This was our second stay at the Westwinds Inn. We stayed for 5 nights in a King Deluxe, room 405. This room is located upstairs in a street front building to the right of the main building. Our room was located on the backside of the building. Street noise was minimal, but yes the roosters will wake you up in the early morning hours. The Westwinds Inn provides a nice breakfast option of bagels, muffins, cereal, hard boiled eggs, fruit, coffee/hot tea and juice. This year they added a poolside Happy Hour on Wednesday - Friday from 3-4:30pm with beer, wine and some canned cocktails. It was a nice social time to meet others in the late afternoon. I hope they continue to have this for guests. The property is well maintained and our room was clean. The housekeeping staff made up the room everyday while we were out and provided fresh towels. The bathroom was nicely renovated with a blow dryer in the drawer and small bottles of shampoo, conditioner and body wash. The room itself is pretty tiny with a very small amount of walking room along one side of the bed. It made it slightly difficult to use the cabinet for your clothes on that side of the room. If you are a larger person or have mobility issues then this room is not for you. Resting in bed and looking out to watch the tops of the palm trees sway in the breeze was a lovely view. Again, we rented bikes from Eaton bikes (on the corner) which is convenient. Westwinds also has a large bike rack in the property to use. read more

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We've stayed at Westwinds Inn at least four times in the past four years, and we absolutely love this little hidden gem in Key West. Yes, the furniture doesn't match and the place isn't shiny and new--but that's EXACTLY the charm. It's cozy, quaint, clean, and ridiculously comfortable. We won't stay anywhere else. The beds are super comfortable, everything is always clean, and the two heated pools feel like your own private backyard oasis. Seriously... it's giving "secret resort vibes." We've stayed in four different room styles, and every single one had its own personality and charm. The continental breakfast is small but sweet, and the women who run it are lovely. Bonus points for letting you park your rented golf cart right on the property--huge win. And being just four blocks from Duval Street? You really can't beat that. I've read some of the negative reviews and honestly... if you're looking for brand-new, crisp, modern, Instagram-perfect hotel vibes, this is not your place--and that's okay. There are plenty of shiny new hotels down the road. But if you love charm, comfort, character, and a laid-back Key West feel, Westwinds is it. 10/10. Highly recommend. Would stay again. And again. And again. read more

Westwinds Inn - Hotels Near Me - Key West, Florida

This is the place to relax. With lots of small rooms and bungalow type buildings there is tropical luscious plants in between so it feels like an intimate resort. Two pools adorn the property (one heated) . Rooms are smaller yet comfy. Staff is nice and helpful with tips. Breakfast is scant yet enough to start your day. It is a place to kickback and relax . read more

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Hard to see how this was rated 2 stars when we booked it. We had great accommodations, the room had a fridge, sink, et,. There were two pools, one cool and one warm. All that and it looked this this. read more

Westwinds Inn - Breakfast nook next to pool - Hotels Near Me - Key West, Florida

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This hotel is a great Key West location on Eaton St just five blocks from the center of the Duval Street strip. A true bed and breakfast with two large buildings with several small rooms and several cottages with two tropical pools in the back of the property. Each morning they serve a simple breakfast at the pool area. The front office staff provides eats and attraction information. Bikes are for rent very close. This property is well kept and priced mid to high depending on the booking months. Best to stay during the weekdays for better pricing. My family has stayed here for Fantasy Fest for over twenty years. read more

Don 't waste your money! Dirty! No USB receptacgles in room. No soap dishes in shower. Had kitchen but no knives or towels . Poop on pool cement for 3 days. Took him 4 hours to clean up the poop. Called Manager and Emailed but he was not resolving issues. asked for a refund. no response. staff does not speak English! poor non existing management. use to be nice but not now! they have not kept up! I was told that Key West is not for me by desk. Stayed a week and it cost me over $4,000. Never again. Breakfast was continental and had to ask for juice and milk. got sick for 2 days on what they had. no refrigeration on condiments. poor judgement! dirty floors. heard a lot of complaints from others. read more

Westwinds Inn - Hotels Near Me - Key West, Florida

Amazing hotel in key west! Perfect for a weekend getaway, walking distance to everything, but also next to a bike rental place that was awesome! Quiet hotel, 2 beautiful pools, great AC in the room, amazing maid service, and a free continental breakfast! Would defiantly recommend this hotel!! read more

Westwinds Inn - Hotels Near Me - Key West, Florida

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Great quiet hotel. We had a room upstairs of the house which they all have their own bathrooms and mini fridge. Pools were awesome! One heated one not and the plants were beautiful read more

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What a beautiful and peaceful inn. Good location, within walking distance to just about everything. Had an absolutely lovely vacation. read more

