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    Havana Cabana

    3.4 (214 reviews)
    Open Open 24 hours

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    Lo by
    Lee W.

    Was really happy with this hotel. Booked a last minute trip to Key West and was happy I found this spot. Great value for the price. Beautiful lobby and pool area. The staff were very attentive and friendly. Check in was easy and the room was cute with comfortable beds. We had drinks at the pool bar which was great. Loved the pool and were happy to unwind with a swim. The pool is so pretty and there are lots of cute floats. There is a shuttle that goes to Old town and back every half hour. This an easy way to avoid the parking situation around Duval Street Nice hotel for a good price.

    Roula H.

    Perfect spot for a Key West vacation. About 10 min from Duval, they have a shuttle every 30 minutes. The rooms and grounds are very clean. The pool is awesome and so are the drinks. Loved the fact that it's adults only and pet friendly.

    Emily S.

    Love love love this resort! Came here with 3 girlfriends for my 30th birthday and we had a blast. We shared a pool view, 2 queen bed room, and the room is fairly small, but it didn't bother us since we spent very little time in there. The pool area is gorgeous, and it was great to have some group games available on the pool deck when we had a chillier evening. The bar was very fun, and the drinks were delicious and reasonably priced. The food was *okay* but nothing different from your standard bar fare. We chatted with several bartenders throughout our stay, and they were all super great and fun to talk to. The only downfall is the breakfast service is very, very slow. There was one server for the bar and dining area both, and it took forever and a day just to get a cup of coffee. Other than that, the stay was wonderful and I would absolutely stay again!

    Cigar Bar view
    Steve C.

    Havana Cabana is a great place to stay, Great Pool, Pool Bar, and incredible Cigar Bar with very nice happy hour prices.. and fun Bartenders The Room is Havana themed as is the whole Resort, and the staff is attentive, fun and made the place a great experience!!

    Jooy C.

    This place is not bad. We booked because it was one of the more economical options in Key West, but experienced inconveniences along the way. The pool is pretty big and nice but not heated, which made it hard to enjoy when the weather was in the 60-70s. But it was still nice to lay around there during the day. I liked the daily coffee, smoothies, snacks (popsicles were meh but churros were good), and free shuttle rides to and from the city and airport, all included as part of the $55 daily resort fee. The rooms were clean overall, and the staff were also very nice and accommodating. A few things that could have been better: 1. There is no gym as they tore it down for the restaurant. The website says guests can access a gym, which is actually the Margaritaville gym, for which we had to specifically ask the shuttle driver to drop us off there. Not sure how we would have gotten picked up if we had decided to do this? 2. Plumbing is a bit questionable. During the first two days, the pipes made a very high-pitched noise every time the rooms next to us used the water. We asked the front desk to fix this on multiple occasions but this was not addressed. This made working in the hotel room very difficult. 3. If you pay extra for poolside view, they will blast music very loudly from 9 AM to 11 PM. This also made it difficult to work at the hotel. 4. Our room key wristbands stopped working everyday, and we had to ask the front desk to reset them every single day. Minor but somewhat annoying inconvenience. All in all, this is a good place if you're looking for a decent place to lounge around for a couple days. It's missing a few key pieces I was looking for in a hotel, but perhaps it will be more enjoyable during the warmer months and when I don't plan to use the hotel to work.

    Wandering L.

    Anniversary Bliss at Havana Cabana We stayed at Havana Cabana for 4 days/3 nights to celebrate our anniversary, and it was such a great choice. From the Cuban-inspired hospitality to the thoughtful champagne waiting for us, every detail felt special. Our ocean-view room on the 1st floor was quiet and relaxing, and the bed + pillows were perfection. The shuttle to downtown Key West was convenient, and we loved that the resort was close enough to the action but far enough to feel like a peaceful retreat. Minor negatives: NYE lacked excitement, and we were disappointed there weren't better late-night food options--they even ran out of beer! But otherwise, it was paradise. Definitely recommend for a relaxing getaway!

