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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
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  • Reviews (276)
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Pilot House Guest House
Ranked #21 of 98 Key West B&B and Inns
Certificate of Excellence 2014
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276 people have reviewed this hotel

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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
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English first
There are newer reviews for Pilot House Guest House
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dade city florida
4 reviews 4 reviews
5 of 5 stars Reviewed July 4, 2012

We had a wonderful time our room was right by the pool. spent several nights there. Loved that the pool and spa are clothing optional. Within walking distance every where. only draw back was the parking you had to look for it but we where able to find it a block a way and did not move the time we... More

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Horsham, Pennsylvania
Top Contributor
65 reviews 65 reviews
14 hotel reviews
23 helpful votes 23 helpful votes
5 of 5 stars Reviewed June 25, 2012

But far enough away to be quiet. Excellent experience at the pilot house. Virginia was very helpful and accomodating when we had to arrive late due to train delays. Our room (next to the pool) was awesome and off street parking ($) was available. The room even had a kitchenette which allowed us to have bagels and coffee in the... More

Was this review helpful? Yes 2
Miami, Florida
2 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed June 22, 2012

Clean, updated, fun, staff exceptional.(Virginia is the best). Hot tub was a perfect late night skinny dip. Only had one night there but are planning many more. A short stumble from duval but far enough from the noise.

Was this review helpful? Yes 2
Buffalo, NY
2 reviews
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed June 21, 2012

I have stayed at about every hotel in Key West over the years but my favorite is by far the Pilot House. It is a beautiful, well maintained property with the friendliest staff on the island. The staff will greet you by your first name and will bend over backwards to help you with anything. The rooms are spotless and... More

Was this review helpful? Yes 2
2 reviews
9 helpful votes 9 helpful votes
5 of 5 stars Reviewed June 18, 2012

First time in Key West and the Pilot House for a well needed vacation. Going over all the details on the phone with Virginia and it sounded perfect, so I booked immediately (even though only 2 out of the 3 nights were available). Got to the Pilot House and could not be more pleased with our room (#9 one of... More

Was this review helpful? Yes 1
Tequesta, Florida
Top Contributor
115 reviews 115 reviews
14 hotel reviews
45 helpful votes 45 helpful votes
5 of 5 stars Reviewed June 16, 2012

This was our second trip to key west in a month. Our previous B and B was great but there was no pool. Pilot House is not a b and b because there is no food. It is a 100 yr old house with a new addition of cabanas by the pool. We stayed in room 4 which is on... More

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Spotsylvania, Virginia
5 reviews 5 reviews
4 hotel reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed June 14, 2012

We traveled to Key West and stayed at the Pilot House during the third week of April. First, thank you to Virginia and Daniel for the hospitality during our stay. Taking the time to chat with the guests every once in awhile was a very nice personal touch on their part - not too much or too little. We felt... More

Was this review helpful? Yes 2
Milford, Connecticut
13 reviews 13 reviews
4 hotel reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed June 13, 2012

We enjoyed 7 wonderful days at the Pilot House Cabana Guest House. Virginia, Daniel, and staff were very friendly and always willing to help. This being our first time in Key West, Virginia and Daniel were very helpful in suggesting attractions, and giving us an overview of the immediate area. The location of the Pilot House can't be beat. It's... More

Was this review helpful? Yes 1
Cocoa, Fl
14 reviews 14 reviews
4 hotel reviews
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed June 10, 2012

I've been going to the Pilot House for at least 15 years now, and have always enjoyed every minute of my visit. It's great to see Daniel and Virginia every summer, and the staff takes care of us. The location cannot be beat; I have noticed other customers mentioning it's like a B & B without the breakfast. I prefer... More

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Fort Myers, Florida
2 reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed June 3, 2012

Pilot House in Key West is my choice of hotels while visiting there and has been for almost 3 years. The staff, lead by Virginia, is excellent. The rooms are always clean & needs are promptly addressed. The clothing optional pool & hot tub are features, but the word optional is key. There are people of all shapes, sizes and... More

Was this review helpful? Yes 3
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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

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Hotel & grounds (30)
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Bathroom (3)
Pool/beach area (6)
Dining (1)
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Hotel & grounds (10)
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Family/play areas (2)
Pool/beach area (8)
Room/suite (14)
Bathroom (2)
Other (31)


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 
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