Hotels with Swim-up Rooms in Key West

The private pool, & public roof pool/bar makes this resort stand-out! Very friendly & helpful staff that took immaculate care of our room/pool multiple times a day! Made for a phenomenal honeymoon get away!

The staff was so friendly, the private pool was wonderful and we had a fantastic time at the roof top bar and pool. We can’t wait to come back!!!

Location, rooftop pool, private plunge pool.

Great room, nice private pool, beautiful and relaxing rooftop pool, lush landscaping, AMAZING service by everyone working there!

The private pool attached to our suite was great, the courtyard at the hotel was really nice and the hotel staff was very freindly and pleasant. We really enjoyed our stay here and will stay here again when we return to Key West without our children.

All of the employees from the hot towel boy to the helpful front desk went out of their way to make sure we had a good experience. I stayed in two different suites and they were both beautiful. I love the beach access room and the pool access room was gorgeous too. The downtown shuttle was easy and the driver was friendly. A++ experience

Loved the room with two king bedrooms, each having their private full size bathroom and also halving a 1/2 bathroom. The pool and pool bar were amazing! We had the best time hanging at the pool in between going into town. The guitar player singing in the afternoon by the pool was a great touch and we really enjoyed his music. Loved the location. Close enough to the airport and all that we wanted to do at the main attractions. Ubers were always available to take us to where we wanted to go and were reasonably priced. When leaving our flight wasn't until 3:00 pm, so front desk offered to put our stuff in a room by the front desk so we could go out and spend our last day doing what we wanted without worrying about our luggage. The bartenders were great!!

Overall a really nice experience. Nice ocean view from the ppol, the rooms were clean and spacious, with easy access to parking garage and pool. Staff was friendly and non-intrusive, and maintenance issues were addressed promptly. The nightly $25 parking fee for the parking garage was excessive considering the cost of the rooms and the distance from all the action in Key West. The pool waiters tried to enforce the no outside food, drinks and coolers rule even though drinks were between $7- $15 a piece, which just angered everyone that was poolside. Due to the everglades wildfires, we left a night early, and brightwild promptly returned the last night's room charge, which was really generous. Overall 4.5 out of 5 stars.

When we arrived at this property, we already felt it was a beautiful place. Not knowing really what we were going into, then we opened up the door to our room. We were amazed, have such a beautiful place that we are going to stay. The pool is beautiful. You get service at the pool. There's the pool bar, there's also the ocean right next to it. Everything you need is in our room. We are truly happy. We had extra days at the end of our trip. And we chose to come back and spend a second 4 days here, instead of somewhere new it was that good.

I recently stayed at this hotel and was impressed by how beautiful all the areas were – from the well-maintained grounds to the elegant interiors. The overall atmosphere was relaxing and enjoyable. However, the pool area and bar could use some improvement. Both seemed understaffed during my stay, which led to delays in service and made it hard to fully enjoy those amenities. With a few more employees, the experience would be much smoother. Overall, it's a lovely place with great potential. I’d definitely return, especially if service at the pool and bar improves.

It's just a very expensive bed and breakfast- so why do i want to win the lottery and just move into room 202 for a year or two? The breakfast- not with anything even hot- just strawberries- blueberries- blackberries- yogurt- cereal- very special bagels- and maybe the best pastry i have had anywhere. The huge room with picture window facing the sea-- the great 4 poster bed- so clean and fresh. The pool- i don't know why but it was as warm as any thermal water pool . I swam laps every day. The fairly new food truck- near the pool- that i thought would be a real negative- wasn't. The molding..the pink and blue decore... nice Now let's talk about Nina ( the manager- who i assumed must be the owner ) around 8PM the air conditioner stopped working and the room got very warm- As there is no one at the desk after 9- i called her around 10 and probably woke her up. In 10 minutes she was there- found an empty room so we could sleep well on our last night. Do i recommend spending your last dime at this place- you bet your life.

We can't say enough great things about this hotel. As soon as we arrived, we were welcomed by the staff and received excellent service throughout our stay. The Mansion itself is beautiful and our room (204) was perfect. The pool and access to the adjacent bar were fantastic for our "pool days." The pool never got crowded and there were plenty of lounge chairs and beach towels provided. The hotel is conveniently located at the (quieter) end of Duval Street and it's an easy walk or Uber ride to dinners, etc. We also appreciated the complimentary breakfast provided every morning - it's definitely a step-up from the typical continental breakfast provided by many hotels. Truly, we look forward to staying here again in the future.

Ok let me start by saying if you want the clean lines of a modern room. This is not for you. This is a historic part of Key West. It is old. It has old beauty. I have included pictures. We rented 301 the tower room but when the air conditioner broke they gave us 302 to use as well. It may not be what we signed up for but it was still great. The beds here are FABULOUS. The staff even more amazing. The third floor can sometimes have an off smell when going up the stairs to it. Not all the time. And there is no elevator so what you bring you carry up three flights. The last flight is long and steep. Worth it for the tower room. The Cuban coffee is not what I was expecting as I am accustomed to real Cuban coffee. It is cafe bustelo. Was still good. The breakfast the first day was not as impressive as the second day. I know $27 for breakfast is high but two eggs on their own in the area can be $12. Things are expensive here. Don’t come if you are looking for cheap. Seriously. The pool is deep, I don’t recommend for kids. The ocean view from it is nice. If you never leave the mansion grounds you will still have a good time. Next to the pool are amazing drinks from a small bar(not free). You will see sea birds, chickens, iguana’s and hear roosters. The place may be old and historic but they do keep it clean. I was unsure of our choice when we arrived but now I never want to leave.