    Frank S.

    Checked in to Havana Cabana and John a super friendly host helped me out with a great room. He addressed all my needs ... very cool looking room and nice bars and pool. Good spot socfar!

    Pina Coladas poolside
    Angie M.

    It's a tropical paradise at Havana Cabana!! We always try to stay here if it's available. The property is gorgeous, the pool is stunning (I THINK it's the biggest pool In Key West), the rooms are beautiful and the beds are so comfortable. But what truly sets Havana Cabana apart is its staff. From the moment we arrive, we're greeted with warmth and hospitality. The bartenders are great, and we can't say enough about Nick at the pool - he is always there when you need something. Chris G. and team also went above and beyond to make our trip special. The shuttle will take you to all action in Old Town, but you won't want to leave the pool and pina coladas!

    Poolside view
    Lisa M.

    Where do I begin?? Ah yes, back when I was planning my wedding over a year and a half ago... My now husband and I chose Havana Cabana to work with when picking wedding venues, not only for the awesome wedding package options, but for the huge pool (largest on the island), the cleanliness/comfort of the rooms, the food, and the eagerness of the staff to help and make our Wedding day (and beyond) perfect. We worked with Jackie on all of the wedding planning and Jody-Kay on the room block arrangements. I will tell you hands down, that both of these ladies are amazing and went above and beyond to make everything perfect and seamless. Fast forward to our first wedding anniversary, and Jackie, Jody-Kay, Brittany, and Nakayla all helped get our trip back to Havana Cabana planned. They each helped us tremendously and even when we had an emergency (causing us to miss our flight), they went out of their way to assist. We really appreciated their help, kindness, and understanding in our situation! The whole staff at HC is great, a few more to shout out to are Annette, Iliana, Taishia, Avery, Vadim, Costa, Val, Vashawn, Nick, Jackson, and Hubert.. Thank you all for making our stay amazing! We visit Key West a couple times a year and we will definitely stay at Havana Cabana again. We absolutely recommend this hotel!!

    Lobby
    Rick K.

    Excellent Hotel - Kick Back, Relax and Float Down Stream Love this Hotel, location 10 minutes from Duval Street (Where all the action is). The ambiance is naturally a Cuban feel, old Chevy's parked out front (lCuban theme interior - well done). Checking in was a breeze the Concierge was full of information and super helpful. The Hotel offers a free shuttle down to the seaport where you can find sunset cruses, snorkeling, fishing ect.... The shuttle starts at 9am and runs every hour on the hour. Room: Our room amenities, Fridge, Safe, Microwave, Keurig Coffee market, complimentary water (note: anytime we needed water we would ask the front desk, it was at no charge. We booked a room with two Queen beds, it was on the ground floor and it exited to a Lanai - (Room 120) - ground floor) perfect location to get to the pool & bar. The AC worked great - Beds super comfortable. - The Hotel is quiet, never heard any noise from the pool/bar area ( they close down at 11pm). The shower had strong pressure, (the handle took a little time figure out) Pool: Pool area is spread out with plenty of lounge chairs - they offer drink & food service (its not as steady as I would have liked but decent) - all of the staff was super great - friendly, professional, helped with all questions. They offer games, like ping pong & corn hole - that was cool. Bar was outstanding - the food from the Floridita Food Truck (located just off the bar) was very good. The have a small menu, but enough choices to please everyone - we ordered a Cuban Sandwich (they call it "Shaved Cuban Mix - mojo marinated pork loin with ham & cheese) was one of the best I ever had & it was huge. You can order up your food at the bar an they'll bring it to you. Havana Cabana is a very cool hotel, we loved it & will be back.

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    Review Highlights - Havana Cabana

    Bar was outstanding - the food from the Floridita Food Truck (located just off the bar) was very good.

