I stayed here for 2 nights. I have mixed reviews... my credit card had an offer that was $250 off any stay. My partner and I chose this hotel based on the location and how close it was to Duval ST. (This location was very worth it as it was walking distance and we could walk around key west without to uber) We also chose this location based on how lush the property is! This is true- the property was full of trees and we even got a treetop view! I loved how immersed we were. it truly felt like a vacation! However my cons for this property would be the fact that if I didn't have that $250 credit I would be furious. We paid $260 out of pocket for 2 nights. I don't think it's worth it. Our room door did not open unless you held it a certain way. We only found that out on our last day. The room was pretty small as well and the decor was interesting.. the bathroom had stains and in my opinion is not worth $200+ a night. You also have to pay $30 a day for parking... I found that insane. My partner and I just accepted that if breakfast was free then we are saving $30 anyway... I give this place a 7/10 if you are spending less than 100$ a night but if you are paying more I would say 5/10. read more

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Winslow's Bungalows has beautiful grounds, poor service, and was a major letdown... We recently stayed at Winslow's Bungalows in Key West, drawn in by the charming photos and glowing descriptions of beautifully restored white-washed bungalows nestled among lush landscaping, multiple serene pools, and inviting common areas. And to be fair, the property itself is as lovely as advertised. The grounds are immaculate, the pools are peaceful, and the bungalow we eventually stayed in was exactly what we had hoped for. Unfortunately, the customer service and overall experience fell far short of what we expected--especially at a steep $600 per night. We booked our two-night stay months in advance, fully expecting (based on the name and the imagery online) to stay in one of the standalone bungalows. However, upon arrival we were led down the street to a completely separate two-story house, up a flight of stairs, and into what can only be described as a glorified closet. The room was tiny and the "queen bed" was definitely not a queen--closer to a full size, and barely fit for two adults to sleep comfortably. As a senior, hauling luggage up stairs to a cramped space we never agreed to was frustrating and unacceptable. To make matters worse, we had arrived at 3:30 p.m. for a 4 p.m. check-in, hoping to get situated a little early. The woman at the front desk was curt, unhelpful, and refused to answer any questions or even start the check-in process until the clock struck 4. Her tone and attitude left a very poor first impression. When I called the front desk to complain about our room, I was told there was nothing available that night (we suspect due to a wedding on the property), and that we'd be moved to a bungalow for the second night. We were also offered $100 off the first night--which I appreciated, but it didn't come close to making up for the experience. The second night we were finally placed in a beautiful ground-level bungalow--the kind we believed we had booked all along. It was everything we'd hoped for: private, charming, and comfortably appointed. But by that point, the damage had been done -- our experience was soured. Breakfast is included, and while it was fine (think: Hampton Inn), it didn't add much to the experience. The open-air bar had live music, which was a nice touch, but the bartender clearly didn't want to be there. No smile, no welcome, and he was out of basic staples like scotch, bourbon, and rosé. In summary, Winslow's Bungalows is a beautiful property that badly needs a reset in customer service and honesty in booking. For $600+ per night, guests should feel welcomed, respected, and get what they paid for--not shuffled off to a glorified attic room and treated like an inconvenience. Two stars, and that's only because of the lovely setting and the much-improved second night. Sadly, we won't be returning and would never recommend this place to anyone! read more

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We had a wonderful stay at the bungalows. Check-in was in was friendly and comprehensive. The grounds itself are charming; everyone's rooms look a little different with paths cutting through gravel to reach each nook, and 3-4 little pools that give the grounds a potential for more private gatherings. The room was immaculate, very stylish, with shutter blinds; not great soundproofing unfortunately but a well-ACed plaace to sleep. The included breakfast included a variety of dishes and an acoustic band playing next to the bar. Unfortunately we didn't get to use our bar tokens which were probably part of the exorbitant resort fee but overall would recommend this place to fellow travelers looking for a unique and personalized stay. Our check-in guy was nice enough to waive parking since we stayed only for one night. read more