Westwinds Inn - Hotels Near Me - Key West, Florida

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Awesome place and Staff. We had an issue with our room on the first night and we were quickly moved to a much more acceptable room closer to our friends. This truly made our trip and was particularly nice since my wife had never been to Key West before. Kudos Westwinds! read more

Westwinds Inn is a wonderfully quiet & quaint boutique inn that is nicely furnished, diligently cleaned & cared for. It has 2 pools and each suite is well decorated & appointed. The only thing I can say that it needs is another blanket for each bed. After being in the hot sun, the AC can freeze you to death. But we had wonderful & amazing time! Will stay again!! read more

We have visited other B&B's in KW and this is by far the worst. Spent 5 days here for Thanksgiving 2021. Most noteworthy issues. * This is not a Bed & Breakfast, the $5 voucher they give you for breakfast does not cover the cost of Coffee and a Scone at the local bakery. * The Bed was extremely uncomfortable, without a headboard and was on wheels and not fixed to the floor or wall so moved. * Absolutely no parking unless you get there nice and early and find street parking........ good luck with that. * Paper thin walls, maid ( housekeeping) banging on the door at 8:30/9:00 am. On a positive note the grounds are pretty. read more

such kind staff and beautiful location. Parkings a little difficult so be prepared to walk, but overall very homie and seclusive. It's about a 10 minute walk to the main road of devaul street which isn't bad at all but i prefer driving around the island for the beach anyways. My favorite part about this hotel is the breakfast vouchers for the bakery down the street- best danishes i've ever had in my life- and the pool which was pretty much always empty when I was out. great find for my family! read more

Westwinds Inn - Hotels Near Me - Key West, Florida

This boutique hotel steps away from Duval Street is the perfect little hidden gem! The rooms are nicely sized and the pool in the middle of the property is perfect for relaxing and mingling with friends and guests. If you prefer to be in a more quiet place, the 2nd pool is the perfect place for that. The hotel staff was just lovely, they made our stay welcoming and comfortable. The breakfast at Old Town Bakery just steps away was delicious! I will be recommending this place to all my friends and family! I can't wait to come back! read more

Beware when making reservations for this hotel especially if going through Booking.com They take your money, make your reservation and then never let you cancel unless they can keep your money! Booking.com says "talk to Westwinds " while Westwinds says, "talk to Booking.com"! I thought there was a law where a person has 24 hrs to cancel any purchase/contract with a full refund however this place gives no refund and charges you 9 months in advance. Very poor customer service!!! read more

Westwinds Inn - Hotels Near Me - Key West, Florida

My wife and I stayed at the Westwinds Inn in August 2018. The room was clean and airy. The bed was comfortable. The (included) breakfast was nice. Not too much, but enough to get your day going. The pool was nice, the water was warm and inviting. The staff was super friendly and helpful. Answered all of our questions and even helped book a sunset cruise for us! We did have to go to the main desk to request towels be put out by the pool, but that took them 2 minutes to fix. read more

Very nice hotel. The rooms are separate buildings on about two city lots. Outside landscaping was beautiful with two swimming pools. Inside our room was spacious with a nice couch, four chairs and table, large king size bed, and small desk area. The bathroom was also spacious with a walk-in shower. They state no children under 6 and with children between 6 and 12, you just have to sign a form understanding there are no lifeguards or fence around the pools. If anyone was looking for a very comfortable and special place to stay for their trip to Key West, I would highly recommend staying here. read more

Westwinds Inn - Hotels Near Me - Key West, Florida

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Pros: Location was good. Room was airy, and clean. The staff we met were great to us. Blankets were in the closet which made Baker more comfortable (she is always cold!). They did have a parking pass for the garage two blocks away for $14/day. Cons: The bathroom was so small you pretty much stepped into the shower stall to close the door. Provided a luggage rack that was to big for the closet and there was no other place to put it in the room. Beds were not comfortable. There were no towels for the pool. All the reviews seemed to rave about the Gauva Tarts....hmmm seemd to be missing for us and breakfast....what a carb loaded disappointment. When you are charging a high price the bar is raised and sadly this was a miss. read more

The customer service is terrible. This is the third year we have stayed and apparently is under a new Managment. Frozen muffins, stale cereal, but the hard boiled eggs were warm(nasty). They did not restock room with toilet paper once during our stay. Someone apparently was to bed around 3pm nightly and up at 7am with tap shoes on all week above us. read more

Westwinds Inn - Hotels Near Me - Key West, Florida

I had a very bad experience with this hotel. Booking.com had the price of $662.00 for 3 nights. I had a question about parking so I called the hotel directly and talked to Imeala who was very nice and said she can book the room and match the price. I said if you can hold the room and I will call you back in less than a hour, she put a hold on the room. I called back in 30 minutes and she had to ask her GM a question. He yelled at her and said he wouldn't honor the price. He raised it to $889.00 and took down the booking off Booking.com. I asked to talk to the GM, Aaron. When he finally got on the phone he was very rude and refused to understand my disappointment. I WOULD NOT STAY AT THIS PROPERTY. BE CAREFUL read more

