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“Love this Place” 5 of 5 stars
Review of Pilot House Guest House

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Pilot House Guest House
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2.0 of 5 Bed and Breakfast   |   414 Simonton Street, Key West, FL 33040   |  
Hotel amenities
Ranked #23 of 92 Key West B&B and Inns
Certificate of Excellence
Dunedin, Florida
Level Contributor
12 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
“Love this Place”
5 of 5 stars Reviewed July 10, 2012

Back again for our annual trip to Key West for the 4th of July week, We stayed in room 8 this time. We loved this place so much when we stayed there last year that it wasn't even a question where to stay this year. The location is perfect close to Duval and all of the attractions there. Short walk to the wharf or any other places on the island. Virginia is the best along with the fun couples that we have met there. The funny thing is that we saw some of the same people staying there this time that we met there last year which really made it fun. Will be calling Virginia back soon to book our room for next year in July and maybe a quick trip a little sooner. See you soon Mike and Sonia

Room Tip: We really like the Cabana Rooms by the pool, but I don't think there is a bad room here.
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  • Stayed July 2012, 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.
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337 reviews from our community

Traveler rating
    258
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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 (116)
Date | Rating
  • English first
  • French first
  • Italian first
  • Any
English first
Palm Beach Gardens, Florida
Level Contributor
12 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 7 helpful votes
5 of 5 stars Reviewed July 9, 2012

My wife and I spent 7 nights in the Attic room this past June. Virginia, who manages the facility is a funny and caring person. The location is perfect, just off Duval, so the noise level is non-existent. The room was very clean and the maid service was excellent. There is a grocery store just a few yards away. The Pilot House has everything a couple could want in a guest house. I highly recommend this guest house and I will stay there again.

  • Stayed June 2012, 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.
Jacksonville, FL
Level Contributor
5 reviews
common_n_hotel_reviews_1bd8 15 helpful votes
5 of 5 stars Reviewed July 7, 2012

Just left from Pilot House where we enjoyed our 8th stay for 4 nights. We've tried other B&B's (Simonton Court, Heron House, Cypress House) and have consistently returned to Pilot House now for last 6 or 7 years. The location is just one easy block from Duval, easy walk to marina area, it's just a perfect location. We've stayed in the cabana rooms and rooms 2a, 2b, and 5 in the Mansion. Prefer the downstairs cabana rooms but none were available this year. Still the Mansion rooms are comfy with great AC, kitchens/kitchenettes, and great linens. Virginia and Daniel are both very welcoming calling us by first names and welcoming us back. Virginia runs a tight ship with proper activity around the pool area (clothing optional, but not a nudist resort) and ensures it's always clean and friendly place. Never an issue that they don't do the breakfast part of B&B...there are so many great breakfast options close by that it's never something we've missed. Plus with Faustos Grocery literally 30 steps from the back gate having snacks in your room to enjoy by the pool is never a problem. The pool is an active gathering place. Couples strike up conversations, or just lounge quietly. Most do exercise the optional part of "clothing optional pool" but no one is ever intrusive, rude, or anything more than just chillin, and enjoying the sun and cooling off in the pool. If you're offended by the lack of swimsuits around a pool, this likely isn't a place for you, but guest who stay here year after year do so because it's an option that is available and respectfully well managed. If you drive there, yes, the parking is $20 a day but literally right out the back door. Throw your blender and poolside plastic cups in the backseat and enjoy. A softside cooler is handy out by the pool if you're not in a cabana room. Another plus is they have bikes always at the property to rent and are in great condition. Love you Pilot House...until next year!

Room Tip: Downstairs Cabana rooms are best. Or upstairs in the Mansion.
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  • Stayed July 2012, 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 2
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
dade city florida
Level Contributor
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 were there

  • Stayed June 2012, 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
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Horsham, Pennsylvania
Level Contributor
96 reviews
17 hotel reviews
common_n_hotel_reviews_1bd8 31 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 morning. The pool was a great place to get together with other guests after visiting all the sites along duval street. We will definitely be back again in the future

Stayed June 2012, traveled as a couple
Was this review helpful? Yes 2
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Miami, Florida
2 reviews
common_n_hotel_reviews_1bd8 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.

Room Tip: Room 8 opens right to the pool.
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  • Stayed June 2012, 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 2
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Buffalo, NY
2 reviews
common_n_hotel_reviews_1bd8 8 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 affordably priced. The hotel is only a block from Duval, and a short walk to the main attractions like Sloppy Joes, and Mallory Square. At night it is quiet and peaceful. Try it, I can assure you that you will love it! Tom W., Buffalo, NY

Room Tip: I love the room on the second floor above the jacuzzi...great morning breeze on the balcony.
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  • Stayed May 2012, traveled solo
    • 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 2
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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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 #23 of 92 B&Bs / Inns in Key West
Price Range (Based on Average Rates): $$
Hotel Class:2 star — Pilot House Guest House 2*
Number of rooms: 14
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

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