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    Simonton Court Historic Inn & Cottages - Our comfy cottage

    Simonton Court Historic Inn & Cottages

    4.3(82 reviews)
    2.7 mi

    Loved my stay here so much that I am already talking about going back next year for a longer stay…read more Jonathan and Violet provided personalized service that makes guests return often. You will not get this at a larger property or resort. Our accommodations were better than we expected. Continental breakfast was a nice touch. The grounds are peaceful and nicely manicured. Secured at night as well. Convenient to center of town. One mile in either direction to the water

    Just got back home after staying a few nights at Simonton- again. Our previous stay was so good we…read morehad to go back Now we won't consider any other lodging in Key West. Jonathan and Violet ( surprisingly not the owners!) treat everyone as a welcome guest in their home and willingly do whatever they can to make your stay perfect. The entire staff is friendly and willing to help in any manner. It's located one block from Duval, convient but away from noisy late night revelers. The grounds are beautiful but not that artificially manicured look, more tropical and natural. The included breakfast has a great selection including Bloody Marys and Mimosas - for a small fee. Each room is unique with amenities you wouldn't expect like a small fridge, a coffee pot and an honor selection of snacks and beverages for purchase. The rooms are clean and have great water pressure and lots of hot water unlike most hotels. And it's an adults only facility for those of us looking for a peaceful space. They even offer their own adjacent parking for a small fee. You won't regret choosing Simonton Cottages .

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    Simonton Court Historic Inn & Cottages - Beautiful uplighting in the courtyard.

    Beautiful uplighting in the courtyard.

    Simonton Court Historic Inn & Cottages - Sitting area MA5

    Sitting area MA5

    Simonton Court Historic Inn & Cottages - Entry at night

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    Entry at night

    The Galleon Resort - View from C53

    The Galleon Resort

    2.9(39 reviews)
    2.7 mi

    Hop aboard The Galleon and set sail for a wild ride around the Florida Keys! Wait, wrong type of…read moreGalleon. The one I'm writing about is more of the grounded/foundation/building kind, and on my recent trip down to Key West I had a pleasant experience at said establishment. My travels were with a handful of coworkers as we escaped the NY cold to get some Florida sun. They had come to The Galleon two years prior and stayed in quite an odd and anything-but-enticing room. Luckily, adding me into the mix gave the need for an upgrade to one of their larger quarters that faced the marina. We walked in and there was some awe to our reactions. Maybe it was all the negative convos I had overheard about their previous place, but this was quite the space (too much rhyming?). Multiple bedrooms and bathrooms, a spiral staircase, a kitchen and dining area, and a breathtaking view (complete with balcony). We kept those balcony doors open most of the time just to really drive in that balmy feel. Beyond our rockin' room was the pool and beach area. Well, the pool was exactly as stated (a pool), but that beach? It was more of a tiny, sandy spot with a few chairs and no real waves. Hey, it was a way to get into the ocean and there was one of those floating wooden docks you could climb up on so it had that going for it. The rest of the outdoor area included a deck with plenty of tables and lounge chairs as well as the majority of this exterior section: the tiki bar. Hanging out back here really let the laid back Key West feeling sink in. So why not five stars? Despite the beauty of the room, by the third day, you could notice some wear and tear in spots that took away some of that original luster. Plus, it should be noted that The Galleon is really more of a timeshare, so housekeeping isn't an everyday occurance (we learned the hard way when we ran out of towels). Staff is also few and far between, but we ran into no big issues so this wasn't a problemo for us. Overall, The Galleon does deliver the essentials for a relaxing time when in Key West. You've got everything you need right there (including a nice happy hour special at that tiki bar) and a short walk away from the bustle of Duval Street. My coworkers are planning a return trip in two years and you can bet your bottom dollar we'll be shacking up again aboard the ship...er, um establishment that is The Galleon.

    Disappointing at best. We had reservations for a five night stay. My husband had a medical…read moreemergency on the first night and was taken by ambulance to Miami. I returned to the hotel to check out early, only to be told I had to pay for the full 5 night stay. We had only spent one night. Just be aware the management will only allow refunds during hurricanes. In addition, the unit was run down and seriously outdated.

