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 97 Key West B&Bs / inns

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
  • Overview
  • Reviews (283)
  • Photos (171)
  • Similar Hotels
  • Amenities
  • Q&A
  • Room tips (95)
  • Location
  • More
Pilot House Guest House
Ranked #18 of 97 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

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
OLATHE KANSAS
Senior Reviewer
8 reviews 8 reviews
6 hotel reviews
22 helpful votes 22 helpful votes
5 of 5 stars Reviewed 1 week ago

this is going to be a review and a trip report combo: for the past 5 years my wife and i had a week that we split between miami southbeach and key west kidless. this year we decided just to stay in key west for the whole week based on key west's crime rate and the pace of the place... More

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

Miami and Key West are both awesome places to vacation. They are quit different in what they offer. Key west is a more relaxed recharging kind of place, an island destination. The pilot house is perfect for what ever type of holiday you want Central to everything on Duval no need for a car. Private inviting pool to chill out... More

North Carolina
Senior Reviewer
10 reviews 10 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed 1 week ago via mobile

This was our first visit to the Pilot House. Attic suite was great- loved the private deck. Enjoyed all of the amenities ! Daniel and Virginia were so helpful. All of their recommendations were excellent. We will be back!

Was this review helpful? Yes 1
Horsham, Pennsylvania
Top Contributor
75 reviews 75 reviews
15 hotel reviews
27 helpful votes 27 helpful votes
5 of 5 stars Reviewed 1 week ago

As the title says, this was our third visit and it was another fantastic stay! Virginia and Daniel made sure our stay was great. The closeness to duval street makes it easy to pop out and visit a bar or two come back for a break and then head out again. Guests are friendly as well.

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

Third visit, fantastic! We really appreciate all the guests who have tried the Pilot House and decided to stick with us. We are a small guest house and lucky to be situated in the heart of Old Town Key West. The property has 14 rooms all with private bathrooms and kitchens or kitchenettes. Depending on the weekend and the guests,... More

Arcadia, Florida
Reviewer
3 reviews 3 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 1 week ago

We love staying at the pilot house. It is peaceful and relaxing. A great place to get away from children. lol You meet awesome friends and keep coming back every year for meet up. Staff is outstanding as well. Virginia is great. Rooms very clean and housekeeping keeps your rooms neat. Can't wait till next years trip

Was this review helpful? Yes
1 review
5 of 5 stars Reviewed 2 weeks ago

We went to the pilothouse for our honeymoon, it was great. For an older property it is well kept. we stayed in the attic suite and found it to be a great choice. its a climb, so if your not able to climb stairs, not good. the clothing optional pool was a first for me and my wife, it was... More

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

Go up the stairs till you can't go any further. It feels like being in the tree tops looking out over the Island You see the Light house and the Old Customs House roof. If a cruise ship is docked you look straight across at it resting in Mallory Square. This is your private getaway. Your own jaccuzzi and sundeck.... More

Farmington, New Hampshire
1 review
5 of 5 stars Reviewed 2 weeks ago

This was our second year at Key West. 1st at The Pilot House. We stayed in the Cabana and couldn't have been happier. The room was clean, cool, and comfortable. Huge walk in shower, kitchenette with coffee pot - microwave- and sink. The staff was excellent from checking in to housekeeping. They were knowledgeable about the island and places to... More

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

Our Cabana rooms Rock!. The Huge showers, the Jacuzzi bath tubs. Having a kitchenette is a bonus but with so many great restaurants a 1/2 block away on Duval and in the surrounding neighborhood most guests just stock up on drinks. As a guest house we don't provide any food or beverage totally un necessary so close to all the... More

Sarasota, Florida
1 review
5 of 5 stars Reviewed 2 weeks ago

We just came back yesterday from our first trip to not only Key West but also to the Pilot House Guest House. We can't say enough about the Pilot House! The rooms were immaculate and the decor was so Key West. We loved the tropical setting of the pool and, spa. Not to mention the clothing optional aspect of the... More

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

Welcome to the Pilot House family. Glad to to hear you had such a great stay. This past weekend was a blast with a fab mix of regular guests and new visitors. This was a stay that we can't take all the credit for. The Pilot house is a small guest house offering a friendly space to relax central to... More

Ft. Lauderdale
1 review
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed 4 weeks ago

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 2
Wayne, Pennsylvania
Senior Contributor
38 reviews 38 reviews
5 hotel reviews
21 helpful votes 21 helpful votes
5 of 5 stars Reviewed 4 weeks ago

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 2
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 5 weeks ago

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
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)
Hotels you might also like...
Check In Check Out
Price Your Stay
Select tags to find the hotel that's right for you.
All
hotels in Key West with
any amenities

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

Questions? Get answers from Pilot House Guest House staff and past guests.
Posting guidelines
Typical questions asked:
  • Can tickets for local attractions be purchased at the front desk?
  • Do you have to pay extra for a mini-fridge?
  • At what time does the pool open each day?

See which rooms travelers prefer