Ridley House - Key West Historic Inns

Enough light coming in the room to keep it lit all night long!
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Panorama of the Deluxe King Room at the Cypress House Hotel: Key West
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Fully refundable before Sun, 28 Apr
Breakfast included
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RM 2,150
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About

4.0
#49 of 55 hotels in Key West
4.4 of 5 bubbles
Location
5.0 of 5 bubbles
Cleanliness
4.1 of 5 bubbles
Service
3.5 of 5 bubbles
Value
Once the estate of a prosperous industrialist, Ridley House is tucked behind classic picket fences and low-hanging trees. Here you’re immersed in a verdant oasis of ease and refinement. Of our five Key West Historic Inns Collection hotels, Ridley House is the most elegant—ideal for honeymooners and VIP stays. Key West is a one-of-a-kind island, and Key West Historic Inns gives you five authentic ways to enjoy the carefree fun. Fanning across the heart of Old Town, our diverse collection of historic buildings each has its own tale to tell—and its own unique offerings. From the low-key luxury of Ridley House to the quiet, expansive experience of Winslow’s Bungalows, there’s truly something for every mood. Tying them all together are bohemian style, glimmering pools, lush gardens—and hospitality that is as warm as sunshine on a palm frond. We invite you to discover the Key West Historic Inns hotel that fits you best, and escape to this land (and sea) of pure enchantment.
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Property amenities
Free High Speed Internet (WiFi)
Wifi
Pool
Pool / beach towels
Free breakfast
Breakfast buffet
Adults only
Baggage storage
Outdoor pool
Newspaper
Non-smoking hotel
Outdoor furniture
Sun loungers / beach chairs
Sun terrace
Room features
Air conditioning
Private balcony
Safe
Wake-up service / alarm clock
Refrigerator
Flatscreen TV
Hair dryer
Room types
Non-smoking rooms
Good to know
HOTEL CLASS
Star ratings are intended to indicate the general level of features, amenities, and services to expect. This property is classified according to Giata.
3.0 of 5 stars
HOTEL STYLE
Quaint
Historic Hotel
Languages Spoken
English
63Reviews25Q+A20Room tips
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Detailed Reviews
Ron C wrote a review Jun 2021
Aiken, South Carolina5 contributions
5.0 of 5 bubbles
Outstanding updated old homeplace for a secure and terrific stay within easy walking distance to KW's main attractions and restaurants. The staff was excellent. They assisted us with our reservation, getting our car parked (which we never had to move for the three-day visit), and provided a great complimentary breakfast to start each morning. The view from our upstairs porch became an excellent evening wind-down point first with the complimentary beverages (they were excellent) and then with choice local beverages.
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Date of stay: May 2021
5.0 of 5 bubblesValue
5.0 of 5 bubblesLocation
5.0 of 5 bubblesService
Room Tip: Our second floor suite had a porch with great views
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Cheryl Martin, Owner at Ridley House - Key West Historic Inns
Responded 2 Jun 2021
Sure appreciate the wonderful 5 star review. Ridley House is so special and I am happy you enjoyed the experience we provided. Plan another trip back soon.......Paradise is waiting for you.
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Tammy M wrote a review Jun 2021
6 contributions
+1
5.0 of 5 bubbles
Wonderful! I work in the travel industry and booked a weekend getaway for myself and daughter at the last minute to celebrate her (24th) birthday. Kimpton properties are always a go-to, and the Kimpton Ridley did not disappoint… Craig was fun and welcoming, thought my daughter was 17, so I did have to ask for the boozy welcome… we had a King porch room (#10), that was lovely and private at the back of the property, just steps from the inviting pool. Our room was very small, yet cozy for two and did have a nice-sized closet complete with bath robes. Bed and linens were top-notch, the room was cute and comfortable and the included breakfast offered a nice variety for a light meal to start the day. The location is just PERFECT, with a handy parking lot less than a block away, and just steps to Duval. Although we were extremely pleased with our stay, I have to admit I am hesitant about sharing such a glowing review and booking future clients here… would rather keep it our little secret! Thank you!!
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Date of stay: June 2021Trip type: Travelled with family
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
kelsie wrote a review Sept 2022
Tuckerton, New Jersey336 contributions10 helpful votes
5.0 of 5 bubbles
We had a late night check in mid week, the end of August. Eddie & his Assistant Fen, who is part American Buldog were in the office to welcome us. Fen was so happy to be able to say hello to both my husband & myself & run around.