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    The Galleon Resort - C53

    C53

    The Galleon Resort
    The Galleon Resort - Sunset from tiki bar

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    Sunset from tiki bar

    The Southernmost Beach Resort

    The Southernmost Beach Resort

    2.2(11 reviews)
    2.7 mi

    We come to Key West often, sometimes twice a year and on our last visit, while walking to Lousie's…read moreBackyard, we passed this waterfront resort and really liked how it looked. It's quite large and also had a few pools, nice beach, and the attention to detail (upkeep mainly) appealed to us, so we decided to stay here on this most recent trip. We selected the Le Mar house, which is sort of like a B&B with your own bathroom in each room. The house's décor is excellent... the upkeep is equally as nice! We heard that these houses (the Le Mar and the Dewey) were recently renovated and we could tell, as everything was shiny and clean, but overall, the staff does a nice job keeping things polished on a daily basis! The bed was comfy and the bathroom was spacious and nicely tiled. The shower pressure wasn't that great, plus it took forever to get hot water to the shower head, but we didn't mind, as it was so clean and nice and the shower was still effective. They have a nice selection of soaps/shampoo called Bee Nice, which offered a nice smell and effective wash. The towels were soft, clean, and kept stocked up in our bathroom. The décor in the room itself was beautiful and reminded us we were at the beach. The only issue with the room itself was that the TV uses WiFi to connect and it was horrible. We like to fall asleep and wake up to the TV, but it kept buffering and mostly didn't work. Plus, there was no sleep function accessible from the remote. The resort offers 3 pools... We chose the tranquility pool the first day, which was nice until a group of loud mouth guys got in and just became very obnoxious. They ran off most of the couples there by being condescending in a southern tone and constantly telling each other to hush as this was the tranquility pool, yet being on opposite sides of the pool to constantly yell back and forth... Juveniles! These types of people are generally why we don't like large resorts like this, they're often loaded with people to drink too much and don't know how to act. So, the next day we opted for the Shores pool, which is definitely a lot louder, as it's got music playing, about 5 times more people in it, a bar, and even live music a few hours each day. But the guests were all much more pleasant in this pool and we enjoyed being here a lot more. Plus, this pool is huge, so it's easier to spread out and have more space in the pool, with plenty of lounge chairs and umbrellas too. The only issue here were the 3 different guitar singers that came in each of 3 different days... they were all horrible! (Note to resort - save your money, just play the regular music from the speakers, yacht rock was great, but these guitarists were very bad!) The report offers full service at this pool with a full food & drink menu. They also have a spa, which is location just off the side of this larger pool too. Housekeeping on point! She would notice when we left the room to go to the pool and she'd refresh our room, making it smell citrus fresh too! I left out checking in, but that too was friendly and efficient. They gave us a ride to our room and took our luggage up. The one thing I wish they would offer is a ride down to the "downtown" area of Duval, as it's pretty hot and to walk 7/10th of a mile every time you want to go out is a bit much, especially for those in heels. We noticed that the staff was always cleaning and keeping things straight around the resort. There were painters constantly touching up and it was evident, as there was hardly any rotted wood railing or chipped paint to be found... Again, great attention to detail! Lastly, the resort did a great job keeping in touch... sending texts throughout the day telling us what was coming up. They had plenty of activities, some looked really fun and the entire staff was very engaging. We'd definitely return here!

    This was the worst hotel I've ever stayed at in over 50 years! A complete rip off is too kind a…read moreterm for this place. It took over $1300. For 2 nights for a substandard king room. That was after we were offered their first room behind a second floor stairway which we refused. Add on to that $45. Per night parking charge followed by a $60 per night "amenities" charge? Where do I start? Noisy room air conditioner, no water pressure in the shower, over 1 hour waiting in the lobby to check in. The beach was filthy. Save yourself the time and aggravation and go somewhere else.

    Photos
    The Southernmost Beach Resort
    The Southernmost Beach Resort
    The Southernmost Beach Resort

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    Havana Cabana - resorts - Updated June 2026

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