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Winslow's Bungalows is a fine hotel. The location of our room on the edge of the property was superb. The pool was close by and not over crowded. The space inside was adequate. Free breakfast was minimal, but we received two free dinks at the bar - mine a glass of a low grade, red wine. I thought the total costs of the stay were high given what we received, but we made our reservations late and were happy to find a well located, local place. When you put on the bar, be prepared to pay. My greatest complaint is the number and sizes of the hidden surcharges - including resort fees and parking charges. I understand such costs are now common, but the practice is reprehensible, in my opinion. Not first class behavior. read more

The property is great. Avoid room #40 because the air conditioner unit is very loud, not relaxing! Parking is $30 a day. Ouch.

Very nice property with 3 pools. Great location. A really nice complimentary breakfast is served 8-10. It was nice to have free cold water fill stations. Our room was at the quiet end of property. Unfortunately the room itself needed attention. There was a huge stain on the chair and the bathroom fan did not work. There was a lightbulb out above the sink. The shower did not drain properly, not the actual drain but the floor seemed crooked so water remained on tile. Very odd. There was no desk in room. The light above the door/ closet flickered so you could not leave in on. For the price paid the room should be in perfect condition. read more

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We are so thrilled that we stumbled across this fantastic accommodation. The property, the grounds, the service, the rooms, the complementary breakfast. All five star. Sonya was so personable, professional and amazing. She put us in the most perfect room to celebrate our anniversary. We are so thrilled about this beautiful property and will definitely be back. read more

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Windows Bungalows previously were a Kimpton. Since the conversion not too much has changed. You get small bungalows some with a small garden area. There are pools and a free morning breakfast which is decent as far as "free" is concerned. The staff are very laid back probably because that happens when you are on an island. The air condition wall units are exceptionally loud which can be distracting if you want to sleep. read more

My husband and I spent 2 nights this past week at Winslow's Bungalows. The location was perfect, the grounds are beautiful, the bar area and breakfast are outstanding. As soon as we walked into our room we noticed a very musty smell. I went to the front desk to request moving to another room, but they were sold out. I was told to go first thing Tuesday morning to see about a switch then. No rooms available. The cleaning people may have sprayed a deodorizer, but that didn't last long. I looked at the air conditioning unit outside and it was very black. I'm thinking it would benefit from a deep clean. My husband and I both agreed that we loved everything about Winslow's Bungalows accept our room. We paid over $600 per night for our little get away. It was very unfortunate that we didn't feel like we could rest well because of the aroma. I hope that management will look into this and make the necessary upgrades or changes to rectify this problem. Respectfully, Ann Couch read more

Very nice place. It is old but well maintained. Vibe is very much old Key West. Bathroom updated and bed fairly comfortable. No elevator. Narrow stairs. BE warned if you book through travel sites like Expedia. There are hidden daily fee of $45 a day. Non refundable for ancillary amenities. Not sure what those are. Also parking is not free. $30 a day. However there is free parking on Elizabeth street and on Truman right in front of School. Breakfast is nothing amazing and does not change day to day. But coffee is good. Bar on site is good but not cheap. Pools unused which is weird. We basically had our own private pool. We would likely stay here again. Good location. read more

Great location near downtown, but the stay had several disappointments. Pet "friendly" really meant pet tolerant--no beds or bowls available, no relief area, and the only grass on property was marked no pets allowed. Rooms are tiny, and the larger room we moved to had a strong mold/mildew smell that made it hard to breathe. Breakfast was weak--mostly carbs, no labels on coffee, and hot items came out late. Parking was a hassle, often full. Roosters are loud all throughout the night and not controlled on the property.. light sleepers beware! Staff were kind and helpful, and the property is cute, but overall, it's not worth the price until these issues are addressed. read more