Took my wife to this beautiful and historic hotel for her Birthday. Was treated royally by Beth on our arrival as she informed of the history and gave us a full tour of the property and our room. She also lugged one of our suitcases up to the second floor to our room. Our room, #201, was beautifully appointed. It overlooking the pool with a terrific ocean view. the pool was fabulous and warm. Our room and ensuite bathroom was very clean and the bed was comfortable with more than adequate air conditioning. The room came with a back deck porch with comfortable chairs and tables. Continental Breakfast was top notch with great coffee, orange juice and a complete choice of a mostly healthy fare. Dean was fantastic and very attentive and informative. Nina, the GM was friendly and very helpful. The only negative was no elevator. We are in our 70's however. Younger people would do fine. I very highly recommend this hotel as it is in walking distance to everything that Key West has to offer. We paid for onsite parking which was very convenient. Would definitely go back and stay. We were there for three nights.

We wanted to have a few days away to unplug and relax. We spent most of the days in the great pool where we could be in the pool and gaze out at the water. With the palm tree providing filtered sun in the mid afternoon, it was a place I could have stayed for days. The rooms were great and clean. The staff was very pleasant, helpful and accommodating.

It’s a nice, smaller, boutique property. Decent, free breakfast. Good value if you like peace and quiet and mixed clientele. If you are a fan of the more social, all male vibe of the Island House or Equator, you may be disappointed. Pool is not clothing optional although there are two remote decks that are. Never saw anyone use them though as they aren’t convenient. Free happy hour at 4:30. Super nice staff. Couple of notes: the pool is accessible only by ladder. Awkward for anyone with mobility issues. The bedside clock radios are not USB compatible.

We loved our stay at Alexander’s. Upon arrival Tim helped us with our bags and showed us the facilities. He also made some recommendations for restaurants. The breakfast and happy hour were fantastic. We had fun meeting the other guests. While there a tropical storm came through the area, Laura communicated with us via text the entire morning to make sure everything was ok. She even ordered lunch for the entire resort when the power went out. I can not say enough about their customer service. Our room was delightful. It was beautiful, comfortable, and had everything we needed. The pool area and sun decks had plenty of space and were beautifully decorated. The lobby area was also gorgeous. The resort is at the quiet end of the street. We were able to walk to almost everything we wanted to do. They resort does have bikes on property for rent, which was convenient. We loved our stay and have already booked our return. I highly recommend this resort.

From arrival through departure our stay at Alexander’s Guest House was amazing! We felt like we were staying with the most thoughtful friends. Breakfast was superb, a variety of choices and always fresh fruit and delicious coffee. The pool temperature was perfect, cool enough to be refreshing and not so cool as to be shocking. We enjoyed the nightly happy hours too. Our room was clean and well furnished, we loved the daybed! A special thank you to Tim who helped us book a sunset cruise and delicious dinner at Latitude!

Wonderful place to stay! We were greeted at the door, offered a welcome cocktail while we checked in, which was great because we had just ridden our bicycles 50 miles! The room was clean, beds were extremely comfy, pool and hot tub were wonderful, the grounds were beautiful. We were unable to attend happy hour and are sad to have missed it. We had to leave early in the morning, but coffee and breakfast were already available for us. We would definitely stay here again.

Absolutely wonderful destination fir a relaxing stay while in Key West. Can not say enough about the great staff— friendly, helpful, just happy to be working here. They could not be more accommodating!! Add to that complimentary wine in your room, daily happy hours by the pool, and full service cooked breakfasts that easily saves you hundreds of dollars on a 4- day stay. Can not give this place enough praise. We are already planning a return trip.

Excellent location! Half a block off Duval. Auxillary off-street parking available first-come-first served at a cost of $25. Super friendly staff, very accommodating. Our room was the smallest I've ever stayed in with a shared bath, but we only slept and showered there anyways. Nice continental breakfast, cold a/c, quaint accomodations. Nice, private backyard pool area that is open 24 hours. Will definitely stay here again, but will upgrade to a second floor room or private pool house with a private bath.

Over all we r happy customers.We did enjoy our room 12, next to the pool(guest house). There was something wrong with our bed, it was a drop in the ocean compare to fun what we have had. Wonderful pool, warm water in it. Quite house .Clean.Nice decoration around the pool. Amazing location!!!!

Wonderful, whacky, just a perfect Key West hotel! great welcome, lovely breakfast, pool and lobby honesty bars, pool towels (and sunscreen) fruit always avaiable in lobby. the ladies were just brilliant, great recommendations from them.Perfect location too.

WOW....don't hesitate staying here....we were in the height of Covid19...and this place had all the protections in place. Now we did not have maid service everyday...but that was understandable.....all we had to do is ask for clean towels and it was granted. Starting withbreakfast..wow....hard boiled eggs, ham, salami, cheese, french toast, yogurt, granola, bagels coffee, orange juice....NOT just a continental breakfast...and it was served because of Covid. In the afternoon around 330...we had complimentary wine....hanging out near the pool was relaxing....and during wine time, she delivered it to us! Now that is service. We did not hear/see any ghosts..and that was ok with me. The room was comfortable....if you looking for a modern hotel room, don't look here...this is over 100 yr old house....if you want quaint, ambiance, and great service.....Marrero's is your choice. What made it very special is the two ladies that service the front desk....hospitality and welcoming....thanks for a great stay!

I spent two nights at this beautiful historic B&B mansion with a friend. We were so thrilled with the grounds, the home, the pool area and the staff. Wine Happy hour everyday at 3:30, a beautifully setup continental breakfast each morning, taken on the viranda, if so desired, and so conveniently located to Duval street, that you don't need transportation to enjoy the action. Our room was quaint and very small ( our choice to make our budget work), but have no complaints about it, really. I rather enjoyed the loft bed! Our stay was a real joy, and we would definitely stay there again. The 21 and over requirement for staying there was a plus, lending itself to a relaxing, quiet experience! A

I loved the pool access room. We spent the morning in the pool after eating breakfast on the patio and it was really nice.