Great customer service, great facility and location. However the regular maintenance of the suites have been lacking as far as the room suites. However cleanliness was fairly good. read more

My parents have been staying here for years and absolutely love it. They brought the whole family down this year and it was just lovely. The pool is gorgeous, with lush landscaping and hidden away off the busy street. This is a nice quite spot for those who are in Key West to relax, not to party. It feels like you're staying in someone's guest house. I will say it does not feel like a hotel at all. This is good and bad. Personally I prefer more of the hotel feel (it makes me feel like I am really on vacation!) but if you like the casual homey atmosphere then this place is for you. Good service, clean rooms. Not fancy at all though. We skipped the breakfast as my parents warned us it wasn't so great, but there are tons of amazing breakfast places within walking distance. read more

Ohhhhh I just loved this hotel. Great looking place... Nice pools.. Friendly staff... Awesome location!! I'd go back there! read more

Westwinds Inn - Hotels Near Me - Key West, Florida

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My buddy and I stayed here based on the price and location. It's a few more blocks off duval street then I prefer (10 min walk ) but we had a great 2 night stay. We were in a jr queen suite that had a community front porch for the 2 rooms upstairs. We seemed to have it to ourselves and was the best part of staying there. As far as the pools, laundry, breakfast etc we're all great. There is no parking onsite but a garage a few blocks away for $17 a night or if your lucky you can find street parking. The staff were really young but helpful when needed. I'd recommend this place and perhaps rent scooters like we did ! read more

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Had a very enjoyable stay at this historical inn. We stayed in a "junior king" suite, which was large, clean and comfortable. This quaint hotel is a quiet, peaceful little oasis in the heart of old town Key West. There's no parking at the hotel, but the city parking garage is a short walk away, and there is a circular driveway in front of the hotel for loading/ unloading of luggage. The two oasis style (salt water) pools are practically private compared to the pools at large hotel chains. A simple continental breakfast is served poolside. The only minor annoyance was the very loud bathroom fan. The A/C was nice and cold - awesome, as this hasn't always been the case at some older hotels we've stayed at. Highly recommend Westwinds Inn !! read more

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Myself and 2 sisters all around 40ish stayed 6 nights in the queen sweet.The desk guy was awesome and the property is gorgeous. That being said I wouldn't visit again or reccomend. Because: The room was up a flight of old wood creaky stairs past every room inside the main building. The rooms private entrance was actually a community entrance located at the top of the creaky stairs it was up stairs either way you go so be warned.The TV is on the wall right next to the door so it can't be too loud. We had gotten a noise complaint and warning of cops and a fine if happened again. If you're not going to bed at 11pm do NOT stay here it is impossible to be quiet.We had to request housekeeping after the 3rd day and it seemed uncustomary, yet there was a tip envelope for it left on the dresser the day we arrived? The library/lounge wasnt available to guests.There is no freezer in the mini fridge but ice buckets and signs for an ice machine .. but NO ice machine. Instead of onsite breakfast, vouchers are given for the bakery down the street only open from 7am-3pm in the opposite direction of everything else so it was out of the way and they were never used. One of the 2 pools were heated so no one wanted to use it obviously, the fountain wasnt even operating. There were lights wrapped around the palm trees on the property that would have been beautiful if they were ever turned ON. So in my opinion unless you're single or a couple of 60+ this isn't the place for you in Key West! read more

Loved this quaint little spot and will definitely return in the future. Clean room, great pool area and well maintained grounds! read more

Westwinds Inn - Hotels Near Me - Key West, Florida

We did go last week and the Hotel is great. Clean and the rooms are beautiful we did love the atmosphere. And the Breakfast was great. Very nice landscape and two pools very special. You should be once there guest. Hubert the person on the reception was very nice and has given us great tips and information. Thank you very much. We will come again we loved it! read more

Westwinds Inn - Hotels Near Me - Key West, Florida

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Prior to posting this review, I tried to get a hold of the owner/mgr regarding our stay via phone and email with no luck hoping they would see how the stay was unacceptable. We had a 1-night reservation with a King size bed. We ended up taking a different room that was available which was supposed to be a queen-size bed but was in reality it was small. (This room was their Suite). We were told there would be a discount by taking the "queen" bed but in reality, the discount ended up being the $240 we had already paid but an "upgraded" room that was a nighmare! That evening when we decided to finally enjoy our "relaxing" evening after swimming, shopping, watching the sunset which by then we were exhausted, we found out the master ceiling fan didn't work, the second room was hot with no AC, the TV did not work and there were bugs in the sink multiple times throughout our quick stay, the place smelled like smoke at one point, you received only one washcloth and as people came in throughout the night, it was very loud as people walked up the wooden steps, the place is old so the doors didn't just shut smoothly, you had to pull hard to get them to close so it was loud enough to wake us up multiple times. VERY disappointing! I should not be shocked noone returned any messages. I'm sure they are very aware of the issues they have. Sad. read more