Our daughter generously gifted us a trip to Winslow's Bungalows. The positives: The check-in staff was friendly, and the location was convenient to restaurants and local attractions. The downsides: No iron or steamer was available in the room, so I had to use my own hair dryer to try and smooth out wrinkles. The lock on our room door didn't function properly, and at one point someone opened the door unexpectedly. We're still unsure whether it was an employee or not--thankfully, my husband was present. We were never informed that bicycles were available for guest use or that we were entitled to two complimentary off-site dinners. We only found this out after our stay, in conversation with our daughter. At nearly $1,000 for two nights, the experience did not meet expectations. I contacted Winslow's Bungalows through the contact information on their website, and after two months, I have received no response. Overall, we were deeply disappointed by both the accommodations and the lack of communication. The indifference to our concerns was especially frustrating. Sadly, we won't be returning. We recommend that future guests confirm details in advance to avoid similar disappointments. read more

We adored everything about Winslow's except for the incredibly uncomfortable bed! It was weirdly soft and felt off-kilter or something, I don't know. There was also a bizarre flashing light on the ceiling all night that was coming from outside, but I'm not sure where! Otherwise, service was fantastic, both at the front desk and at the bungalow bar. The grounds are SO cute, as are the rooms. Location is close-ish to Duval, probably best to rent a bike or scooter like we did. If it weren't for a rough night of almost zero sleep it would have been a five-star experience! read more

Amazing breakfast !!!! The room was clean and quiet. Ac worked great . We stayed the night with our children and they enjoyed the nostalgic room. This is a historic bungalow meaning it will have its quirks but we go with the flow . I'd say a 4.5 is an honest score read more

Please treat yourself here. Absolute 5 stars! I even wanted to post 6 stars the first two days here. Breakfast, coffee nook, poolside bar, and more pools. Felt small getaway feeling with big city accommodations; staff was SUPER polite, gracious, attentive, and helpful. along side real peace and privacy. Super great location to old town / Duvall st, rentals and such. Won't stay anywhere else next time. YOU ALL MUST treat yourself and STAY HERE! read more

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After the first night I do not have one negative thing to say. Room=Amazing People=Amazing Complementary breakfast=Amazing read more

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We were shocked to be shown to room #53 after paying over $500 per night to stay at Winslow's. I would have been upset to pay $200 a night for such a tiny room, much less $500! Our room looked nothing like the beautiful pictures on their website. After moving our suitcase into the room we didn't even have enough room to easily move around the bed. The bathroom only had a sink and a toilet, so nowhere to put any toiletries. The room itself needed a lot of maintenance: there was peeling paint and rust in the bathroom, lots of messy cords and crooked outlets by the air conditioner. There was a big, awkward step up into the bathroom. Oddly, only two of the shower walls were tiled, so the full spray of the shower hits the plaster wall across from the shower head, disaster waiting to happen. You should not be renting room #53 to anybody! After we complained, we were moved to another room of the same room type for the remainder of our stay and the other room was at least double the size! Unfortunately, it was right on Truman Ave. and there is zero soundproofing against the traffic noise. We were woken up all night by sirens and trucks and then roosters at 5 AM. The beds were comfortable but what good is that when the noise keeps you awake anyway. We were somewhat happier with our stay after moving rooms until our final day when we sat down at the bar with our friends. I merely asked the bartender a question about one of the food items listed on the chalkboard and he snapped "I wouldn't know!" He then got busy with other customers and when he finally came back to us he snapped, "it's after 2pm now and my chef leaves at 2pm." We were ready to order well before 2 pm. Our entire group got up and left. I don't have an issue with the hours but with the manner in which this employee chose to inform us he wasn't going to serve us. I wasn't going to leave negative reviews on this stay but this extremely rude bartender changed my mind! read more