First time we stayed the Perry Hotel when we travel to Key West again definitely choose to stay again. Staff was friendly location enough far away the back pool like our private pool room so clean and comfortable. They had the dog park love everything about this place. Thank you again! Price really affordable!

We absolutely loved everything about our stay at the Perry Hotel & Marina. From the moment we checked in the process was easy. They welcomed us with a bottle of champagne to celebrate our anniversary. Our room was very nice & roomy. Our view looking over the pool and Marina was perfect! View from our balcony at night was spectacular. Housekeeping staff were friendly. Loved both restaurants. Fernando at Matt’s went above and beyond to make our 40th wedding anniversary special. All the staff at Matt’s were wonderful. Zach at the Salty Oyster was great, he made us feel so welcomed! Loved the pool, met so many nice people. Loved that we could order food & fun drinks poolside. Arthur was very friendly & helpful on places to explore while we rented a golf cart during our stay. It was so fun driving it Oceanside to downtown Key West. Johnny, the concierge was super helpful when we rented a golf cart and our schooner sunset cruise- which was amazing.

our room was clean and the view of the marina was perfect. the pool was great, as was the pool bar. the service was kind and fast. the pool itself was warmed and clean. my wife and I spent a few hours a day lounging.

The location of the Perry hotel is great if you want explore Key West but stay somewhat outside of the very busy areas in downtown. The Perry team was warm and welcoming. Our room was clean, very spacious and with a nice view on palm trees, the pool and overlooking the marina next to the hotel. For our room the pictures on Booking.com were real. Also a gym is available which was clean and provides all the essential stuff. At the pool we never had an issue to find plenty of free deck-chairs and one day there was even a live band playing. A shuttle bus to Key West downtown was available but we did not use it. Parking is also available but comes at an extra fee. Breakfast was not included, but this was no issue for us.

The hotel is gorgeous! It is set on a wide section of beach, like no other hotel in Key West. They have 2 pools, one adults only and the other is for families. They have waiters wandering around to take food and drink orders. There is a pier as well as a water sports rental facility located on the property. The restaurant is open air and located between the pools. The food tastes great. The rooms are very spacious and are equipped with a coffee maker and mini fridge. The bathrooms are the smallest I've ever squeezed into. The staff is very friendly but service is a little slower than expected. The cons: We had to ask 4 different people over 2 days before we actually were able to secure a luggage rack for our room and got our luggage off the floor. The ac in our room went out and they did fix it, but it took over an hour to get someone there with the tools he needed to fix it at midnight... Our room also had a table with a single chair. We asked for a second chair, but in the 4 days we were there, we never received one. For the thousands we spent to be there for a long weekend, you would think the room would have 2 chairs and a luggage rack. Overall the hotel was gorgeous, room was spacious (except for the bathroom), and we like that the location was a little off the beaten path. We enjoyed our stay minus a couple if inconveniences. I would recommend staying there, but I would say bring your patience if you have any requests.

White Lotus meets Palm Royale in a five-star experience that rivals any luxury resort. I haven’t encountered this level of service or sophistication since before the pandemic—until last week. My husband and I, along with our two 18-year-olds, spent four unforgettable nights at this incredible resort. It’s beautifully updated yet retains the timeless charm and classic architecture envisioned by its original designers. I could easily imagine my grandparents sipping gin martinis here, listening to the soft notes of a piano echoing through the grand lobby. The rich mahogany hardwood throughout the lobby is warm and inviting—it truly transports you. And the view? One of the best I’ve had in Key West. I’ve stayed at several top-tier resorts near Mallory Square, and this one stands out. The service was impeccable—from housekeeping to the pool attendants and everyone in between. Breakfast each morning was delicious, and we enjoyed multiple lunches poolside at Dorada, the resort’s vibrant restaurant. The experience offered incredible value for what we spent and far exceeded our expectations. Tip: Get the ocean view room. Each evening, our kids joined us in the Canary Lounge for pre-dinner cocktails and mocktails while we played cards—moments we’ll never forget. Don’t miss the Hemingway Daiquiri.

We stayed during hurricane Debby, the resort lost power for two days, but they kept slinging drinks, walking people to their rooms, then comp’ed half our food and bev tab for the entire stay! Staff remembered our names and drink orders. Pool attendants set up pool chairs with covers, extra towels, and cold waters. The coffee cafe woman (French accent) was so incredibly kind and got our mornings started off positive and strong (caffeine ;) ) Erick and Patrick at the desk, 10/10. Great job guys!

I booked a family cabana by the pool for the day. Ayla was our recreation attendant and did a fantastic job. She was attentive to our needs while still allowing the proper privacy. She also played pool games with the kids, which allowed the adults to take a break. Giorgio was our server and was also attentive to all of our needs and had such a friendly demeanor and great attitude. We enjoyed it so much that we booked another cabana for next week.

My husband and I stayed for 4 nights to celebrate our 10th anniversary. From start to finish, we thoroughly enjoyed all the resort had to offer. We especially enjoyed the daybed option at the adult pool. All of the staff were attentive and helpful, especially Christian at the pool.

Full disclosure - we stayed in a condo through Airbnb versus through resort. We stayed for 3 weeks during holidays 23-24. Location is perfect - a block and a half from southernmost point. Nice rooms, although the rooms in the two-story, two BR, 2 1-2 bath condo we stayed in were a bit small. Needed a place to set up a work station (working vacation) and no great options. Nice pool, but beware it’s not heated! There seems to be a no cigar policy by the pool but unfortunately it is not enforced….. :-(. Even though we didn’t have access to the resort amenities by the pool since we were airbnb residents, the staff seemed mostly very pleasant and accommodating - small bar and towel service. Lots of kids during our stay. First week was very windy in key west but since the pool is in the middle of the condos it was perfect weather shielded from the wind! We will probably look for a different place for our next 3-week trip for various reasons, but this place is worth consideration!!!

