrected it the next morning to be surprised that I was now going to have to pay for parking that night as well as the following night. When asking the staff why I had to pay for the previous night, her response was "nothings free DUDE!" I dont mind paying for parking however if I had never mentioned where I had parked, I would not be paying for that night. Honesty got me no where at that point. honetlsy I wouldnt saty here again because of the last expierence, the only thing going for this place anymore is the clothing optional pool and jacuzi, and unless your with some appealing looking friends, you may want to skip it altogether.

Room Tip: find parking before you get there!
See more room tips
  • Stayed April 2011, traveled as a couple
    • 3 of 5 stars Value
    • 5 of 5 stars Location
    • 1 of 5 stars Sleep Quality
    • 2 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 1 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Hotels you might also like...
mm/dd/yyyy mm/dd/yyyy
Price Your Stay

Been to Pilot House Guest House? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Pilot House Guest House

Address: 414 Simonton Street, Key West, FL 33040
Location: United States > Florida > Florida Keys > Key West
Amenities:
Free High Speed Internet ( WiFi ) Kitchenette Suites Swimming Pool Wheelchair access
Hotel Style:
Ranked #18 of 97 B&Bs / Inns in Key West
Price Range (Based on Average Rates): $$
Hotel Class:2 star — Pilot House Guest House 2*
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 
Also Known As:
Pilot House Guest House Hotel Key West

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.