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Catastrophe. Run away. Let me count the reasons: 1) The pool tiles were filthy dirty greasy. For 6 days. We stayed there for 6 days and they were never cleaned. See the pictures.. 2) Towels at the pool would run out by mid-morning and the front desk just told us to wait because they have to wash-and-dry the old ones. At 11am on a weekday? Every day? For $600 to $700 per night, no one should have to wait for hours for towels. And the staff was entirely indifferent to this. See the picture.. 3) "Welcome drink" was a can of cheap beer. And for my daughter? No non-alcoholic options available.. What a disappointment 4) For $600-$700 per night, the fanciest part of the breakfast was hard-boiled eggs. Hard. Boiled. Eggs. Oh, I guess the microwaveable single-serve oatmeal was pretty fancy too 5) I contacted General Manager Joy Boyd to go through these entirely correctable issues and my call was not returned So here we are. Do yourself a favor and stay ANYWHERE else. Oh well at least the location was decent read more

Winslow's Bungalows - Greasy filthy dirty pool tiles - Hotels Near Me - Key West, Florida

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Beautiful property but I was put in a room that was on the outskirts of the main property rickety stairs! Room did not cool down at night until well I to the early morning. Noises of kritters on roof woke me on several nights! Beware of the $37 a day resort amenity fee! Not paying for much with that! I went to the pool to be interrupted by crew coming to power wash! Cleaning of my room had to be requested and was poorly done. Floors were filthy! Location is the best part of this property along with outstanding breakfast and bar service! As an older traveler the desk should have noticed the location of my room and changed it! Lots of other choices in the same area! read more

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This place is wonderful and Kirk the weekend Bartender is beyond amazing. If you ever need recommendations on what to do or see he's your guy for everything cool going on around town! read more

Tiny rooms. Almost zero storage (no closet, only a few drawers). So if you like to unpack, or come from an average to above average sized home / bedroom, this will be super disappointing. Service was good....but still....wish we'd stayed home instead... read more

Quaint accommodations that is close to Duval St...they have three pools, a bar, and complimentary breakfast. Would recommend and we will definitely be coming back to get our Key West fix! read more

Just returned from Key West, 12/30/24 our first trip, and we loved Key West. Its a fun place to go. Our accommodations at Winslow's Bungalows were a big disappointment though. We were given Room 61 (if you decide to stay here, make sure to request to NOT be put in this room). The room has no natural light (no windows) and it is very tiny. There is no closet or even hooks for clothes to be hung. The bathroom has very little counter space for toiletries. If you stay, be sure to be specific to have a room with a window and room for your clothing (there may be other rooms like this one at Winslow's), Who knew you had to ask for a window in a room? Is it even legal to rent a room with no window?? You can imagine the humidity in the room after showering, and no way to get rid of it. So overall, the room smells musty. We were there for 5 days, and every item of clothes we had smelled musty when we left. The landscaping on the property is very nice, and most of the staff, also nice. We did have to call for housekeeping service on once day after arriving back to the room at 3:30pm to find it hadn't yet been made (I was told "they work till 5pm".) Um, we have dinner reservations and would like to freshen up. I really wanted to love this place, it's a historic inn, the photos on Expedia and the reviews in general were good, but that wasn't our experience sadly, so I wanted people to be aware before they go. You will love Key West though! read more

Great hotel and location, one of the best in key west. Front desk staff is amazing. The only reason for the 3 stars is one of the bartenders. His name is Keith and he was just absolutely rude to the guests. I think he is trying to inject humor but he is just condescending and rude. It was very uncomfortable for us and the other people at the bar. Maybe he was having a bad day but it was so bad i took the time to mention it . We luckily came back to the bar a day later to give it another try and glad we did. Different bartender was working...captain Kirk! He was amazing. Fantastic drinks and service. Gave us recommendations to vist during our stay ( so many great ideas) and was just overall a pleasure to be around. He was so welcoming to not just us but everyone at the bar. We made some friends with other guests and they said the same thing. Each night before we went out we hit the bar to see kirk and have a drink. . Captain Kirk thank you so much for everything you do. We have booked again for February. read more