The central courtyard and pool space of the resort is almost magical and we loved hanging out by the pool surrounded by the beautiful plant life. The staff at the resort were so friendly and helpful. We especially enjoyed the poolside happy hour and nightly turn down. Additionally, the location is perfect for walking to all the downtown Key West destinations, but inside the resort, you feel transported to a peaceful oasis.

Very nice pool, homemade muffins every morning very nice! Pool very clean and pool area very nice. Location not bad, very close to water and a block off Duval. Plenty of great restaurants close by!

Our room was perfect! The entire property is super clean. Upon arrival, we were greeted by the very nice Matilda, the front desk receptionist. She was very friendly, and was able to accommodate our early check-in! Once she got us quickly checked in, we told her after driving all day, we were starving. She recommended a great place down the street to eat with lobster pizza. Great recommendation, as it was delicious. After the good meal, we enjoyed happy hour at the pool with Wilfredo serving us all delicious drinks. He made sure we had anything we wanted during our time at the pool. Very good bartender! Azul also did a great job filling in for the front desk and the bar. She did a great job. Housekeeping kept our rooms tidy and proper every day. After staying at a different property the previous trips we took to Key West, I think that my family has found our go-to spot in Key West!

Condo, like with some hotel amenities such as pools and pool-side bar. Fully stocked condo - felt like home. In our villa 2 bedroom and 2.5 bath with a separate kitchen and living area. Bar seating in kitchen.Also has washer and dryer inside unit with laundry detergent provided. The hospitality and helpfulness of the staff are awesome. Will assist with luggage storage for early check-in until the room is ready. Matilda is exceptional. Assist with transportation and assist with scheduing activities if needed. Location and access to sites and the Duval Loopis great. Warm muffins and dove bars each evening delivered to your room each evening. Kitchen stocked with bottled water and coffee for the keurig. All in all, it was a great experience. FYI, if you require an ADA room, notify when booking because several villas are two levels and require steps to access.

The property host was very friendly and helpful. We arrived about 30 minutes before check in and were accommodated. There was a bottle of wine chilling in our room but we did not receive an upgrade or anything else for the VIP access. The grounds were nice and the room was lovely. The bed was quite uncomfortable, though and I missed having access to a pool. Also, the neighborhood the property was in was quite far from anything of note. I don't think I would stay again for the price we paid - not worth it.

Nice place , Staff was very friendly and walked us to room and good parking for Key West . Only knock is not real close anything and no pool . Otherwise great !

Initially booked a 3 night stay but added on 2 more days (booked cheaper room). The manager let us stay in the bigger room at no charge. The room was really nice and spacious, outdoor patio is beautiful and the breakfast was just right. We spent a few nights on the patio enjoying wine, Jamon and cheese. Very relaxing environment. My favorite part was the free parking. Only downfall they have 6 spots in front of the hotel and 10 units so if they get taken they have more parking spots a half block away. One of my favorite restaurants, El Siboney is a block away so we enjoyed dinner there a few nights. Also if you take Grinnel street south you’ll run into tennis courts, nice public beach and a pier that has stairs that go into the water for people wanting to swim. Only downfall is the property next door is getting remodeled so around 0800 in the morning it can get loud. Overall pleased with the Grand Guesthouse and will be back.

My partner and I stayed at The Grand Guesthouse recently for 3 nights. It was really wonderful. From the moment we arrived (sweaty and on bikes!) Jason made us feel very welcome and at home. Every detail has been thought through and there are lots of nice little touches like torches and umbrellas in the room, and staff recommendation boards. On a few nights a week they have a happy hour drinks reception, with free beverages for guests, and actually we turned up on a day this wasn’t scheduled, but instead of turning us away, we were kindly offered a beer and some snacks. There is a basic continental breakfast and a lovely courtyard area to sit in the shade, and a coffee machine that’s available all day for guests to use. The location is great - a short walk from all the action on Duval Street but in a very quiet and relaxing street. We would definitely make a return visit if we’re in the area again.

We really enjoyed our 2 night stay at the Grand Guest Guesthouse . There was plenty of parking either in front of the house, or down the street. Our room located on the side of the house was clean, had a hair dryer, iron, TV, Mini fridge, shampoo, conditioner, & body lotion. All perfect for our 2 night getaway. A light Breakfast in the morning was good to start the day, as well as 24 hr coffee. We rented bikes for a small charge, and that was so convenient to ride to all the local sites. We also walked to Duval from the guesthouse. Always felt safe. Jonathan the GM was awesome. Jonathan was very helpful in guiding us on where to go and very knowledgeable of Key West. We really recommend the Grand Guesthouse! We will be back!

My wife and I stayed at Almond Tree Inn for our honeymoon, and it was an amazing experience! The property is quaint, cute, and clean, with a small but beautiful pool and spa. We got a lot of use out of the pool/spa with the wonderful touch that this property is adults only, no kids to stress you out, and we were definitely relaxed here! Check in was smooth, all hotel staff we interacted with were friendly and professional, and they provided us with a fruit basket and champagne on our first day out on the town. Nice breakfast included with actual food (boiled eggs, fresh fruit, assorted breads, etc). They also provide a nightly free drink at happy hour, which was a nice supplement to the already steady steam of liquid. Location was perfect, just steps away from Duval Street, where we spent a a lot of time. Everything is mostly within walking distance (although you may want to rent a scooter or take a trolley to the beaches). A CVS is conveniently next door if you need any essentials. Bed was very comfortable, and the shower head was the best we have experienced. There was a nice, cold fridge in the room, but oddly no microwave, so plan for that while you are eating out. Almond Tree Inn is a perfect choice for visit to Key West, we look forward to coming back with a bigger group next time!