I had asked for a 1st floor level room when I booked since both of us have medical conditions & we would have difficulty climbing stairs. Ridley House, like many older homes throughout KW don't have elevators. Even though we could not expect a particular room we were able to get on the first floor. Our room was perfect with a small outside patio with couch & 2 lounge chairs. We had a nice room & private bath. The A/C worked fine & the bed was like sleeping on a cloud. My husband said he doesn't remember getting such a good night's sleep. The bedding and pillows were perfect. Continental breakfast is served from 7:00-10:00 am. There is a very nice assortment of muffins, pastries, etc.

The next morning we were met by Craig .who told us where all of the local restaurants & attractions are. We have been coming down for over 25 yrs., so we were quite familiar with a lot of them, and knew that most of our favorites were 2-3 blocks walking distance.
There isn't parking at The Ridley House, but for $20/day you can park around the corner in the parking lot. Mike, the Attendant was very observant with all of the cars & since it was a Holiday weekend he made sure he always had a space for us. The nice thing is that you can park & come and go as you please. This was a total plus.

We went to Ridley's sister property, Winslow Bungalow's that was a short distance away & listened to music at their bar & had food from Mike, who owns the food truck there on the property. The food & drinks Keith Ross made were delicious. Thank you Neeta for taking care of us when Keith had a day off.

We were extremely happy with everything the Ridley House & it's sister hotel Winslow had to offer us & we are looking forward to returning in the Spring.