My boyfriend and I booked a room here at the last minute for an overnight in Key West and we were not disappointed! The staff was friendly and helpful and the rooms were clean. From the inn, you can walk to Duval St. in ten minutes or less! My favorite part was the continental breakfast served from 8-10 am. Food options were limited, but the outdoor area is so beautiful and peaceful! read more

After an aggressive and intense online search for a nice hotel in key west, I stumbled upon this gem. I booked it in a matter of seconds, and was pleasantly surprised. The entrance itself looks like a bed and breakfast place (although it's not), but discovered that there are multiple guest houses in the back. The rooms were very bright and clean, and the bed was soooooo comfortable! The Filipino lady at the front desk was so sweet, I was sad to have to leave after only one nite. The walk to duval street (kinda what bourbon st is like in NOLA) isn't too far, and you get to see a lot of shops and bars. It is close enough to enjoy the sounds of the city, but far enough to be able to sleep ;) Other 3 star hotels in the area cost at least $330, but I got to stay here for half that price! read more

Best place to stay on key west if your looking for a quaint bed and breakfast. Quiet, quaint and friendly.

Price on par with others in the area, though the rooms were tiny (we were staying in the main building, upstairs from the reception)-- imagine a queen sized bed plus about 2 ft of space around the bed. The gardens and pool provide a lush outdoor space, and since Key West is less about being indoors and more about the outdoors, it didn't matter too much... read more

Very disapointed in Westwards. Our room was so plain, no pictures on the walls and a couch that would not let the bathroom door open all the way. The employees at the reception were cold, and when I inquired about the discounted parking they were holding for us, the looked at me like they swallowed a canary! Will NOT recommend. read more

We really enjoyed our 3 night stay in Feb. Looking for 'inexpensive' lodging in KW, we chose a small room here, but it had everything we needed--comfortable beds, clean, good AC/fan and TV. Breakfast was good--especially the hot guava empanadas!! Not a fancy cooked breakfast but plenty of choices. Loved the outdoor spaces--lush landscaping and two pools. We prefer this type of old hotel to newer cookie-cutter chains, and loved being in old KW, close to everything. No parking on site but a public lot 1/2 block away. We left the car and rented bikes at Eaton Bikes on our corner; rode to all sites beyond 5-6 blocks. Thank you to the pleasant and helpful staff at Westwinds! read more

This was about my 6th time visiting the florida keys and my 2nd time staying at Westwinds. I will not stay at any other "resort/hotel". This is the place where I get the most for my money. They are the friendliest people to work with, in the office. Hubert and Suzie are so kind and accomondating. Suzie was quick to call me upon my arrival asking how I liked the room. I went down for breakfast on MOnday and I heard her questioning soe of the guests if they were me. She was looking for me personally to welcome me. I loved that! The staff, Fatima, Josie and Rick are very friendly and appreciative. There is always a big smile from them every morning, even if you are a little late going to breakfast. They understand that the nights in Key West may make the moringing a little hard. The breakfast is fabulous! They offer the freshest fruit, an array of danish and breads (I had a cruisant every morning! I was on vacation). There are two pools to enjoy while there. A cool pool and a warm pool. The warm pool has jaccuzzi jets that are perfect after a long day of exploring the island. And, the location is awesome. You are two blocks from the "boardwalk" and about 5 from Duval Street. Close enough for stumbling home and far away that you don't hear the noise of the night life. And, because it's the West end, there aren't as many roosters that will wake you at 5am. Oh, I don't want to forget Pumpkin. She is the sweetest cat you will meet on the island. If you have any questions about what to do or where to go, the folks at Westwinds will point you in the right direction. Did I mention that they have a great gas gril for the nights you would rather cook yourself? OH, I don't believe there are children under 12 there. You may want to check with them about bringing your kids. I could go on and on. If you are going to Key West, stay at Westwinds on Eaton street! read more

love this place. listen book on Trivago. close to old town this place is just blocks from Duval at where all. We had a great time highly recommned read more

My 5 star rating is for the service!!! Ladies at the front desk were awesome, especially Emily! I would definitely recommend spending the extra money for a room with a kitchen and a view. read more

Heads up- only children 12 and older are welcome here, even though online booking sites recommend this place for kids. They are accommodating though, and small pools are lush and pretty. Nice location. read more

Had a great time! It's a bit older but for a place to lay your head (after a day, or night, of drinking) and grab a quick shower, it's perfect. Less than 10 min walk to Duval Street and within walking distance of a lot of great places to eat. It's quiet, has 2 small pools and continental breakfast. We will definently be staying here again! read more