This was our second trip to Key West and our first to the Almond Tree. The hotel is in the midst of the action on Truman and one block off Duval. Even so, you feel far away while lounging by the pool. It's quiet and relaxing. The pool area is well laid out, with fresh towels on the lounge chairs every morning. The continental breakfast is good with fruit, pastries, and good coffee. The 5:00 Happy Hour is great with an assortment of beer and wine. There is a different "main course" plus cheese and fruit. The room was good-sized, though we had booked a double in the hopes our adult children might be able to join us. The sheets, towels, and bathrobes were top-notch.

This property was exceptional - had 3 rooms for our girl’s trip and everyone raved about this place! Clean, modern rooms - beds were sooo comfy - high end toiletries and bathrobes were much appreciated! Breakfast was fresh and plentiful with many options and their happy hour with free drink and charcuterie was a nice bonus! Pool and hot tub were clean - pool noodles were available to use and free sun screen was a nice touch! All staff was friendly and helpful and seemed really happy to be there and willing to do anything they could to enhance our stay. Location is perfect - very walkable with many restaurants nearby and just one mile down Duval to the Harbor area. Overall this place is amazing - we highly recommend!!!

loved the staff, location, pool and comfortable, clean rooms. The staff that took care of the breakfast service every morning were extremely pleasant and I loved the white tablecloths and flowers on the tables. Everyone from check in and housekeeping, to pool maintenance had a bright smile and kind word every single day. Our stay was truly amazing and extremely serene and relaxing.

The staff was excellent! They were friendly and offered suggestions on activities in the area. The pool is clean and all the lounge chairs were clean and in good condition. The pool and surrounding area was quiet we seldom heard noise from the outside. The greenery was well kept and offered the right amount sun and shade. The room was well equipped and comfortable with daily cleaning and restocking available. Overall it was a tropical paradise!

Great key west resort. We stayed in MA1 and had no complaints about the room. Pretty quiet at night as well. The private porch was fantastic. Great complimentary breakfast. I kept going for the bagels and hard boiled eggs. We got one free drink which was also nice. Assortment of pools to choose from. My ONLY complaint is that it was warm during our trip and they still had the pool heaters on. I asked the front desk if they could turn it down and they said no. However, another guest at the main pool asked the pool maintenance man and he was able to do it. I don’t know why it couldn’t have been for the others. Regardless, loved our stay and we’d definitely come back. Looking forward to it!

We just returned home from our 3rd stay at the Simonton. Hands down the staff here are the best. From Jonathan at the front desk who found me a yoga mat to use in my room during our stay right down to every housekeeping staff member or groundskeeping crew. Everyone says hello whenever you pass them. The housekeepers inquire as to if you need anything specific (towels, always towels lol). Which is great when you don’t need the entire room serviced. We love the historic and rustic nature of this hotel. We’ve found our favorite room that we’ve stayed in twice. With all there is to do in Key West it can be difficult to take advantage of all the included amenities they have. From yoga by the pool, your complimentary drink, the various sip and paints, or the food tour. They offer it all. And of course, 4 pools on the property! They’re small but rarely crowded. And if one is there are 3 more. The black bottom pool is definitely our favorite. Great included breakfast as well. Nothing fancy but lets you ease into the day perfectly. And don’t forget the cutest hotel cat. Thank you to Jonathan and rest of the Simonton family for being so amazing that we come back year after year. See you in 2026!

The walkway just past the front gate is magical. Full of lush trees, plants, and orchids. At night it is lit with beautiful lighting. The heated black bottom pool was our favorite and seemed secluded as there are not a ton of guests and there are 4 pools to choose from. The staff was very friendly and helpful. Lots of complimentary breakfast options, you put in an order, and they deliver it to your outdoor table by the pool or on the mansion porch. This was really the getaway my husband and I needed to decompress, recharge, and soak up the tropics.

This was our second year at the simonton court. There are so many things about this location we love, I don’t know where to start. They are accommodating, polite, the grounds are beautiful! Complimentary breakfast by the pool is a relaxing way to start the day. The location is close to all the action, but set remotely for quiet privacy. I love all the pools at their different temperatures and the 24 hour accessibility. The concierge will call you a cab, get you discount on a golf cart, and bring anything you need to your room. You can even use one of their bikes for a day to explore the island. Thank you to everyone that made our vacation there wonderful !!!❤️

Where do I begin!? First, the staff at Simonton Court are wonderful - they are caring, kind, and so accommodating to all guests. Specifically, Jonathan and Violet really went out of their way to make our baby moon the most memorable trip! Second, the hotel itself is so beautiful! We loved the tranquil setting, the pools, and the lush greenery. Third, the breakfast is fantastic! It was so peaceful to come to the beautiful poolside patio every morning to eat a big breakfast. I would HIGHLY recommend Simonton Court to anyone traveling to Key West for the most peaceful and relaxing stay:-)

Lovey large room and large bathroom. Plenty of towels for bath, pool, and beach. Having the food truck restaurant and patio bar onsite was wonderful. The bar hours of 11-7p were perfect We could listen to the single musician music during the afternoon but all was quiet after 7p...perfect. The location was absolutely perfect - only a few steps away from the Southernmost Point buoy and from a small almost private beach. Being on Duval meant that the pedal cabs and Ubers were always only 2-3 minutes away. Being at the lower end of Duval meant it was a little quieter than the other end with all the bars and restaurants, but still within walking distance of everything. The heated spa pool was nice. The included breakfast was such a bonus - I never expected such a full breakfast and it was always good.