Thank you Eddie, Fen & Craig for a wonderful stay!!
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Date of stay: August 2022
4.0 of 5 bubblesRooms
5.0 of 5 bubblesService
Room Tip: Note: hotel does not have elevator
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Sarah wrote a review Apr 2021
1 contribution3 helpful votes
1.0 of 5 bubbles
We understand that this is a historic site and when we came we didn’t expect the place to be perfect, however we didn’t expect the place to be a free for all. My partner and I came for our honeymoon since we couldn’t go out of the country. Our room was tiny and uncomfortable. l to the point where we felt uncomfortable being in it. They don’t do any room service because of Covid and it was hard to even get fresh towels. They say there is a bike service but we could never actually get one. Whenever I would go try to ask for something it felt like the front desk didn’t really know or have the answer. It didn’t really feel like I was staying in a hotel. There was no cleaning up of the pool area from people’s shenanigans from the night before. Glasses were left out on the tables and it made me wonder if they were actually cleaning the space. The pool was also pretty dirty.
The main problem we had was the other guests. It says this is a non smoking site, but guests are really allowed to smoke wherever they want and smokers took over the entire place. They were smoking in the pool and in their rooms, so we could smell it in our rooms. Some guests had taken our table that was outside our room and moved it to the front of their room so they could smoke at it. When we complained to the night desk staff there was nothing that was really done about it.
Me and my partner stay at a lot of Kimptons and this really did not feel like a hotel experience, let alone a Kimpton experience. I really think that management needs to start prioritizing the guests, especially at the price point they have.
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Date of stay: March 2021Trip type: Travelled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Cheryl Martin, General Manager at Ridley House - Key West Historic Inns
Responded 19 Apr 2021
Ouch, we really dropped the ball on your recent stay and I am very sorry for that. I appreciate the details so I can refocus my team and make immediate improvements as we are normally much better than what you experienced. Cleanliness is a high priority for us. I hope you will forgive our mishaps.
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Cspigle1 wrote a review Dec 2022
Ashburn, Virginia67 contributions26 helpful votes
2.0 of 5 bubbles
Positive: Location. Very close to all of the Duval Crawl locations, plus the waterfront.
Negatives: Most notably, this place is simply dirty. From the moment you walk in to what should be a beautiful property, advertised as a spot for VIP’s, you notice that the floors are dirty, carpets dirty and beautiful wood work coated in dust. It may be hidden a bit with the near non existent lighting in the hall.
We were pleased with a large room with a lovely balcony. We quickly realized that our feet were getting dirty when barefoot in the room due to the filthy floors. When the room was tidied daily, hopefully by 2 or 3pm, it became clear that actual cleaning wasn’t taking place. We saw one vacuum, but never saw it actually used.
The staff were not welcoming and were actually apathetic. We let them know that the phone in the room didn’t work and nothing was done. The person handling breakfast literally acted as if she was bothered by our presence. And the kitchen was filthy, so I am not sure what she did after breakfast concluded each day at 10:00am.
While I mentioned the lovely balcony, our room faced the street and it was extremely noisy, basically all hours of the day and nearly all night.
As mentioned in other reviews in 2021, there is no security in this property. This is a very busy street. Anyone can walk into the building at any time of the day or night.
The pool and lounge area is very small. If you really want to spend time lounging by the pool, this property isn’t for you.
When we encountered staff, we were never asked how our stay was or if we were enjoying our trip. One of the front desk staff people just spent the day across the street smoking on and off all day. We did not feel welcomed at all at this property.
The TV’s need to be updated to Smart TV. There is no streaming option available.
Overall, this was a major disappointment. Most disappointing is the sheer potential of this property. Luckily, we’ve stayed at other beautiful properties in Key West and we won’t ever use
Ridley House again.
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Date of stay: December 2022Trip type: Travelled as a couple
Room Tip: Don’t stay at Ridley House
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Lights99 wrote a review Jul 2021
31 contributions19 helpful votes
2.0 of 5 bubbles
Good location, nothing else is good. Very old house, you may need to carry your luggage yourself to upstairs, no lifts, pool is a joke, so small, no in-house restaurant or bar. Breakfast area is pathetic. No in-room coffee maker or microwave. You have to walk to the breakfast area to heat up any or make your early morning Coffee. And :-( !!!! breakfast room opens at 8am only, there’s a back side opening though!, but it is a pain . Completely valueless for the amount you may pay. No parking, though there is a private parking available near by, which may get filled quickly on busy days. Not good toiletries, but large bathroom. You may see bugs and ants along the walkways, which I feel common in this area. Very noisy as the property is at a busy corner, you may hear vehicles honking at times. Nice balcony and good Front desk staff.

If you are an early morning coffee drinker, want to drink coffee in room directly from bed, better buy a camping self heating coffee can.