We had a lovely big room on the ground floor. Was well decorated and comfortable big bed. Staff were very friendly. Room was nice and clean. Was at the end of Duval street but far enough away not to be disturbed by noise from bars. Free parking and a small pool. We only discovered the pool on the day we checked out, maybe at checkin staff should make people more aware of the facilities.

This little Guest House was the absolutely BEST location!! Got to fulfill my husband's BucketList for our 50th Anniversary by getting to the southernmost point of the USA which was just 1 block away from our Guest House. Key West was a bustling little community but all laid back. Our room was perfect! We were in room 3B, the Palm King, overlooking the pool/patio area. Very peaceful and quiet but just around the corner from all the fun! The king size bed was very comfortable, the room was a very nice size, was equipped with a fridge, microwave, iron and ironing board, a room safe, a big screen TV, hair dryer, and bathroom essentials. And it was SPOTLESS!! Oh, and there were flowers on the dresser on our arrival!! Breakfast was great!! Eggs, sausage, fresh fruit, hot and cold cereal, sticky buns, waffles, and toast were all offered!! The staff was extremely nice and helpful!!! They all get an A+!!! My favorite was being able to set on the verandah, listen to the live music, and watch all the people passing by. So would we recommend Southernmost Point Guest House?? You better believe it!! And we will be back!! FYI...please do not confuse the lovely Guest House with the Southernmost Point Resort....two completely different vibes!!! Thank you to all who helped us have such a pleasant stay❤️💐

Wonderful bed and breakfast situated a stones throw from the southernmost point marker at the very end of busy Duval St.. All staff was A+. Upon check in we were gifted 2 drink tickets to the attached outdoor bar/cafe and was told breakfast was complimentary. Cafe was outdoor covered eatery with a food truck stationed all day and the food was great! Also some excellent entertainment with a singer/guitarist. Small pool outback. Complimentary breakfast was very good and it was nice to sit outside with all the roosters! The room was spacious and bed was comfy. Huge bonus, free parking in site . We plan to stay again!

We chose a small room, but it was all we really needed as we were on the go a lot. Nice amenities! It was very clean and quiet in Room 8. Nice cool AC! Loved the live music, food truck, outdoor bar, pool. The property was beautifully maintained. Friendly staff. Enjoyed the fresh fruit and coffee in the morning. (Most days we ate at some cafes that were recommended to us by friends. Just hanging out there was a good time!

This place is super cute and the staff is so friendly and helpful. My husband and I did a little anniversary trip we got there no problem checking in friendly front desk staff. We walked into our room which was not huge but really clean and cute. It was enough room for us. The bed was really comfortable. I usually miss my pillows at home but these were surprisingly perfect. They had a coffee maker which we really didn’t use much since we could walk right out the door to the pool patio area where there was coffee and water every morning. They also provided 2 bottled waters and left Oreo snacks each day when they cleaned the room. The pool area was not crowded and chairs with pool towels available everyday. They even provide sunscreen and after sun lotion in the pool area. In the pool courtyard area was a small bar where we could use our complimentary drink we received at check in. They had a happy hour each day with some light snacks. The bar also served as the location for the breakfast that was included. Food was good , good variety and the staff was amazing! Overall good pick and we would definitely stay again!

My bestie and I recently enjoyed a wonderful week at the Orchid Key. From the desk staff at check in to the bartenders and housekeeping staff everyone was friendly and helpful. Randy and Niall at the bar served up awesome drinks. The continental breakfast from 7-10 was good with fresh fruit, pastries, dry cereals, toast and bagels. The extra added touch were the tablecloths on the tables around the pool at breakfast time. Always fresh water for drinking by the pool and the pool chairs always had a towel waiting for someone to use. And let's not forget Pete the Cat. Sweetheart. We had a King Deluxe room by the pool, with refrigerator and microwave along with a Keurig for coffee. Also 2 nice bathrobes were provided for use during our stay. Hotel is located on the corner of Duval and Truman walking distance to many/all attractions.

We just returned from our stay at the Orchid Key Inn. What’s not to love! This place is perfect! Right on Duval, close to shops and restaurants! We rented a golf cart to tour around one day and the front desk arranged for the golf cart to be delivered, which was great! We loved the pool and the pool bar. The bartenders were great and drinks were delicious. We had a room poolside, which was nice. Fridge in room with keurig coffee maker. Breakfast was good too, with amazing fresh fruit, pastries, bagels, English muffins, cereal, hard boiled eggs. Perfect to start your day. The staff was incredible as well. Customer service was top notch. We will definitely be back!

This is a fantastic hotel, right in the middle of everything! We will be back. The staff were amazing, special shout out to Chris who worked the bar.. his cocktails were the best I’ve ever had. The room (115) over looked the pool, was super clean, comfortable and the bed was extremely comfortable too. The pool is small but just what you need there were always free beds around the pool. Breakfast had everything you could want and all the visitors were friendly, we made so many friends while we were there. Thank you Orchid Key Inn for a wonderful trip

nice room, super pool and pool service. the Happy Hour with complimentary wine service is rare in key west. Nice touches as ice cold water and fruits and sun lotions provided by the pool area!

The ladies at the front desk were so sweet, I spoke with 3 of them. They gave us extra room keys, they helped us with bike rentals. They gave me extra pool towels and let us keep our bags in the office after we checked out and before we left for our flight. The woman who worked for housekeeping was very sweet as well when she came in to clean up and change our towels. We absolutely loved the atmosphere, the historic building and large porch that our room had. We loved the courtyard area with the ponds and fish, the water machine was great. The pool was amazing and loved that there was a bathroom and multiple showers by the pool. The bike rentals worked perfectly for us. One of my favorite parts was our little black kitty friend who came to visit us. The location near Duval street was absolutely perfect. Loved this place!