Net net, very difficult to recommend to anyone.
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Date of stay: July 2021Trip type: Travelled as a couple
Room Tip: Near by parking is there, $25 to 35 per day, depending on the crowd. Walkable to most places,...
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Cheryl Martin, Owner at Ridley House - Key West Historic Inns
Responded 6 Sept 2021
As a historic hotel, it appears we missed the mark on your expectations. I am very sorry for your unhappiness with us, but thank you for mentioning that my staff was good. If you do ever want to stay again, we can certainly send a Nespresso coffee maker to your room upon request for your "coffee in bed".
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E C wrote a review Nov 2020
2 contributions2 helpful votes
1.0 of 5 bubbles
This place is completely unprofessional and using the Kimpton name. If you cancel within the cancellation policy timeframe you will still be charged. And if you try and contact management you will never get to anyone. It's completely ridiculous and unprofessional. I had to fight them through my credit company. I can't believe this is a Kimpton. They are totally going down hill. Not worth the price, save your money for a real hotel.
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Date of stay: November 2020
1.0 of 5 bubblesService
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Adam Osborn, Owner at Ridley House - Key West Historic Inns
Responded 17 Dec 2020
Dear Vacationer, We want to firstly thank you for taking the time to share your thoughts and perspectives with us, as we are always looking for new ways to improve ourselves and the stellar Kimpton experience we have become known for. We would also like to sincerely apologize that you feel let down by your experience working with our team, and while we may not be able to adjust the past, we would love to provide any context that may better illuminate the situation moving forward. As you may recall, we did have a less-than-easy time maintaining contact with each other, but were happy to discuss the details of the reservation with you once we finally could connect. We had discussed that your reservation’s cancellation policy in particular was quite atypical, so when you cancelled your booking on the day of arrival a few hours prior to check-in time, we went ahead and followed our usual cancellation procedure which is to charge any applicable penalties. Notably, our systems also indicated this was the correct action to take, as the cancellation policy you were sent and the one in our system were not matching. That said, when we were finally able to connect with you, you were able to provide us with your confirmation email which showed cancellation was actually allowed on the day of arrival itself with no penalties. Working with new information and context, we were happy to reverse the charge immediately in full and share that information with you. Being that this was the main concern in regards to your booking, we were relieved that we were able to assist you in that matter and make things right. We sincerely hope that this miscommunication has not skewed your perspective of Kimpton as a whole, and we certainly would hope that you would consider us in the future to stay in-house with and experience all of the wonderful things Kimpton Ridley House has to offer. We do offer many of the typical Kimpton luxuries found in our more traditional-style hotels, and would love for you to contact us directly to coordinate a truly Key West-esque experience at our unique, historic Kimpton hotel. Again, we are infinitely grateful for your thoughts and perspectives on this matter, and hope that sharing ours with you will help shine new light on things past. Should you be gracious enough to consider us in the future, we kindly encourage you to contact us directly at 305-294-6969 so that we may provide you with the utmost in Kimpton hospitality. Safest and warmest regards to you, Adam Osborn
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Jackieb3 wrote a review Jan 2022
Birmingham, Alabama38 contributions37 helpful votes
2.0 of 5 bubbles
It was quite cold at night and the heater didn’t work. We had to ask 3 times to have it fixed. If everyone is using the hot water you won’t get much. The real problem is security and the front desk. The main house with most of the rooms you enter though a front door and it’s not locked. There is a lot of people on the streets here and anyone can enter. It should have keyless entry on the front door. The other issue is when you text the staff to get help you just get an ok. There is no follow up to make sure your problems are being handled. This is strange for a Kilimpton. Ella’s and Windslow cottages are secure and the staff is super good. If you have a choice for the money pick one of those and skip the Ridley house
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Date of stay: January 2022
3.0 of 5 bubblesLocation
1.0 of 5 bubblesService
3.0 of 5 bubblesSleep Quality
Room Tip: Pick Ella’s or Winslows cottages
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Monika Pearson, Other at Ridley House - Key West Historic Inns
Responded 8 Feb 2022
Dear Jackieb, I am very sorry to hear that we did not met your expectations. We take our guests feedback to heart and I can assure you we will look into mentioned issues immediately to improve upon moving forward. Again my apologies for your less than exceptional experience.
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gramm2007 wrote a review Jun 2023
Decatur, Illinois57 contributions69 helpful votes
+1
5.0 of 5 bubbles
I really loved this hotel! Amazing staff and the rooms were very modern with it being in a historic home! The pool was very nice nestled in with palm trees that gave a little much needed shade in the afternoon! I will say that the street noise was a little loud but I think wherever you are in Key West you will have that problem. You are 2 blocks from Duvall. 2 blocks from the hot spots. Close to Hydrothunder golf cart rental. Beds are comfy. Showers were hot with great water pressure! Very clean. If the showers are slick just ask for a rubber mat. I would stay here again.
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Date of stay: June 2023Trip type: Travelled as a couple
Room Tip: Smoking only allowed on sidewalk!
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Monika Pearson, Owner at Ridley House - Key West Historic Inns
Responded 5 Sept 2023
Dear Gramm2007, Thank you for 5 star review and for staying with us. We are so happy to hear you enjoyed your stay with us and the location and vibe of Ridley house. We hope to see you soon.
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Jessica B wrote a review Aug 2021
3 contributions2 helpful votes
5.0 of 5 bubbles
We stayed at the Kimpton Ridley House for 2 nights this past weekend (July 30 to August 1) and had a wonderful experience. Every single person at the front desk was welcoming and charming, check in was a breeze (even though we got delayed and showed up 30 mins after they were supposed to close, THANK YOU for waiting for us!) The room was a pure delight! Extremely clean and well maintained with a lovely Key West atmosphere. I'm not sure if it was because we just got off a three day charger with no AC and tinnny rooms, but it may have been the most comfortable bed I've ever laid in! The best part is how close it is to everything - a short block or two walk to the main marina and Duval Street - makes it incredibly convenient but tucked away enough you aren't bothered by the noise when you want to relax. All in all would highly recommend this little gem!
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Date of stay: July 2021
5.0 of 5 bubblesLocation
5.0 of 5 bubblesCleanliness
5.0 of 5 bubblesService
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Cheryl Martin, Owner at Ridley House - Key West Historic Inns
Responded 6 Sept 2021
Thanks jessicabV2401BT. I just loved reading your review, you sound like the perfect Key West visitor! Plan another trip back sooner than later.
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J E wrote a tip Feb 2024
Fredericksburg, Virginia8,980 contributions664 helpful votes
2.0 of 5 bubbles
"There's hardly any sun exposure at the pool during the day, do to the tiny yard area, tall rooflines and foliage "
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gramm2007 wrote a tip Jun 2023
Decatur, Illinois57 contributions69 helpful votes
5.0 of 5 bubbles
"Smoking only allowed on sidewalk!"
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hikerbecky wrote a tip May 2023
Wisconsin121 contributions23 helpful votes
4.0 of 5 bubbles
"Use the pool between 2-4pm, very few people using it! Grab pool towels whenever you see them available!"
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Greg P wrote a tip Apr 2023
Key West, Florida1 contribution
1.0 of 5 bubbles
"Not uncommon for there to not be any towels…"
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Karen C wrote a tip Mar 2023
2 contributions
5.0 of 5 bubbles
"Use the privately owned parking lot half a block away to park your car and walk everywhere if possible."
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PRICE RANGE
RM 1,744 - RM 2,471 (Based on Average Rates for a Standard Room)
ALSO KNOWN AS
cypress house hotel key west
LOCATION
United StatesFloridaFlorida KeysKey West
NUMBER OF ROOMS
22
Prices are the average nightly price provided by our partners and may not include all taxes and fees. Taxes and fees that are shown are estimates only. Please see our partners for more details.
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RIDLEY HOUSE - KEY WEST HISTORIC INNS (R̶M̶ ̶2̶,̶9̶0̶5̶) RM 2,385: UPDATED 2024 Hotel Reviews, Price Comparison and 83 Photos (FL) - Tripadvisor