It felt so tropical and comfortable. The pool area was nicely shaded in the afternoon and the pool was clean and nice. The staff was extremely kind and accommodating.

Our first stay at the Island City House won’t be our last. The rooms are spacious, the gardens are gorgeous, the staff are professional and courteous, the pool is warm, and if you visit over the holidays, the decorations are exceptional. We spent a week in a king suite in the Cigar House. It’s comfortable, not chic, and I wish the bathroom had a vanity rather than a pedestal sink. The pool area is unremarkable but the gardens and outdoor seating areas, both private and communal, are lovely. An added treat was chatting with Mickey, the wonderfully friendly grounds guy who was constantly hanging lights and decorations for the holidays. It was an outstanding week!

The staff were friendly and professional. Good location in relation to activities. The property needs updates.. the ceiling paint was stained and peeling, the mattress was terribly lumpy and uncomfortable and the furniture was very dated. There was construction happening at the property next door that was very loud- every day, all day for the 5 days we were there. Loud machinery, hammering, loud music from the workers. This was right next to the pool and could also be heard in our room. I was very disappointed that I wasn't able to relax and enjoy peaceful time by the pool.

This was our first trip to Key West... and it didn't disappoint!! And that's mostly because we had a great start at the Island City House Hotel!! The buildings are gorgeous architecture. They've really tried to preserve the old world charm while updating for modern tastes. We stayed in the 2 bedroom suite with my sister and her new husband. The living/dining room was plenty large for us to sit and hang... and we didn't need it, but the couch was a pull out to accommodate 2 more people. The kitchen was fully stocked and usable with a microwave, stove, refrigerator, sink. They offer complimentary coffee, water, snacks, and stock daily. The bathroom was so cute and well decorated. The water pressure was quite good!! I'm not used to that on an island. The bedrooms were nice. A bit smaller but we don't need a lot of room. There are tvs in both bedrooms. THE BEST PART.... is the bicycle rentals... these bikes... saved our world lol. They are $15/day. By far the best money we spent down there!! Cars are basically unusable... bikes are a must on the island!! The grounds and gardens... are spectacular. Absolutely amazing. It's so calming to sit in the sitting areas and just hear the water, birds, wind.... love it. The pool was nice, private, great furniture. We also received a $5/day coupon the the nearby bakery (3min walk)... which had the BEST croissants I've ever had... We will definitely be return customers. Thank you so much.

Exceptional property. All employees were top tier in service and kindness and being overall very welcoming. Everything is clean and excellently laid out and the rooms are wonderfully appointed and have excellent features such as a top tier Nespresso machine. Free water bottles are abundantly available. The pool is heated and really big and the service at the pool cabana is always excellent. The location is good in the sense that you’re a bit away from the heart of the town so you can relax here and go have fun in town when you want to via a $10 or so ride share. The bed was outstandingly comfortable and the property was quiet. Furniture in the room and in the resort/pool area was top notch overall.

The Capitana was absolutely gorgeous! We couldn’t have been more pleased with our stay. The staff was very warm and welcoming. They made sure we always had everything we needed. The facility is clean, inviting, and decorated nicely. The breakfast was good every morning and always different. It was way more than continental and always tasted great. The pool and hot tub were clean and we spent a lot of time in both. The tiki bar had both good food and drinks. Our room was clean, quiet, and decorated nicely. It had a refrigerator, microwave, and a Nespresso machine. The bathroom had a walk in shower with a rain head as well as a hand held sprayer. Our balcony looked out over the pool, but also had a view of the ocean. We had room service daily and in the evenings they come by to empty trash, replenish towels, and leave small pieces of chocolate “tuck in” service. Such a nice touch! We will definitely staff here again in the future.

We had such an amazing experience here! The breakfast was delicious with so many options to choose from. The pool was spectacular — fresh towels always available, a bar conveniently right next to it, and even drinks served to you while you relax in the pool. The property sits right on the water with a sandy area that’s perfect for lounging or letting kids play. Cold bottled water was provided at every ice station, which was such a thoughtful touch. The coin laundry and fitness center were both super convenient. We tried the on-site food and it was fresh, flavorful, and well prepared. The concession area is stocked with everything you could need, and we loved the text service where you can request items straight to your room. Our room was very clean, with linens and towels refreshed twice daily. Every detail was taken care of, and the staff really made our stay effortless. We can’t say enough great things about this place — highly recommended!

Loved everything about our stay Some highlights include 2 days prior to our visit I received a text asking if I had any special requests and I replied with a request for early check in. The morning of our arrival I received another text requesting an estimated time of arrival at the property and when we in fact arrive, our room was ready for us. Nightly turndown service, hydration stations, continental breakfast, poolside food and beverage service and free popsicles were amenities not readily found at many hotels in current times. All staff were extremely friendly and accommodating. The facility was spotless. Only wish was the property was in walking distance of Duvall Street but was only a $10 Uber ride so not a big deal. Pool, small beach area and balcony rooms overlooking the water provided that “resort feel” Not only will I return to the Capitana I look forward to staying at other Opal properties in the future!!!

Clean, comfortable bed, loved the soap and shampoo (smelled like a spa), nice pool, loved the ocean view, loved that there was kayak rental on the property and a bar by the pool area, breakfast and coffee was good, bottled water were readily available when needed, loved that the room key is on a water proof bracelet, fast easy check in and check out.

The location was excellent, so close to Duval St, easy walking distance to the square and pier but so quiet we had no problem sleeping. The hotel was lovely, unique and a piece of history. The reception area had fruity water, different each day and the room had everything we needed. Breakfast in the courtyard was a gorgeous start to the day, with a range of choices from bagels to waffles, fruit, cereal and yoghurt, as well as pastries. The owners were welcoming and super helpful giving advice on where to visit and their advice on hiring bikes was invaluable. We didn’t use the pool but it looked fabulous. We cannot recommend this hotel highly enough.

The room was comfortable with ample space for clothes, and high ceilings that helped maintain a comfortable temperature. Room equipped with a nightstand, chair, luggage stand, television, and hot beverage tray. Spacious bathroom with shower and vanity with good water pressure and plenty of towels. The included buffet-style breakfast was well stocked with a waffle maker, salmon and capers, bacon, fresh bakery items, hard-boiled eggs, etc. with freshly brewed coffee. Wonderful outdoor seating in a beautiful patio garden space to relax and enjoy the meal. Access to the pool was available at the adjoining property and looked inviting although time constraints did not allow me to enjoy that amenity.

Tg here was no breakfast, pool was very clean, had steps from our bedroom down to the bathroom, luckily we had a night light that we plug in so we could see the steps at night.

Awesome breakfast. No pool at the hotel but around the corner at a partner hotel.

Great welcome to the hotel. We stayed in the Saratoga suite which was lovely and had its own shaded patio area which was private, being surrounded by beautiful trees. The suite itself was well equipped and clean. There was plenty of coffee, sugar etc. & of course a coffee making machine. There was also a fridge and ice available from an ice machine nearby. The room was serviced daily and the bathroom was equipped with a nice range of complimentary shower gel, shampoo and conditioner. Breakfast was included which could be taken out on the large patio area or inside if preferred. There was plenty of variety in choice of breakfast. Staff were helpful and friendly. We parked in a nearby (discounted) public parking garage which was fine. We were able to use the pool in the sister hotel (villas) which was a couple of minutes walk away. The property is just off Duval Street which is a great location for restaurants, bars, shops and in walking distance of the main tourist attractions. We would definitely recommend Old Town Manor and would stay here again.

The bed was very comfortable, we had all the amenities in our room (mini-fridge, microwave, coffee), lovely robes provided, our room was close to a more private pool (room 4) and in general everything was within walking distance.

Beautiful hotel in keeping with the area, perfect location in the middle of everything you’d want to see, everything within walking distance. Parking at the hotel was available when we arrived although very limited and a charge for this. Lovely pool areas 2 separate pools, 1 being more of a plunge pool but was lovely and peaceful.

Great location just a few streets from Duval and between the marina and Hemingway House. We stayed in the Treetop suite which was in the annex across the street from the main B&B. It was very quiet and the small pool was basically a private pool since we were the only guests in the building. Appreciated the cold, filtered water stations throughout the property. The breakfast offered included hot options like eggs or pancakes and was better than most of what we’ve experienced in Key West.

Loved the oasis-like feel. So close to restaurants, shops, grocery, yoga studio and bars but super quiet. Pools right outside your door. Air conditioning was great in Katie’s cottage. Breakfast pool-side was a treat. Staff are super friendly and accommodating. Ice machine and filtered water dispenser were a pleasant surprise. Only negative is that the pools bleached my expensive bathing suit in 90 minutes…watch out!

This was a jewel of a hotel set almost in the centre of Key West, and within easy walking distance of the main attractions. The rooms in our apartment were quite large. Cooking facilities were limited, but we ate out most of the time. With a pool just outside our apartment, it was easy to change and get in and out of the pool. The breakfasts were extremely good, and replenished regularly, with plenty of tables around the pool where you can eat.

We liked the location in cleanliness of the property. We also liked the layout and the location of our room which overlooked the pool. The pool area is close by a lot of palm trees and greenery, which was very soothing. Pool was extremely clean and warm. We were offered freshly baked croissants and coffee every morning.

The hotel and the grounds are impeccable. The pool was clean. The water was comfortable. The rooms were large. The beds were comfortable. The bathroom was large. We had a king suite. We had daily made service with an abundance of bath towels, and pool towels. The design of the resort is very unique with with staircase is connecting the buildings making it very convenient to get around the resort easily. I didn’t partake in the continental breakfast, but the coffee was a little disappointing. Fortunately, the Key West Cuban coffee shop was a few doors down. In walking distance from everything so very centrally located. When our flight was canceled, we were able to get an extra night at a discounted rate. Will definitely return it and highly recommend.

We loved the whole ambience of the hotel, a quiet oasis in the heart of Key West. The breakfast poolside was amazing with fresh croissants and quiche, the staff was so attentive and even knocked on our door to bring us bottles of water in the afternoon. Happy hour with wine in the evenings was a bonus and we loved dipping in the pool and laying out before getting ready for dinner. The location cannot be beat! We literally walked everywhere from our front door at the Truman Hotel. We explored Duval Street, Mallory Square, the Southernmost Point, the Hemingway House and Lighthouse are two blocks away, too many restaurants to name, bars to get drinks, and SO much more. I would 10/10 recommend this hotel.

Fabulous location of hotel. The interior designer did a great job with everything. I loved the comfortable sun loungers and easy access between pool area and rooms. They have a happy hour every day! The pool was clean, warm and a good size - my daughter could splash around while not getting others too wet. Breakfast was good with a selection of drinks, pastries, granola/yoghurt or a savoury option to start the day.

Breakfast was great . The lady in charge of the breakfast was very nice and did a wonderful job keeping things stocked. Pool area very clean, as well as all grounds and rooms. Very walkable to Duval Street. Cold water available all afternoon at the pool was great to keep hydrated on a very hot day! All of the staff were very friendly and professional.