Frequently Asked Questions about Ridley House - Key West Historic Inns Collection
Which popular attractions are close to Ridley House - Key West Historic Inns Collection?
Nearby attractions include Mallory Square (0.5 km), Rodriguez Cigar Factory (0.3 km), and Heroes Bar & Liberty Lounge (0.5 km).
What are some of the property amenities at Ridley House - Key West Historic Inns Collection?
Some of the more popular amenities offered include free wifi, free breakfast, and a pool.
Which room amenities are available at Ridley House - Key West Historic Inns Collection?
Top room amenities include air conditioning, a flat screen TV, and a refrigerator.
What food & drink options are available at Ridley House - Key West Historic Inns Collection?
Guests can enjoy free breakfast during their stay.
What are some restaurants close to Ridley House - Key West Historic Inns Collection?
Conveniently located restaurants include The Breakfast Club, Too, Keys Coffee Co., and Fisherman's Cafe.
Are there opportunities to exercise at Ridley House - Key West Historic Inns Collection?
Yes, guests have access to a pool during their stay.
Is Ridley House - Key West Historic Inns Collection located near the city centre?
Yes, it is 0.6 km away from the centre of Key West.
Are there any historical sites close to Ridley House - Key West Historic Inns Collection?
Many travellers enjoy visiting Truman Little White House (0.5 km), Key West Garden Club (2.2 km), and West Martello Tower (2.0 km).
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